“A man can do all things if he will.”

This was the prevailing sentiment during the time of the Renaissance, a time of great flourishing in the arts, sciences, literature, and all of the subjects that drive a culture forward towards the true, good, and beautiful.

Leonardo da Vinci gave us the Last Supper, and Michelangelo produced the ceiling of the Sistine Chapel; both revolutionized art through realistic human bodies, dramatic lighting, and a new sense of depth and perspective. The rise of Copernicus birthed the heliocentric model, and Galileo Galilei took the blueprint and finished the job. Gutenberg invented the printing press, providing books with a level of accessibility that once seemed comical. The revival of Roman architectural forms led to some of the most beautiful European Cathedrals like the Florence Cathedral, engineered by Filippo Brunelleschi. Major advances in mathematics proceeded intense intellectual duels between men like Gerolamo Cardano and Niccolo Tartaglia. The Church underwent the Counter Reformation, weeding out much of the corruption and moral laxity through the Council of Trent, drawing on great minds like St. Augustine and St. Thomas Aquinas.

The advancement in so many different areas meant that many of the greatest minds from this era were experts in multiple fields.

Leonardo da Vinci was more than just a painter - he engaged in anatomy, engineering, mathematics, and military design, as he was known for designing flying machines, tanks, and hydraulic systems. Galilei was a high level engineer, mathematician, and philosopher in addition to his astronomical endeavors. While Galilei and da Vinci may be more notable historically, Leon Battista Alberti may have the best resume, as he was an architect, polymath, linguist, cryptographer, philosopher, artist, and an athlete. While he didn’t engage in any organized sports, he was the best horseback rider in town and could allegedly vertically leap over a standing man. He is where the preceding quote originates and rightly so.

The common traits among these men were intellectual curiosity, a desire to learn, and the belief that man–a strange hybrid between an immaterial / intellectual angel and beast-like animal–was a special creation from the fingertips of God whose essence was unlike any other being on this planet. The combination of man’s intellect and will, his faculties that separates him from the other animals, was what drove this ability to be rational yet creative and not only strive for expertise in a specific area like art, math, science, theology, or philosophy but all of them at the same time.

This man is not just any man; he is the Renaissance Man.

Shakespeare was something of a Renaissance man himself given his deep knowledge of law, psychology, politics, philosophy, theology, and of course, poetry. If this is the case however, why is he quoted as saying the jack of all trades is a master of none?

What people often forget is the quote is typically utilized in its incomplete form: “the jack of all trades is a master of none, but the jack of all trades is better than a master of one.”

Now this makes more sense.

Rather than pursuing the mastery of one sport, Casey Hayward began his sports journey as the jack of all trades. After all, the strive for greatness in multiple areas within the intellectual or athletic lanes is still highly admirable in today’s time. One can easily argue that Deion Sanders, through his ability to play both football and baseball professionally, is a more impressive athlete than Tom Brady, the consensus GOAT for football, as more people could conclude that Sanders’s feat of hitting a home run and scoring a touchdown in the same week is more impressive than Brady’s rings.

Born in Perry, Georgia, Hayward was a high level track & field athlete, competing in the 100 meter dash, long jump, and triple jump, where he finished second place at the prestigious Patriot Invitational with a jump of 45.5 feet. He was also a four-year varsity player on the basketball team, playing a pivotal role at the combo guard spot. Lastly, he was an animal on both sides of the ball for football; his senior year he totaled nearly 2,600 yards at QB, while rushing and passing for 18 touchdowns each. On defense, he was even better and was recruited by several schools to play cornerback. After receiving offers from Troy, Southern Mississippi, Duke, North Carolina, and Vanderbilt, the choice became obvious to him, as only one school had high level academics and played in the best conference in the country.

Hayward played during his freshman year and started his sophomore year, but it wasn’t until his junior year that he became one of the best corners in the country, as he ranked first in the SEC and third in the country in passes defended, earning 2nd Team All-SEC. The following year he was even better, being named an All-American after tying the Vanderbilt career interception record with 15, doing so in epic fashion in his last game as a Commodore. While his time at Vanderbilt was filled with accolades, the only regret he has is not beating Tennessee, despite paving the way for those who came after him, with Vanderbilt winning five out of the next eight matchups with the Volunteers.

After being drafted to the Green Bay Packers in the 2012 NFL Draft’s second round, Hayward got busy right away, recording an unbelievable six interceptions, including four in a three game stretch. He was named to the All-Rookie team and finished third for Defensive Rookie of the Year. Hayward spent three more years in Green Bay before signing with the San Diego Chargers, where he again immediately burst onto the scene in a new environment. His 2016 and 2017 seasons included back to back Pro Bowls, 11 total interceptions–including a league best seven in 2016–nearly 100 tackles, and being named to the notorious NFL’s Top 100 Players list. When asked about what he remembers most vividly from his career, he cites Tyreek Hill’s speed and a Thanksgiving game victory against the Cowboys in 2017 where he had several notable pass break ups and an interception in the 4th quarter to seal the game.

When asked how he is able to collect so many interceptions, he keeps it simple:

“You either have it or you don’t… it’s always been something I was good at…with me, you know I’m going to get to the ball.”

Hayward wrapped up a successful 11-year career in 2022 after spending a season with the Las Vegas Raiders and Atlanta Falcons each. It was now time for the next chapter. He knew he wanted to get into investing, he just needed to determine which asset class. After some deliberation, there was a clear winner: real estate.

The first reason was more practical than anything else: his cousin had put together an impressive real estate career, so he didn’t need to spend precious time and energy organically building a deal flow channel nor pay anyone for deal access. Rather, he would rely on his cousin’s pipeline in the beginning and over time understand how to source deals. He also was highly attracted to the income component of real estate, as the continuous stream of rental payments was something that immediately caught his eye. Not only were the income streams continuous, but he also noted the tax advantages that come with real estate that many other asset classes can’t boast of. Thus, the combined appreciation potential, steady cash flow, and strategic financial flexibility was enough for him to pull the trigger on the asset class.

Once real estate became the target, single-family homes became the focus, not only because the access was the highest due to pricing points, but also because he was most bullish on the space because of the unique demand for single-family units. Thinking about it at a high level, he intuited that the persistent demand for homeownership along with the limited housing supply in most markets creates a compelling long-term opportunity.

Hayward admits while he has purchased existing assets before and many have turned out to be successful investments, the satisfaction of building a unit from the ground up is hard to match. There is a unique fulfillment, he says, in taking a project from a raw piece of land to a fully realized community that families can ultimately call home. For Hayward, development is not just about financial returns, but about creating something tangible and lasting through vision, execution, and patience.

He also acknowledges the profound impact attending Vanderbilt has had not only on his life holistically but specifically in business, as many of the relationships he cultivated when he was at Vanderbilt and the Commodore connections he has made since graduating have served him well in his real estate journey.

Getting into some more specifics on what he looks for in the deals he does, he tells us the following:

“Location is obviously a massive component of real estate analysis, but for me it goes one step further than just which location is seeing growth…I have to be familiar with wherever I’m investing in. Most of my deals are places close to me [within a few hours of Perry, GA] because the insight that I have on these places serves as a potential alpha generator…the right information can be the difference between a project’s failure and success. You can receive all of the information in the world from someone else about places you’re not familiar with, but the level of trust in that information will never stack up against the information you’ve learned by yourself first-hand.”

“When it comes to return targets, it depends on what the project is. For standard single family units where the goal is to hold and receive cash flow through rent, the target is usually between 8 to 12 percent [internal rate of return]. On the other hand, I’ve been getting into flipping duplexes recently–with a time frame of 8 to 12 months–and we’ve had higher targets, typically 15% or above. We’ve been carving out a niche of affordable housing, typically $375K and below, that has served us well and will continue to keep executing.”

While the athlete investing wave we’ve seen recently has helped spark intrigue among many athletes, it isn’t always clear to younger athletes what the first step to getting a foot in the door actually is. Klay Thompson notably remarked that early in his career he wanted to get involved in investing but everyone made it seem like all you needed to do was “throw your money in a microwave and watch it grow.”

Thus, when asked about the advice he would give to younger athletes looking to get started, he has many thoughts. First, he underscores the importance of engaging with an asset class that you either have an advantage in, whether it is through your skillset or network, or one that you are highly passionate about and are willing to go above and beyond consuming everything there is to know about it. In the same way it makes sense to pursue the sport you have the most natural talent in and then continuously work to improve, the opportunity cost of engaging with asset classes that you’d be less successful in is extremely high, especially since a few percentage points in returns over decades amounts to very large sums of capital. He also advises athletes to strike while the iron is hot; in other words, don’t wait until you are retired to begin making connections, as meeting with people in the industry you’re looking to build in is mutually advantageous to both parties. For the players, meeting people who have decades of hands-on experience is obviously valuable both from a network and knowledge standpoint, but having connections to athletes from the business owners’ perspective is also key for the same reasons. Lastly, he urges athletes to have a well thought out plan for the short, medium, and long term but also not to be scared to iterate when things don’t go according to plan.

It is safe to say Hayward has done well within the real estate world. But that same desire to conquer all the fields that drove da Vinci, Alberti, and others during the Renaissance is simmering within Hayward. Just as da Vinci is known for art, Hayward’s investing legacy will likely be headlined by real estate. However, Hayward will soon branch into the other asset classes that he initially ignored to pursue a mastery in real estate because the pursuit for mastery in different domains seems to be hard-coded in our DNA.

Or at least hard-coded in the DNA of the greats.

Hayward has already passively invested in a few early stage funds in addition to investing in a few restaurants and acquiring a handful of Starbucks. Private equity / credit, hedge funds, art, and even crypto seem to be on the horizon for Hayward. As an athlete, he started as the jack of all trades before eventually transitioning to the master of one. With regards to his investing career, it has become inverted, starting as the real estate guru before beginning his metamorphosis into the multi-faceted investor.

Long live the Renaissance Man.

He is inevitable.

A quarter of a millennium later and we’re still pushing.

Since the very beginning, we’ve always been unique. Not in the sense a revolution preceded our birth; that is an ordinary occurrence throughout history.

What is unique is that innovation was present from the first moment.

The concept of democratic principles had been around for thousands of years, spanning back to the Ancient Greeks. Nobles and aristocrats making decisions was no novel concept. A single leader with centralized authority was a tale as old as time.

But it had been a while since anyone put together all three.

To observe the last time it was executed, we must traverse back to Rome.

Similar to the Americans, Rome was founded after the overthrow of a despotic tyrant, Lucius Tarquinius Superbus, and thus were cautious of consolidation of power in the hands of a single individual. The two consuls served as the decisive co-monarchic leaders, especially in wartime, working alongside the aristocratic Senate and democratic popular assemblies. However, the turn of the millennium marked a shift in which the emperor began to accumulate more power, and by the late 3rd century during Diocletian’s rule, historians agree that the Senate and popular assemblies were just there for show. But for a while the Romans had a good thing going. The Founding Fathers identified this and took some notes.

Hence, innovation isn’t always producing something completely new, but rather it can be looking backwards and bringing old ideas to life with a new and original twist.

The rule of one was through the president, the rule of the few was by the Senate, and the rule of the many was represented by the House of Reps. The system fit into this box much cleaner pre-17th Amendment, as before this, Senators were elected not by the people but rather by the state legislatures, serving as a longer term ruling elite blocked off from the passions and demands of the people.

The key addition to the Roman model was a written Constitution that clearly enumerated the separation of powers to ensure that the roles of the different bodies weren’t left to oral tradition so that separation of power could not slowly be eroded as with the Romans. Moreover, the concept of federalism meant that there were not only checks between the different branches of federal government but also between the federal and state governments as well.

The new and improved Rome was ready to go.

The 1780s and 1790s saw the formulation of the Constitution, Bill of Rights, and Washington’s warning about excessive partisan divisions. The 1800s and 1810s consisted of expansion through the Louisiana Purchase and proving the Revolutionary War wasn’t a fluke through a draw in the War of 1812, producing our anthem of “The Star-Spangled Banner.” The 1820s and 1830s gave us the establishment of authority in the Western hemisphere through the Monroe Doctrine and economic growth that proceeded from expansion of railroads, canals, factories, and banking. The 1840s and 1850s resulted in even more land, acquiring western states like California and Nevada through the Mexican-American War victory, leading to the compromise of 1850. The 1860s kicked off with a victory from Abraham Lincoln, causing southern states to secede and sparking the bloodiest American war to date, claiming the lives of roughly 700,000 Americans. The 1870s and 1880s marked the Reconstruction Age, as the South began to be reintegrated back into the Union, as well as the rise of business tycoons, with Carnegie controlling steel, Rockefeller monopolizing oil, and Morgan dominating banking. The 1890s and 1900s saw another American victory over a foreign adversary, claiming Puerto Rico and Guam in their victory over Spain as well as Teddy Roosevelt leading the charge to break up monopolies created by the aforementioned moguls and their associates. The 1910s and 1920s included the formalization of federal income tax, US’ entry into World War I, the beginning of American global dominance, Ford producing the model T, and the economic boom that was the Roaring Twenties. The 1930s showed us what comes up must come down, with the Great Depression erasing the previous decade’s gains and more, not just in the US but around the world. The 1940s and 1950s saw the US enter back into global combat, finishing off the war with the infamous bombing of Japan, as well as the population boom that proceeded from soldiers returning home. The 1960s and 1970s changed the entire fabric of the nation’s culture, as race, gender, and cultural relations would never be the same. The 1980s produced supply side economics and heightened paranoia surrounding the Cold War until the Berlin Wall eventually fell. The 1990s and 2000s were all about technology, from the rise of the computer–and stocks associated with it–until cell phones dethroned its popularity. The 2010s saw a recovery from the Global Financial Crisis as well as a continuation of the previous decades’ technological advancements with cell phones continuing to advance and the proliferation of social media and entertainment apps on said devices. Lastly, the 2020s gave us…

The first trillionaire on record.

Very fitting that the milestone comes on the cusp of the nation’s 250th birthday.

His trillionaire status will likely continue to oscillate as post-IPO volatility is to be expected but the point still remains.

What many are keen to forget is that just a few years ago, Jeff Bezos was the man to beat. Most thought he would hit the big T status before anyone else, as from 2017 to 2021, Bezos always reigned supreme on the annual Forbes list. The spring and fall of 2021 was the year of the Tesla stock boom that put food on the table and Tesla’s in garages for the pandemic day traders with good timing. The rivalry is hard to ignore, as both have their “main company” and their respective space companies on the side, as both have publicly claimed they will “conquer” Mars before the other. Not only has SpaceX thoroughly outperformed Blue Origin but its valuation is on par with Amazon, briefly passing it before retreating.

Bezos is not just sitting idly by but rather recently came out of retirement, sliding into his first operating role since he stepped down from Amazon in 2021.

Bezos has begun working on Project Prometheus, a company building an artificial general engineer meant to be the physical AI for the industrial economy rather than chatbots and consumer applications. By modeling, simulating, and optimizing sophisticated physical products, they aim to bring efficiency to the “design-build-test” loop across the most capital intensive industries. Created in San Francisco in November of 2025, they’ve hired nearly 150 employees from companies like DeepMind, OpenAI, Meta, and Nvidia. Despite being pre-product, the company raised a $6.2B Series A funded almost entirely by Bezos in November and are currently raising a $12B Series B at a $41B valuation with participation from DST Global, BlackRock, JP Morgan, and ARCH Venture Partners.

Only time will tell if / when Bezos will reach trillionaire status as well.

For now, Musk stands alone.

Now that Musk is a trillionaire, the scrutiny has of course increased, with a sizable increase in Twitter commentators urging him to liquidate his assets and single-handedly solve world hunger. In fact, the streets are saying that sum of money could solve world peace; after all, simply present both sides of any conflict with billions of dollars, and they have no other option but to call a truce.

In all seriousness, it is interesting to see the changing attitudes towards notable milestones of wealth being amassed.

John Jacob Astor is widely regarded as the first American millionaire, generating a net worth of $20-$30 million before his death in the early to mid 19th century. Born in Germany in 1763 before venturing to America after the Revolutionary War, he was your favorite salesman’s favorite salesman with the ability to sell wings to a bird. He entered the fur trade, initially sourcing from Native Americans himself before eventually importing from Canada and selling the fashionable beaver fur hats domestically and internationally. After the British destroyed his trading posts during the War of 1812, he pivoted and entered into a more lucrative trade: opium. Between 1816 and 1825, he sold hundreds of thousands of pounds of the illegal substance through bribing port officials before exchanging it for Chinese goods like silk and tea that he would sell domestically. After years of engaging in the “fair, honorable, and legitimate trade,” according to fellow American businessman Warren Delano, father of FDR, he washed the money through New York City real estate before calling it a career and admiring his work.

Rather than inquire about the shady dealings, the public admired him and praised the fact that wealth at this scale could be produced by an individual, rivaling the notable European businessmen of the day.

“There are few men whose biography would prove more instructive or more acceptable for the present age than the life of John Jacob Astor.”

There was a similar reaction to the emergence of billionaire titans like Rockefeller, Carnegie, and Vanderbilt. Most Americans viewed these men as examples of the outlandish but rightfully earned outcomes that could happen to anyone who was enterprising, dedicated, and intelligent enough to build a good business from the ground up. Tides would eventually begin to shift as the anti-competitive measures that many of these figures engaged in began to surface, with famous The History of the Standard Oil Company by Ida Tarbell marking the official turning point of public opinion. They would eventually slightly improve their images through highly conspicuous philanthropy and contributions to education, with Rockefeller creating the University of Chicago and Vanderbilt establishing the “Harvard of the South.”

Fast forward to today, and the public’s perception of these business magnates is more negative than positive for sure.

My gut tells me Elon doesn’t really care at this point; most of his energy is likely going towards smoothly transitioning SpaceX from the private to public lifestyle.

Elon is undoubtedly the biggest winner of the IPO but there are of course many winners. Firstly, a big shoutout to the SpaceX janitors that will now see their net worth swell to well over seven figures. The executive team and earliest hires are the next winners, with their longstanding devotion to the company paying off handsomely to the tune of hundreds of millions of dollars, if not billions. Last but not least, the early stage investors that will be seeing their long-held investments realized at last.

While firms like DFJ Growth and Valor Equity Partners invested at the earlier growth stages and bigger fish like Sequoia and Andreessen Horowitz would come in later in the game, the biggest investor is likely Peter Thiel’s Founders Fund. SpaceX was on the brink of bankruptcy in 2008 after three consecutive failed Falcon 1 launches and needed funding immediately. Musk called his former PayPal associate Thiel and he invested $20M, before investing more than $600M over the company’s lifespan. The firm now owns roughly 3% of the company resulting in a roughly $60B stake.

The effects of an outcome like this in a liquidity starved venture environment are monumental. The DPI boost that these massive firms will be able to boast of will likely drive concentration of LP capital to a place people didn’t think was possible. Everyone is already aware of this existing concentration but the trend will become even more pronounced. Now throw in the reality that OpenAI and Anthropic are eyeing IPOs as well, and things could get spooky for the non-mega funds’ access to capital. The pitch from mega funds to prospective LPs becomes simple: the number of generational companies that can reach trillion dollar outcomes is increasing and we and a small number of select investment firms are the only ones who can consistently access them. With the previous three companies as examples of realized capital at these astronomical valuations, institutional investors, in theory, will put the emerging and mid-sized manager deployment on pause and re-up with the big dogs. Are there actually companies being conceived of at this very moment that can actually reach these valuations? The answer to that isn’t entirely obvious but doesn’t seem to be relevant, as these investors will likely hand over the cash regardless.

In addition to the blockbuster IPOs that have happened and are on the horizon, notable venture backed M&A activity has ticked up as well. SpaceX acquired Cursor for $60B in stock as a way to bolster its AI vertical after several controversies and mishaps with the company’s original model, xAI. The $60B price tag is the largest VC-backed M&A transaction ever recorded, providing investors like Andreessen Horowitz, Thrive, and Accel with some DPI as well.

Within the span of a month, we’ve seen the largest IPO and venture backed acquisition in history.

The tides are definitely shifting but the real question mark is whether exit opportunities will open back up for the market as a whole or will it continue to be the biggest fish feasting while everyone else starves.

That is to be determined.

Speaking of shifting tides…

This country has seen a lot, been through a lot, and most importantly achieved a lot.

The list is too long; we’ve dominated in just about every field, and sports is no different. To quantify this dominance, the US has won more than 3,100 medals in the Olympics, over 1,000 more than both Russia and Germany, the next two in line.

The only relevant sport that we are lackluster in is soccer. This likely has to do with the fact that Americans tend to focus on the major sports that were created in the U.S. like basketball, football, and baseball. After all, this seems like the patriotic thing to do, thus benevolently allowing foreigners maintain superiority in soccer.

Accordingly, the USMNT has seen many ups and downs, and although there is likely a higher frequency of downs, their first World Cup in 1930 started with a bang, reaching the semifinal game before settling for a 3rd place finish. The team’s goalkeeper, Jimmy Douglas held Belgium scoreless, posting the first shutout in World Cup history, making the entire city of Newark, NJ proud. Its neighbor within 10 miles–New York City–must have been proud too.

In fact, now that New York City is mentioned, the Knicks’ recent championship is highly relevant to this discussion.

In hindsight, it was the Knicks’ year. Despite the better-than-expected regular season, Boston seemed very beatable without Tatum, and even when he returned, he didn’t look 100%. The Sixers were inconsistent all year, and it is difficult to flip the switch and gel together when everyone’s healthy. The Pistons completed their rebuild and put together a 60 win season but had minimal playoff experience. Despite all of this, the Knicks really weren’t on anyone’s radar because…well they’re the Knicks. Even with the relatively new roster construction and a steady captain in Jalen Brunson, most people expected them to probably make the semifinals, maybe even the ECF if we’re being gracious, before settling into their ostensibly eternal destiny: disappointment.

But this time was different, and the New Yorkers would tell you that they could feel it in the air. But how did they know? They could rattle off the reasons why other teams weren’t going to win, similar to what was listed earlier; but the real reason was an intangible gut feeling that this was the year, end of story.

The same can be said about the USMNT.

Firstly, it is on our home turf.

Yes, the country hosted the tournament in 1994, and we didn’t win, but the result is significant. In 1950, the team failed to reach the elimination stage, sparking a decades-long drought of not qualifying that would finally end in 1990, where they were once again knocked out before elimination play. However, once we had the home field advantage in 1994, they advanced to the round of 16 for the first time since 1934. Since then, they’ve had solid performances including reaching the quarterfinals in 2002 and reaching knockout play in 2010, 2014, and 2022.

Thus, this is the year where we go from reaching the elimination stage being a win to transforming into a real contender, with the catalyst being the home advantage.

To top it all off, the nation’s 250th anniversary is approaching, so we have no other option but to bring the cup home in honor of the Founding Fathers and make a truly remarkable statement of American supremacy over the rest of the world.

God bless America and let’s get the job done.

Today marks the end of Q2, and there are a number of developments to catch up on. First, Starcloud rides SpaceX tailwinds into a $2B valuation, officially the most valuable company listed on Watchlist this year.

Starcloud becomes a unicorn, twice.

On March 30, 2026, Starcloud announced their $170M Series A at a $1.1B valuation, led by Benchmark and EQT. The company is now in the process of raising a $200M Series B round valuing Starcloud at $2.2B, reportedly led by Manhattan West. Caplight’s pricing engine is showing lots of secondary demand from investors, with an implied $3.3B valuation based on the flurry of bid action. Starcloud was previously covered in the January edition, and at the time, the company was only a seed stage prospect, having raised $24M from Sequoia, Y-Combinator, and In-Q-Tel. When the Series A round was announced in March 2026, Starcloud became the fastest company to reach unicorn status in Y-Combinator history. Starcloud’s primary goals now are to develop large, low-cost deployable radiators and make high-performance chips work in a higher-radiation environment. Multiple second movers are now raising fresh capital to try and take advantage of the influx of investor interest:

• Orbital raised a $5M pre-seed round from a16z speedrun to build AI data centers in low Earth orbit.

• Cowboy Space Corporation raised a $275M Series B round at a $2B valuation, led by Index Ventures. Cowboy was originally Aetherflux before pivoting from space-based solar power delivery to orbital data centers. Led by Robinhood co-founder Baiju Bhatt, Cowboy Space is actually building their own rockets to launch space data centers, as they believe rocket availability is the true constraint.

It will be interesting to watch how the competitive dynamic unfolds, specifically between Cowboy Space and Starcloud; Cowboy’s vertically integrated approach could either pose a threat or prove unsustainable in contrast to Starcloud’s reliance on SpaceX. Nonetheless, true commercial scale eludes the category for the near future.

OpenRouter breaks through to unicorn status.

