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.

Legacy is a mainstreet media series featuring private conversations with athletes building wealth, influence, and impact beyond sports.

Subscribe to join 4,500+ athlete-investors, founders, and operators shaping what comes next.

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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.

Edited by Allen Lee

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.

Horizon is a mainstreet media series told in the athletes’ own words - ideas, perspectives, and personal stories from those preparing for what comes next before the final buzzer sounds.

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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.

Legacy is a mainstreet media series featuring private conversations with athletes building wealth, influence, and impact beyond sports.

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Acquihire.

In June 2025, Meta spent $15 billion to acquire a 49% stake in Scale AI, also hiring Scale CEO Alexandr Wang in the process.

In July 2025, Google paid $2.4 billion to hire the Windsurf leadership team and license their technology.

In December 2025, NVIDIA gave Groq $20 billion to acquire key assets, technology and talent from the inference chip developer.

Not to mention the Google-Wiz deal ($32 billion), the Microsoft-Inflection AI deal ($650 million) and select others.

The rationale behind these deals is that an “acquihire” consolidates extremely valuable talent pieces while avoiding the antitrust scrutiny that comes with blockbuster acquisitions. Since Google/Meta/NVIDIA aren’t technically acquiring the company outright, federal regulators aren’t able to pounce and stall said transactions, which is important, because the largest technology platforms need top AI talent right now. It’s like the Lakers and the Celtics are playing in the Finals and through a loophole, the Lakers are able to acquire Kevin Durant for the rest of the series. If this trend continues, the feds will likely evolve. But until then

We are beginning to examine these acqui-hires to make sure they are not an attempt to get around the agency’s merger review process.

Kevin Ferguson, FTC Chairman

Benchmark, a storied Silicon Valley venture firm, just added the acquihire move to its bag.

Last week, the firm announced that it was hiring Jack Altman, Sam Altman’s brother, and Alt Capital founder.

In a LinkedIn post, Jack made it clear that he was bringing his team from Alt Capital, which raised a $274 million fund just five months ago, with him.

• Bala Chanrasekaran, a UIUC computer science graduate who worked at South Park Commons then Alt Capital, will be joining Benchmark.

• Vivek Katara, a Yale computer science graduate and former software engineer at Rippling, will be making the transition from Alt Capital to Benchmark.

• Nate Collins, a Furman BA who was previously Chief of Staff at First Round Capital, will be transitioning from Head of Operations at Alt Capital to an unspecified role at Benchmark.

Although the post made it seem as if the entire Alt Capital team is being absorbed into Benchmark, this is not the case.

Elaine Dai, a Harvard graduate and Alt Capital partner who previously worked at Norwest Venture Partners for five years, was not mentioned as one of the members moving over to Benchmark.

There is also some opacity around what will happen to the recently raised fund. According to anonymous sources on other media outlets, uncollected capital will not be called, and Alt Capital will not make any new investments.

In addition to investing in startups, a lot of the value from Alt Capital can be traced back to Jack’s podcast, Uncapped. The podcast has spanned over forty episodes after launching in 2025 and featured venture moguls like Marc Andreessen, Keith Rabois, Garry Tan, Sam Altman, Elad Gil, and more. It is quietly becoming an industry staple, alongside known incumbent 20VC. And the Uncapped pod is now a shiny asset on Benchmark’s balance sheet.

To understand the significance of this hire, it is critical to understand who Benchmark is.

Benchmark is an old dog.

Founded in 1995, they are one of the only firms that can say they have invested across every era: eBay, Uber, and Snapchat are all trophy names in their portfolio.

Benchmark still keeps a small partnership, with no more than six general partners at any given time.

Benchmark still prides itself on being the best Series A investor, not B or C or D or E.

Benchmark still keeps a low profile, with minimal online presence.

And for a firm of its caliber, Benchmark has not been the busiest bee in this new AI age.

In terms of status, Benchmark lags behind the new cats, Thrive, a16z, Founders Fund, et al.

So Benchmark bringing on a media first, AI focused personality in Jack Altman, along with most of his team, is quite a signal to say the least.

Alt Capital closed on a $150 million Fund I in early 2024 before the $274 million Fund II in September 2025. The platform invested in more than 52 companies during its relatively short life. Standout companies include:

• Legora:

  • a collaborative AI platform for lawyers

  • $150 million Series C at $1.8 billion valuation

• Rogo:

  • an AI platform for investment bankers

  • $75 million Series C led by Sequoia

• David AI:

  • proprietary audio datasets to power AI lab models

  • $50 million Series B led by Meritech

• depthfirst:

  • AI native cybersecurity platform for enterprise

  • $40 million Series A led by Accel

Benchmark isn’t just buying an AI centric investor, Sam Altman’s brother, a hot podcast, or fresh blood… It’s buying the same product luxury handbag companies sell.