On May 26, OpenRouter announced their $113M Series B at a $1.3B post-money valuation, led by CapitalG, Google’s growth equity arm. OpenRouter provides developers access to over 400 AI models, claims over 8 million global users, and processes 100 trillion tokens per month. Their revenue has more than doubled since February. The company’s focus for the rest of the year is to develop their enterprise (B2B) business, as many large technology companies are overspending on AI and OpenRouter’s product allows access to a wide range of models for a low price. OpenRouter was previously covered in the January edition.

Benchmark Makes More Moves.

A few months ago, we wrote a short memo about Benchmark slowly breaking away from their old ways by adding Jack Altman. The brand evolution has accelerated in real time; two weeks ago the firm raised $2B in new funds, by far its largest ever haul, including a $1.25B growth fund for a thirty year old firm that has never done a growth fund before. The early stage fund ballooned to $725M, nearly double the firm’s typical $425M fund size. Venture capital’s most disciplined high profile fund has opened the floodgates, a sign of the times if there ever was one. Andreessen Horowitz, Thrive, Founders Fund, Battery Ventures and Lux have collectively raised $36B in the first quarter of 2026, about 80% of venture capital raised in that time period. The top venture firms have significantly expanded in fund size over the past few years, forcing Benchmark to reassess their historical position on deliberately smaller sized vehicles. Paired with the Altman hire, all signs point to Benchmark intentionally shaping a new era for the platform going forward.

On a related note, Jack Altman made his first investment as a Benchmark partner in May, leading a $50 million Series B into Monaco, an AI company building “the future of sales” for startups, and also joining the board. More on that deal below.

June 2026 Watchlist.

Monaco

• Company Overview: Monaco is an AI native sales engine for startups, built by former Brex CRO and Founders Fund investor, Sam Blond. Monaco launched in February 2026, announcing both its $10 million seed and $25 million Series A, both led by Founders Fund. The company has reportedly been adding seven figures of annual recurring revenue each month since launch. As mentioned previously, their latest fundraising round was a $50 million Series B round led by Benchmark, with Jack Altman taking a board seat.

• Founders: Sam Blond - co-founder and CEO of Monaco, former Partner at Founders Fund, former CRO at Brex; Brian Blond - co-founder and Chairman of Monaco, Investment Partner at Human Capital, former Managing Director at Sutter Hill Ventures; Abhishek Viswanathan - co-founder and CPO of Monaco, former CPO of Apollo, former CPO of Qualtrics; Malay Desai - co-founder and CTO of Monaco, former Senior VP of Engineering at Clari.

• Investors: Benchmark, Founders Fund

• Amount Raised: $85M+ (Series B stage)

• Headquarters: San Francisco, CA

Probook

• Company Overview: Probook is an AI operating system for home services. The company uses one AI system to optimize bookings, leads, and onboarding for home services businesses in HVAC and plumbing. Their desired outcome is to increase customer EBITDA post-installment. Probook claims their engineering team “is more talent dense than early Ramp,” with ICPC World Finalists and IMO Gold Finalists.

• Founders: George Eliadis - co-founder and CEO of Probook, Wharton graduate; Lewis Zhang - co-founder and CTO of Probook, Senior ML Engineer at Roblox, UC Berkeley graduate; Ben Cervantez - co-founder of Probook, Wharton dropout.

• Investors: Andreessen Horowitz, Sequoia

• Amount Raised: $40M+ (Series A stage)

• Headquarters: San Francisco, CA

Ploy

• Company Overview: Ploy is a marketing platform that turns startup websites into a growth engine. Founded by former Webflow co-founder, Bryant Chou, whose experience building a multi-billion dollar website platform will prove useful. Ploy raised $27 million in a seed round after participating in Y-Combinator’s Spring 2026 batch.

• Founders: Bryant Chou - founder and CEO of Ploy, former co-founder and CTO of Webflow ($4B private val.), former senior software engineer at Intuit.

• Investors: First Round, Y-Combinator

• Amount Raised: $27M+ (seed stage)

• Headquarters: San Francisco, CA

Caplight

• Company Overview: Caplight is building the institutional standard for private markets pricing. With $5B in daily live secondary transaction opportunities and 700+ institutional market participants on the platform, Caplight has built both the leading secondary trading marketplace and price discovery platform. The company recently announced a $16M Series A led by BlackRock and Fin Capital with participation from UBS. The investment from BlackRock unlocks collaboration across its private markets ecosystem, specifically Aladdin and Preqin.

• Founders: Javier Avalos - co-founder and CEO of Caplight, former Deutsche Bank Investment Banker, former Forge Senior Vice President of Marketplace; Justin Moore - co-founder and CTO of Caplight, former Engineering Manager at Forge.

• Investors: BlackRock, Fin Capital

• Amount Raised: $26M+ (Series A stage)

• Headquarters: San Francisco, CA

Critical Energy

• Company Overview: Critical Energy is building modular power plants that convert heat into electricity, starting with geothermal. The systems ship in standard containers and install in weeks instead of years. The first power plant is scheduled to be completed by 2027 and will be installed at an existing geothermal site much like the ones in Northern California or Iceland. Founded by former SpaceX propulsion engineer Spencer Jackson.

• Founders: Spencer Jackson - founder and CEO of Critical Energy, former Senior Propulsion Engineer at SpaceX, Rose-Hulman Institute of Technology graduate.

• Investors: Susa Ventures, Upfront Ventures

• Amount Raised: $22M+ (seed stage)

• Headquarters: Los Angeles, CA

OffDeal

• Company Overview: OffDeal is an AI-enhanced investment bank for small and medium sized companies, focused on sell-side M&A advisory. OffDeal equips young mid-level bankers with technology systems to run sell-side processes for businesses that are too small for traditional investment banks. Their proprietary tech finds 1,000+ relevant buyers on average and the company services profitable, owner-led businesses ranging from $5-100 million in revenue. A 5% success fee is applied when a transaction closes, but no retainers or upfront costs are dedaucted from sellers. OffDeal recently closed the sale of LG Logistics Solutions to Fura, an AI powered logistics service provider.

• Founders: Ori Eldarov - co-founder and CEO of OffDeal, former Investment Banking VP at RBC, UBC graduate, HBS graduate, Y-Combinator W24; Alston Lin - co-founder and CTO of OffDeal, former Meta software engineer, University of Waterloo graduate, Y-Combinator W24.

• Investors: Radical Ventures

• Amount Raised: $17M+ (Series A stage)

• Headquarters: New York, NY

I drove the lane at UVA and at the last second pulled it back to kick it out.

I don’t even remember the pass. But I remember the landing.

I felt a pain so loud it drowned everything else out. I couldn’t bend my knee. I couldn’t think. Then came the fear and panic - the kind that hits before your brain catches up.

Three days later, I was back at practice, moving slowly, with no idea what the MRI would say. Then Dr. Safran called and pulled me in.

“Patellar tendon, more than 50% torn. You’re done for the season.”

Just like that, my senior season was over. I walked into practice thinking I was managing an injury. I walked out knowing my year was gone.

What I didn’t know yet was that those few seconds at UVA were about to give me something I never really had before…

Time.

I’m four months out from surgery now - rehab twice a day, every day. But the space in between is where this whole other life has been quietly taking shape.

I’ve always known I wanted to invest in early-stage startups. Turns out, my injury moved up the timeline.

To date, I’ve met with more than 30 VC investors. I wrote my first check into an early-stage sportstech startup. And I’m building a network that’s growing faster than I can keep up with.

I’m still new at this. I’m still learning. But I’ve been getting reps in.

And for any athlete sitting on the same itch I had, wondering whether there’s actually a path into the VC world, here’s what I’ve learned so far.

Pattern Recognition Comes From Getting Your Reps In

Judgment in early-stage investing is a muscle. And like any muscle, it gets built through volume.

One piece of advice I keep hearing from veterans in the space is this: if you want to develop an eye for great startups, you need to see a massive number of deals. Take multiple founder meetings a day. Study the original pitch decks of companies that ended up becoming huge.

This feels like familiar territory, because it’s the same thing I’ve been doing my whole life. You take hundreds of shots until the motion becomes automatic. You practice alone in an empty gym so that when the buzzer’s about to go off and the lights are on you, your body already knows what to do.

Early-stage investing works the same way. You sit in enough founder meetings and eventually your brain starts picking things up - which founders have what it takes, which problems are real, and which market opportunities feel inevitable.

There’s no shortcut to pattern recognition.

VC is a Relationship Business

The best investors operate as nodes in a highly trusted network.

From the outside, this industry can look cold, cutthroat, and closed off. But once I started getting inside the rooms, it felt surprisingly relational.

I’ve had countless meetings where the next steps rarely involve anything transactional. Sometimes, one conversation turns into another introduction, then another. Over time, those relationships started opening doors I never would’ve found on my own.

One of those introductions led me to Eric Chen at OVO Fund, which eventually led to me writing my first check into a startup called The Intelligent Search Company.

VC is a relationship business. Being welcomed into the industry requires proving you can built trust. Once you have it, the industry becomes far more collaborative than people realize.

Skate to Where the Puck Will Be

After studying the history of VC, I realized that a lot of alpha comes from looking past the current hype cycle.

It’s important to become an expert in something that’ll be hot in five years. Hardware. Engineered biology. Whatever the next thing is. Build expertise in that space before it goes mainstream.

This is challenging but also exciting. It forces a different kind of patience. It demands a shift from reacting to what everyone is currently talking about to figuring out what they will be talking about.

Puneet Agarwal at True Ventures talked about a similar idea through the lens of contrarian thinking: some of the best founders can see something the market hasn’t fully priced in yet. Because by the time everyone agrees a sector is hot, most of the alpha is already gone.

This is probably the lesson that’s hardest for me to put into practice right now. I’m still figuring out which sectors are worth going deep on. But I know that’s the right question to be sitting with.

At the Earliest Stages, You’re Investing in the Founder

This has been the single biggest mindset shift for me.

At the pre-seed and seed stage, you’re not investing in a product. You’re investing in a founder’s character and their sheer force of will. The product is probably going to pivot 25 times before it finds product-market fit, and the only thing that survives all those pivots is the person at the top.

Charles Hudson from Precursor Ventures shared one of the clearest frameworks I’ve heard for evaluating founders. He focuses on three things:

1. Market knowledge: do they actually understand the space they’re in?

2. Their “why”: is there a real, personal reason they’re building this?

3. Unfair insight: do they know something the market doesn’t yet?

Steve Bowsher also introduced me to the idea of the “personality thermometer”. When he evaluates founders, he’s not just listening to the pitch - he’s reading the room. The presence. The composure. The way they handle pushback.

And separately, he looks for evidence of excellence in any domain. It could be previous jobs, athletics, music, anything. Because winners tend to keep winning. The arena changes, but the underlying traits often transfer.

A lot of these conversations ended up shaping the lens I used when I eventually wrote my first check.

Conviction Comes From Stacking Signals

Here’s the thing nobody tells you about writing your first check: you’re not waiting for one big “yes” moment. You’re stacking smaller moments of conviction until the answer starts to feel obvious.

I learned this writing my first check into Pick and Roll AI, the first product developed by The Intelligent Search Company. The platform uses AI to help basketball programs evaluate players, organize scouting information, and make smarter recruiting and transfer portal decisions.

Looking back, I can map exactly what stacked up.

First, the opportunity came through a warm introduction from, Eric Chen, someone I trust and continue to learn from. And when I saw other investors I respected getting involved too, it created another layer of validation. Their conviction didn’t replace my own thinking, but it gave me confidence the opportunity was worth taking seriously.

Second, I realized I had a form of unfair insight that a lot of people on the cap table probably didn’t. The transfer portal is chaotic. Coaches are overwhelmed with film and scouting reports. I’ve lived inside that world. I know what coaches are looking for. I know what players care about. I know how fragmented the process feels from both sides. Pick and Roll AI was solving a very specific and real problem.

Third, the founders, Arpan and Moe clearly knew the space. But what stood out even more was how they responded to pushback. The second I challenged something, they leaned in instead of shutting down. They had a combination of knowledge and humility, which left a real impression on me.

None of those things alone would’ve been enough signals.

And even after all that, it still feels scary having put capital behind an idea that’s still early. But I think that’s part of the game. Conviction doesn’t mean certainty. It just means you’ve done enough work to believe.

I’m four months in and one check deep. A lot of what I’m operating on is still instinct. And the more reps I get, the more I realize instinct is just a starting point.

I’m still building my own thesis, and that’s going to take time.

But I’ve realized that the same things that made me a basketball player - discipline, coachability, obsession with reps, comfort with being uncomfortable - are the exact same things the VC world rewards.

Lately, people keep asking me how I balance chasing the NBA while building something off the court.

Truth is, there are 24 hours in a day, and basketball is non-negotiable. But there are still hours left in the day. And I wanted to spend them building something that could grow alongside basketball, not after it.

Investing hasn’t taken anything away from basketball. If anything, it raises the stakes in a way that makes me want it more. The better I perform on the court, the more access I have, the more doors stay open, the more opportunities I get to learn from incredible people.

The two worlds feed each other.

Rehab has a way of slowing everything down.

Every morning, I wake up and rebuild the knee a little more.

And somewhere between the film sessions, founder calls, weight room, and rehab table, I realized I’ve been building something else too.

Chisom

Chisom Okpara is a NCAA Division I basketball player at Stanford. Alongside his pursuit of professional basketball, he spends his time investing in early-stage startups. To keep up with Chisom, follow him on LinkedIn and Instagram.

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Cursor owes its success to Steph Curry.

Jalen Suggs dribbled down the lane, slowing down for just a second on the fastbreak to load up for a dunk. As he approached the rim, he accelerated then twisted his body in the air for a 360 slam. Now it was Chet’s turn. The gangly seven footer brought the ball down the court with his right hand, stopped just in front of a much smaller Steph Curry, went behind the back to his left, then quickly behind his back again to his right, beating Curry off the dribble and coming down the lane with momentum. Help defense was useless at this point, and Chet swooped in for a two handed dunk, landing on the floor instead of his feet. The clips of Steph and Chet going back and forth went viral that summer.

At the time, Chet and Jalen were just high school standouts proud to share a court with Steph at his annual Curry Camp. The program is an invite-only event that showcases the best high school players in the nation before they become superstars at the college and NBA levels. In past years, Anthony Edwards, Cade Cunningham, Cooper Flagg, AJ Dybantsa, Dylan Harper, Stephon Castle, Amen Thompson, Ausar Thompson, Jared McCain, and Jalen Green have all participated at the camp as high school prospects. In some sense, getting an invitation to Curry’s summer sessions is harder to do than making a McDonald’s All-American game. Curry invites 16 boys and 16 girls, across multiple classes of high school, while the McDonald’s All-American game consists of 48 players, all seniors, half boys and half girls. No other basketball program, be it Nike EYBL or even Team USA National Teams, can truly rival the talent density that Curry puts together each summer. If you want to watch a future NBA all-star in person, this is the place to be.

The program originally launched in 2014 as the SC30 Select Camp. The first few years were nothing to write home about, but the time spent built a foundation that would serve future generations. In 2016, Steph Curry was socializing at a cocktail party at SF’s City Hall, when he found himself talking to a technology entrepreneur about basketball talent networks. The tech executive, Ali Partovi, was actually attending on behalf of his twin brother Hadi, who missed the event due to a flight delay. Ali talked about how scouting for basketball was similar to scouting for software engineers, but basketball had robust talent discovery networks like Nike EYBL, endless high school camps, Team USA, etc., while the tech scene lacked depth. Ali had been thinking about starting a talent network-investment fund hybrid for years before that conversation, but he didn’t have the courage to do it himself. Steph said he was interested in learning more, and the next day, Ali began a ten year journey to construct the Curry Camp for technical talent.

Cursor’s 25-year-old CEO just inked a $60 billion deal with SpaceX.

In perhaps one of the most interesting deals of the year, SpaceX agreed to either acquire Cursor for $60 billion or pay the company $10 billion for their work together. Both outcomes ensure that Cursor does very well as a company in the near term, and by extension, provides their investors with generous security. Before the Musk stimulus package, Cursor was slowly losing steam to Anthropic’s Claude Code, and the business’s unit economics were in a state of flux. Since Cursor was using other artificial intelligence models to power their AI coding tool, they were subject to the foundation models from a pricing perspective. Anthropic could, relatively speaking, afford to serve consumers at more competitive rates since they owned the technology. Cursor was renting the technology and was losing money as users spent more time and compute on the platform. The media narrative pre-SpaceX deal was “Cursor’s dead.” The media narrative before that was “Cursor is the greatest of all time:” the company went from $0 to $100 million of annualized recurring revenue in twelve months and sent the venture capital ecosystem into a frenzy. Prominent partners at top firms started appearing on podcasts and saying things like “going from $1 to $3 to $9 million is not interesting (anymore). You have to go $1 to $15 to $100 million.” The Cursor cap table is a who’s who of growth equity: Thrive, a16z, Coatue, Accel, DST. Some of these funds stand to generate respectable multiples should the $60 billion buyout go through. Yet no one stands to benefit as much as Michael Truell.

Truell attended Horace Mann, a prestigious New York prep school, then MIT, where he completed a summer internship at Google. During his summer internship in 2018, Michael met Ali Partovi, a former technology founder who was now recruiting star engineers for the second cohort of his pre-accelerator program. Ali was captivated by Michael, who completed a coding test in record time. Ali admitted Michael to the program and vowed to invest in any company Michael founded. Three years later, Ali Partovi was the first investor in Cursor. The rest is history.

New eras usher in new models for educating the youth. Most Ivy League institutions were created for the purpose of training religious clergymen: Harvard and Yale trained Congregational clergymen; Princeton trained Presbyterians; Brown was for the Baptists; Columbia was the Anglican response to the growing influence of Protestantism. As the country underwent societal shifts (Civil War, industrialization, a rise in popularity of the German education model), colleges evolved into secular academic grounds circa 1850. Latin, Greek, and Christian theology took the backseat to medicine, law, and science.

The most interesting educational trend in this day and age is the accelerator model. Y-Combinator has grown from a Cambridge summer program to funding more than 600 new startups every year, and a significant proportion of those founders are too young to buy liquor. UC Berkeley, Cornell, MIT, and Stanford watch dozens of students take leaves of absence each year to try and raise millions in funding at YC. No other accelerator has their reach: 5,400+ companies funded including Stripe, Airbnb, Coinbase, Doordash, Reddit, and Twitch. When you talk about startup schools, you have to mention Y-Combinator.

Partovi studied at Harvard alongside now Sequoia partner Alfred Lin. He understood if Y-Combinator was already the fun, successful state school, he needed to come up with a new school, a smaller, private Ivy League for the most technically gifted young startup founders. He named it Neo.

Neo is a Greek derivative that means “new,” also short for neophyte, a beginner or rookie, typically used in fraternities or secret societies. And, by no coincidence, Neo is the main character in The Matrix series, played by Keanu Reaves. Ali is training the next generation of world shapers.

Neo vs. Y-Combinator:

• Selection Criteria:

  • Neo: two pathways, Neo Scholars and Neo Residency. The Neo Scholars program accepts roughly 25 highly technical students (~2% acceptance rate) into a year-long program of events and mentorship to accelerate their careers as founders. Scholars also get acceptance into the Residency, Neo’s Y-Combinator competitor that selects 15-20 startups per year (~1% acceptance rate) and gives them $750,000 on an uncapped SAFE, much better economics than Y-Combinator.

  • Y-Combinator: 150+ companies per cohort, with four cohorts a year. $125,000 for 7% of the company, with an additional $375,000 at whatever valuation the next round is raised at. Incentivizes YC founders to maximize their seed valuations in order to prevent additional early dilution.

• Notable Alumni:

  • Neo: Cursor ($30B private val.), Cognition ($26B private val.), Kalshi ($22B private val.), Chai Discovery ($1.3B private val.), Applied Compute ($1.3B private val.)

  • Y-Combinator: Stripe ($159B private val.), Airbnb ($80B market cap), Doordash ($69B market cap), Coinbase ($45B market cap), Reddit ($27B market cap), Kalshi ($22B private val.), Deel ($17B private val.)

• Returns:

  • Neo: Neo 1.0, the 2018 vintage fund, is at a 7.5x net MOIC while Neo 2.0, a 2021 vintage, is at a 6.5x net MOIC, according to a profile in the Wall Street Journal. The two funds turned a combined $150 million into $1.2 billion, top-tier returns especially during a tough 2021 vintage; safely top 1% funds performance wise. The smaller cohort sizes have worked in their favor, as Y-Combinator is deploying capital into 20x the amount of companies and needs both more frequent and larger winners to match their top of class returns.

  • Y-Combinator: harder to piece together as they have not been as transparent with their results. Historically, the camp has released data snippets showing that Y-Combinator is “the best asset class in venture” and consistently top quartile. Safe to assume their returns are very respectable but nowhere near Neo’s recent success. Y-Combinator also has significantly higher AUM.

Steph never invested in Neo after indicating interest in doing so, and by extension, missed Cursor as well.

But the brief moment of validation was enough to motivate Ali to get started.

In a decade, he’s built a small educational institution with a venture arm, visible only to certain students on certain campuses. Across the past three cohorts of Neo Scholars, 82 students were accepted (~27 each year on average), with just three colleges accounting for almost half of all Neo Scholars. Harvard has sent 14 students to the Neo program over the past three years, while Stanford has sent 13, and MIT has sent 10. Other schools consistently represented across cohorts include the University of Michigan (6), Yale (5), Columbia (4), UC Berkeley (3), and UPenn (3). As mentioned earlier, only students with extraordinary levels of computer science aptitude are encouraged to apply; a rigorous coding test weeds out the ordinary folk before an interview is even granted. Which means, most students are simply not interested in the program to begin with. Ali’s training lab is underground, out of sight, out of mind, with no plans to eventually become as mainstream as Y-Combinator. He only wants to find the next Tarek Mansour before Kalshi, the next Michael Truell before Cursor, the next Russell Kaplan before Cognition. If just one scholar in every few cohorts can break the matrix, then maybe, just maybe, Ali can rest easy knowing the next fund will generate a tenfold return on capital.

Everything comes back to Latin.

A mystery is often defined as something that is not meant to be understood, a puzzle, a conundrum, something beyond our human understanding, perhaps, understood only through divine revelation, reserved for higher life forms, the angelic bodies. But a word can mean one thing to one man and a second thing to the next. Within a theological context, the word mystery refers to something that cannot be fully unraveled within the temporal realm. For instance, the Christian mystery of the Holy Trinity: even if two knowledgeable monks were to discuss truths and wisdom on the three persons of God, nonstop from now until death, they would hardly scratch the surface of the ocean. To say a mystery in this context is something that cannot be discussed would not be accurate; rather, a mystery is something that cannot be fully uncovered even if the most luminous minds collaborated for hundreds of years. A mystery is as deep as the Atlantic and as wide as the equator in terms of the levels of revelation. The fundamental depth of mysteries is why early Christians in Rome and Byzantine would compile Biblical commentary from multiple respected monks, scholars, and bishops, and string them together like a chain to attach one holy man’s understanding to the next, in a humble effort to strengthen the faith of ordinary people. The compilations became known as “catena patrum”, Latin for “chain of the Fathers.”

In this chain, unity is the syrup gluing one good thing to another and, without added goodness, bringing about an all-together sweeter goodness through its togetherness.

As mentioned earlier, a word might mean one thing to one man and a second thing to the next. For Sean Neville, a co-founder of Circle, “chain” is simply shorthand for blockchain technology. Which explains why his new startup is named Catena Labs. For those not familiar with Circle, the company was founded in 2013 as a consumer finance company using blockchain as a payments platform. They raised around a billion dollars in venture capital before going public, are the second largest stablecoin company in the world, and have a market cap of $25B+. Neville left the company in 2020 but remained on the board. Around 2022, he began working on what would become Catena. In 2025, a16z crypto won the right to lead Catena’s seed round, an $18 million financing that saw participation from Breyer Capital, Coinbase Ventures, Circle Ventures, and Tom Brady. Just last week, Catena announced their $30 million Series A round co-led by a16z crypto and Acrew Capital, with participation from Breyer Capital, General Catalyst, and QED.

Catena is building the bank for AI agents.

Before actually engaging with the thesis and market opportunity, let’s talk about how we got here. For about 98% of Americans, a bank for AI agents is nothing less than a hallucinogen-induced nightmare, an episode in the modern day remake of Alice in Wonderland. Some Americans interact with artificial intelligence by occasionally toying around with ChatGPT, very few use it daily in their workflows, and even fewer know what OpenClaw is. But within the circles that fund startup ideas, the consensus is that AI agents will eventually be as commonplace as human workers, and therefore, the agents need the ability to transact. Keep in mind that venture capitalists make the most money from funding ideas that are not entirely obvious yet. So Catena is trying to capitalize on this assumption before the future and the present intertwine.

Catena’s thesis is that today’s payment protocols were designed to keep bots out through fraud prevention systems, and therefore, an entirely new system must be built to service autonomous agents. Additionally, the key constraint is building trust with companies and proving there are standard frameworks for verifying agent identity and enforcing spending policies. For agents, Catena provides verified identities, accounts, dollar balances, and the ability to send and receive payments across fiat currency and stablecoin. For companies, Catena provides a control panel with auditable transactions and the ability to approve, deny, and halt activity. In an interview with Fortune, Neville said “I think the main learning has been, as we evolved from thesis to reality and moving real money, is that giving an agent a wallet is pretty easy compared with giving a business a governed way to trust it.” Along with the fundraise, Catena filed for a national bank charter with the OCC (U.S. Office of the Comptroller of the Currency).

In addition to Neville, Matt Venables, an early employee and SVP of Product Engineering at Circle, is the CTO and co-founder at Catena. Adam Berrey, a former CPO at Circle, joined as COO. Jessica Chiu serves as VP of Partnerships, after senior partnership roles at Pinterest, Spotify, and Airwallex. Andrew Hungate, a former Brex Product Lead, joined as Product Lead. Molly Sterns, a compliance executive with experience at Bank of the West and Chipper Cash, joined as VP of Compliance. The team continues to grow.

The market is still hard to decipher. As mentioned above, Catena is assuming that agentic finance will be a multi-trillion dollar market in the next 7-10 years. A joint report with Keyrock, Coinbase, and Tempo found that AI agents processed around $73 million in the past year, with ~98% of those transactions settling in USDC. This is far from a sure bet; the market needs to have multiple inflection points that can catapult confidence in an agentic finance future. But if the market catches up, Sean Neville is the man for the job. $48 million from a16z isn’t a bad start either.

Quartermaster

• Company Overview: Quartermaster is building the world’s largest maritime awareness network. Founded by Neil Sobin, formerly defense deployment lead at Scale AI, Quartermaster uses video capture, location authentication, sensors, and artificial intelligence to provide unprecedented visibility across the world’s oceans. Their product is known as “SmartMast” and it is far more advanced than AIS, the current industry standard. The company announced their $43M Series A last week, co-led by First Round and Quiet Capital, with participation from BoxGroup and TMV Logistics.

• Founders: Neil Sobin - founder and CEO of Quartermaster, UChicago graduate, former Scale AI Defense Deployment Lead

• Investors: First Round, Quiet Capital

• Amount Raised: $45M+

• Headquarters: Alexandria, VA

Hanover Park

• Company Overview: Hanover Park is the leading AI-native fund operations platform. Hanover leverages technology to handle back office operations efficiently for mid to large venture capital and private equity funds. The company recently crossed $15B AUA and their last fundraise was a $27M Series A round from Emergence Capital with participation from Lux, announced in March 2026.

• Founders: Chris Hladczuk - co-founder and CEO of Hanover Park, Yale graduate, former Goldman Sachs investment banker, former CRO at Meow; Nick Puljic - co-founder and CTO of Hanover Park, Columbia graduate, former SWE at Oscar Health, former YC W22 founder

• Investors: Emergence Capital

• Amount Raised: $31M+

• Headquarters: New York, NY

Accordance

• Company Overview: Accordance is developing software that helps tax professionals do their jobs better. The software is trained on public tax data and also learns from customers’ own financial histories. Companies like Figma and Quora use Accordance. Khosla, General Catalyst, NEA, Sequoia, and Anthropic all participated in their $13 million seed raise.

• Founders: David Yue - co-founder and CEO at Accordance, Stanford dropout; Finsam Samson - co-founder and CTO at Accordance, Stanford dropout

• Investors: Khosla, General Catalyst

• Amount Raised: $16M+

• Headquarters: San Francisco, CA

Venture capital has a branding problem.

From the outside, it looks like a game of big checks, fast wins, and headline investments.

From the inside, it’s something else entirely: a grind built on repetition, pattern recognition, and a kind of invisible work that rarely gets talked about.

That gap between perception and reality is where most new investors struggle, especially athletes.

Keaton Nankivil didn’t come into the industry with a finance background, a business degree, or a traditional network. He started as an intern at Alumni Ventures after a professional basketball career in Europe.

Nine years later, he’s a Senior Principal leading the firm’s sportstech thesis.

In this conversation, he breaks down what venture capital actually looks like, where athletes can experience challenges, and the lesser known skills from sports that can make athletes exceptionally valuable.

This Q&A has been lightly edited for clarity and length.

Venture capital is often described as a game. What do people, especially athletes, misunderstand about how it’s actually played?

Keaton: The first thing is understanding what venture capital is.

It’s a part of the financial stack that’s historically been hard to access, but it’s also where a lot of value creation is happening now, in private markets. If you’re looking for asymmetric upside, this is one of the best places to find it.

But it’s not for everyone.

The biggest mistake I see is people entering the space without understanding their role in it.

You don’t need a formal degree. But you do need to understand how returns are generated and be honest about your risk tolerance. It’s high risk and high reward. You should have a genuine capacity to take some risk with your money knowing that there is potential upside.

Because the reality is: a small number of investments actually create returns.

Before you entered VC, what did you think the job was? And what does it actually look like day to day?

Honestly, I had zero context going in.

My perception was mostly from what I heard - aggressive, sharp-elbowed, the “vulture capital” stereotype... And to be fair, parts of that exist. Luckily, most of the people I’ve met in this field are genuinely motivated by helping founders build extraordinary companies.

But the bigger disconnect is the work itself.

It’s a lot like professional basketball. From the outside, it looks like a glamorous job.

In basketball, you see the three-pointers, the dunks, the game-winners. What you don’t see is the warmups before practice, the repetitive drills during practice, and the post-game rehabs.

VC is the same. You hear about the headline investment. But the day-to-day grind before and after the investment is the actual job.

I still cold email founders every week. I take hundreds of calls a year to find a small number of opportunities that fit our fund strategy. And a lot of the job is tracking companies, supporting founders in moments no one hears about, and maintaining LP relationships over long periods of time.

It’s repetitive. And that’s the point. Because every now and then, that repetition compounds into something meaningful.

Very few people are willing to start from the bottom when they transition careers. You chose to start as an intern at Alumni Ventures. What gave you the conviction early on to commit to this path before you had any real proof it would work out?

Honestly, I think “chose” is such a generous word. I didn’t have a clear path after basketball and kind of just stumbled into it.

The internship opportunity at Alumni Ventures came through people I trusted, and that mattered more than anything else. I believed in the people before I understood the asset class.

Looking back, that was enough to get started.

There’s this idea that you need conviction upfront. I don’t think that’s true, especially for athletes transitioning into something completely new.

A lot of this was just showing up, doing the work, and stacking reps until things started to make sense.

The hardest part actually wasn’t the lack of conviction early on. It was accepting that while I was a high-level operator on the court, I was a beginner here. I had to earn the right to compete and win in this space.

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How did your experience as a professional basketball player shape the way you think as an investor today? What skills transferred over well to the investing world? Was there anything you had to unlearn?

The biggest thing that transfers is an appreciation for the dirty work that doesn’t show up on the stat sheets.

I remember a game in Spain where I wasn’t playing well, and a coach pointed out that a screen I set created a key three-point shot for a teammate. That really stuck with me.

VC works the same way.

A successful investment might trace back to a cold email, a relationship built months earlier, or internal work that helped the team move faster. It’s the result of invisible, dirty work that happens long before a check is written.

On the flip side, what doesn’t translate as well is structure.

In sports, there’s a clear chain of command. The coach calls the play. I would execute the play. And for a long time, that’s exactly what makes me valuable to a team.

In VC, the most successful investors tend to be the independent thinkers - the ones that can look beyond the status quo and push boundaries.

They generate alpha from challenging the general consensus, forming original ideas, and trusting their own instincts.

That’s something I’ve had to learn over time.

You now lead the Sportstech thesis at Alumni Ventures. Where has your background as an athlete given you a real, non-obvious edge when evaluating companies?

Context.

As an athlete, I’ve been fortunate to experience almost every part of the sports value chain.

I’ve played in youth sports. I’ve gone through the recruiting process as a college recruit. I’ve been part of teams at different levels. I’ve used performance technology as a pro. I’ve been a fan consuming sports from the outside.

So when I look at a company in this space, I’m not imagining the user. I’ve been the user.

That helps me quickly understand who a product is really for, where it fits, and whether it solves a real problem.

But there’s a trap in that too.

My experience might feel universal, but it usually isn’t.

What worked for me, or what I would have wanted as an athlete, isn’t always representative of the broader market.

So I try to treat my experience as an input. It gives me a starting point, but it doesn’t replace doing the work. If anything, it just helps me ask better questions and build conviction faster.

Athlete-investors tend to gravitate toward Sportstech and CPG due to familiarity. What’s the most common mistake they make?

I love this quote from Mark Cuban on Shark Tank: “I’ll be a consumer, but I’m not going to be an investor.”

As an athlete-investor, the most common mistake is investing in products I would have personally wanted - a youth training app, a performance supplement, a fan experience product - and mistaking that for real diligence.

Just because I like something doesn’t necessarily mean it’s a good investment.

Take CPG as an example. You can build a great business there. But the structure of these companies can make it hard to achieve venture-level returns.

Margins are tighter. Growth is more linear. Capital requirements are higher.

That doesn’t make them bad businesses. It just means they may not fit the venture model.

The second mistake is ignoring portfolio construction.

The reality is, most investments won’t work. That’s just how the asset class works.

Venture is a portfolio of opportunities. You need to see enough deals to understand what “great” actually looks like, and then let the great investments balance out the ones that never reach escape velocity.

You’re building an apprenticeship model for athletes at Alumni Ventures. Why is that the right model for venture, and what does it unlock that traditional education doesn’t?

First, the trust factor. You meet a fellow athlete and the bond is almost immediate - there’s shared values, shared communication, shared experience. That’s multiple layers of affinity. It matters when you’re learning something hard and unfamiliar.

Second, and I say this with real conviction, is that athletes are among the smartest people I’ve ever worked with. A lot of my former teammates didn’t attend top business or finance programs. They are just as sharp as many of the people I work with today. The issue has never been intelligence. It’s been access and exposure.

Third, venture is a craft. Kobe Bryant used to talk about basketball as a craft - you are a craftsman, and you hone your craft over time. Investing is the same. You need feedback loops. You need a space to make mistakes safely. You need someone who has been through it to guide you.

Ultimately, my goal is to help athletes become a formidable part of the venture ecosystem. Venture capital shapes the future economy, and athletes deserve a seat at that table.

The capability is already there. I’ve seen it up close. What’s been missing isn’t the talent. It’s access, exposure, and the opportunity to prove it.

This dynamic shows up more often than people think. Athletes bring real context, especially in areas like sportstech. The challenge is turning that context into sound judgment over time.

That’s what Keaton is focused on, helping athletes build reps through apprenticeship. With the right guidance, the next generation of athletes won’t just participate in venture. They’ll play a active role in shaping it.

To learn more about VC and sportstech investing, connect with Keaton on LinkedIn.

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I. 2:36 at Sotheby’s.

In 1986, Claude Monet’s Meules (1890) painting sold for $2.5 million, or $7.34 million in today’s dollars. It was kept in a private collection until Tuesday, May 14, 2019. On that day at the Sotheby’s in New York, Monet’s impressionist painting sold for $110.7 million, a 44x return on investment in 33 years. The internal rate of return was over 12%, outperforming the S&P 500’s 9% during that same timeframe. The piece was bought by Hasso Plattner, the German technology billionaire who founded SAP, a $200 billion public company.

Meules doesn’t even make the top thirty list of most expensive paintings sold. To be considered for the top five, a piece needs to surpass $200 million in final clearing price, for instance, Klimt’s Portrait of Elisabeth Lederer ($236 million) purchased by the estate of Leonard Lauder of Estée Lauder, or Cézanne’s The Card Players ($250+ million via private sale) purchased by the State of Qatar, or Kooning’s Interchange ($300 million via private sale) purchased by Citadel’s Kenneth Griffin. Less than 150 individuals in the world can compete in the highest end of the market, with sufficient discretionary funds to scoop up $50 million masterworks like a ground ball. But that number - 150 - has grown significantly from 30 years ago. Wealth is increasingly concentrated in the hands of multi-billionaires, making $100+ million art sales a semi-normal occurrence at Sotheby’s. And, sovereign wealth funds, particularly in the Middle East, are now buyers as well.

It is important to understand, however, that art is a mediocre investment as a whole. There is a statistic that “blue-chip” art returned almost 14.3% annually between 1995 and 2020, while the S&P 500 returned 9.9%. The issue with art indices that calculate returns is that they rely on art pieces with “repeat-sales”, which are exclusively the highest demand pieces, like our friend Meules, skewing the return profile upwards. Less than 10% of art pieces ever appreciate in value at all, while 90% lose value. Furthermore, artworks priced at over $1 million (the top 1% of transactions) account for 58% of total market value. Yet even at the highest end, returns are not guaranteed. For every Monet painting that was bought for $2 million and sold for $100 million, there is a Giacometti sculpture that was expected to sell for $70 million and failed to find a buyer. A few Middle Eastern sovereign wealth funds might learn this lesson soon. Perhaps they already did with LIV.

II. Neon Boudeaux’s Revenge.

There goes Happy heading for the cash machine! Oh yeah he’s gonna get himself another linebacker! That guy’s got the best players money can buy! The best players money can buy! You know, I’ll tell you something else. You know, someplace, someplace in America right now, there’s some 10 year old kid. He’s out there on that playground, and he’s playing, he’s dribbling between his legs, he’s going left, he’s going right, he’s already above the rim, he’s stuffing it home. You know what’s gonna happen to this kid? Five minutes from now, he’s gonna be surrounded by agents, corporate sponsors and coaches. You know, people like me. Just drooling over this kid because he holds our future employment in his hands. I mean, that’s what we’ve made this game. That’s what we’ve done.

Pete Bell, Blue Chips (1994)

The concept of paying college football and basketball players is nothing new, it was done pre-NIL, and Shaq even starred in a movie called Blue Chips that used the moral tension of paying college players illegally as the core plot.

But no one ever thought that they would take it this far.

In this past transfer portal cycle, a handful of clear first round NBA picks opted to go back to college instead, each pocketing upwards of $4 million, and in one case, $10 million between traditional revenue sharing, an unprecedented collective deal, and pre-arranged sponsorships with university-affiliated corporations. Said player stood to make approximately $3 million by getting drafted in the back half of the first round, but now he will get paid roughly the same as Cameron Boozer (projected 3rd pick) before factoring in Boozer’s endorsements. In a market where all but the top-10 picks could make significantly more money going back to school, one cannot help but wonder about the second-order effects of inefficient pricing. Think about this: a borderline starter at a high major school can find an offer for $1.5 - 2 million at a different school. That pay range is significantly higher than most second round draft picks, who are, broadly speaking, better at basketball than the average college basketball starter. At essentially every level of high-major college basketball, programs are overpaying for talent. Now, you might be tempted to question the assumption here… How do you know they’re overpaying? The simple answer is that the NBA has far better price discovery than college basketball programs - it is a more efficient market than NIL, and if college teams are doling out 2x+ the price for the same caliber of player, they are overpaying. Of course, there are clear incentives that can explain why this happens.

Shiny object syndrome kills rationality. Never before could wealthy college alumni be as influential in bringing a championship home to their alma mater. This is FanDuel at the highest level; gambling $5 million for a collective to sign the star point guard and watching the team break school records as a result. Plus, it’s tax deductible. Mark Cuban funded Fernando Mendoza’s NIL package to bring a championship home to Indiana. Probably put the trophy up in his dining room like a Klimt painting. For those unfamiliar with the wildly complex financing mechanisms in college sports, there are three key ways players get paid. The first is revenue sharing, which dictates NCAA teams can share up to $20.5 million annually with their student athletes. The majority of revenue sharing goes to men’s football (~$14M+) and men’s basketball (~$4M+), but for the top spenders in each sport, for example, Texas in football or Louisville in basketball, this is simply a drop in the bucket. Louisville’s basketball team signed Flory Bidunga, a top 5 transfer, for an estimated $5M+, plus top 50 recruits in Oregon guard Jackson Shelstad, Arkansas wing Karter Knox, and Iowa forward Alvaro Folgueiras, who will collectively cost between $7-8M, before factoring in returning starter Adrian Wooley and five-star high school recruit Obinna Ekezie, who should cost at least $4M combined. All in all, Louisville’s basketball team is rumored to be spending as much as $20M on their roster, which means that a revenue sharing package is not enough. In order to fill the gap, top football and basketball programs turn to collectives for a significant source of revenue. And when I say revenue, I mean donations. Wealthy alumni or university affiliates hand out millions to support their programs and play a part in championship seasons, or, in most cases, average seasons. The University of Texas collective, for instance, raised $22M for their football and basketball programs in 2024, and that number has grown significantly in the past two years as bidding wars for players have spiked prices. The final and least developed method of financing rosters is by making legitimate connections with businesses so that players can advertise for said businesses and get paid to do so. In essence, the actual name, image, and likeness deals that started everything have become dwarfed by eight-figure collectives and revenue sharing.

Trophies usually lose their shine as time goes on. Reality is a tough pill to swallow, but when it goes down and works its way into the system, collective money will dry up for all but the top high-major programs that are actually competing for championships and can sustain unsustainable levels of funding. At some point in time, 80% of college basketball teams in the country will regress to far more modest compensation numbers when programs acknowledge they can’t outspend Michigan and Tennessee. Ivy League programs offer no pay-for-play arrangements, or even scholarships, yet Yale’s basketball program was ranked 81 in the country last year (KenPom), above multi-million dollar programs like Minnesota, Syracuse, Notre Dame, Rutgers, and Oregon. In the past two years, multiple Yale basketball players have graduated to the NBA, including first round pick Danny Wolf, and two-way players John Poulakidas and Bez Mbeng. Building a winning program without large capital reserves is doable, teams just need to find their unique advantage and lean into it. The most likely future scenario is a tale of two cities: a few big spenders bidding on trophy assets at the auction and a lot of penny pinchers playing moneyball at the flea market.

And I don’t know if it’s just me, but I’d heard where you climb the ladder and you say ‘Is this really it?’ And it was worse. It was less than ‘it.’ The journey was so much better than the destination… Literally it’s such a blur because there’s no time to celebrate. You meet with your seniors, you do exit meetings, you’re meeting with your players and trying to figure out what your vision with them will be for the following year. Plugging holes in your roster, trying to make sure you’re generating NIL opportunities and attracting businesses and things of that nature.

Dusty May, Michigan coach, to CBS Sports on winning March Madness (2026).

III. Quid Pretium.

When a billionaire wants to buy expensive art, the process truly begins with finding a reputable advisor. This could be an art advisory team like Schwartzman&, Athena Art Finance, a boutique shop, or a single reputable curator. The right advisory team makes a night-and-day difference in lighting up an awfully opaque market. Hundreds of questions must be answered with ballistic precision, such as, is this one of the artist’s top works? What do comparable sales look like? Will there be heavy interest from other buyers at the auction? The list goes on until daybreak, at which point, the ultimate question meets its much anticipated answer. What’s the price?

The right price can make or break the transaction in entirety. Art advisory teams take anywhere from 5-10% of the purchase price, and if the transaction ages well, it’s another stamp on their resume.

Information is the currency by which art advisory teams transact. It is the single most important asset on their balance sheets. They must collect it with a passion, collect it as their clients collect Picassos and Warhols. All of their qualitative and quantitative data points feed price discovery capabilities. Price discovery is all there is.

After a price is uncovered, the team must work to protect themselves from passion. An auction room’s architecture is designed to draw increasingly higher bids from its participants. Some buyers stay at home and allow their professional advisory team to represent them, oftentimes enforcing a ceiling bid that will not be surpassed. Some buyers acknowledge that the transaction is not an economic one, but rather, an exercise of bravado and spectacle, and they allow animal spirits to run wild. Yet, both of these bidders are justified; it is the one who lies in the middle that will suffer remorse.

The private markets, venture capital in particular, is becoming a tale of two markets. On one end, the biggest players are morphing into pure capital factories and raising money as quickly as possible from the largest investors, most notably, sovereign wealth funds, and then deploying the billions of dollars raised into startups that can handle a few hundred million dollar injection early on. Rinse and repeat, like a Ford factory in the 1920s. Price is no longer important for these buyers, because their singular incentive is to have bought the next OpenAI or Anthropic while the valuation is still sub-$10 billion. A $100 billion valuation is the minimum acceptable outcome for their winning pieces. $1 trillion is a lot cooler. On the other end, smaller programs will have to get smarter about their roster construction; Yale cannot compete with UConn for players, but that does not mean Yale cannot have highly successful seasons. Sophisticated limited partners, including a number of college endowments, are increasingly searching for boutique venture funds with specialized strategies that can deliver impressive returns. There is a top 15 endowment that has altogether stopped new capital commitments into venture “mega-funds”, and instead writes $2-20 million checks into boutique and emerging managers. An interesting stipulation for said endowment is that (a) they employ this strategy in order to get direct exposure into their funds’ winners and (b) they terminate relationships when a fund manager gets too large. On the first point, let’s say the endowment invests in ABC Fund, which invests in Ramp at the seed and Series A stage. When it becomes clear that Ramp is a winning prospect, the endowment then takes allocation at the Series B stage directly, bypassing the fund manager, meaning, the endowment isn’t paying any fees to invest. Direct deals like this can be extremely lucrative for endowments; the University of Michigan directly invested $20 million in OpenAI and the stake is now worth $2 billion, enough money to fund their basketball team for one hundred seasons. And with megafunds increasingly turning to sovereign wealth funds for capital, more endowments will be searching for boutique managers and direct exposure. Systems for price discovery will only appreciate in value.

What would change the game more, making the hoop 12 feet or removing the 3 point line?

On its face, the question is ostensibly a thought provoking question. However, once pondering for more than 30 seconds, the correct answer becomes clear.

If the height increases from 10 to 12 feet, there would be some friction and shooting percentages would decrease across the board in the short term. However, one can credibly argue that over time, it would gradually approach previous percentages until settling, if not at, close to normal marks.

On the other hand, if the three point line faded away, everything about the way basketball is played would drastically change.

The Duncan Robinsons and Sam Merrills of the world would likely fade into obscurity, as the expected PPP (points per possession) on their 28 footers would fall off a cliff, falling from roughly 1.2 to .8. Thus, the current hunt for 3 point specialists would likely move towards seeking the next paint dominating big man.

In an alternate universe, Hunter Dickinson finishes his NBA career as one of the all-time greats.

Between the changes in scouting, analytics, coaching style, assortment of the five players on the court, and even the positioning, it’s safe to say that the game would change dramatically. The difference between this scenario and the previous one is that these changes would be permanent, whereas changing the goal height would provide an immediate negative shock to offensive output but would slowly creep back to normalcy.

But of course, this is exploring a hypothetical world, and as we know, the real basketball world we live in revolves around the three point arc.

The first thought is to discuss Steph Curry’s impact on the game and analyze how the implementation of the 3 point arc facilitated his ascent to top-10 of all-time status. But the ramifications are much wider than that. Along with the increased pace, the shift towards increasing the proportion of 3s shot has allowed an entire generation of players to place themselves in a pristine position to surpass their idols in a very pertinent category: total points scored. Furthermore, the earlier in their careers when the analytics revolution occurred, the more they stand to benefit.

Let’s take two high scoring young players as examples: Jayson Tatum and Anthony Edwards. If we assume a constant scoring output over their careers, an 18-year career, and roughly 70 games played, they are projected to score 34K and 32.6K points respectively, landing them in the top 10 very comfortably, with Tatum being on the cusp of top five. The flimsiest assumption is likely an 18-year career, and while it is difficult to predict a player’s career length, an entire generation of stars from the 2010s are still playing and seem to have plenty of gas in the tank. Steph Curry, Russell Westbrook, Kevin Durant, James Harden, and Demar DeRozan are just a few examples of older players that have silently put together lengthy careers of 15-18 years who don’t get enough recognition for it simply because LeBron James is still one of the best players in the league in his 23rd season.

So as the game has shifted more towards the three and pace increases, getting to 30 on any given night has become easier; and even if one argues that the difference is marginal, marginal differences compounded over time expand into wide gaps. Thus for the current game, the 3 pointer has become the foundation, making the game simpler, smoother, and more enjoyable for the end consumer.

Plaid is the 3 point line for financial technology.

Plaid functions as the connection later between the ever increasing number of consumer fintech companies and the bank data needed to use the apps, essentially serving as the underlying foundation of these apps. While retrieving consumers’ bank data seems easy enough, without Plaid, developers found the task rigorous because the data wasn’t aggregated and different banks used different systems. Thus, Plaid does all of the dirty work through using its API to unify all of the different bank data into one format through a process that includes aggregating, categorizing, and standardizing the data. Their real advantage lies not from being able to do this with the largest players but having the coverage to do this process with all of the smaller, less notable regional banks as well.