Relevance

Here’s how you rob a professional athlete:

Keep salaries secret. Hide market rates. Make sure they can’t compare notes. Tell them “this is standard” when it isn’t. Collect your 5-10% cut. Repeat.

It’s worked for decades.

The global sports industry generates hundreds of billions in revenue every year. Most athletes see a fraction of that, if they’re lucky.

Jori Davis and Julie Wojta spent a combined 29 years playing professional basketball internationally. They were good. Really good. But they were getting screwed.

When they finally figured out how the machine worked, they didn’t write a Twitter thread to complain about it. They built a weapon to dismantle it.

It’s already spreading across international sports. 300 athletes in 14 countries are uploading contracts, comparing salaries, and arming each other with data.

And the gatekeepers who’ve been profiting off athlete ignorance? They’re about to get exposed.

The Betrayal: Broken Representation

Here’s a dirty secret in professional sports: sometimes your biggest opponent isn’t on the court. It’s the person sitting next to you at the negotiating table, wearing a suit, calling themselves your agent.

Jori still remembers the Facebook message that changed everything.

First season in Israel. She’d finished 10th in league scoring against WNBA-level talent. She was expecting an invite back to training camp.

Instead, she got ghosted.

She was home, unsigned, training alone, working a 9-to-5 at Paychex to pay rent.

Then a coach messaged her: “Why aren’t you playing? I thought you’d already signed with another team.”

She hadn’t signed anywhere.

Turns out, when Jori tried to leave her agent, the agent’s partner in Israel started telling teams she was “too expensive” and “already committed elsewhere.”

Her opportunities didn’t dry up by accident. They were sabotaged.

And just like that, Jori found herself at the peak of her career, frozen in limbo, waiting for a phone call that never came.

When she finally got back on the court, she discovered something equally brutal. Her performance kept rising, but her pay stayed flat.

League after league. Year after year. Top scorer in Switzerland twice. Top scorer in Italy’s Serie A.

Her stats screamed elite. Her contracts told a different story.

The person who was supposed to fight for her? They were the ones holding her back.

The Pattern: Negotiating Blind

Julie’s breaking point came at an athlete offsite in 2019.

She had a killer resume - years playing in top leagues across Italy, Spain, France, and Belgium. From the surface, it looked like she had it all figured out.

She didn’t.

For years, Julie did what she was taught: work hard, play well, trust your agents to get you what you’re worth.

Every negotiation came with the same soundtrack: “Trust me, this is standard. You’re getting the higher end for someone with your experience. I got you the best deal they could offer.”

She nodded. Signed. Assumed that was enough.

Then Jori told her story. And suddenly, Julie saw her own career in a new light.

She hadn’t been actively blocked like Jori. But being kept in the dark? That was exploitation too. Silent, invisible, perfectly legal, and wildly profitable for everyone else.

Around the room, other athletes started sharing. Different leagues. Different teams. Same stories.

Julie realized the pattern wasn’t isolated. It was systematic.

Some agents played favourites, quietly burying offers from teams to steer clients toward deals that maximized commission. Others crafted multi-year contracts designed to trap desperate athletes from overseas, locking them into below-market deals with brutal buyout clauses.

And then there were the teams that couldn’t be trusted. Moldy apartments labeled “housing.” Promised cars that showed up three months late. Sometimes, amenities only ever existed on paper.

Most athletes had no idea they were being screwed until it was too late.

One FIBA player later told them, “When it came time to fight for my money, my agent hadn’t tracked the missed payments, hadn’t documented the breaches, and and hadn’t been submitting the paperwork for a proper legal process. I was on my own.”

And that player’s agent? Still taking a cut of everything he earned.

Enough was enough. Julie decided she was done negotiating blind.

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The Revelation: Information is Power

As Jori and Julie compared notes with more athletes across Europe, Asia, and Africa, the answer became obvious.

Everyone in the industry had leverage except for the athletes.

That’s it. The entire machine in one sentence.

This wasn’t the NBA or NFL, where players’ unions, collective bargaining agreements, and public salary caps created baseline transparency. This was international sports. The wild west.

Thousands of athletes playing across hundreds of leagues in dozens of countries, with zero salary disclosure, inconsistent regulation, and agents who operated however they wanted.

The problem wasn’t talent. It wasn’t skill. It certainly wasn’t performance.

It was information.

The difference between a sky-high opportunity and a below-market deal came down to one thing - who knew what.

Some athletes knew exactly what to negotiate for. Most didn’t. And if they didn’t? They left money on the table. Enough to change where they lived. How long they played. Whether they could afford to retire.

Jori and Julie weren’t outliers. They were the norm.

The industry didn’t just exploit athletes. It trained them to protect the very system exploiting them. Fear of being labeled “difficult.” Fear of losing their roster spot. Fear of speaking up.

The machine ran on silence.