Interestingly enough, building the backend for consumer fintech companies was not the original plan for Zach Perret and Will Hockey. In their eyes, the biggest and most notable tech companies at the time were consumer facing, so it only made sense to start in this lane.

Perret studied hard sciences at Duke, earning a BS while being heavily involved in campus leadership and student government before working at Bain for a short stint. While he was there, he met Hockey, a computer science grad from Emory, and although neither of them had a traditional finance background, they immediately bonded over a common theme: the outdated nature of financial infrastructure.

The initial concept was some form of a financial budgeting application, as after they left college and entered the real world, they realized how opaque something as simple as paying your bills could be. But Perret quickly ran into two problems. The first was rather simple: while people theoretically wanted to save money through budgeting and smarter spending, Perret concluded that practically speaking when it came to actually doing it, most people didn’t actually want to. More importantly, he also experienced firsthand just how difficult it was to build custom integrations for different financial institutions, so they realized that building the API that would simplify that process could have a higher expected value of success than another consumer fintech app. Because they were building a consumer app, the ideal situation is to spend a majority of the time figuring out ways to onboard customers and then continuously curate the product to retain them, but this wasn’t the case at all. They were spending so much time and effort trying to access the data required that they couldn’t onboard customers at the rate they wanted to. To make the decision even easier, they showed the head of engineering at Venmo their app and he told them the consumer-facing aspect “sucked,” but he wanted to license their backend and would pay for it.

This was all the validation they needed to go all in on the infrastructure play.

An important piece of context to paint the picture was the recent establishment of the Dodd Frank regulation after the Great Financial Crisis. All you need to know about Dodd Frank is any story about the glory days of Wall Street from the typical managing director always starts with a reminiscent sigh and “you see, back in my day before Dodd Frank…”

In addition to a wide variety of new rules that Wall Street now had to play by, the most pertinent change that directly impacted Plaid was the mandate that consumers could access their financial data at any time. The only problem was that it wasn’t actually clear on how exactly this would happen mainly because it still needed to be interpreted and clarified by the newly minted Consumer Financial Protection Bureau. Because of this, most of the banks held off on building APIs to retrieve consumers’ financial data, which ultimately meant that in order to make the data retrieval process work, Plaid would have to “screen scrape,” manually logging in to consumers’ accounts as a bot and essentially pretend it was the consumer himself logging in. Banks also didn’t go out of their way to build APIs because they initially weren’t fans of the fintech space in general. The tale of the hostility from the old, established titan towards the ascending newcomer is one as old as time, and this is exactly the lens through which the banking system viewed fintech. The perfect example was the antipathy towards Robinhood, as the free commission platform, while not making a major dent, was “stealing” just enough order flow from the incumbents to become annoying. Knowing this friction existed, there needed to be serious growth for the banks to take the newcomers serious, because when this happened, they would have to capitulate and either build the APIs or have Plaid do the job for them.

It is safe to say that the ecosystem did in fact grow, ushering in the golden age of consumer fintech. The growth of Plaid was directly tied to the growth of the ecosystem as a whole, as the company not only depended on more players entering the space but also existing members onboarding new customers. The growth of both led to Plaid crossing 10 million consumer account connections in 2017 and north of 20 million by the following year. By the end of 2019, it had integrated data from more than 11,000 financial institutions and over 5,000 fintech apps were using the product. An important part of the GTM was “selling through the basement,” known as identifying lower level developers and creating a smooth, frictionless experience for them and hoping they would advocate the product to the rest of the organization. Plaid’s business model consisted of a stable “per user per month” fee as well as “per action” fees that includes every time initial signups or payments occur.

After similarly impressive growth numbers in 2019, 2020 started off with a surprise: a $5B acquisition offer from Visa.

The story played out exactly how every startup imagines: experience a problem first hand, build a product or a service to combat it, experience exponential growth for several years, and then smoothly sail into the liquidation event where the founders, employees, and investors all strike it rich.

Visa had been an investor in the company, mainly because they really weren’t a direct competitor; Plaid had no interest in issuing any sort of card to eat into Visa’s market share, so the partnership had been purely synergistic.

Over the next few months, the requisite paperwork was slowly being completed with an interesting twist in the fine print: a “pandemic clause” that ensured that even in the case of a potential pandemic, Visa would still be obligated to go through with the deal.

Before accusing Perret and Hockey of being a part of the secret cabal that rules the world and orchestrates future global events, it is safe to say that there were enough murmurs about a potential pandemic even in January of 2020 that it made sense to include this possibility.

Because of this clause, Plaid had optionality in the deal which proved to be critical.

Firstly, the deal was looking even more appetizing from Plaid’s perspective because as soon as the pandemic hit and stock prices crashed, the percentage ownership of Visa Plaid shareholders would get dramatically increased. The deal was majority cash but included a stock component that was dollar denominated; because the dollar amount remained fixed, as the stock price decreased, the more shares those same dollars would amount to.

Before the excitement could grow too large in the Plaid offices, there was another twist: the DOJ stepped in and requested for the transaction to be reviewed by the FTC for a potential antitrust violation. This wasn’t necessarily a big deal initially, as most deals over a certain nominal amount will typically get flagged with an initial request, but what was unexpected was the second request, which signaled that this one was more serious than normal.

As the year went on, the process became more and more drawn out, and it became clear that this lawsuit could last all of 2021 as well. This scenario was less than ideal for Plaid, mainly because their company was exploding during the COVID era, as multiple tailwinds were hitting their business at once. Firstly, not only were financial assets booming due to the free money flowing through the financial environment but also people had free time to finally learn about what stocks and crypto were and why they were booming. Additionally, the near zero rates not only meant surging asset prices but more directly gargantuan amounts of funding for fintech startups, providing an incentive for more of them to pop up and immediately use Plaid to link accounts.

Thus, as the company began growing and the valuation multiples continued to expand, the $5B valuation price that was agreed upon began to become more of a call option for Visa that would undeniably be a bargain if it was exercised. Luckily, there was another clause in the contract that stated if a year passed after the initial agreement, Plaid could walk away from the deal.

While they would eventually leave the deal on the table, it wasn’t as much of a no-brainer as it would seem mainly because the expectation of both employees and investors was that they were going to liquidate their positions and buy the dream house overlooking the Bay that they had been dreaming about for years. As Perret expected, when he announced over Zoom that the deal was not going through, many employees were not particularly happy. However, to lighten them up, he ensured that a fraction of people’s positions could be liquidated through secondaries, so instead of a full cash out for the new crib, everyone would have to settle for a Tesla Model S Performance.

And maybe a Model Y if you were a young buck.

Three months later after walking away from the deal, the company raised at a $13B valuation, executing on the secondaries promise through this fundraising cycle.

Interestingly enough, when the deal was initially being negotiated with Visa, the CEO of Intuit at the time gave him a call and told him congratulations on achieving the pinnacle of success for a first time founder. Before hanging up, he left Perret with an interesting caveat: even if it doesn’t go through, things are going to turn out great as well.

Almost like he knew the deal would fall through.

As mentioned earlier, working with banks and fintech companies meant that Plaid was very much tied to the broader financial macro environment, which was a major boost in the early days after the COVID breakout.

Thus, they were tied to the finance macro for better and for worse.

When rates quickly increased in 2022, Plaid experienced real adversity for the first time in a while, as although they were still able to maintain positive growth, the rate of growth slowed quickly. Their revenue from the per user per month and per payment remained relatively stable, but the top line from new sign ups took a nosedive. In theory, people should actually flock to consumer fintech apps when prices drop to acquire assets for pennies on the dollar, but reality is far from theory and the herd behavior is of course to sell. They maintained the slower growth phase up until roughly Q3 of 2023, where they saw growth approach normal levels.

One positive from those slower growth years was the focus on growing additional products outside of their main “Link” service. The common denominator among these new products is the vast amounts and variety of data they come across, with the two most notable being fraud detection and credit scoring.

Plaid can easily monitor activity through different apps, so they quickly realized their customers would pay for early fraud detection based on suspicious activity not only within their apps but other apps as well. Additionally, FICO has been using much of the same data and systems since the 80s and 90s, but Plaid’s access to personal financial data far surpasses it. FICO doesn’t include other information like new raises or higher paying roles, spending levels, or other secondary pieces of information that helps paint a more holistic picture of someone’s creditworthiness in real time.

Sometimes, Plaid will act as temporary contractors, doing a variety of different tasks for their customers because as soon as a company would try to build a certain product, they would simply ask Plaid to do it for them due to Plaid’s unique access to such a large quantity of data.

Thus, building the infrastructure for these different products in these slower growth years allowed these new products to account for roughly 1/5 of the company’s ARR in 2024. In a world where companies are constantly engaging in side quests that prove to be epic failures and only result in millions, if not billions, of dollars wasted, this is a massive feat for Plaid.

More growth. More products. Stronger business.

Yet, a lower valuation.

Significantly lower.

In 2025, Plaid raised $575M at a $6.1B valuation, seemingly contradicting the idea that their business has massively grown in quantity and quality.

Before the haters begin to chirp, Perret insists this cut in valuation is simply due to compression in multiples, as the previous round was raised in 2021, also known as the year of free money. While the valuation drop-off is not ideal, it was still a good signal to see most of their existing investors re-up during this round, as they likely viewed the valuation as a bargain. Rather than being a sign of internal weakness, the discount is rather an opportunity for Perret to go back to the drawing board and plan the company’s next steps.

Speaking of returning to the drawing board, many teams are thinking about doing something similar. With the advent of the Steph Curry revolution and the ensuing Warriors dynasty paired with the Boston Celtics’ 2024 championship run, the consensus around front offices quickly became to shoot as many 3s as possible. However, with the recent success of the Oklahoma City Thunder and the ascending San Antonio Spurs, a new philosophy could be on the horizon, as both teams are built in a similar fashion: a clear number 1 and 2 option that catalyze the bulk of the offensive creation and a wide array of defensive talent, particularly at the wing spot that have the defensive versatility to match up with guards, wings, and even smaller bigs. Neither team crack the top 10 in 3 pointers attempted (#13 and #14 respectively) but both are in the top 3 in defensive efficiency. The New York Knicks–whom many are labeling as the third best team in the playoffs–also land outside of the top 10 in 3s attempted and are top 5 in points allowed. This is not to say that the 3 pointer’s role within the game is going anywhere; it is the rock that the game is built upon and to strip the game of its foundation would be too drastic of a change that would likely negatively impact all of the constituents within the game. However, the spray and pray model of the early 2020s may be shifting, and the magnitude of the shift will depend on the success of the two 60-win Western Conference behemoths.

Let the new age rivalry begin.

“I just gave the city life. It ain’t about who did it first, it’s about who did it right.”

Drake, Wu-Tang Forever

MySpace then Facebook, Blackberry then iPhone, Blockbuster then Netflix, Napster then Spotify.

The list could go on forever. For every example of first mover advantage, there exists a parallel instance of second movers stealing the spotlight. Being first is only advantageous when a competitor correctly identifies the high ground in an arena, and sets up barriers to protect then compound the advantage.

One of these great corporate battles is taking place in real-time: OpenAI versus Anthropic. While OpenAI came first, Anthropic has made a series of calculated decisions that allowed Dario Amodei and his troops to capture the enterprise market and induce panic in OpenAI’s heart. Now there are a number of outstanding questions that will determine who wins. For instance, which is more important in the AI market, the consumer or the enterprise? Will OpenAI’s compute advantage materialize in the medium term? If scaling laws hit a wall, does Anthropic have the upper hand? Is it easier to go from enterprise to consumer or the other way around? You could spend an entire week debating the merits and still not have an exact answer. For now, Anthropic has closed the gap, and investors are allocating accordingly.

On a smaller scale within the artificial intelligence domain, another war is being waged.

Legal software, headlined by Harvey, versus AI-law firms, also known as “neofirms”, headlined by Crosby.

Harvey is an $11B startup that raised money from Sequoia, Coatue, a16z, and Kleiner Perkins to run AI legal workflows. Harvey is used by the majority of AmLaw100, over 500 in-house legal teams, and 50 asset management firms across 60 countries; a total of 100,000 lawyers across 1,300 organizations. They reached over $190M in annualized revenue at the end of 2025. Harvey co-founder Winston Weinberg was working at O’Melveny & Myers and Gabe Pereyra, his co-founder, was working at Meta. When GPT-3 came out, the two friends tried to do chain-of-thought prompting on California landlord-tenant statutes, took 100 questions on the topic from Reddit, ran the AI prompt, and gave the question-answer pairs to a few landlord-tenant lawyers. The lawyers said that 86 of the 100 questions were perfect answers, no edits needed. On July 4th, 2022, the duo pitched OpenAI’s executive team and got their first investment. The rest is history.

Crosby is a $400M startup, an AI native law firm that reviews and redlines contracts in under an hour, pairing large language models (LLMs) with in-house lawyers who take on direct liability for their work. In the past year, Crosby has grown from 0 to 100 customers and processed tens of thousands of contracts. They raised $26M from Sequoia, Bain Capital Ventures and Elad Gil in both seed and Series A funding, before raising $60M last month in a Series B led by Lux Capital and Index Ventures, at a $400M post-money valuation. Lux’s Grace Isford wrote in a LinkedIn post that “what convinced us what when Crosby publicly launched last year and our portfolio companies were clamoring to use the product. By the time they signed their third Lux portfolio company and were recruiting some of the best talent in NYC, we’d seen enough.”

The tension between Harvey and Crosby is about strategy precision; it’s less about one being right and the other being wrong, and more about who is more right or who is less wrong. Harvey’s two year headstart has proved fruitful in signing law firms, but critics are quick to note that their tech is built on a foundation of sand, or more precisely, OpenAI’s foundation models. They are, in some sense, renting today’s revenue, an expensive gamble. Crosby is going after a fundamentally different customer and has fundamentally different unit economics. Crosby sells directly to startups (Ramp, Cursor) and enterprise (Tishman Speyer, Starwood), charges on the basis of work rather than billable hours and is designed to process large volumes of contracts quickly. They hire lawyers in addition to engineers. The Crosby thesis is that traditional firms bill by the hour, don’t optimize for long term equity value, and distribute profits to partners rather than re-invest, which leads to a lack of innovation. For context, America’s top 100 law firms made a combined $69B in profits through 2025, which was larger than Google’s R&D budget ($62B). Crosby is positioning itself to take advantage of improvements to artificial intelligence by pairing lawyers with AI engineers, charging customers for outcomes rather than billable hours, and re-investing into innovation for long term value creation. The primary customer at this stage is a well-funded startup; Cursor, Clay, Listen Labs are all paying Crosby to get their legal work done in a timely and cost-efficient manner. As more customers send more legal work to Crosby, the company’s technology systems get smarter, work gets done faster and more accurately, and the lawyers theoretically deliver a better product to clients that incumbent firms can. The bull case for Crosby relies on a number of probable assumptions, but perhaps the two most important assumptions being made are that (a) artificial intelligence improve significantly over time and (b) they can expand from their wedge (NDAs, MSAs, DPAs for high growth startups) into more complex upmarket work. As of right now, Harvey’s position is much stronger given their revenue scale, while Crosby is simply more interesting.

The 100th largest law firm in America by revenue did $697M in 2025 while employing 1,025 lawyers. If Crosby can creep anywhere near the incumbents, their valuation would warrant a much higher multiple given the fast growth and tech-enabled narrative. That day is still many years away from coming to fruition.

After less than two years of operations, Crosby is headlining today’s edition of Watchlist.

In the next two years, expect their price to increase tenfold.

The San Francisco Compute Company

• Company Overview: The SF Compute Company is a marketplace for compute that allows companies to buy GPU/compute capacity on flexible, short-term contracts while enabling data centers and enterprises to sell excess capacity. Their $40M Series A round was led by DCVC and Wing, and their seed round was led by Alt Capital. Their post-money valuation following the Series A in late November 2025 was $300M.

• Founders: Evan Conrad - co-founder and CEO of The SF Compute Company, Gonzaga graduate, Y-Combinator Summer 2019 (Quirk); Ethan Anderson - co-founder and COO of The SF Compute Company, Rhode Island School of Design graduate, Y-Combinator Summer 2019 (Fynn)

• Investors: DCVC, Alt Capital (acq. by Benchmark)

• Amount Raised: $52M+ (Series A stage)

• Headquarters: San Francisco, CA

Nevis

• Company Overview: Nevis is a unified AI platform for wealth management. They help advisors complete operational work end to end, including meeting preparation, client follow-ups, account openings, and ongoing service. Nevis supports advisors that manage more than $50B in assets. The company raised a $35M Series A from Ribbit, Sequoia, and Iconiq.

• Founders: Mark Swan - co-founder and CEO of Nevis, University of Edinburgh graduate, ex-Revolut; Ivan Chalov - co-founder and COO of Nevis, Novosibirsk State University graduate, ex-Revolut, ex-Deutsche Bank

• Investors: Sequoia, Ribbit, Iconiq

• Amount Raised: $40M+ (Series A stage)

• Headquarters: New York, NY

AfterQuery

• Company Overview: AfterQuery is a research lab that delivers datasets and reinforcement learning environments to top AI labs. They work with subject matter experts to translate human knowledge into reasoning for artificial intelligence systems, similar to Mercor ($10B valuation). The difference is, AfterQuery is focused on judgement density and producing frontier data in finance and coding, while Mercor is higher volume and automates the hiring of professionals to train models. The company surpassed $100M in annualized run rate a month ago, and is in line for a high-end Series B round soon.

• Founders: Spencer Mateega - co-founder and CEO of AfterQuery, ex-Silver Lake, ex-Morgan Stanley, Wharton graduate, Y-Combinator Winter 2025; Carlos Georgescu - co-founder and CTO of AfterQuery, ex-Meta, ex-Citadel, University of British Columbia graduate, Y-Combinator Winter 2025

• Investors: Altos Ventures, Y-Combinator

• Amount Raised: $30M+ (Series A stage)

• Headquarters: San Francisco, CA

Yuzu

• Company Overview: Yuzu is a healthcare tech company that provides a third party administrator platform for businesses to create and manage their own health plans. Their ultimate goal is to drastically decrease the amount of time and cost of processing a health insurance claim, which is currently around 30 days. The company raised a $35M Series A led by General Catalyst and Chemistry VC, and their company headcount is around 52.

• Founders: Max Kauderer - co-founder and CEO of Yuzu, ex-Bain, ex-Capital One, Haverford College graduate; Ryan Lee - co-founder of Yuzu, former product engineer at Lithic, Harvard College graduate

• Investors: General Catalyst, Chemistry VC

• Amount Raised: $40M+ (Series A stage)

• Headquarters: New York, NY

SmartBricks

• Company Overview: SmartBricks is an AI-powered real estate platform that provides a comprehensive intelligence layer for global real estate investing. The company built autonomous deal agents, underwriting agents, execution agents, and portfolio intelligence agents to increase ROI for real estate investors. After raising a $5M pre-seed round led by a16z speedrun, SmartBricks reached $12M in annualized run-rate revenue.

• Founders: Mohamed Mohamed - founder and CEO of SmartBricks, ex-McKinsey, ex-Bain, University of Warwick graduate, London Business School MBA

• Investors: a16z speedrun, 500 Global

• Amount Raised: $5M+ (seed stage)

• Headquarters: San Francisco, CA

How do I prepare for what’s next while I’m still fully committed to soccer?

That question has been sitting with me for a while now.

I’m 24. I’m in year two of my pro career. And I’m already thinking about what comes after it.

I know how that sounds.

I’m still all in on the game I love. That hasn’t changed. But I’d be lying if I said I haven’t thought about what happens if it’s taken away from me.

Not when I’m ready. Not on my terms. Just gone…

When you’re a pro athlete, your life is pretty structured.

Training. Recovery. Games. Travel. Repeat.

Outside of that, everyone fills their time differently. Some guys play Fortnite. Some golf. Some just unplug and spend time with family.

I do all of that too. But part of me can’t fully switch off.

Because I keep coming back to the same thought:

What else could I be building right now?

I think that’s why I’ve always been drawn to athletes who don’t wait until the end. The ones who are already exploring something else while they’re still in it.

Some invest. Some advise. Some write. Some just start figuring it out in public.

At first, I found myself asking a lot of questions.

How did they get started? How did they get into those rooms? Why that particular path?

But the more I paid attention, the more it stopped feeling separate from what I was doing. Because my own path into pro soccer didn’t look that different.

I went from MLS Combine invitee, to being undrafted, to going on trial, to finally signing my first professional contract, to starting the first game of my first season.

There’s nothing linear about my career. I had to roll up my sleeves and figure it out as I went. So I’m doing the same thing off the pitch.

For a long time, I thought building something off the pitch meant writing checks.

Growing up, I watched guys like Kevin Durant, Stephen Curry, and Andre Iguodala operating in the Valley, and I thought that was the model.

You make it, you earn, then you invest. That’s when you’re allowed in the room.

I believed that for a while. Most athletes my age still do.

Then I started paying closer attention to the athletes around me who are doing it without the spotlight. They aren’t necessarily the ones with the biggest bank accounts. They’re the ones who figured out their unique edge and went to work with it.

The legend Mr. Johan Cruyff said it best: every disadvantage has its advantage.

I don’t have a ton of capital to deploy yet. What I do have is a front-row seat to locker room conversations and access to people building things around a global sport in real time.

That’s a different kind of currency.

Three guys, in particular, are shaping how I approach my work off the pitch.

Jeremy Ebobisse, who played at my boyhood club, Bethesda SC. He uses capital as a learning tool. Every investment is a rep. Win or lose, he walks away sharper. I might not be writing the same checks yet, but I can still get the reps. Every room I enter, every conversation I have is a rep.

Spencer Jones I knew from Stanford. Before he became a rockstar on LinkedIn, he’d been thinking out loud about investing and sharing lessons he’s learned from his work off the court. Watching him confidently yet humbly build in public has been a good reminder that I can turn my platform into a magnet for opportunities.

Casey Toohill takes a different approach. He writes opinionated blog posts about opportunities in sportstech and emerging market trends. What I’ve taken from him is that a sharp point of view can open doors. He made me realize that proximity alone isn’t enough. You also need a perspective.

Off the pitch, I’m building. I’m building relationships, building experience, building judgment.

I now sit on the board of Spekt, a protective performance sock brand built for athletes. I help validate demand with other pros, give product feedback, share future product ideas. I’m also supporting the business development team at Game1 AI as a brand ambassador and raised money for a non-profit supporting young students to learn STEM.

My early stage work isn’t the shiny or scalable kind that makes headlines. But it’s work that I deeply care about and invested in.

Most of it is me in rooms I wasn’t in a few years ago - asking questions, listening, trying to add value however I can.

Some days I wonder if I’m doing the right things. Whether a 24-year-old in year two has any business even writing a piece like this.

I don’t know yet.

What I do know is that Jeremy, Spencer, Casey, the guys a few steps ahead of me, probably didn’t know either when they started. But they didn’t wait to feel ready. They used what they had and figured out the rest along the way.

So I’m doing the same, understanding that many failures and breakthroughs lie ahead of me. But that is the point, to learn those lessons now and use it as a trampoline for later.

I’m still all in on soccer. That part hasn’t changed.

But I’m not waiting for the final whistle to start the next chapter.

When the time comes, I want to already know the rooms. And I want to have earned the right to be in them.

Noah

Noah Adnan is a professional soccer player currently playing for Loudoun United in the USL. To keep up with Noah, follow him on LinkedIn and Instagram.

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There’s a lot in a name.

Technically speaking, Anthony Edwards, Draymond Green, and Domantas Sabonis are all “basketball players.” To someone who does not watch basketball, the assumption is that these three players do similar things for a living. That assumption, as basketball viewers know, is absolutely false. Anthony Edwards gets paid to score from all three levels - near the rim, the mid-range, and the three pointer - and occasionally jump over unsuspecting opponents like an NFL athlete.

Draymond Green gets paid to anchor the defense, frustrate the other team’s best player, and orchestrate the offense. His mind and attention to high level game strategy are arguably more important than his physical tools. Domantas Sabonis is paid to get a double-double every night by using his size advantage to finish around the rim, grab rebounds, and create offensive advantages as a screen setter in pick and roll actions. Anthony Edwards, Draymond Green, and Domantas Sabonis are all basketball players, but they do very different things for a living. This is why positions were created to better describe roles. Anthony Edwards is a shooting guard, Draymond Green is a forward, Domantas Sabonis is a center. As the game got more complex and “position-less”, more creative ways to precisely label players began to emerge. Rashad Phillips is a Detroit Mercy Hall of Famer for his basketball career there; at just 5’9, he was one of the leading scorers in school history with 2,319 career points. He played a year in the NBA’s Developmental League before embarking on a ten year overseas journey across Germany, Turkey, Greece, and Saudi Arabia. He retired in 2010, but recently found a new lane doing scout analysis as an independent outlet under the Twitter handle @RP3Natural. One of his major contributions is re-defining traditional positions, which he does in his book, Basketball Position Metric: The Evolution Is Being Televised. Instead of point guards, shooting guards, small forwards, power forwards, and centers, Phillips introduces a much wider slate of options to label more complex players: traditional guard, point guard, hybrid guard, combo guard, shooting guard, small forward, dual forward, stretch big, hybrid post, power forward, center, and point center. Lebron is a dual forward, Chris Paul is a point guard, Steph Curry is a hybrid guard, Karl Anthony Towns is a stretch big. Over time, the way analysts label and evaluate players becomes increasingly specific in order to accurately assess different skillsets.

A similar evolution is silently taking shape in venture capital. Limited partners and founders are starting to wake up to the different forms of venture capital outside of traditional investing parameters. For instance, accelerators are not the same as pre-seed investors, even though they invest in startups at similar stages. And some of the general partners running alternative strategies are sick of being labeled as “venture capital funds”.

Jack Abraham is one of those general partners.

The serial founder launched Atomic VC in 2012 with $10M of his own capital.

The outfit most recently raised $320M for its fourth fund in 2023.

In a Harvard Business School article, Atomic VC partner Chester Ng rejects the idea that Atomic is a venture fund: “We’re definitely not a venture capital firm… We’re not an accelerator or incubator either.”

There isn’t much you can find online about Atomic.

You can search for their fund announcements and Techcrunch will tell you how much they raised recently. Or you can look up their team roster and see that Jack Abraham is the founder and CEO, Chester Ng is a general partner, and Kristin Schaefer, a former Postmates CFO, is their most recent general partner hire. You can even go on their website and look at a couple of companies that they’ve invested in - or, more appropriately, built, or even more specifically, conceptualized… perhaps there’s no word in the English language to precisely describe what Atomic does. But if you put your reading glasses on, you’ll quickly realize that the companies listed on Atomic’s site are outdated; the fund only lists companies they’ve backed in the past that were successful. 15 out of the 17 companies listed were founded between 2012 and 2021, and the two other companies were founded in 2024.

You would also struggle mightily to find data on fund level returns: Atomic has done a great job of barricading public limited partners - U.S. public pension funds or public university endowments - from investing in their vehicles, because public LPs are required to disclose fund level data to the public, so if Atomic had public LPs, the data on their fund returns would be available to anyone. Instead, Atomic’s LPs include the most famous venture capitalists in the world, such as Peter Thiel and Marc Andreessen, and institutional investing firms like Stepstone Group ($149B+ AUM), with the latter accounting for 90% of the fund’s capital.

To cap it off, Atomic operates out of Miami, Florida, a detail that initially seemed insignificant until placed next to other pieces of damning evidence on the conspiracy board. Upon further examination, it seems as if Jack Abraham tried to run as far away from San Francisco as possible, with the hope of evading any undercover agents that could erode the information advantage his fund has. A firm this focused doesn’t move to Miami for the weather.

We were very annoyed in the last cycle where we would start companies and there were literally other studios that would send spies into our studio.

Jack Abraham, Atomic founder, to Auren Hoffman

Secrecy shrouds Atomic like a mushroom cloud; it is the Manhattan Project for startups.

Magid Abraham was born in 1958 and raised on a fruit farm in Machghara, Lebanon. The town’s name roughly translates to “strong and abundant flow of water,” a reference to the springs that power Machghara’s agricultural economy. Nearly 30% of Machghara is agricultural land, and the main crops are fruit - apples, grapes, pears, and cherries - so Magid’s upbringing on a farm was common. At a young age, Magid’s father taught him that it was better to own something than to work for someone else. Magid’s father owned multiple fruit orchards and spent days working hours in the sun, doing manual labor. It was a small town at the time, and still is today; no more than roughly 9,000 people live in Machghara on a full-time basis.

At the ripe age of thirteen, Magid moved from Machghara to one of the largest cities in the Middle East. He went to Beirut by himself, searching for the best high school education in Lebanon. His journey as a scholar was one of consistent excellence. After grinding his way to the top of his class as a teenager in Beirut, he traveled to École polytechnique, the top engineering school in France, where he excelled and then moved on to a MBA and PhD from MIT. While studying at MIT, he slept on a concrete floor in a sleeping bag. Magid was a relentless learner… In 1985, he joined Information Resources, Inc (IRI), a data analytics company that delivered market research on consumer shopping patterns to corporate clients. Just a year after joining IRI, Magid and his wife Linda welcomed their first child to the world. They named him Jack. In 1995, ten years after initially joining IRI and nine years after Jack was born, Magid and Linda founded Paragren Technologies, a marketing automation software company, which was later acquired by Siebel Systems in 2000, and Siebel was later acquired by Oracle in 2006. In 1999, Magid co-founded ComScore, a market intelligence company that he eventually took public in 2007. ComScore’s valuation on the first day of trading was around $640M and it hit a peak valuation of $1.6B in early 2016. Magid’s trophy room includes a “40 under 40” award from Crain’s Chicago Business, a “Technology Pioneer” award from the World Economic Forum, “Entrepreneurship Hall of Fame” induction from Ernst & Young, and the “Buck Weaver Award” from MIT Sloan School of Business. Magid’s life story is an American Dream case study. The son of Lebanese fruit farmers traveled thousands of miles across the world and found wealth beyond his wildest fantasies. If Magid Abraham’s life was a movie, Jack Abraham had the best seat in the house.

At the ripe age of thirteen, Jack started working nearly full-time at ComScore alongside his father. He was working with college graduates and other people twice his age, learning valuable skills such as programming and data visualization. The confidence Jack developed from having a seat at the table allowed him to constantly live outside of the box. Even as a high school student, he came up with his own changes to the processes his dad let him run.

Jack also got early exposure to the volatility of managing a startup company. During the summer of 2002, Magid, Linda, and Jack took a vacation to Outer Banks, a chain of barrier islands off the coast of North Carolina, now known for the Netflix series named after the region. Magid was the furthest thing from relaxed; even a young Jack could sense his angst, but his father would not tell him what the problem was. Unbeknownst to the kid, Magid’s company had two weeks of cash left in the bank and he was frantically dialing the phone to find new investors. The market for funding startups was drier than Machghara in July. The dot-com bubble was still fresh in the psyche of technology investors, and Magid was facing a near death experience. ComScore ended up surviving, but the experience of seeing just how sticky things can get stuck with Jack forever.

In 2004, Jack started college at Wharton.

He didn’t graduate.

In 2007, he dropped out to start a local product search engine company called Milo.com.

Today, it’s easy to gloss over the last sentence. Dropping out of college to start companies has been normalized, even championed in many circles. Programs like Thiel Fellows and Y-Combinator have created pathways for elite students to take a break from their academic lives and see if they can build a revenue generating company. If not, they simply return to their ivy-coated campuses, finish their degrees, then either try again or get a job at Ramp. But dropping out of a college like Wharton in 2007 to start an unproven company was extremely rare and high risk. The only ones dropping out were the ones who couldn’t see themselves doing anything else - they were willing to die to be a founder.

Milo.com was a site that enabled shoppers to research online with the purpose of buying local. It gave users real-time inventory and availability information for local products, basically bringing an Amazon feel to supporting nearby retailers. Jack was living in an apartment on University Avenue in Palo Alto, and he was introduced to high-profile founders like Jawed Karim (YouTube co-founder) and Keith Rabois (Slide founder, venture capitalist), who helped him focus his value proposition. Milo launched in 2008 and site traffic grew roughly 70% month-over-month, going from roughly 2,000 visitors per month to over 1,000,000 in a year.

Milo.com was acquired by eBay in 2010 for a reported $75M.

At just 24 years old, Jack was a young prodigy at eBay. It was in the midst of this transition, from the frenetic pace of startups to a more stiff corporate environment, that Jack’s mind began to linger to another world. He had heard too many stories of his founder friends who get acquired, join a larger company, and become vegetables, mere shells of their former selves without any guiding motive in life. He decided that would not be his story.

Jack started doing whatever he wanted to do at eBay; he had an epiphany and realized the worst case scenario is he would get fired, which was not a terrible thing in his book. At the peak of the madness, Jack riled up his co-workers Boston Tea Party style and convinced everyone that cubicles were holding them back from their fullest potential, and in a matter of minutes, eBay employees were ripping cubicles out and throwing them on the front lawn at eBay’s San Jose campus. No one was fired.

The pranks were just a way of passing time. Jack’s mind kept coming back to building new products. He dreamt of a world where he could ideate on multiple concepts at once, have teams of engineers and product managers build them out, and steer these numerous ships with ease, like a teenager dominating his friends in Call of Duty, ejecting the disk, inserting Madden, and dominating them some more without losing a single iota of focus. Jack dreamt of a world with no constraints to building new things, where he could seamlessly deploy human capital to create new solutions to expensive problems and he could deploy financial capital to double down on things that are working. Money wasn’t real.

He pitched the CEO of eBay at the time, John Donahue, to let him build out multiple products using different teams. The results were almost all positive: Jack and his teams built products that translated to real revenue and brought good press to the company, consequently driving up stock prices. In one episode, Jack convinced Donahue to let him fly out six eBay employees to Sydney, Australia, rent an Airbnb, turn it into a hacker house, and build a product for two weeks straight. The resulting product became the feed and homepage for eBay, which became the primary discovery mechanism for the 130 million people using the site.

What I remember about Jack was that very early on he was very enterprising. When he was 3 years old he would go and talk to his friends, and he would convince them to exchange an old quarter for a shiny nickel… He went to a national marketing competition [in high school], and he was a finalist. He realized he needed to have a jacket, and he didn’t have time to go back to his hotel. So he convinced a total stranger to part with his jacket [and won]. He showed confidence, chutzpah, salesmanship.

Magid Abraham to Forbes

Private equity, as a word, is typically used to describe leveraged buyouts, a transaction in which a leveraged buyout fund acquires a controlling stake in a relatively mature company using a mix of debt (leverage) and equity (cash), with the goal of improving operations and financial structure before selling the company to a new buyer or taking it public and getting a return on initial capital. The inclusion of debt amplifies the cash return, making the transaction more lucrative than a simple “buyout.” When you hear about private equity in the mainstream media, pundits are almost exclusively talking about leveraged buyout firms like KKR, Blackstone, and Apollo. But private equity linguistically includes a wider range of strategies, such as growth equity, distressed private equity, and venture capital. Private equity technically includes any private stock financing, not just leveraged buyouts.

While leveraged buyouts get all the “private equity” media attention, early stage venture and growth equity get all the “venture capital” media attention, and less covered strategies such as incubators, distressed private equity, and secondary buyouts sit in the shadows of their famous family members. Everyone knows Stephen Schwarzmann from Blackstone, Henry Kravis from KKR, Josh Harris from Apollo, Orlando Bravo from Thoma Bravo. Likewise, Marc Andreessen and Peter Thiel have become household names. But the average business savvy American cannot name a single high profile investor who founded a venture studio, distressed private equity firm, or secondary buyout firm. There are a few ways to explain why there’s a lack of attention on these lesser known private equity sub-sectors.

The sheer deal volume and transaction size for the leveraged buyout industry makes it low hanging fruit for media outlets. It’s easy to write an article whining about the risk leveraged buyout funds pose to the American economy and use Schwarzmann’s latest $21B buyout fund as a data point to drive the point home. Everyone wants to talk about how these decabillionaires amassed so much wealth through financial engineering, and private equity moguls are happy to make the rounds on CNBC, Bloomberg, WSJ. Venture capitalists are famous due to their involvement in defining technology companies. Peter Thiel invested in Facebook, Palantir, Stripe, LinkedIn, Spotify - all companies that create products used by countless everyday Americans, businesses, and in Palantir’s case, governments. Shiny objects attract eyeballs, eyeballs drive the media cycle, and venture capitalists pay people to build more shiny objects. There are also few stories as powerful as the story of a few people going from nothing to something. From students in a college dorm room to a trillion dollar public company. From a quiet startup in Sweden to displacing the entire music industry. From two young Irish villagers to processing trillions of dollars in global payments. The startup story captures the human heart, and the heart controls the mind, and the mind directs media consumption.

Distressed private equity is far too technical to capture the heart of the average individual. In practice, distressed investing is an academic pursuit that legalistic financiers celebrate in their designated corners. Only a few skilled directors can take a distressed deal and come back with a Disney movie. Secondary buyouts are even further removed from winning hearts; at least with distressed deals, there is still tantalizing upside to be earned through savvy maneuvers and sharp litigation tactics; secondary buyouts are lifeless transactions, leveraged buyouts’ boring big brother that no one wants to hang out with. Telling someone you work at HarbourVest Partners will not ring a single bell, unless the person you’re talking to works at Lexington.

Risk and returns generally tend to increase when moving from highly passive investing to highly active investing, and from old, mature companies to new, unproven companies. So a pre-seed investor (new companies, very active) should have a higher risk/return profile than a secondary buyout investor (old companies, fairly passive).

What does this have to do with Jack Abraham?

In 2013, after ruffling feathers and shipping products at eBay, Jack Abraham had compiled enough business ideas to last a lifetime. During his commutes from San Francisco to San Jose, he would allow his mind to run wild with possibilities. When he left, there were more than two hundred and fifty ideas in his vault. At least one hundred of them were very good ones. He wanted to act on all of them, in a twisted mad scientist kind of way. He wanted to do what he couldn’t do at eBay. This is how Atomic came to be.

Atomic is a venture studio that takes ideas from concept to revenue, and then spins their companies out to raise additional capital from venture firms.

They do this by testing out ideas on their idea list, and then spending money, usually in the hundreds of thousands of dollars, to validate the ideas with end customers. When they get confirmation that an idea solves a painful problem for customers, they invest some more money, up to a few million, to go to market and generate revenue. At this point, when the company is running on its own and needs a larger check to accelerate growth, Atomic spins the company out of its studio and the company raises money from other venture capitalists. If the company is successful - let’s say an IPO - it works in Atomic’s favor because their ownership percentage is extremely high at the beginning, so even with dilution over time, a smaller outcome is still significant relative to capital invested. The fund math is more favorable from the ownership perspective, but on the other hand, the studio is time-intensive and typically has less portfolio companies than a venture fund, which is good for IRR metrics but usually results in a lower cash-on-cash return since exits are harder to come by with less shots taken.

Venture studios have one of the highest risk/return profiles within private equity and the opportunity set is dwarfed by traditional venture capital. Investors don’t build as many venture studios because (a) it requires a rather unique skillset and (b) there is no clear path to $5B+ AUM. If you follow the numbers, though, there has been a quiet uptick in the amount of capital flowing to studio platforms.

Andrew Dudum was born in 1988 and raised by Palestinian American parents in San Francisco. His primary ambition as a child was to become a rockstar and play guitar in a Billboard charting band. His mother, an astute woman, convinced him that in order to master the guitar, he must start with the fundamentals and learn the cello first, then in a few years, the transition would be seamless. Andrew ended up being an elite cellist and never touched the guitar nor a rock band. Instead of rocking the stage with Van Halen he toured the country with Villa Sinfonia, an orchestra that played at the Carnegie Hall, private concerts, and occasionally, weddings.

Andrew’s music resume helped open the door to arguably the most coveted undergraduate business education in America, Wharton. You can probably connect the dots here now - Andrew Dudum met Jack Abraham at Wharton. Like Jack, Andrew dropped out of Wharton to work on a startup. TokBox was a Sequoia Capital backed company that enabled business conference video chats, and it was acquired in 2012 by Telefónica.

In 2013, Andrew joined Jack at Atomic.

They raised $20M for its first fund, with a significant chunk coming from Jack’s earnings on Milo’s sale to eBay.

In addition to Jack and Andrew, there were two other partners. Chester Ng previously founded an app development company called SweetLabs and Andrew Salamon previously worked for Bridgewater Associates. The studio was located in San Francisco’s Presidio Park at the time, not too far away from Peter Thiel’s Founders Fund office (Thiel was an early investor in Atomic). The model was as follows: either start a company using one of the several hundred ideas the team had on a list, or partner with an intriguing founder to bring the founder’s vision to life.

In 2016, Andrew Dudum had an idea.

Epiphanies come in many forms, but a specific kind of epiphany takes place when an individual independently realizes that the textbook is wrong. Certain assumptions made on a societal level are not true, and when an individual realizes this, there is a sense of enlightenment; a similar feeling to uncovering a long lost secret or finding hidden treasure in your backyard.

Andrew Dudum knew there was an extraordinary opportunity to improve on the healthcare model. In a world where Amazon delivers same day packages, the traditional timesuck of a doctor’s visit didn’t make any sense. The issue is, healthcare has a ton of inefficiencies for a reason; regulatory constraints make the sector a graveyard for overly optimistic founders. There are general partners at Tier-1 venture firms who have sworn off investing in healthcare startups entirely. So Andrew took some time before taking any action. He decided what to build only after the vision became clear as day.

Andrew’s core realization was that healthcare is failing men for a few reasons:

• Culturally, men do not seek out medical help unless there’s an emergency, which translates to worse healthcare outcomes for the demographic as a whole

• Stigmas around certain health issues further perpetuate this cycle

• Men actually do care about their health, but the inconvenience and stigma of dealing with it prevent treatment

Andrew figured if he could come up with a way to (a) de-stigmatize getting treatment for issues like baldness and prostate health and (b) make the treatment products desirable, then Atomic could build a generational healthcare brand from this wedge.

In 2017, Atomic launched Hims, and the brand did $1M of sales in the first week.

The brand did generational numbers in record time, raising $200M in venture funding from Thrive, 8VC, and Founders Fund.

Revenue scaled from $0 to $100M+ in less than three years.

• 2018: $26.7M

• 2019: $82.6M

• 2020: $148.8M

Profitability also improved drastically from 2019 to 2020.

• 2018: -$75.8M (loss)

• 2019: -$72M (loss)

• 2020: -$18.1M (loss)

It’s easy to gloss over the simply incredible growth trajectory that Hims hit in such a short amount of time, but I refuse to do so. In hindsight, the company is one of the top five fastest growing consumer brands of our time and probably the most underrated venture backed company considering both the explosive growth and longevity.

Hims & Hers ended up going public in 2021, just four years after initial launch. You would be hard pressed to find another company in the past ten years that graduated from private markets faster than a Wharton student graduates from undergrad. This is, to be clear, a record time, according to Atomic VC’s website. Incredible stuff.

• Hims & Hers Founding Date: November 2017

• IPO: January 2021 (via SPAC)

• Time to IPO: 3 years, 2 months

• Valuation at IPO: $1.6B

The sprint from incubation to IPO is impressive on its own, however, while I was reviewing the IPO S-1 filings, I found another gold nugget that adds to Atomic’s legend.

Oaktree, the renowned asset management firm led by Howard Marks, took Hims & Hers public via a SPAC in 2021.

If you are familiar with Howard Marks, you can feel the shock value in that statement. Marks is an exceptionally conservative investor that primarily made its money in credit - distressed debt, high yield loans, and private credit. Marks is nearly synonymous with taking intelligent risks, sitting out on easy money booms, and aiming for 15%+ IRR year over year. So why was he taking a venture backed startup public via SPAC in 2021? I thought this was Chamath Palihapitiya’s lane?

This reminds me of a conversation I had a few months ago with a friend. We were talking about the Warriors - Cavaliers rivalry from back in the day, and the topic eventually rested on the Game 7 when the Cavs miraculously beat the 73-9 Warriors team in what was one of the best basketball games of recent times. At one point during this discussion, my friend mentioned that Draymond led the Warriors in scoring that game. I responded as any rational person would, and said, no, that’s not true, let’s not make things up. I clearly remember Lebron pinning Iguodala’s layup off the backboard. I remember Kyrie’s shot over Steph Curry. I remember it was a gritty low scoring affair where every point mattered. But I couldn’t remember Draymond scoring 32 points.

Turns out he did; and not just 32 points, but 6 for 8 on three pointers, 11 for 15 on field goals, 15 rebounds, and 9 assists, nearing a 30-point triple double while shooting 75% from 3, 73% from the field, and just two turnovers, in Game 7 of the finals. When no one else could score, he provided more points, rebounds, and assists than Steph Curry and Klay Thompson combined. Draymond isn’t known to be a scorer, 32 points is the second highest scoring performance of his career, his career average is just shy of 9 points per game; he also isn’t known to shoot the three, he’s a solid 32% shooter on moderate volume (2.7). But in the biggest playoff game of the past ten years, he played like a completely different player - a flatout superstar. And I completely forgot.

From 2019 to 2023, Howard Marks and Oaktree were uncharacteristically active in the SPAC market, launching three SPACs - Oaktree Acquisition Corp, Oaktree Acquisition Corp II, and Oaktree Acquisition Corp III Life Sciences - while investing in a few others. The results are hard to detangle given the low sample size - Oaktree III Life Sciences pulled out of the market before acquiring a company - but if you take an average of the two primary vehicles, things are looking solid due to Hims & Hers strong stock performance.

Atomic is one of the few studios that can boast of successfully taking a company from incubation to IPO. The Hims & Hers exit returned 150x+ to the fund; as a result, the aggregate portfolio returns have been rock solid. In 2017, pre-Hims & Hers, Jack said Atomic’s IRR was at 65%, and in 2018, Atomic partner Chester Ng said their Fund I had a 70% IRR. Not much detail has been revealed since then.

Fund sizes have grown accordingly - from the initial $20M fund to a $150M Fund II to a $260M Fund III and most recently a $320M Fund IV.

As mentioned in the beginning of this breakdown, it’s difficult to decipher what Jack Abraham and the guys are building now. They’ve intentionally kept things stealth, treating each startup incubation as a military grade project unfit for the public’s eyes. The most recent unveiling is from 2024: Exowatt is a company that builds modular, dispatchable energy systems that capture solar energy, store it as heat, and use it to meet demands of AI infrastructure. A much more technically gritty endeavor than selling hair loss supplements, but I guess that just goes to show the range with which Atomic operates. After initial funding from Atomic, Exowatt raised a $20M seed round from a16z, Sam Altman, and Leonardo DiCaprio in 2024, then closed on a $70M Series A led by Felicis in April 2025, before raising another $50M from MVP Ventures and 8090 Industries in November 2025, for a total of $140M in two years. Energy efficiency for AI infrastructure is a massive problem for some of the deepest pocketed tech companies of all time, and by extension, a massive market to go after.

On the topic of AI, there is arguably no better time to own a venture studio. The biggest drawback of the studio model, according to multiple venture capitalists who have incubated companies, is the time cost. Instead of sitting and waiting for the right opportunity, reviewing tons of pitches and then allocating capital to the highest growth opportunities, the incubation model lifestyle looks much more like a professional early stage founder than an investor. Days are filled with customer meetings, user research, pitching investors to buy in at the seed stage, and other time intensive tasks usually reserved for people building companies. Of course, another executive is brought in to lead these tasks, but the investor’s typical routine is disrupted nonetheless, and there is a question of whether incubating while actively investing full-time is desirable, or even sustainable for optimal returns. With artificial intelligence, studios are able to iterate faster, test things quicker, and start more companies.

Since Atomic launched in 2013, the venture studio model has blown up.

From 2015 to 2025, the number of venture studios grew 15x+, from around 65 studios to over 1,000.

From 2022 to 2025, the number of venture studios as a percentage of new venture funds grew fourfold, from 3% to 13%.

Copycats began to flood the scene, and Jack Abraham moved to Miami to avoid them.

Who can truly tell us where ideas come from.

Ideas are like rabbits. You get a couple and learn how to handle them, and pretty soon you have a dozen.

John Steinbeck

New scientific ideas never spring from a communal body, however organized, but rather from the head of an individually inspired researcher who struggles with his problems in lonely thought and unites all his thought on one single point which is his whole world for the moment.

Max Planck

If you guys want these crazy ideas, these crazy stages, this crazy music, this crazy way of thinking, there’s a chance it might come from a crazy person.

Kanye West

When I am … completely myself, entirely alone… or during the night when I cannot sleep, it is on such occasions that my ideas flow best and most abundantly. Whence and how these ideas come I know not nor can I force them.”

Wolfgang Amadeus Mozart

The air is full of ideas. They are knocking you in the head all the time. You only have to know what you want, then forget it, and go about your business. Suddenly the idea will come through.”

Henry Ford

Inspiration comes from the Latin root “inspirare”, meaning “to breathe into”: in = “in”, spirare = “to breathe”. The word originally described divine influence; God breathing ideas into us, akin to how God blew life into Adam in the book of Genesis, and how Jesus blew the Holy Spirit into his disciples in the book of John. Inspiration eventually wandered away from its original meaning over time.

But maybe

In January 2011, Goldman Sachs invested $1.5 billion into Facebook, roughly a year before the social media giant’s IPO, at a $50 billion valuation.

In addition to a $450 million principal investment, Goldman Sachs also created a special purpose vehicle (SPV) with the intent of giving their private wealth clients access to the hottest company in the world. Goldman looked to fill the SPV with the outstanding $1 billion.