But there was a blueprint for dismantling it.

Rich Barton had done it three times already.

Expedia - killed the travel agent stranglehold. Now worth $20+ billion.

Zillow - demolished real estate’s information monopoly. $10 billion company.

Glassdoor - made salary transparency mainstream. Sold for $1.2 billion.

Same playbook every time. Find an industry where gatekeepers hoard information. Give the people the data. Watch the gatekeepers panic.

Different industries. Same move.

If it worked there, why not sports?

The Rebellion: Dismantling the Machine

After years of watching the machine chew up athletes, Jori and Julie faced a choice: keep turning the crank… or tear it wide open.

They chose the latter.

That’s how WEVOLV was born. The Glassdoor for athletes.

Athletes upload contracts. Compare salaries. Review agents and teams. Rate housing, payment reliability, contract terms.

For the first time, athletes could negotiate from a place of power instead of blind faith.

“With WEVOLV, data stops being a mystery and starts being leverage,” Jori says.

No more sitting in meetings while someone slides a contract across the table and says, “It’s standard, don’t worry.”

No more squinting at legal jargon, wondering if that “performance bonus” comes with strings attached.

No more chasing down your own money while someone else collects a commission.

The app launched quietly. No big PR push. Just word of mouth between athletes who were tired of getting robbed.

300 athletes signed up across 14 countries.

The agents who’d been coasting on information asymmetry? They started getting defensive.

But WEVOLV isn’t trying to kill all agents. Just the bad ones.

Too many agents in international sports fall into one of two categories: incompetent or corrupt.

The incompetent ones forward contracts via email and call it “representation.”

The corrupt ones act like gatekeepers - hoarding information, keeping athletes dependent, and skimming 5-10% off the top while adding little value.

Those agents are about to become obsolete.

The good ones? They’re not worried.

They aren’t scared of informed athletes. They’re scared of competing with scammers who give the whole profession a bad name.

A good agent knows which teams actually pay on time and which string you along for months. They’ve got direct lines to coaches and GMs. They negotiate performance bonuses that actually trigger and buyout clauses that don’t trap you. They understand visa complications, tax treaties, and contract law that changes depending on which league you’re in. They map your career like a chess game - knowing when to sacrifice money for playing time, when to chase the bag, when to position for a WNBA look.

WEVOLV doesn’t threaten those agents. It empowers them.

“I’ve had incredible agents who fought for me and earned every penny of their commission,” Jori says. “The problem is, I’ve also had agents who did none of that, and I had no way to tell the difference until it was too late.”

Julie puts it bluntly. “A great agent with an informed athlete is a superpower. You skip the ‘trust me’ tap dance and get straight to opening doors.”

An informed athlete knows what they’re worth. And when they sit down with a good agent? They’re not wasting time on basic questions. They’re strategizing. They’re building. They’re maximizing.

WEVOLV isn’t eliminating the agent model. It’s eliminating the agents who never deserved to be agents in the first place.

The Future: Athletes In Control

Here’s what happens next:

300 athletes today. 3,000 next year. Eventually, every professional athlete on the planet will know exactly what they’re worth, which agents deserve their trust, and which teams are worth their talent.

Every bad agent is one viral screenshot away from obsolescence.

Every exploitative team is one review away from being exposed.

Every shady contract is one upload away from becoming evidence.

An athlete thinking about playing in the UK versus China? They’ll get the real story from players who’ve been there. Choosing between two team offers? The community will tell them which coaches actually develop talent and which just talk. Wondering if an agent is trustworthy? The community has receipts.

It’s athlete intelligence - built by players, for players. And it exists because no one else in the system has any incentive to create it.

“Athletes need to take control of their own careers,” Julie says.

She’s right.

For decades, the sports industrial complex has extracted billions from the people actually doing the work - the athletes scoring the points, filling the arenas, generating the revenue.

They got away with it because information was locked up. Because agents and teams controlled the data. Because athletes negotiated alone, in the dark, hoping the people across the table weren’t exploiting them.

That era is ending.

Jori Davis spent 15 years getting underpaid. Julie Wojta spent 14 years negotiating blind.

Now, one by one, they’re arming athletes with the truth.

“Once athletes have access to the whole game,” Jori says, “they’ll never go back.”

And the people who’ve been profiting off the lies?

Their clock just ran out.

To follow Jori and Julie's journey, connect with Jori on LinkedIn or Instagram, and Julie on LinkedIn or Instagram. To learn more about WEVOLV, visit their website.