For some reason, Goldman’s email to their clients did not mention the company (Facebook) by name, and when the suspicious client email got leaked to the media, the SEC started digging around. Goldman folded. Under SEC rules at the time, private placements came with a strict prohibition on mass solicitation, and not mentioning the company by name, as well as using language like the “opportunity of a lifetime”, gave regulators the impression that Goldman was trying to pull a fast one. Goldman ended up filling the SPV with foreign dollars to avoid further scrutiny, but the damage was done - Facebook was embarrassed. The most prestigious investment bank in the world would no longer be the lead bookrunner for Facebook’s IPO.

One of the most notable fumbles in modern investment banking.

Morgan Stanley went on to be the lead-left bank, JP Morgan was second, and Goldman Sachs fell to third.

Divesh Makan was technically working at Morgan Stanley at the time. Well, he actually had a history working for Goldman Sachs as a wealth advisor in San Francisco, a job he took after a Wharton MBA in 2001. Makan wanted to do investment banking or private equity, but the job market was tough post-dot-com bubble. He made the most of his Goldman gig, hustling to meet the next big tech entrepreneurs in the Bay Area before they became big fish. He met Mark Zuckerberg around 2004, when Facebook first landed in Palo Alto. While at Goldman, Makan was known for going above and beyond the typical wealth advisor duties, often helping clients with the extracurriculars such as doing business school applications for clients’ kids and planning bachelor parties. This full-service style approach is considered acceptable at private family offices, but Goldman’s stiff structure meant Makan butted heads with the compliance team and colleagues at several points during his tenure. In 2008, he was fired for a “loss of trust”, according to representatives at Goldman Sachs. Makan has publicly stated that he left over a “workplace disagreement.”

Morgan Stanley picked him up quickly, paying a reported $20 million signing bonus to get the deal done. Chad Boeding and Michael Anders, two of his trusted colleagues at Goldman, followed him to the new platform. As Zuckerberg and other high-profile tech execs began to grow in stature, Makan’s network became a highly legible asset to the Morgan Stanley wealth business. Zuck was getting wealthier each year, and Makan was his primary advisor. The trio had more autonomy at Morgan Stanley, but there was still friction. In 2011, when it became crystal clear that Facebook was going to be one of the most valuable IPOs of all time, higher-ups at Morgan Stanley made plans to give Makan the wealth management equivalent of Frank Quattrone’s deal at CSFB, with the aim of retaining Zuckerberg and other Facebook executives in as wealth management clients. But Makan, obviously a student of the game, decided to walk away from Morgan Stanley in his prime and build a family office platform around Mark Zuckerberg. Anders and Boeding joined, and they launched Iconiq at the same time as the Facebook IPO, which Morgan Stanley led.

This is a story about how Makan’s decision to leave Morgan Stanley spiraled into a $100 billion platform.

The United States is expected to experience a financial advisor shortage in the next ten years.

A report from McKinsey estimates that by 2034, the advisor workforce will decline to the point where the industry faces a shortage of roughly 100,000 advisors. For context, there are roughly 300,000+ active advisors in the U.S. right now. The industry is heavy with older professionals, and retirement is outpacing recruitment, as graduates are steering away from the field.

On a firm level basis, there are 15,000+ SEC registered investment advisor (RIA) firms in the U.S.

The most common business model for an RIA is to charge ~1% of assets under management (AUM), and the percentage typically decreases as the amount of assets go up, to incentivize larger accounts. The median RIA manages ~$393 million and has 8 employees. To break into the top 5% of RIAs, a U.S. based firm must crack the $1 billion assets under management mark. At $10 billion assets under management, a U.S. based firm is now flirting with top <0.2% status, safely within the top 50 largest RIAs in America.

Within the upper stratosphere of wealth managers, there are two dominant strategies.

The “mass-affluent” model focuses on relationship quantity, drawing in tens of thousands of clients who have, from a wealth management perspective, smaller accounts and thus lower margins for the platforms that manage them. Some examples of firms in the mass-affluent space include Moneta ($37 billion AUM, ~$900,000 average account size, ~41,000 clients) and Savant ($26 billion AUM, ~$1.7 million average account size, ~15,000 clients).

The “UHNW” model focuses on relationship depth, usually measured by lofty average account sizes and breadth of services. This model prioritizes selectivity and going above and beyond for the select clients they work with. Circle Wealth ($10 billion AUM, ~$11 million average account size, <1,000 clients) is a good example.

Iconiq is the most extreme version of the UHNW model, with somewhere around $70 billion AUM across less than 300 families, implying an average account of more than $230 million. It is, perhaps, the most capital efficient RIA in modern history, the most concentrated formal network of wealth in America, and the most valuable brand in the industry.

Although $70 billion is a reasonable estimate of RIA AUM, this number is tricky to pinpoint given Iconiq’s opaque nature. On public materials, the firm lists $100 billion AUM, but this number includes both the wealth management and investment arm. In 2024, a Fortune article reported that Iconiq had $60 billion AUM on the wealth side and $20+ billion AUM on the investment side, for a total of $80+ billion total assets under management. No matter how you slice it, Iconiq is a case study worth examining closer.

When Makan, Boeding, and Anders split from Morgan Stanley, they did so on good terms with their former employer. On day one, Iconiq actually struck a deal with Morgan Stanley Wealth Management for back office support and proprietary deals. The launch came with approximately $1 billion across roughly a dozen clients, and within two years of launch, scaled to $7 billion across roughly two dozen clients. The foundation to their growth was, at first, Mark Zuckerberg, and then, the Iconiq network. Mark Zuckerberg as a founding client opened every door they wanted. The easy thing to do after bringing Zuck on would have been to optimize for the quantity of accounts above a set threshold, for example, a $15 million account minimum. But the doors to Iconiq remained closed, open only to the top dogs in technology, finance, and entertainment. Over time, guys like David Bonderman (TPG founder), Jack Dorsey (Twitter, Block founder), Henry Kravis (KKR founder), Satya Nadella (Microsoft CEO), Will Smith, Ashton Kutcher, and Justin Timberlake signed up as Iconiq clientele. And to provide palatable contrast to their high profile accounts, the firm remained as lowkey as possible.

The question is, why is there only one Iconiq? Surely, a number of extraordinary entrepreneurs exist outside of Mark Zuckerberg… Where are the other Divesh Makans at GS/MS/JPM that have a single highly valuable relationship and can spin out into their own shop? By the end of this piece, the answer will be clear. But first, the most notable basketball executive you’ve never heard of…

Malice in the Palace will forever be remembered as the modern NBA’s most violent night. A hard foul by the Pacers’ Ron Artest on the Pistons’ Ben Wallace escalated into a brawl, then fans got involved, and Ron Artest rushed the stands in an attack on a fan that threw a drink at him. Stephen Jackson followed, punches were thrown, and utter chaos ensued.

Ron Artest was suspended for 86 games afterwards and lost $5 million in salary.

In the midst of this black swan event was a man with no formal affiliation to the Pacers, the Pistons, or Ron Artest. The man in the gray suit pictured below is William Wesley, one of the most powerful men in basketball, popping up out of nowhere to try and restrain Artest.

Wesley grew up in Cherry Hill, New Jersey, and as a teenager, worked at Pro Shoes, a high-end sneaker shop. He would use the gig to build a network of basketball royalty, from up and coming high school stars like Milt Wagner to current NBA players on the Nets and 76ers. In the early 1990s, Milt Wagner, now an NBA player, introduced Wesley to Michael Jordan. Jordan gave Wesley a job at his basketball camp, and by 1993, he moved out to Chicago full time. In Chicago, Wesley became friends with the Clintons, Phil Knight, basketball executives, and anyone in between. William Wesley has been credited for brokering peace between 76ers coach Larry Brown and star player Allen Iverson, helping John Calipari land high school phenom Dajuan Wagner, and building Creative Artists Agency into a basketball powerhouse.

His most notable feat is as follows. Aaron Goodwin is from Oakland, California. Which means he had a front seat to watching Lebron James dominate the AAU circuit as a member of the Oakland Soldiers. Goodwin built a relationship with Lebron’s family in high school and ultimately won the right to represent him in May 2003, right before the NBA draft. From a distance, Wes watched and observed. Well, actually, Wes was pretty close to the action. Wes became friends with Lebron’s surrogate father, Eddie Jackson, built a friendship with Lebron himself, and eventually introduced Lebron to Jay-Z, a dream come true for the young hooper. In 2003 Wes moved to Cleveland for proximity. In 2005, Lebron cut ties with Goodwin and signed with Leon Rose, who, less than two years after, moved his business to CAA. Rose almost exclusively represented players that had ties to Wesley. And, important to note, Leon Rose was William Wesley’s lawyer; the two grew up in New Jersey together. CAA signed Wes as a “consultant” and became the default agency for basketball superstars. This is the story of how “Worldwide Wes” put CAA on the basketball map for good.

The relevant part of this story, however, as it pertains to Iconiq, takes place in 2012, around the same time that Facebook went public. On September 13, 2012, Lebron left CAA, and Leon Rose, to be managed by his longtime friend, Rich Paul, who, without coincidence, was a former CAA employee under Leon Rose. The timing was critical, Lebron just won his first championship, was coming off an MVP season, and was, without reasonable doubt, the best player in the world. Paul was a childhood friend of Lebron’s and learned the game from William Wesley. At the peak of Lebron’s power, the two decided to start a platform of their own, in the same year that Facebook went public and Makan-Zuckerberg made an analogous move.

Klutch Sports, Rich Paul’s agency, now manages $7 billion in athlete contracts, and has expanded past basketball. Clients include Lebron James, Jalen Hurts, Tyrese Maxey, Anthony Davis, Draymond Green, Odell Beckham Jr., Myles Garrett, and more. Klutch is a top five agency in North America by contract value and commissions.

The key reason why Klutch worked so well is because there is only one Lebron James, and the move was made in his prime. Outside of Michael Jordan and perhaps Kobe Bryant, James is the most high profile NBA player of all time, and Rich Paul was able to capitalize on this right after he won his first championship. Klutch probably wouldn’t work as well if it were founded today. Timing was of the essence. This was Lebron’s IPO equivalent.

With that in mind, it’s important to understand just how dominant Zuckerberg’s run was in the early 2000s.

Facebook was the most highly valued tech startup in history leading up to its IPO.

And it was being run by a 28 year old Zuckerberg the year of its IPO, the same year that Lebron won his first championship.

Prior, Zuckerberg became the world’s youngest self-made billionaire at age 23, the same age that Lebron won his first scoring title.

From 2005 to 2012, Zuck set the precedent for founder control:

• 2005: Series A by Accel, $13 million at ~$100 million valuation

• 2006: Series B by Greylock, $27 million at ~$527 million valuation

• 2007: Microsoft Strategic Investment, $240 million at $15 billion valuation

• 2009/2010: DST Growth, $200 million at $10 billion, $500 million at $15 billion

• 2011: Goldman Sachs, $1.5 billion at $50 billion valuation

Raising $2.5B before an IPO was unheard of before Facebook, but the most ludicrous part was Zuckerberg’s infamous ownership structure. Before the IPO, he owned 28.4% of the company yet controlled 56.9% of voting power through the dual-class share structure he instituted in 2009, designed to prevent investors from ever ousting him.

Zuckerberg walked so Kalanick, Neumann, Chesky, and Altman could all fly private.

And to cap it all off, this was Zuckerberg’s first company. He had no experience prior to founding Facebook, he is the startup equivalent of going straight from high school to the league. This is a significant part of the reason why Iconiq worked; there were no enduring business relationships Zuck had built from selling past companies or working under others, Makan was the only advisor that was there to take a chance on him early, and when Makan decided it was time to leave Morgan Stanley, Zuck followed suit.

In 2013, roughly a year after Iconiq launched, Dave Goldberg encouraged Divesh Makan to launch an investment arm alongside the wealth advisory brand. Dave was a technology executive and husband to Iconiq client and Facebook COO, Sheryl Sandberg. Goldberg went on to recruit Will Griffith, a longtime venture investor at TCV, to join Iconiq and lead the venture efforts. Iconiq launched its first growth fund that year, a $509 million vehicle, with 67% of investors coming from the wealth management side.

The strategic thinking was pretty sharp. Many of our clients are the biggest names in technology and top founders already want them on cap tables. Our clients also dabble in venture investing and come to us for deal introductions, so why not launch a fund to make things more straightforward? We’d win any deal we want, because who’s going to say no to Mark Zuckerberg and Jack Dorsey? Growth stage also reduces risk and allows for larger check sizes. The fee structure is more favorable, an additional 20% through carried interest, as opposed to just the 1.5% fee that Iconiq charges clients for public markets action.

With every advantage comes disadvantage, and from the perspective of other wealth managers, the disadvantage was too obvious to ignore. Iconiq operating a private investment fund that they shop to their wealth clients is a blatant conflict of interest. A wealth manager is, by SEC’s RIA rules, required to adhere to the fiduciary standard, which necessitates a manager acting in his client’s best interest. Other wealth managers offer a few select funds and allow clients to choose. While Iconiq theoretically does something similar, they are conflicted and incentivized to push forward their own products, and this has only gotten more pronounced as the firm added other asset classes in addition to venture/growth, such as real estate. The reason Iconiq is legally allowed to operate in this gray area is because of their full disclosure to clients that they are indeed “conflicted.” Makan, obviously a student of the game, graduated with honors from Goldman Sachs and Morgan Stanley. Chad Boeding, however, one of Iconiq’s founders alongside Divesh Makan and Michael Anders, actually decided enough was enough. In 2018, Boeding left Iconiq to found Epiq Capital - he couldn’t resist the -iq ending - and cited his reason for leaving Iconiq as “an intense commitment to avoiding conflicts of interest commonly found at major banks and large advisory firms.” Boeding scaled Epiq to $5.9 billion in assets and then sold the firm to IEQ Capital in 2024.

In 2013, Iconiq did a limited number of deals: SurveyMonkey’s $800 million growth round, Flipkart’s Series E, The Honest Company’s $25 million Series B, and Modern Meadow’s $2.5 million seed round. In 2014, the firm tripled the amount of investments made, deploying capital into twelve deals and ten unique companies. 2015 saw a similar amount of deals, 13, with a critical Series A investment in Figma, done at a $77 million valuation.

The funds have overperformed, especially considering the focus on growth, which typically warrants a lower return profile:

• 2013: 2.7x MOIC

• 2014: 5.5x MOIC (top-decile)

• 2017: 5.4x MOIC (top-decile)

• 2019: 1.9x MOIC

Consider top-tier fund Thrive Capital and their early returns, albeit TVPI, not MOIC:

For the early funds, 2013, 2014, and maybe even 2017, MOIC and TVPI should be relatively comparable, as these funds should be mostly or completely realized. TVPI for a given fund is lower than MOIC until full realization, so Thrive is ever so slightly disadvantaged in this comparison. But all of that to say, Iconiq is not simply “Zuck’s family office” anymore. The numbers tell a clear story: Iconiq took their advantage and turned it into a top growth equity platform. Back-to-back 5x funds on $500+ million pools, closed on a $6 billion fund in 2024, and attracted so much demand for their last fund that the proportion of LPs from the wealth arm withered to 20%.

Nowadays, Iconiq has been focusing heavily on both artificial intelligence and financial technology.

Stage-wise, they are flexible as ever, investing from seed to Series F and beyond. Most of their activity is clustered in the B, C, and D rounds.

Something interesting to watch is how active Iconiq has been in the first few months of 2026. So far, they’ve already done more volume wise than entire previous years - 2023 and 2024.

This year they’ve led 8 rounds:

• Whirl AI | $9 million seed round

• Standard Template Labs | $49 million seed round

• Quince | $500 million Series E round

• Grotto AI | $10 million seed round

• Braintrust | $80 million Series B round

• Outtake | $40 million Series B round

• Rain | $250 million Series C round

• Swap | $100 million Series C round

Time flies. Over the course of fourteen years, Iconiq evolved from a boutique RIA with a growth equity arm to a multi-faceted investment firm managing more than $100 billion. No thesis, no stage focus, no financial engineering, just a network that had Zuckerberg as the central node, quite literally the Klutch Sports of technology investing. From that initial network foundation, Makan built various structures to capture value, embraced conflicts of interest without any remorse, and delivered highly respectable returns to his clients, white glove style. Klutch is now built to outlast Lebron, and perhaps even Rich. Only time will tell what Iconiq’s next chapter holds. Now onto a more explosive subject

America was booming.

Specifically the population, as the country had just concluded a gruesome war that saw many of its soldiers sacrifice their lives.

But we are not referencing the frequently scapegoated baby boomers and WWII.

The scene is post Civil War.

Between 1860 and 1890, the country’s population more than doubled from 31 million to 63 million. This caused several notable effects, but the most pertinent was a drastic increase in food demand. Thus, many saw where the tides were shifting and set their sights on becoming farmers.

Since many of these prospective farmers–who were now journeying westward–calculated that the growth in demand for food would be stable in the short to mid term future, taking on debt from east coast banks seemed like the cheapest way to grow their economic prospects.

Things were going according to plan until they weren’t.

Global competition and overproduction led to falling crop prices, monopolized railroads began to hike transportation prices, and droughts rendered significant portions of farmers’ crop supply useless.

Farmers began going bankrupt left and right.

After seeking help from the government, specifically to regulate the railroads, the politicians yawned and told them to get lost because it wasn’t their problem. While sounding cliche, the farmers had no other option but to band together and advocate for themselves. They used the help of labor unions and worker organizations to expand their reach, creating The People’s Party in 1892.

American populism was born.

Over the years, it was used strategically by left wing figures like James B Weaver and Huey Long as well as right-wingers like Joseph McCarthy. After McCarthy, it hit a bit of a lull but it would soon resurrect.

“For too long, a small group in our nation’s capital has reaped the rewards of government while the people have borne the cost. Washington flourished—but the people did not share in its wealth. Politicians prospered—but the jobs left, and the factories closed. The establishment protected itself, but not the citizens of our country. Their victories have not been your victories; their triumphs have not been your triumphs. That all changes—starting right here, and right now, because this moment is your moment: it belongs to you.”

Donald Trump

“We are going to create an economy that works for all of us, not just the 1%… We will all come together to say loudly and clearly that the government of our great nation belongs to all of us, not just a few wealthy campaign contributors. That is what this campaign is about… that is what the political revolution is about.”

Bernie Sanders

Populism awoke from its slumber in the mid 2010s. Donald Trump quickly garnered a loyal fanbase by creating a clear bifurcation between the constant stream of corrupt politicians that enriched themselves at the expense of the people and himself, a political outsider that could theoretically not be puppeteered by outside lobbying influences due to his financial independence. On the other side of the political aisle, Bernie Sanders became popular among the youth with a similar yet distinct socialist outcry of the financial and political elite conspiring to keep the masses oppressed. Both Trump and Sanders benefitted from a relatively stagnant economy, growing popularity of social media platforms, and growing distrust of the Mitt Romneys and John Kerrys of the world.

More than a decade later and the populist bug is still in the air.

Some argue that it hasn’t left the political scene and both sides still await their true populist messiah.

But where it is undeniably present is in the private investing world.

In a surprising turn of events, many voices have begun to ask the question of “How do we increase retail investors’ access to private assets?”

But what if retail investor access isn’t actually the goal? More importantly, if the actual goal is simply to increase fund manager access to a new–and rather large–capital source rather than retail investors’ access to private funds, does that actually matter if access is gained nonetheless?

This move would only make sense if fundraising became noticeably more difficult in recent times.

As the data shows, private capital raised across the board has seen a downward trend since the 2021 peak, with venture capital and private equity following the trend. Not only has the total amount raised between the two assets decreased, but their share of capital within the private ecosystem has decreased as well, as LPs have shifted to assets like infrastructure, secondaries, and private debt, given the lack of cash flow PE and VC has provided recently. PE specifically has seen fundraising decrease to $414.2B in 2025, a 38% decline from the 2021 peak. In VC, the biggest players increased their share of capital raised, as 22% of commitments were closed by 10 funds, the highest since 2012.

Thus, one cannot say that the executive order signed in 2025 aiming to expand access of 401Ks and other retirement plans to private assets was a coincidence. It doesn’t take a genius to realize why all of the loudest voices for democratization were nowhere to be found in 2021 when institutions were handing out cash like everyone’s favorite uncle on their birthday.

While no major shifts have occurred yet, regulators have been working overtime to figure out how to actually implement these changes while the biggest fund managers are curating specific products catered towards them.

While many of the biggest PE funds are gearing up for this shift, several of their friends up the capital stack tapped into the trend slightly before the noise became loud. Private credit funds like Blue Owl, Cliffwater, Apollo, and others have steadily allowed high net worth individuals to access their products through evergreen funds, mainly BDCs. These structures differ from the typical private funds in that they allow a limited % of assets to be redeemed per quarter, usually around 5%.

The dynamic between these HNWIs and the funds was unproblematic for a while until the murmurs about software companies’ vulnerabilities to the AI revolution became louder in recent weeks, with software stocks undergoing a noticeable correction. Most of these funds lended a decent chunk of their assets to software companies and some investors became spooked and decided to redeem the assets.

Similar to your average bank, these semi-liquid structures are only functional when a relatively small portion of investors redeem their cash at the same time, as nearly all of the original capital has typically been deployed to the companies. Thus, the funds will typically draw from either new LP cash, their relatively small portion of funds held in cash or its equivalents, or through credit facilities with the underlying loans serving as collateral.

As the demand for withdrawals has surged far past the traditional 5% limit, these funds are faced with a decision: either increase investor confidence through granting requests or protect themselves and prevent all of the requests from being granted. While the first option seems like the “right” thing to do, many of the firms would likely have to increase their leverage exposure.

Blue Owl has taken the safer path, limiting redemptions in one of its most notable funds, although they were able to satisfy some requests through selling a third of the fund’s assets for 99.7 cents on the dollar. While coming that close to par was likely a best case scenario, many in the industry are still nervous about the portion of the fund’s assets that needed to be sold.

Cliffwater and Morgan Stanley also limited their withdrawal requests as well, with both funds exceeding the typical 5% but not accepting all requests. One of Cliffwater’s funds–holding $7.6B in assets–saw withdrawal requests shoot to 14%, in which they honored about half of them. Morgan Stanley’s situation was similar, fulfilling about 46% of the 10.9% request figure.

The problem with these types of structures became obvious. Firstly, they are more opaque than many investors realize, as not only do the investors redeem shares at NAVs that are determined by the fund managers that can inaccurately price these assets that rarely trade, but many evergreen funds buy secondary interest in other managers’ drawdown funds, creating a fund-of-fund type structure that many investors aren’t aware of. For instance, Blackstone’s new hedge funds for “mini-millionaires” will have roughly a third of the fund’s assets invested in other hedge funds, creating a less than ideal double fee structure.

When good times abound, most don’t pay attention to these types of issues.

But it’s a different ball game when things turn downwards.

When the market deteriorates, while fund managers have to worry about the value of their assets decreasing, they typically don’t have to worry about all of their investors rushing to their door, demanding they get their money back, as the institutional investors that back these funds know they signed up for the long time horizon that will ideally be rewarded through increased returns. However, as the share of capital through these semi-liquid evergreen funds increases, in downturns, managers will not only have to deal with declining NAVs but also a flood of withdrawal requests that will likely not be feasible. The system has already shown vulnerability based on weakness in a specific industry, so only time will tell what happens when the broader macro environment is hit with a negative shock. We’ve seen a spike in requests simply based on fears of future software performance, and the fact that most of the underlying loans themselves in these major funds are healthy seems to be irrelevant to the sentiment.

While the bears have been predicting a recession since late 2022, many economists have an active eye on the macro conditions, especially with the low consumer sentiment due to increased gas prices from the Iranian conflict.

In addition to the apparent gap in the armor, many have been discussing the paradox of increasing private assets access to the masses. Specifically when analyzing the relationship between public and private equity, as more investors gain access to private equity through structures that provide some sort of periodic liquidity, private equity begins to look more like public equities, as the lack of liquidity is one of the key features of private equity. Additionally, as the retail capital floods the private scene, there is an increased likelihood that it may lead to bidding up the entry prices, thus competing away the excess return that private equity–in theory–provides relative to its public counterpart. The entry price is obviously one of the key metrics when determining rates of returns and the inverse relationship between return and purchase price could potentially eliminate the attractiveness of private equity. This is highly theoretical, and the practical doesn’t always fall in line with the theoretical, but it is nonetheless something to keep an eye on.

Thus, the verdict of whether retail investors should access private assets en masse, and if so how, becomes unclear. Access of some sort seems inevitable at this point, but the real mystery lies in how to create a mechanism that will provide access without creating potential headaches for both the investors and managers.