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Considering the enormous power he is believed to wield, it’s remarkable how few people have heard about Josh Wolfe. In technology investment circles, Wolfe, the managing partner and co-founder of Lux Capital, is one of the most important men alive. But mention his name to the everyday American and they will wonder whether or not you’re talking about his more famous namesake, Josh Wolf the comedian. Among the power players that pump capital through the market’s myocardium, Josh Wolfe’s name is met with unbridled admiration and respect. In May 2025, as the government slashed funding for science, Lux Capital committed $100 million to support promising early stage research with commercial potential. Over the course of twenty years, Lux has expanded from New York City to Silicon Valley, amassed more than $7 billion assets under management, written checks ranging from $100,000 to $100 million, and made boatloads of money for the college endowments, scientific research foundations, and medical systems that actively invest into the firm’s vehicles.

Lux’s reach in private capital is not its only source of sway. $7 billion is impressive, but perhaps equally as impressive are their government ties. James Woolsey was the CIA’s 16th Director of Central Intelligence, from 1993 to 1995 under President Bill Clinton. A Stanford grad, Yale Law School grad, and Rhodes Scholar, Woolsey’s intellectual curiosity led him to the most vaunted rooms in government, and he served as a delegate at large to the U.S. - Soviet negotiations in the 1980s. In 2011, Woolsey joined Lux Capital as a venture partner and advisor.

Through a combination of expertise, capital, and government affiliations, Lux Capital has become the silent kingmaker of our nation’s most technically complicated startups, often funding products with national security implications. The firm was an early investor in Anduril Industries, the $30B defense tech outfit led by former Oculus VR founder Palmer Luckey. Anduril builds autonomous systems capable of monitoring all realms of war - air, space, land, sea - and sells them to entities such as the Department of Defense and U.S. Special Operations Command. Lux tapped Brett McGurk, a former Biden advisor and Middle East diplomat, to join the fund as a venture partner last year. The fund also collaborates with U.S. national laboratories in discrete pockets like Los Alamos, New Mexico, to commercialize the technologies that emerge from research. On September 29, 2025, Wolfe met with Israel’s Prime Minister Benjamin Netanyahu to discuss the use of artificial intelligence to boost Israel’s military strength.

If Josh Wolfe is currently at the forefront of deeptech venture capital, he has achieved this position largely in the shadows. His public persona is dwarfed by other giants of industry such as Marc Andreessen, who recently raised $15 billion for a16z, or Josh Kushner, who announced a $10 billion raise for Thrive earlier today. When examined closely, Wolfe’s presence can most accurately be compared to Alfred Borden in Christopher Nolan’s The Prestige: always behind the curtain.

The truth often hides in plain sight, but people walk by it without any acknowledgement.

Or in today’s world, scroll by it.

Josh Wolfe is working on creating superheroes: designer humans who are able to go without sleep, withstand injury and disease, think faster than quantum computers, and possess alien body strength.

In a 2022 article with Institutional Investor, Wolfe says that the X-Men movies were a point of inspiration for him: “It got me thinking: If there’s a one-in-a-billion chance in real life that somebody has a special trait, with seven and a half billion people on earth, there should be seven or eight people walking around that have the ability…” He then wondered if these mutant genetic traits could lead to biological breakthroughs in disease treatment. While the article is from 2022, the anecdote dates back to 2018. After pondering the possibilities, Wolfe went through his network of builders in science, government intelligence, and finance, then assembled a team to work on “developing lifesaving therapies by studying the genetics of diverse populations that are outliers for health-related traits.” The company was named Variant Bio, and Lux Capital invested $1 million in 2018. Variant Bio has gone on to raise $130M+ through the Series B stage and boasts strategic partnerships with Novo Nordisk and The Bill & Melinda Gates Foundation.

Technically speaking, Lux’s portfolio company, Variant Bio, is not building designer humans.

But if you stand outside Lux offices and listen closely enough, whispers of transhumanist fantasies will buzz around your myringa like bees looking for honey. We turn sci-fi into sci-fact. What’s more science fiction than billionaires running around like Batman and Ironman, with superhuman recovery times, the inability to feel stress, and mind control? The total addressable market would be huge…

For now, the firm has to settle for more realistic endeavors.

Like turning $3 million into $300 million.

In 2008, Wolfe went down the rabbit hole of finding solutions to nuclear energy generation. He employed first principles to deduct that the world was reeling from incredible energy consumption coupled with a limited supply of fossil fuel. The best alternative energy solution was nuclear, which, considering the externalities, was not a great option. Wolfe wondered if there was a way to limit the downsides associated with nuclear waste. After interviewing 300 experts in the industry, it became clear just how expensive nuclear waste was: the Department of Energy spent upwards of $6 billion a year on nuclear waste cleanup. In a similar process to Variant Bio, Wolfe tenaciously recruited a ton of experts in the field - Jacques Besnainou was the former CEO of AREVA Inc., the French nuclear giant, former White House official Jon Foster joined Wolfe’s company as CFO, Gaetan Bonhomme was an MIT PhD in materials science, Aris Candris, former CEO of Westinghouse, joined as well. The company was named Kurion.

On March 11, 2011, Japan’s largest earthquake ever (9.0 magnitude) unleashed a tsunami that wiped out power at the Fukushima Daiichi nuclear power plant. The aftermath was an environmental hazard of epic proportions. Kurion was one of the few companies in the world that could assist with damage control. The team designed, built, and delivered a system to treat the 68 million gallons of radioactive waste at Fukushima, and loaded it onto a Russian military cargo plane to get it to Japan as soon as possible. Kurion workers suited up in full body suits and masks to prevent radioactive exposure, and even then, they could only be on site for a few minutes at a time before retreating to safety. All signs of life around the disaster were gone; even the birds didn’t sing.

The team successfully removed all radioactive isotopes from the site and made their way back to the states to continue growing operations quickly. Josh Wolfe and Kurion CEO Bill Gallo hired aggressively, made a few acquisitions, and opened offices in other countries. Four years later, Veolia, a public French energy company, reached out with an acquisition offer. Veolia bought Kurion for $365 million in 2016. Lux Capital owned around 30% of the company at acquisition, which meant a roughly $110 million windfall for a $100 million fund.

Wolfe’s life was anything but a straight path; it was filled with twists and turns; the bumps left brutal bruises which taught him how to survive. He grew up in Coney Island, the only child of divorced parents, raised in a two bedroom apartment with his grandparents and his mother. His early upbringing was simultaneously dysfunctional and instrumental to shaping his later success. He didn’t have an active relationship with his father. Wolfe directed his energy into academia, and as a teenager, won multiple awards for his scientific prowess, including reaching semifinalist status in the Westinghouse Science Talent Search. He ended up attending Cornell University with hopes of securing a degree in biology.

During a summer internship at Merrill Lynch, Wolfe and his fellow interns spent a day at a Merrill executive’s residence, a Greenwich, Connecticut mansion with decadent displays of wealth throughout. This moment changed his life for good; from that day forward, he vowed to use his intelligence to secure riches for himself. Wolfe would go on to change his major from biology to economics and finance.

He lasted in investment banking for just a year before teaming up with Peter Hebert, a young banker at Lehman Brothers, to launch a venture capital fund together. The year was 2000, the dot-com bubble was bursting, and two half baked investment bankers in their early twenties wanted to launch a venture firm; sounds good, doesn’t work. If you recall from The USV Story, even seasoned venture capitalists were dropping like flies during this dry spell. But the macroeconomic environment was of little concern to Wolfe. The two newcomers pestered one of their college friend’s parents for an introduction to the Carlyle Group’s Bill Conway, and when they met Bill, he gave them $10 million to get started. Wolfe was so excited he quit his investment banking job immediately and forgot to collect his bonus.

On January 7th, 2026, Lux closed on a $1.5 billion Fund IX, its largest fund ever, bringing assets under management from more than $5 billion to $7 billion. Part of the explanation for such a massive fund relative to total AUM is Lux’s recent shift away from companion funds earmarked for growth companies. All investments, early stage and growth, are being made from their flagship as of Fund VIII, which raised $1.15B in 2023. Nonetheless, having the latest fund account for 22% of assets under management is a sign of legitimate pull in a tough market. The fund aims to make 40 - 50 core investments with a median check size of $25 million.

In addition to Anduril, Lux has participated in defense tech funding for companies like Hadrian, an autonomous manufacturing company for aerospace and defense production, Saildrone, a developer of autonomous maritime systems, and Terra Industries, a Nigerian defense tech company founded by 22-year-old Nathan Nwachuku and 24-year-old Maxwell Maduka. Terra Industries designs autonomous systems to help governments monitor and respond to threats. Their $11.75 million seed round was led by former Palantir executive Jon Lonsdale, now founding investor at 8VC. Lux participated in the seed round as well. Just yesterday, Terra Industries raised an additional $22 million of funding, led by, you guessed it, Lux Capital. The company has generated $2.5 million in commercial revenue and is protecting assets valued at around $11 billion.

Lux’s AI bets are also starting to pay off. Hugging Face is valued at upwards of $4 billion, Runway AI is valued at upwards of $3 billion, and Mosaic ML was acquired by Databricks for $1.3 billion in a cash and stock deal.

It would be wise to keep both eyes on Wolfe, lest he vanish into the shadows for his next trick.

The etymology of the word “flex” can be traced back to the father tongue of languages, Latin - “flectere” means to bend, and “flexus”, the past participle, means to bend or curve. Usage of the word has grown sharply over time since the early 1900’s, when it meant to bend or tense a muscle group, most notably the bicep.

The literal definition - a physical demonstration of strength capacity - has been recently refined into a more abstract interpretation derived from urban culture. “Flex” in today’s language economy refers to “a boastful statement or display”, popularized largely by hip hop culture from the 2000s to present, and then officially convocated into mainstream vernacular through social media, i.e. “weird flex” circa 2018.