What is perfectly clear, however, is that the push for retail investor access to private markets was not an organic populist movement but rather the titans looking for their next meal while saving some crumbs for the masses. In a strange way, there could be a scenario in which both parties are satisfied given that crumbs are better than the empty plate they had before. Where it could get dangerous is when the people realize the crumbs they were given were not as they originally appeared, as a revolt is inevitable once they realize it wasn’t real food to begin with but rather synthetic, lab-grown food.

mainstreet hoop labs 001.

Team Caplight beat Team Mainstreet, 107 - 95 in a FIBA style 3x3 basketball exhibition.

Team Caplight:

• Gokul Natesan.

  • Bio: A top 5 all-time scorer at Colorado School of Mines, played in the NBA G-League for Cleveland’s affiliate team, has more than 7 years of experience playing professionally in Taiwan, Finland, Uruguay, and more. A machine learning engineer with a Masters from Columbia University, works for Corning Incorporated with a focus on manufacturing AI and data operations. Also does investment scout work for a sports tech family office.

  • Stats: game-high 44 points and game-high 10 threes made… Player of the game.

• Matt Mooney.

  • Bio: Played college ball for Air Force, South Dakota, and finished at Texas Tech. At Texas Tech, Matt and Jarrett Culver led Texas Tech to its first Final Four appearance ever, where Matt scored 22 points to beat Michigan State… He was named to the 2019 March Madness All-Tournament Team, went undrafted, and ended up playing in the NBA for the Cleveland Cavaliers on a two-way contract and signing a 10-day contract with the New York Knicks. Mooney has more than 6 years of professional basketball experience and is the founder of AthletIQ, a sports tech startup. Read more about Matt here.

  • Stats: 31 points, game-high 7 assists.

• Dylan Jensen.

  • Bio: A BYU psychology graduate, a Utah State University MBA, and founder of Sola Athletics. Sola’s primary product is SoleGripz, a portable traction pod for basketball and volleyball athletes. SoleGripz is used by athletes in the NBA, NCAA, USA Pickleball, and more. The startup did $300,000+ in revenue last year and looks to generate multiples of that number in 2026. Plays pick-up basketball regularly.

  • Stats: 18 points, 7 rebounds.

• Yonas Bayu.

  • Bio: A Harvard Economics graduate, Yonas did internships at Goldman Sachs in both Credit Research and Equity Research before joining Hines full-time as an investment analyst on their opportunistic closed-end real estate fund. He recently joined Columbia Ventures as an associate, where he does both real estate development and investment work. Former club basketball player at Harvard.

  • Stats: 14 points.

Team Mainstreet:

• C.J. Watson.

  • Bio: The exhibition game headliner, C.J. Watson was a former Tennessee basketball standout in the SEC, went undrafted, but ended up establishing himself in the NBA after getting signed to the Golden State Warriors in 2008. With the Warriors, he scored a career-high 40 points against the Sacramento Kings in 2010. He went on to play in the league for ten years, suiting up for the Chicago Bulls, Brooklyn Nets, Indiana Pacers, and Orlando Magic. Since retiring in 2018, he’s been active as an investor, startup advisor, bookwriter, and philanthropist. mainstreet hoop labs 001 was his first time stepping back onto the court since retirement, but no one could tell. Read more about C.J. here.

  • Stats: 33 points on a game-high 50% from 3pt range.

• Ike Okereke.

  • Bio: A Harvard Economics graduate, Ike did internships at Goldman Sachs in investment banking and Oak Hill Advisors as an investment analyst, where he received a full time offer to join the fund. He is currently a co-founder at mainstreet. Ike played club basketball at Harvard before playing in England for Durham University’s BUCS Premier team on a scholarship.

  • Stats: 35 points, 8 rebounds.

• Jakai Tutler.

  • Bio: A Cuesta College (JUCO) basketball player who will be playing in the NCAA next year… Averaged a near double-double at Cuesta.

  • Stats: 19 points and a game-high 11 rebounds.

• Hyeong Shin.

  • Bio: A Pomona College mathematics graduate, worked on $5B+ of transactions at Rothschild & Co. as an investment banking analyst. Worked at Gold Leaf Farming, an agriculture private equity platform, as Director of Acquisitions & Asset Management… Currently on the sell-side of ag M&A, running HS & Co… Plays pick-up basketball regularly.

  • Stats: 8 points, 8 rebounds, game-high 67% FG.

Thanks to our sponsor, Caplight, for their support and dedication to excellence.

Thanks to the University of San Francisco events team for their attention to detail in executing the vision.

Thanks to the guests that attended, including investors, founders, and operators from Wells Fargo, Manhattan Venture Partners, Encord, Forge, Fin Capital, Augment, Incline Partners, IEQ Capital and more.

I knew I was in for a ride the moment Dijon Thompson leaned back in his chair, grinned, and said:

“My first startup experience felt like my first Suns practice.”

That’s when it clicked.

The 2005-2006 Phoenix Suns weren’t just a typical basketball team.

They played like a scrappy garage band crashing Carnegie Hall - breaking rules, ignoring the sheet music, and somehow leaving everyone cheering anyway.

And here I was, sitting across from a member of that legendary team, hearing he’d found that same adrenaline again.

After leaving basketball, he made a bold pivot to the tech world, and quickly found himself immersed in something that felt eerily familiar.

The same energy, pace, and rule-breaking philosophy that made the Suns a religion…

Turns out, he’s back in it - only this time, it’s startups.

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Pace Over Perfection

As I was talking to Dijon, it hit me: the 2005-2006 Phoenix Suns were basically the OG YC batch before YC was cool.

Most NBA teams in the mid-2000s lived and died by structure. The triangle demanded patience. Horns sets required precise spacing. Everything was about controlling pace.

The Suns rewrote the rules. Push the pace. Shoot early. Score in seven seconds or less. (Yes, you read that right.)

It was organized anarchy - the kind of basketball that looked like Mario Kart on hardwood.

Fresh out of college, Dijon was dropped into this system. He’d been drafted by the Knicks, traded to the Suns, and there he was - practicing with Nash, Marion, and Stoudemire in a system that saw D’Antoni turn speed into a weapon.

They won 54 games that year, and Dijon was caught up in that frenetic energy.

“I just had a feeling we were going to win the championship,” he told me.

Then came the gut punch. Not a slump. Not a bad stretch. A full stop.

His knee gave out mid-season. Microfracture surgery. The same procedure that nearly ended Stoudemire’s career. Except Stoudemire had already secured a multi-million dollar contract. Dijon hadn’t.

He was 22 years old. No guaranteed money. No fallback plan. Just a surgically repaired knee and a slim hope he’d ever play professional basketball again.

Highest high. Lowest low. Just months apart.

Fast-forward to 2020. Dijon’s retired after a career that took him across France, Germany, Russia, Ukraine, Vietnam, and Japan.

Then, out of nowhere, Dijon ran into an old friend at cryotherapy. She kept recruiting him to join her startup.

The pitch was wild. Pre-revenue. Small team. Competing against billion-dollar tech giants.

“Don’t worry, you don’t have to know tech. We’ll teach you.”

With zero tech experience and no clue what he was getting into, he said yes.

And boom. Déjà vu.

Sales hyped features that were still three sprints away. Founders tweaked the pitch deck 15 minutes before a meeting. Product shipped with bugs everyone knew about. (Sound familiar, founders?)

At YC, they call this “building the plane while flying it.”

“I realized fast that if you wait for the perfect plan, you’ll always be a step behind,” Dijon told me. “On the Suns, we moved before the play fully formed. In startups, it’s the same.”

Once you’ve played at that speed, everything else feels slow, and slow starts to feel wrong.

Speed isn’t just a style - it’s a strategy. The faster team forces everyone else to react.

This was Phoenix all over again, just in a different arena.

Positionless

In Phoenix, your listed position was basically a formality for the stat sheets.

Marion guarded 1-5. Diaw played center, point forward, and part-time magician. Dijon played the 2, the 3, and even stretch 4 when the system demanded.

You didn’t fit the system. The system stretched around you.

So when Dijon joined his first startup, he already knew the playbook. Partnerships, biz dev, fundraising, product… whatever the team needed, he jumped in.

The Suns taught him to be positionless. Startups don’t just reward that - they demand it. If you need a job description to be useful, you’re already behind.

He laughed when I asked how many hats he’s wearing these days.

“Sometimes I wear more hats than Boris Diaw in a playoff series.” (Trust me, that’s a lot of hats.)

The Suns exploited something most teams overlooked at the time: athletes thrive in ambiguity. New teams. New coaches. New roles. And sometimes even new countries.

“You know, we spend our entire careers moving around and learning to adapt,” he told me. “It’s the same muscle startups need.”

That line stuck with me. Dijon figured this out earlier than most athletes, and turned adaptability into his superpower.

The Nash Effect

There’s one person who made that Suns system click. That person was Steve Nash.

Nash didn’t just bring the ball up the court. He saw angles two steps ahead, turned chaos into choreography, and most importantly, amplified everyone around him.

Every startup needs a floor general. Or, as Dijon puts it:

“Every startup needs a Nash.”

Dijon has learned to spot that same floor-general energy in the founders he works with.

Take Paige at Powered by Point. She saw something in him before he saw it himself and put him in a position to contribute. She also teamed up with her cofounder to level him up. Pitch deck breakdowns, UX debates, post-mortems on growth experiments, even a deep dive into consumer psychology using the GameStop fiasco as the syllabus… Dijon absorbed it all. It was like watching game film.

Now he’s seeing it again at Cache AI. Kobi, the founder, has the rare ability to read the market, pivot on the fly, and keep the team moving in perfect sync. She has a knack for putting people in the right spots - looping Dijon into key conversations, trusting him to run with opportunities, and turning small openings into real partnerships. Under her guidance, he’s gone from learning the ropes to helping land a growing slate of partnerships.

Great founders, like great floor generals, make everyone else better. Dijon learned that lesson from Nash. Now he watches for it in every founder he works with.

Seven Seconds Or Less, Cont.

When I first sat down with Dijon, I thought I was talking to a retired hooper.

By the end, it was clear he hadn’t left seven-seconds-or-less behind. He’d taken that philosophy off the court and into startups.

Move fast. Take risks. Break rules.

The Suns planted the seeds. Startups made them grow.

Dijon didn’t just find a second act. He found the same adrenaline, rhythm, and joyful chaos. Only now, it runs 24/7.

As we wrapped up, he leaned forward with that same grin from the beginning of our conversation:

“Most athletes don’t realize they’re already trained for this. I didn’t either, until Ryan Nece at Next Legacy Partners, told me: the most dangerous thing is an athlete knowing he can compete in another arena.”

He’s right. One pivot is all it takes for an athlete to become a killer startup operator. Once that pivot happens? Watch out, world.

Follow Dijon's journey on LinkedIn and check out how he brings that same Suns-style pace to Cache AI, where he helps athletes and teams make sense of NIL valuations using AI.

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Today’s Watchlist Edition marks the end of Q1 2026.

In celebration, we will discuss a few risers and fallers from the January and February editions, before ending with this month’s selection of leading startups.

Risers.

Starcloud

Starcloud, the space tech company aiming to launch data centers into orbit, is seeking FCC approval to launch up to 88,000 satellites into orbit. The FCC accepted the filing for review on March 13th. For context, Starcloud previously tested an NVIDIA H100 GPU on a satellite in GPU, becoming the first company to train an AI model in space. Starcloud founder and CEO Philip Johnston also sat with key investors from Sequoia Capital, Pat Grady (head of Sequoia alongside Alfred Lin) and Sonya Huang (co-led Sequoia’s OpenAI investment with Grady and Lin), for a 45 minute conversation on why space will become the primary location for AI compute infrastructure within the next decade. The last few months have been generous to Starcloud, and they are quickly rising up the ranks after being named to Watchlist in January.

OpenRouter

An incognito AI model was getting tons of attention on OpenRouter roughly two weeks ago, and there was speculation amongst developers that the model was DeepSeek testing its next big launch. A week later, on March 18th, the model was revealed to be from Xiaomi, a Chinese smartphone company. The model initially surfaced on March 11th under the name “Hunter Alpha” and was described by OpenRouter as a stealth model. Xiaomi’s AI team is run by Luo Fuli, a former DeepSeek researcher. The significance of this event was less about the model and more about the growing influence of OpenRouter in foundational model discovery.

Fallers:

Delve

Perhaps the fastest faller in recent startup history. It started with a viral Substack post with some serious allegations about fraudulent business practices at Delve, the Insight and Y-Combinator backed compliance startup, and things quickly spiraled into a media storm. A former customer alleged that Delve was not actually helping companies clear security certifications - most notably SOC 2 - but rather providing customers with fake evidence, rubber stamping its own reports, and avoiding independent auditing. To add insult to injury, Insight Partners, the $90B venture firm that led Delve’s $32M Series A, deleted an article on their website celebrating their investment into the company.

Fundamental Research Labs

A very mild inconvenience compared to Delve’s more serious troubles; yet, a threat nonetheless. Fundamental Research Lab’s most potent product to date, Shortcut, the AI agent that creates financial spreadsheet models, is poised to hit market headwinds post-Claude. According to co-founder Nico Christie’s LinkedIn, however, Shortcut is growing quickly, 50% month-over-month. Will be something to watch going forward.

March 2026 Watchlist

Novig

• Company Overview: Novig is building a commission free sports prediction market that allows users to trade against one another. It operates as a legal sweepstakes-based platform in over 40 U.S. states with a focus on providing better odds for gamblers. The company most recently raised a $75M Series B led by Pantera which closed at a $500M valuation in February. Prior to that, their $18M Series A was led by Forerunner in August 2025.

• Founders: Jacob Fortinsky - Novig founder and CEO, Harvard graduate and Y-Combinator Summer 2022; Kelechi Ukah - Novig founder and CTO, Harvard graduate and Y-Combinator Summer 2022, Jane Street intern

• Investors: Pantera, Forerunner

• Amount Raised: $105M+

• Headquarters: New York, NY

Savvy Wealth

• Company Overview: Savvy Wealth is building the most advisor-centric platform in wealth management, enhanced by artificial intelligence. The company claims to save up to 19 hours a week for wealth advisors by eliminating manual workflows, leading to 30% more client facing time. In July 2025, Savvy raised a $72M Series B led by Industry Ventures with participation from Thrive Capital, Canvas Ventures, and The House Fund.

• Founders: Ritik Malhotra - founder and CEO of Savvy Wealth, 2x exited founder - Y-Combinator Summer 2012 (Streem, acquired by Box), Y-Combinator Winter 2019 (Elph, acquired by Brex)

• Investors: Industry Ventures, Canvas Ventures

• Amount Raised: $100M+

• Headquarters: New York, NY

Somos Internet

• Company Overview: Somos Internet is building a vertically integrated Internet Service Provider (ISP) in Latin America, starting with Colombia and now launching in Mexico through a partnership with Mercado Libre. The Somos network stack consists of fiber, hardware, and software, and this trifecta unlocks world leading connectivity at a lower cost than other ISPs. The $18M Series A round was led by Union Square Ventures and Ribbit Capital.

• Founders: Forrest Heath - Somos Internet founder and CEO, Y-Combinator Winter 2021 founder, IDEO Co-Lab Design Fellow

• Investors: Union Square Ventures, Ribbit Capital

• Amount Raised: $40M+ (Series A stage)

• Headquarters: Medellin, Colombia

Rainmaker

• Company Overview: Rainmaker is building an end-to-end cloud seeding system to make it rain on demand, with the mission of ending water scarcity. The company’s weather radar and atmospheric sensing system is named Eden, and it contains LiDAR, infrared cameras, and temperature/pressure sensors. Eden is used to target clouds and measure the effectiveness of Rainmaker’s cloud seeding efforts, while Elijah, a weather resistant drone, is used to distribute seeds in the clouds to induce precipitation. The process is monitored by a software system known as Prophet. Rainmaker is licensed and regulated in Utah, Colorado, and parts of California, Texas and the Middle East.

• Founders: Augustus Doricko - Rainmaker founder and CEO, UC Berkeley dropout, former founder of Terra Seco Solutions

• Investors: Lowercarbon Capital, Navil Ravikant

• Amount Raised: $31M+

• Headquarters: El Segundo, California

Natilus

• Company Overview: Natilus is developing next generation aircraft. There is a global shortfall of 15,000+ planes, and Natilus wants to address the supply gap while bringing a new, more efficient design to market. The blended wing body leverages improved aerodynamics, cuts fuel usage by 30%, and has 570 commercial pre-orders worth an aggregate $24B from airlines around the world. Commercial deliveries are expected to begin in the early 2030s. The company raised a $28M Series A in February, led by Draper Associates with participation from Soma Capital, Flexport, and Liquid 2 VC.

• Founders: Aleksey Matyushev - Natilus founder and CEO, former lead aerodynamicist at Piper Aircraft

• Investors: Draper Associates

• Amount Raised: $28M+

• Headquarters: San Diego, California

Caravaggio was a sick man.

The Baroque artist’s name paid generous homage to his Renaissance predecessor: Michelangelo Merisi da Caravaggio.

In the recesses of his heart lived two wolves, one a belligerent murderer and the other an artistic genius.

By artistic genius, I mean the best in the world during his time.

And by belligerent murderer, I mean a man who killed people when he got angry.

Around 1591, Caravaggio committed a murder that forced him to flee Milan and find a new life in Venice, then Rome.

In 1605, Caravaggio injured a notary with his sword during a dispute over a woman.

In 1606, Caravaggio killed Ranuccio Tomassoni during a fight in Rome. Tomassoni was a gangster from a wealthy family, who, like many others that frequented the streets at the time, had his fair share of run-ins with Caravaggio before. This time was different. Tomassoni, a rich man and citizen of Rome, was dead. Previously, Caravaggio could rely on one of his powerful patrons to protect him from the law’s strong arm of justice. His most notable backer was Cardinal Francesco Maria del Monte, a high ranking Bishop with a love of art. But Cardinal Francesco Maria could not save him this time; Tomassoni’s family wanted his blood spilled in retribution. So Caravaggio was sentenced to beheading, and the authorities placed an open bounty, allowing any civilian who saw him to dismember his head from his body and get paid in the process.

Caravaggio fled Rome in a hurry.

He spent the next four years in exile, bouncing between Naples, Malta, and Sicily. During this time, Caravaggio’s remorse began to leak onto his canvas. He painted a number of works revolving around the themes of beheading, Christian mercy, and forgiveness, including The Beheading of Saint John, The Seven Works of Mercy, The Raising of Lazarus, and Salome with the Head of John the Baptist.

Salome with the Head of John the Baptist depicts the Biblical story where Salome, the daughter of Herodias and stepdaughter of King Herod, dances for Herod and his guests, and after pleasing the King and his company, gains his favor. Herod then tells Salome to ask for anything and he will make it so, and Salome, at the instruction of her mother, asks for John the Baptist’s head on a platter. At the time, John the Baptist, Jesus Christ’s older cousin, was the most renowned prophet in Judea, and it hurt even Herod’s hardened heart to order death to a righteous man. In Caravaggio’s masterpiece, he illustrated his own head as a model for John the Baptist; an aesthetic plea for mercy from the law. Then he sent it to authorities in Malta.

On the run for his life, Caravaggio created some of his best work. It was around the same time as the Salome painting that he painted David with the Head of Goliath, an unusual take on the classic scene. Instead of David basking in the glory of God-given victory over Goliath, the young to-be-king of Judah is sorrowfully staring at the giant’s dismembered head with remorse. Onlookers can barely make out the letters H-AS OS on David’s sword; a Latin inscription short for humilitas occidit superbiam, first coined by Saint Augustine around 400 AD. Humility kills pride. Goliath’s head of course, was modeled by Caravaggio’s own. He sent it to a Cardinal in Rome, and upon seeing the masterwork, authorities decided to remove the bounty from Caravaggio’s head. In 1610, he took a boat ride back to Rome to receive his pardon.

He never made it back.

No one really knows how he died. The most likely explanation is that he got sick with a fever or malaria. Rumor had it that the Tomassoni family caught up to him. What is known, however, is that, when it mattered most, Caravaggio painted with a strong mixture of passion and repentance in a fight to regain his life. The artistic genius sought to create a visual pleasure so powerful that it would remedy any pain caused by the belligerent murderer. And it worked briefly. But the murderer had sown too many seeds this time.

He was buried off the coast of Tuscany, in Central Italy, a fitting resting place for the greatest Baroque painter ever.

Tuscany is roughly 400 miles north of southern Italy.

In the 1880s, more than 300,000 Italians immigrated to the United States.

In the 1890s, this number doubled to 600,000.

In the 1900s, more than 2,000,000.

The migrants largely consisted of young Italian men who sought to earn money in America and then return home. They came from the northern and central parts of Italy prior to 1900, but after 1900, southern parts dominated the Italian exodus to America. Sicily, Calabria, and Campania were a few of the regions in the south that Italians left from. New York, Boston, and Philadelphia were the primary cities they planted roots in.

South Philadelphia was an especially Italian area, overwhelmingly filled with immigrants from Calabria and Campania.

This is where Frank Quattrone grew up.

In 1955, Quattrone was born. His mother, Rose, was a sewing machine operator that quit her job at his birth, and his father, Frank, was a presser in a tailor shop who became a union official. Both were of Italian descent; Quattrone’s grandmother was an immigrant from southern Italy in the early 1900s. The Quattrone family lived paycheck to paycheck.

Frank’s elementary school, Stella Maris, was attached to their local Catholic church, which bore the same name. 98% of the parishioners were Italian at the time. From a young age, Frank was known for his intelligence. As a first grader, he read at a fifth grade level, and when he got old enough, Frank was awarded a scholarship to St. Joseph’s Prep, a boy’s high school in north Philadelphia, where he grew in popularity due to a combination of book smarts, aggression, and quick wit.

He would go on to attend Wharton on a full scholarship. At graduation in 1977, Frank was one of three students to join Morgan Stanley full-time. The firm was even more prestigious at the time than it is today. The young swashbuckler from 9th and Shunk made it to the top of Wall Street, scoring $12,500 a year in the process. After his two year analyst stint, Frank went out west for a Stanford MBA. The immersion in Silicon Valley opened his eyes to the potential of new technology. One of his classmates, Steve Ballmer, dropped out to launch a company called Microsoft with an old acquaintance. When the MBA program reached a conclusion, Morgan Stanley told Frank to come back out east to New York. He refused. Instead, Morgan Stanley ought to come out west, because his wife, Denise, was doing a two year program at a San Jose hospital, and there were opportunities in the Bay Area the firm should explore. Morgan Stanley’s recruiters did not actually believe a junior associate would risk his offer over a wife’s job, so Quattrone doubled down, bought a house in the Bay, and started interviewing with local firms, just to show he was serious. Morgan Stanley folded like a lawn chair at a South Philly cookout. In 1981, Quattrone re-joined Morgan Stanley, working from a satellite office in San Francisco alongside Carter McClelland, the more senior banker that persuaded him to attend Stanford. Quattrone’s pay leveled up to $35,000.

For a few years, things moved slow. Quattrone was a technology banker, and the technology industry was nascent. Morgan Stanley did not care about Quattrone’s deals because the IPOs were tiny tech companies going public at $100 million valuations. The $1-2 million fees were pitiful compared to the RJR Nabisco deal where Morgan Stanley earned $25 million. Bankers at firm headquarters in New York thought Frank was deranged.

As life would have it, a little less than a decade later, the technology financing space started to grow into a full-fledged industry. In the early 90s, Frank reached $1,000,000 in annual compensation, and by 1995, this number ballooned to $6,000,000. His pay only captured a small portion of the economics: Morgan Stanley sold $203 million of technology IPOs in 1990, compared to $5.8 billion of technology IPOs in 1995, a nearly 30x increase. Morgan Stanley’s technology group became the fastest growing business line for their investment banking division, and it was effectively operating as a wholly separate company, from the other side of America, subject to the whims of Mr. Frank Quattrone.

But Morgan Stanley was a white-shoe firm with complex politics. Technology was still not a prestigious industry to cover, and Quattrone quickly got the sense that his success was not being appreciated to the fullest extent. The story of a high performer feeling underpaid is as old as time itself, and in 1996, the union had run its course. Quattrone would go on to join Deutsche Bank, where he hoped for the “flexibility and autonomy to make decisions and build the technology dream team.”

The dream team would last less than two full basketball seasons, and in 1998, Quattrone entered the transfer portal one last time.

This time around, Frank insisted on owning his art. The problem with Deutsche Bank was simply a different shade of the same problem with Morgan Stanley. If Morgan Stanley was crimson, Deutsche was scarlet. Quattrone was trying to create chiaroscuro on the canvas, but who can paint with a patron standing over his shoulder? After all, business is an art. At this point you are probably wondering why Quattrone didn’t simply start his own investment bank. If he’s making that much money for his company, and they’re refusing to pay him fair economics, then perhaps launch a boutique advisory firm? Listen. When a man’s in his moment, the prime of his life, he cannot be marginalized. You can burn tens of millions of dollars building an investment banking business in the 1990s and it still would not touch Goldman level scale. The infrastructure needed at the time - a major bank with a full balance sheet and distribution could be the lead underwriter on any IPO, could hire hundreds of people at a time, and had a large research division to help them win IPO deals - made launching a tech-focused boutique nearly impossible. At the very least, Quattrone would be missing out on tens, if not hundreds, of millions in upfront cash by striking out independently. He already made it out of the gutter as a tech banker when tech bankers used to be bottom of the barrel. How could he refrain from cashing out at the next bank? You ain’t got the answers, Sway.