To flex is to express yourself in the worst way possible

Like buying a $300,000 Maybach, taking the doors down, cutting the roof off, and driving the German landyacht like a car from Mad Max. This is a thorough flex; unapologetically braggadocious, pushing consumerism to the cliff with no regard for human life.

While the meaning of “flex” has remained constant over the past decade, its essence is slowly shifting.

At the root of this shift is increased societal awareness around a medical explanation for our hyperconsumerist tendencies.

Those with experience fasting from food can attest to an interesting occurrence that sometimes takes place: after a few hours of fasting, the hunger pains disappear, and then come back infrequently; when the fast is over and you make the decision to eat again, your mind plays a trick on you, and rather than eat an appropriate amount of food, you binge in an attempt to psychologically make up for not eating the past few meals. Since your body has briefly grown accustomed to a low energy state, the influx of food hits harder than usual. Afterwards, you realize the feeling you were searching for by doubling up on food never arrived. The scientific term for this fatale is “post-fast hyperphagia” or “rebound hyperphagia”, and I have been drawn in by her siren song more times than I care to admit.

The consumerist equivalent of rebound hyperphagia preys on the newly wealthy and the old money crowd alike. Man overspends on unneeded luxuries to compensate for his past pains - a triple black Bentley Bentayga to remind you of all the times your company should have died, a blood red 458 for all the lovers that left, a cream colored Sunseeker to drown out childhood trauma. Spend and then spend some more, the high you are chasing is almost here. Her lies encounter minimal resistance from the mind’s security system because deeply knotted pain is ever present in our somatic memory. So we flex until our arms hurt

Alas, the remedy to any illness starts with recognition.

The people are slowly waking up from slumber, realizing that good things are good up until a certain point, and a societal transition is taking place, moving us away from excess consumption and towards beauty, substance, and peace.

Simplicity is the new luxury.

Clarity is the new flex.

There’s a statistic going around that roughly 10% of Thiel Fellows have founded billion dollar companies and about 33% of Thiel Fellows have started companies valued at a hundred million dollars or higher.

Ceteris paribus, the odds of starting a billion dollar business are 2x higher for Thiel Fellows compared to Y-Combinator graduates (~4.5%), and more than 10x higher for a venture backed startup (<1%).

The most prominent billion dollar Thiel Fellows include Vitalik Buterin (Ethereum), Lucy Guo (Scale AI), Dylan Fields (Figma), Chris Olah (Anthropic), Walden Yan (Cognition AI), Brendan Foody, Adarsh Hiremath, Surya Midha (Mercor), and Austin Russell (Luminar Technologies).

Zaid Rahman will join this list soon.

The former Columbia University student dropped out to become a Thiel Fellow in 2017.

And his company recently raised a $60M Series B to build the financial operating system for an abandoned market.

Flex is building an AI-native private bank for high net worth, middle-market business owners.

The problem Rahman’s solving is deep pain for high net worth business owners; individuals who own middle-market companies have complex financial lives both on a company level and a personal level; managing both is a perpetual grievance. With Flex, owners get a single platform to control all parts of their financial lives at once, while leveraging artificial intelligence to find easy wins that result in tangible cost savings and simplicity.

• Middle market companies employ 40% of Americans yet modern financial tools are typically built for high growth startups or enterprise (Ramp, Brex, Airwallex)

• Those tools are also built strictly for business, not the business owners

• By servicing both the owner and the business, Flex becomes deeply entrenched in the individual’s financial workflows and can unlock additional value easier

The primary product is their Flex Net-60 credit card known as the Flex Card, the first three-in-one business credit card that offers interest free float (an 0% interest loan) for up to 60 days, allowing business owners to get easy money on hand for much longer than any other card on the market, all while retaining the optionality to “flex” between interest-free float time period and maximize personal travel and lifestyle rewards for the business owner. It’s the easiest decision a middle market business founder can make.

This is Flex’s wedge, a Trojan horse into their customers’ financial lives.

Using the Flex Card as top of funnel, the company sucks unsuspecting customers into their vertically integrated financial operating machine. At the heart of the beast is an AI-driven underwriting system that allows for precise risk analysis, which then enables Flex to offer more tailored products outside the scope of traditional banks.

Over the course of 2025, Flex:

• Grew revenue 4x

• Tripled their number of private credit offerings

• Launched Bill Pay (accounts payable automation)

• Crossed $1B+ in transactions

Flex’s story since its founding in 2021 has been one of consistency and steady growth.

It took roughly a year to hit $1M+ in transactions, and then two more years to hit $1B+ in transactions. They acquired Ghost Financial, a finance tool platform for ghost kitchens, in 2023. 2024 was the year of in-person events and brand building.

But Flex is not Ramp.

Ramp’s growth was much more explosive than Flex’s for a number of reasons:

• Ramp’s market - all businesses - is much larger than Flex’s. Even initially, when Ramp was going after fast-growing startups and tech companies, their market was way bigger than Flex’s mid-market business owners demographic. Ramp is horizontal while Flex is vertical

• From an underwriting perspective, Ramp typically has lower-loss severity per customer and can move faster at the earliest stages

• Ramp crossed $1B in transactions after less than 2 years, crossed $10B in transactions after 3 years, and crossed $55B in transactions in less than 5 years

• Flex crossed $1M in transactions in less than 1 year, then crossed $1B in transactions in under 3 years

Flex is not Ramp.

They are comfortable playing in a much smaller initial market than Ramp. They are comfortable with a flatter growth curve than Ramp. They are comfortable serving a forgotten demographic. But Flex’s much smaller initial market is filled with individuals all safely in the top 1% of America net worth wise. Their flatter growth curve meant that Ramp, Brex, Airwallex, and other competitors ignored the opportunity completely. Their forgotten demographic makes for exceptionally loyal customers.

If Ramp is building the business card equivalent of JPMorgan, the world’s largest investment bank, underwriting every major company under the sun, Flex is building Goldman Sachs’ private wealth arm, a trusted financial partner for the high value individuals.

With all that said, an amusing similarity between the two companies is their use of athlete marketing.

We all know Ramp’s favorite spokesperson, NFL running back Saquon Barkley.

Not everyone knows Luke Baldwin, third generation Nascar driver and Flex ambassador.

The partnership is an on-brand activation, leveraging a sport often overshadowed by football, basketball, and even another racing league, F1, to drive awareness.

Flex’s earliest investors are feeling giddy about the upwards momentum.

Jonathan Wasserstrum, founding partner at Unwritten Capital and Flex seed investor, told mainstreet media that “Flex has been a fun one to watch. When we first invested, they were focused on the construction industry. Needless to say, they’re expanding their customer base and product in a massive way. And the most fun part is that they are just getting started.”

Ben Zises, founding partner at SuperAngel.Fund, and Flex pre-seed investor, sent us the following LinkedIn post which tells the origin story of his relationship with Zaid. Per the post, “My relationship with Flex began in April 2020, when I received a DM on X (then Twitter) from founder Zaid Rahman about a new idea he was exploring. At the time, I hadn’t yet transitioned into full-time investing and didn’t have the bandwidth - so I asked him to keep me posted. He did. And I’m glad he did.” In October 2021, Zises made his first investment in Flex, followed by a second check in October 2022 alongside Fifth Wall, Hustle Fund, Not Boring, Banana Capital, and Jonathan Wasserstrum.

Flex’s $60M Series B was led by Portage Ventures with participation from Crosslink Capital, Titanium Ventures, Wellington Management, and others.

Next round could be Zaid Rahman’s biggest flex yet.

Galadyne

• Company Overview: Galadyne is redefining modern missile architecture using scalable liquid propulsion combined with vertical integration. The company’s primary objective is to reduce U.S. dependence on fragile supply chains and strengthen defense capabilities in the process.

• Founders: Chandler Luzsicza - a UCLA aerospace engineering graduate with three years of experience as a propulsion engineer at SpaceX

• Investors: Andreessen Horowitz, Pax Ventures

• Amount Raised: $5M+ (pre-seed stage)

• Headquarters: Austin, TX

Inception AI

• Company Overview: Inception is an artificial intelligence neolab betting on diffusion LLMs. Diffusion architecture already dominates audio, images, and video, but Stanford professor Stefano Ermon is betting that diffusion could significantly improve code and text generation also. The incumbents - OpenAI, Anthropic - are focused on next-token prediction while the Inception thesis is that diffusion will be faster and much cheaper. Inception’s Mercury model is reportedly 10x faster than Anthropic’s Claude 4 Sonnet and Inception’s Mecury Coder model is reportedly 4x+ faster than Grok Code Fast.

• Founders: Stefano Ermon - CEO of Inception, Stanford professor, Cornell MS; Aditya Grover - CTO of Inception, UCLA professor, former Stanford AI PhD

• Investors: Menlo Ventures, Microsoft’s M12, NVentures

• Amount Raised: $50M+ (seed stage)

• Headquarters: Palo Alto, CA

Cubby

• Company Overview: Cubby is building the next chapter of self-storage technology. Cubby’s platform serves as a one-stop-shop for the underserved self storage industry, weaving together revenue optimization, voice AI agents to attend to customers, and e-commerce solutions for storage operators. More than 400 operators managing 450,000+ units in North America use the platform.

• Founders: Matt Engfer - CEO of Cubby, former Director of Client Success at VTS, a CRE technology company

• Investors: Goldman Sachs, Third Prime

• Amount Raised: $69M+ (Series A stage)

• Headquarters: New York, New York

GovDash

• Company Overview: GovDash is the only end-to-end AI system built to win, manage, and deliver government contracts. GovDash customers won more than $5B in contracts during 2025, the company increased revenue 16x since its previous funding round, and the team achieved FedRAMP Moderate Equivalency, an important security milestone that allows GovDash to serve defense contractors.