So when Credit Suisse First Boston came calling, Quattrone signed the best deal of his life, and relatively speaking, perhaps the best deal any investment banker has ever signed. He was guaranteed $10 million annually in both 1999 and 2000, more than twice what Michael Jordan made in 1995. His group was guaranteed 40% of its incremental contribution to firm revenue. The group would also get 10% of revenue that CSFB made from trading technology stocks. Quattrone moved the entire Deutsche Bank technology group to CSFB, and he oversaw an entire bank within the bank: research, equity capital markets, M&A, and private client divisions all reported to him. CSFB would also give Quattrone a $25 million venture capital fund, because, well, why not?

He made more than $200 million in bonus payments during 1999-2000, and at his peak, Quattrone personally pocketed $120 million a year. His pay was roughly 6x what Hank Paulson (CEO of Goldman Sachs) earned in 2000. In the context of today’s dollars, Quattrone earned 5x the amount David Solomon (CEO of Goldman Sachs) did in 2025. All without taking the operational risk of running his own shop.

Now, to be clear, he was the most well paid banker for a reason. During the dot-com boom, no other banker could make it rain like he did. The near decade Frank spent building connections in Morgan Stanley’s basement finally proved useful when the number of technology IPOs reached an all time high. He had every major venture capitalist on speed dial. Sequoia, Kleiner Perkins, Benchmark, the trifecta. Frank knew which portfolio companies were ripe for public offerings and courted them accordingly. The founders also loved him. When Frank was at Morgan Stanley, he took Marc Andreessen’s Netscape public. When Frank was at Deutsche, he took Jeff Bezos’s Amazon public. Scott Cook at Intuit, John Chambers at Cisco, John Doerr at KPCB, Frank’s friends formed the ruling class of technology business.

The problem with money can be explained by incentives. A wise man once declared money a “terrible master but excellent servant”. If my contract awards me for performing “x” action, I am incentivized to perform “x” action as much as possible. Now replace “x” with “take company public”. There are only so many companies that are fit to go public each year. Assume 300 companies should go public a year, and 100 of these companies are technology companies. Quattrone’s contract strongly incentivizes him to take all 100 technology companies public, because doing so would result in multi-hundred million dollar payouts. Now, taking a half step back, in the context of the dot-com boom, the frothiest technology investing environment that modern capital markets have ever seen, the number of technology companies going public increased drastically. According to Jay Ritter at the University of Florida, the data is as follows:

• 1995: 205 technology IPOs

  • 44% of all U.S. IPOs

  • 21.4% average first day return

• 1996: 276 technology IPOs

  • 41% of all U.S. IPOs

  • 16.7% average first day return

• 1997: 174 technology IPOs

  • 37% of all U.S. IPOs

  • 21.2% average first day return

• 1998: 113 technology IPOs

  • 40% of all U.S. IPOs

  • 22.1% average first day return

• 1999: 370 technology IPOs

  • 78% of all U.S. IPOs

  • 80.8% average first day return

• 2000: 261 technology IPOs

  • 69% of all U.S. IPOs

  • 59.4% average first day return

When the opportunity set doubled during 1999, assuming Quattrone could maintain or increase market share, his potential payout would increase significantly. The one caveat is that Frank was incentivized to take bad companies public. This was the quiet part that CSFB forgot to say out loud. If Quattrone could take 300 bad technology companies public in one year, he would make billions. During Frank’s best year at Morgan Stanley, his group did 18 tech IPOs. In 1999 at Credit Suisse First Boston, he did 53.

In January 1999, CSFB’s tech group debated whether they should delete an internal guardrail that prevented them from taking companies public before at least $10 million of revenue in the last twelve months. The debate started because a company called TheGlobe.com had an IPO that shot up 606% to $1 billion in market cap, on just $1.2 million of revenue. CSFB ultimately decided to toss previous underwriting standards out the window. They took CareerBuilder Inc. public in May 1999, with previous twelve months’ revenue of $8.8 million.

Other more prestigious banks were turning down the very tech companies Quattrone was taking public. Credit Suisse First Boston worked on Audible’s IPO, a deal Goldman didn’t even pitch for. CSFB also did Gazooks Networks in mid-1999, and Goldman was notably absent from that bakeoff. Goldman’s conservatism is an important signal. The firm’s strict underwriting meant less short term revenue during a mania but more power in the long run. By doing every deal, Credit Suisse First Boston was building the Wall Street equivalent of McDonald’s. Everywhere at once, short term pleasure, and everyone knows they probably shouldn’t. Goldman was more worried about making sure their Michelin star wouldn’t be taken from them in retrospect. Not to say there wasn’t suspect activity from Goldman Sachs. It just never got near CSFB level. Certain things cannot be measured by traditional metrics. You can analyze the vertical jump, three point percentage, and box-plus-minus of two players and see similar profiles. But one of those players just has “it”. “It” might not be legible to everyone. But peers and insiders always know. Goldman cared about reputational capital just as much as dealmaking volume or revenue per employee. Our name should mean something, it should be a permanent co-sign. So when it came to IPOs, Goldman cared about the Ciscos, the Intels, the Microsofts. Only blue chip names could get the baby blue stamp. Goldman saw itself as the moral authority on Wall Street. They called it “reputational capital” internally. I call it good credit.

At the end of 2000, the party was over.

As the dot-com bubble burst, federal investigators came out of hiding and began to issue subpoenas to various parties. CSFB was at the top of their list.

The charges had to do with fraudulent activity during the IPO allocation process. Rather than offer IPO shares to buyers in a fair process, CSFB was known for giving special favor to clients who had the potential to bring in new IPO business. For example, during a hot IPO, Frank would work with the client services division to make sure they gave significant allocation to technology executives running companies that could go public soon. In turn, the technology executives would choose CSFB to take them public. Remember that during 1999, the average first day return for technology IPOs was 80%+. Investors were fighting tooth and nail for extra shares. Frank’s shrewd behavior of redirecting deals to potential clients was a direct violation of securities law. They called it “spinning”.

Although most investment banks at the time participated in spinning to some degree, CSFB’s technology group was notorious for this behavior. The reason being, Frank’s sweet deal that gave him absolute control over research, private clients, and IPOs also allowed him the autonomy to spin more than Pat Sajak on Wheel of Fortune. Other rainmakers on Wall Street had compliance controls to prevent inordinate abuse. Quattrone’s unchecked power turned into his largest liability. Once prosecutors found enough evidence, they pounced on him, with the intention of making an example out of South Philly’s finest. They treated Quattrone like Barry Bonds after the steroid scandal, and acted like he wasn’t an all-time great. Yes, both were undoubtedly wrong, but in their respective contexts, they were still better than their opponents. No other banker could compete with prime Quattrone.

CSFB settled with the SEC and NASD in 2002 for a fine of $100 million, slightly less than Quattrone’s paycheck in 2000. Speaking of Quattrone, after paying the fine, CSFB threw their primary bucketgetter to the wolves, suspending him from the firm and forcing him to fend for himself as the three letter agencies sought his demise. He fought for his life for 6 years, and after a hung jury, a conviction, a federal prison sentencing, and an appeal, the charges were dropped, and Quattrone returned home to his family a free man, avoiding Caravaggio’s fate. In 2007, he founded Qatalyst Partners, a boutique technology investment bank, the one he should have started in the prime of his career. Sway was right.

Frank Quattrone was named “Financial Dealmaker of the Year” by SF Business Journal in 2012, advising key clients like LinkedIn, eBay, Google, and NetSuite.

Today, Qatalyst consistently ranks as a top boutique investment bank, alongside firms like Centerview, Evercore, and PJT.

Meanwhile, Credit Suisse First Boston dropped the First Boston in 2006, and rebranded back to Credit Suisse.

Then Credit Suisse proceeded to collapse in 2023.

Credit Suisse’s death was the culmination of decades of bad culture. The post-mortem will reference Greensill and Archegos, money laundering and balance sheet mismanagement. But when it comes down to it, Credit Suisse was a bank with weak morals, and post-Quattrone, they had no star player to make up for their lack of structure.

The Swiss government helped facilitate UBS’s $3 billion acquisition of Credit Suisse on March 19, 2023.

Quattrone outlived the machine.

What if basketball ended tomorrow?

I would stay up super late at night thinking about this. I’m talking 2, 3, 4 in the morning. You know that time of night when it feels like the whole world has gone quiet and you’re the only one still up? I like those hours. Because it’s so quiet I can actually think. Or maybe I’m just so tired by that point I can’t overthink. And honestly, that might be better.

I like to write. I would write about the options, the fears, the worries, the hopes and dreams, the past, present, future. It would be me, my pen, and some paper trying to figure out what the hell Miller Kopp is gonna do next. Then whenever my low back had enough of that chair, I would take a shower in the pitch black, brush my teeth, say a prayer, and go to bed, hoping the answer would come to me in my dreams so I could wake up and attack it in the morning.

I’ve been thinking about this question a lot lately. Not because I’m planning to retire anytime soon. I’m not. But because I think there’s something wrong with waiting. Waiting until basketball is over to start figuring out what comes after.

I used to say I don’t regret anything. That was my line. But I think that’s a cope.

I wish I hadn’t worried so much about what people think. Social media is woven so deep into the sports world that I made decisions on what to say, what to post, what to build, what to pursue based on what some nameless gray face on the internet might think of me. It pisses me off just thinking about it. We’re on this floating rock for 80 years if we’re lucky and I’m out here making decisions because some anonymous account might have an opinion?

I wish I would’ve leaned into what I wanted. I did in some areas, but I did so with one hand tied behind my back. Making that shift earlier in my career would’ve allowed me to be further ahead in whatever I build when basketball is over.

I have nobody to blame but myself.

And honestly? It fires me up.

The next chapter’s gonna get played with both hands.

So what would that actually look like?

I’d write more. Build up my Substack. I’ve always had thoughts I wanted to put somewhere - things I think about at 4am that I never said out loud because I was too busy being a basketball player.

I’d make an electrolyte product. Something I’ve used every single day for the last five years. I even got my girlfriend taking it now. Clean ingredients, high quality, dosed right. I like to nerd out on health stuff. Sleep, recovery, hydration, the details most people ignore. If I’m going to build something, I’m going to build something I believe in and would use myself.

I’d also make some calls. Not for a job. For information. I want to understand different industries and see where my skills and passion could help me build something that would disrupt some shit. My first move would probably be to contact Pat McAfee’s assistant and ask to shadow him for 30 days. Then I’d hunt down Todd Graves and do the same thing. It sounds crazy but what better way to learn than to watch. Just sit there and observe. I want to be around people who built something real, on their own terms. People who did it their way and didn’t ask permission.

I’d probably get some calls about coaching, which I’d take and talk through. I love basketball. The leadership, the interpersonal dynamics, the chess of it all. But I’m a builder, and I’m not sure if coaching is the right path for me.

There’s a Mike Tomlin line tattooed somewhere in my soul - “it’s a reasonable expectation to be continually on the rise.” I’ve failed a lot and had some successes, but I’ve always been the kid who wasn’t afraid to look like the “try hard”. The dude who made others uncomfortable with his work ethic. When I set my goals, I never negotiated with myself. One decision took care of every other one after it. Because it’s not easy. Growth is not linear. But over time, I improved… which I know now is just a “reasonable expectation”.

So I think I’d be ready. Because I’ve spent my career building toward something, even when I didn’t always know exactly what.

One of the biggest lessons the game of basketball has taught me is that there’s beauty in pursuit.

Whether I knew it or not, my younger brothers were always watching. My work ethic, my mistakes, my bad decisions, how I treated people, how I carried myself - all of it. The footsteps along the journey can leave behind a roadmap for the people behind you, if they’re hungry enough to follow it.

My days are my life in miniature. Every step I take, every decision I make, leads to the life I create. And more importantly, the life I leave behind.

As cliche as it is to say, I look back and don’t see a string of successes and failures. I see a ton of different experiences. Some days pure bliss. Some just absolute chaos.

Honestly, nobody will remember what Miller Kopp did 100 years from now. The only people I care about remembering me are my younger brothers, future kids, grandkids, great grandkids... I’d want them to feel an urge to live large, to dream big, to read a book then write their own, to ask a question and listen, to be afraid and do it anyways.

Life is greatest when you’re the Man In The Arena. When you’re the kid climbing the tree, running the race, jumping the fence and scarring your face.

There’s a story about Mozart I love.

A 21-year-old kid walks up to Mozart and asks, “How do I write a symphony?” Mozart says, “You’re too young.” The kid goes, “You were writing symphonies younger than I am now.” And Mozart says, “Yeah, but I wasn’t going around asking people how to do it.”

I think that’s pretty funny. And pretty powerful.

It’s all self discovery. That’s how it’s supposed to be.

I’m a poet, philosopher, entrepreneur, coach, teacher, speaker, writer, and psycho trapped in a professional basketball player body. Makes sense why I get confused sometimes. But I’ll take it.

What if basketball ended tomorrow?

I don’t know for sure…. and that’s okay.

What I do know is I’m a builder and builders build.

Touch the fire. Get burned. Build something.

That’s not just the plan. That’s always been the plan. I just needed to say it out loud.

MK

Miller Kopp is a professional basketball player currently playing in the NBA G League. To keep up with Miller, follow him on LinkedIn, Instagram, or TikTok.

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I recently sat down with Jeremy Ebobisse to talk about how he invests in private markets.

A decade ago, that sentence alone would have surprised me. Back then, “athlete investor” wasn’t a recognized category. Athletes earned money. Investors decided what to do with it. The roles were mostly separate. But that separation has quietly eroded. Access has broadened, information is less scarce, and private markets no longer require the same set of gatekeepers they once did.

What struck me about Jeremy wasn’t that he invests, or even what he invests in. It was the how.

When I speak with athletes about money, many of them describe investing as something they engage with opportunistically. Over time, this tends to produce portfolios that resemble drawers of souvenirs: interesting to look through, but without much underlying thesis.

Jeremy approaches investing differently. He treats his portfolio as an intellectual gym - something he shows up to deliberately. He doesn’t wait for opportunities to find him. He actively seeks them out. Different investments train different muscles, and early on, the goal isn’t to maximize immediate returns or secure his retirement. It’s to build the capacity to make better investment decisions over time.

What became clear in our conversation was that the real risk isn’t making a few bad investments. It’s reaching the end of his playing career without having built the judgment to deploy his wealth effectively.

Portfolio Construction: Treating Diversification as Education

Much of the conventional financial advice given to athletes emphasizes wealth preservation. So the prescription is almost always the same: diversify broadly, stick to safe assets, and preserve capital.

So by conventional standards, Jeremy’s portfolio would raise some eyebrows.

Roughly 70% sits in public equities and savings. The remaining 30% is in private investments, which includes venture capital, private equity, and real estate. That’s nearly double the illiquid exposure financial advisors typically recommend.

“It’s more aggressive than what most advisors would recommend,” he said. “But I’m young, and I can afford to learn.”

Most investors use diversification to minimize volatility. Jeremy uses it to broaden exposure. Instead of asking, How do I protect my capital? he’s asking, What do I want to understand next?

Each asset class teaches him something different about how capital behaves. Each investment exposes trade-offs, constraints, and second-order effects that only become visible from having skin in the game.

“This is the phase of my life where learning has the highest return,” he told me. “I’d rather over-index on that now and de-risk later than do the opposite.”

What most people miss, and what Jeremy intuitively understood, is that portfolios can be optimized for learning, not just returns, especially since he doesn’t need the money right away. When approached this way, the logic of diversification changes entirely.

Jeremy isn’t just diversifying across asset classes. He’s diversifying across learning opportunities. And in this phase of his career, that might be the most valuable form of diversification.

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VC Funds: Learning From the Pros

Getting traded from Portland to San Jose dropped Jeremy into the Bay Area’s tech ecosystem. And watching NBA players like Andre Iguodala and Kevin Durant invest in startups sparked his interest.

Like most athletes, he started with what he knew.

The problem is that athletes are magnets for celebrity-adjacent deals like sportstech and consumer brands. Categories like enterprise software, AI infrastructure, and hardware rarely show up in Jeremy’s DMs.

That changed when he connected with Next Legacy Partners. Instead of pitching him deals, they took him under their wing. Through their events and introductions, he got access to the broader tech ecosystem.

Investing as an LP in VC funds was the logical next step. It gave him exposure to a much broader slice of the market, to startups he'd never have seen otherwise.

His first commitment was to 640 Oxford. He liked their thesis: applying technology to antiquated industries to re-industrialize America. So he invested.

The fund has shown strong early returns on paper. But Jeremy got lucky. At the time, he couldn’t articulate what edge the fund had or how to distinguish truly great fund managers from merely good ones.

“I didn’t have a framework yet,” he told me. “I just knew I really liked the team. They also had a strong thesis, which felt contrarian at the time.”

As he evaluated more funds, he started noticing patterns.

The strongest funds had strategies where the math actually worked - the fund size, stage focus, and check size all aligned perfectly with the opportunities they were chasing. The ones he avoided were the funds whose strategy boils down to raising a big fund and chasing the hottest deals.

He looked for fund managers with a distinct edge. Venture returns follow power laws: most of the upside comes from a small fraction of startups. If a fund couldn’t show how it could access the best deals consistently, it’s optimizing for average outcomes in a game designed for outliers.

He also learned to distinguish between people motivated by craft and people motivated by status. In a world full of people chasing the VC investor label, being able to spot who’s actually in it for the long haul matters.

The lessons filtered out bad funds. But the bigger payoff came from what the good ones taught him.

Over time, Jeremy began to view LP investing as asymmetric education. For the cost of a single check, he gained direct access to decision-making frameworks that would have taken years to build on his own - how professionals source deals, build conviction, and know when to pass.

The fund managers he backs aren’t just deploying his capital. They’re also compressing his learning curve.

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Early-Stage Startups: Betting on Lived Experience

LP investing lets Jeremy study the professionals. Direct startup investments are where he tests his own judgment.

South Park Commons helped sharpen that judgment. He spent much of 2024 surrounded by deeply technical founders building companies from zero to one. The community taught him to separate conviction from hype and to think bigger about what’s possible.

He focuses on asymmetric bets rooted in his own lived experience. I call these “Jeremy deals” - investments where the product solves a problem he understands viscerally.

Take Ozlo. As an athlete, sleep isn’t just comfort. It’s a performance requirement. Traveling to busy cities like New York or LA for away games means dealing with noise and inconsistent rest. When Jeremy saw Ozlo’s sleep buds, he wasn’t reacting to a market trend. He was reacting to a problem he’d lived.

The same logic applied to The Realest, a memorabilia authentication platform. Jeremy remembered scoring his first MLS goal and wanting that moment authenticated and preserved. He saw an under-served market that many investors miss simply because they haven’t experienced the problem themselves.

But resonance alone doesn’t justify a check. It gets his attention, not his capital. Before investing, he runs every startup through a framework he’s refined over dozens of deals.

Is the market big enough? Personal problems can make for great products but terrible businesses. Ozlo wasn’t just building for athletes; it was targeting the multi-billion-dollar sleep wellness market. The Realest wasn’t just about memorabilia. It was a bet on bringing trust and liquidity to a fragmented sports collectibles market.

Are the founders mission-driven? Jeremy avoids founders who are “chasing the heat.” The best founders aren’t building companies because it’s fashionable. They’re building because they’ve lived in a problem long enough to see what others miss and can’t imagine not solving it.

Do the founders have grit? For Jeremy, hustle is the baseline. Grit is the differentiator. He looks for founders who are relentless - the kind of people willing to risk rejection repeatedly to move things forward. “Not taking no for an answer has never hurt anybody,” he said. “I was like that growing up. So I look for that when I evaluate founders.”

What stood out to me wasn’t just that lived experience helped him spot opportunities. It was how much it mattered after the framework had done its work.

Because Jeremy has lived the problem, external signals matter less to him. Most investors, deprived of personal experience, fall back on pattern-matching, relying on proxies like founder pedigree, VC backing, and market buzz instead of personal conviction.

Jeremy’s edge isn’t superior knowledge of sleep tech or memorabilia. It’s his ability to act on what he knows and play his own game without outsourcing judgment.

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Sports Ownership: Finding Mispriced Potential

Most investors I know treat sports ownership as a symbol of status. Jeremy sees it as preparation.

He talks about owning a sports team in Cameroon, where his father came from, as something far off, but present enough to shape how he thinks today. There, sports is a cultural force - it can make or break a nation’s spirit. The talent is world-class. But too often, teams are built to optimize short term profit rather than next decade’s infrastructure. Jeremy sees an opportunity to build differently, to create a hub of employment and invest in communities. That goal is years away. But the groundwork starts now.

His involvement with Portland Thorns FC grew organically from his five years playing in the city. He didn’t just see a team. He saw a cultural movement that was still under-priced, and a chance to support the women’s game in the community that helped launch his career.

He believed women’s soccer was at an inflection point, where institutional capital and media rights were finally catching up to demand. He’s betting that over the next decade, the gap closes and the asset outperforms.

A similar logic led him to TMRW Sports - a bet on how golf is evolving through innovative formats and technology to reach a broader audience. “I was bullish on the league as a whole,” he said. “Golf, like many other sports, needs to evolve to eventually capture the younger generation.”

What these investments taught Jeremy wasn’t just patience. It was pattern recognition.

Listening to him talk, I realized that most people think long-term investing means being willing to wait. In practice, it also requires something more specific: recognizing when current pricing reflects old infrastructure, not future demand.

As Jeremy saw it, women’s soccer has world-class talent. It just doesn’t have world-class media deals yet. Golf has massive participation but aging viewership demographics. The gap between where these sports are and where they’re going is the opportunity. The capital required to close that gap is inevitable. Patience is just what you need while the world catches up.

At some point, his mentality shifted from Is this a good asset? to Does current pricing reflect today’s reality or yesterday’s conditions?

That’s the muscle sports ownership is training. It’s preparation for the Cameroon project, where the gap between talent, demand, and infrastructure is even wider.

He’s investing alongside experienced team owners now - absorbing the governance structures, operational discipline, and community engagement models that make sports leagues and franchises sustainable.

What he’s building here isn’t just a portfolio position. It’s the experience and network he’ll need to turn his vision into reality back home.

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Real Estate: Paying for Passivity

If sports ownership taught Jeremy to spot mispriced opportunities, real estate taught him to price his own time.

He owns properties in Columbus, Ohio, and in Williams and Gilbert, Arizona. Each began with the same two questions: Will demand persist? and Can the property adapt if market conditions change?

Columbus was a bet on stability. Ohio State anchors the city permanently, and a growing tech scene is turning it into a Midwest hub. A long-term rental offered predictable cash flow.

Williams was a bet on scarcity. Millions of people visit the Grand Canyon every year, but accommodations for larger groups are limited. A short-term rental captured that gap.

Gilbert was a bet on growth. The city ranks among the top snowbird destinations in the country, and the Phoenix metro sees a surge of winter visitors every year looking for mild weather and the quiet of suburban life. That seasonal influx made a short-term rental look compelling on paper.

“After doing both, I realized that short-term rentals generally have higher financial upside,” Jeremy told me. “But they’re not as passive as you think.”

Gilbert proved that. Frequent turnover, maintenance, coordination - it all added up. What looked passive began to resemble a small hospitality business. So he converted it to a long-term rental. Returns dropped, but so did the mental load. That tradeoff turned out to be worth it.

That experience changed how he thinks about rental properties. Short-term rentals still make sense for Williams given the scarcity and demand dynamics. But he’s no longer defaulting to them just because the potential returns look better on a proforma.

Real estate forced him to price his time. And in some cases, passivity is a feature worth paying for.

Building Judgment: Playing The Long Game

Jeremy’s portfolio doesn’t look like what most advisors would recommend. It’s aggressive, illiquid, and concentrated in areas where he’s still learning.

But that’s by design.

“I’m not trying to preserve capital right now,” he told me. “I’m trying to build the judgment I’ll need to achieve my goals in the next 15-20 years.”

Most athletes spend their playing careers accumulating wealth and their post-playing careers figuring out what to do with it. Jeremy is collapsing that timeline.

By the time he hangs up his cleats, his edge won’t be capital. It’ll be judgment.

That’s what stayed with me after we finished talking. Not whether his portfolio works. But how many people, athletes or not, are spending their best years optimizing for the wrong thing.

To keep up with Jeremy, follow him on LinkedIn, Twitter, or Instagram.

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