• Founders: Sean Doherty - CEO of GovDash, Y-Combinator W22, Boston University graduate; Curtis Mason - CTO of GovDash, Y-Combinator W22 batch, Boston University graduate, former Google software engineer

• Investors: Mucker Capital, Northzone, Y-Combinator

• Amount Raised: $42M+ (Series B stage)

• Headquarters: New York, New York

Empires come and empires go.

The desire to build from the ground up and expand is as innate to man as quenching thirst for water and knowledge.

History seems to be an endless repetition of ambitious men attempting to build massive empires that span the globe.

Many notable empires have come close to dominating the globe, but one after another, they inevitably crumble.

Interestingly, the Book of Daniel describes a mysterious empire that will be unique:

“In the lifetime of those kings, the God of heaven will set up a kingdom that shall never be destroyed or delivered up to another people; rather, it shall break in pieces all these kingdoms and put an end to them, and it shall stand forever.”

Thus whoever is at the top of this empire necessarily will be the King of Kings.

The four empires described before this mysterious empire are widely interpreted to be Babylon, Persia, Greece, and Rome. So the question becomes which empire after Rome will be the chosen one?

After the Western Roman empire fell and the Eastern Byzantines continued to reign, it seemed as if this was the everlasting kingdom. But the Ottomans had other ideas.

The Holy Roman Empire sprung up centuries after the Western empire fell and utilized the name to cement legitimacy, but they too would eventually see their end.

Seizing on the chaos and instability of the French Revolution, Napoleon usurped power from the republic and crowned himself King, defying the tradition of the Pope crowning Kings.

Battle after battle, Napoleon emerged victorious and stretched the empire further and further. At the height of his power, the French empire spanned from the Iberian Peninsula to the border of Russia and from the North Sea to Southern Italy.

The fifth kingdom had been identified. Or so it seemed.

Along the years of consistent conquest, France had made many enemies, and it was only a matter of time before they bound together in the classic “the enemy of my enemy is my friend” maneuver. Russia, Austria, Prussia, The United Kingdom, Sweden, and Spain all joined forces to bring Napoleon’s vision for world conquest crashing down.

After fleeing exile from the island of Elba, near Italy, he came back to the game like Wizards Jordan and tried to get his get back.

He failed.

This time, he was sent to St. Helena, an island between Africa and South America, with 1,000+ miles separating the island from either land mass.

It was officially over.

He spent six years there before eventually passing away.

In the grand scheme of things, six years isn’t a long time. However, for a man whose whole life was dedicated towards constant expansion, leadership, and brutal competition, it begs the question: how can a man like that spend the rest of his life essentially doing nothing?

This is the same question founders ask themselves when they step away from their company after a “successful exit.”

From the outside looking in, the idea that there could be an agent-principal dilemma between founders and VCs can be confusing. After all, the alleged goal for the company is for the founder to come up with the idea, source capital from investors to build the product and scale, and then finally both enjoy the wealth that proceeds the exit, either through M&A or an IPO.

But it’s not that simple because founders and investors unsurprisingly have different motivations.

VCs have their own investors that they need to appease, so the liquidation event is always the end goal. In recent years, investors have grumbled over the lack of action surrounding these two mechanisms for liquidity, but things seem to be reversing course a bit.

In 2025, there was a strong rebound in M&A, reaching a deal value of just under $5T, thanks in large part to the record level activity in Q3 and Q4. Mega transactions–exceeding $5B–saw a notable uptick, with 122 occurring, a sharp uptick from the 76 and 74 in 2024 and 2023 respectively. Strategic buyers through corporate M&A rose to $2.73T, representing roughly 60% of total deal value.

The IPO market also improved from the past few years, as the 354 total new public offerings far surpassed the 218 and 145 in 2024 and 2023 respectively. $44B was raised by non-SPAC offerings, compared with $30B and $20B in the two previous years, with healthcare company Medline winning the gold medal after raising $6.26B in their IPO. Although the capital raised through public markets in 2025 don’t come close to 2021 figures, it was still significant enough to surpass every year between 2015 and 2018.

Thus, investors seem to be a bit more optimistic based on this data and are hoping to see the trends continue on this trajectory. After all it is a simple equation: more exits leads to more money for the LPs and thus more money for the GPs.

But with founders, it can be a bit more complicated than that.

This complication occurs because many of the most successful founders build companies as a tool to do what they want to do. This seems obvious and cliche but still needs to be said nonetheless. For the rest of the founder population, the means is the company and the end is wealth and status, which is why there seems to be an imbalance between people building companies and truly revolutionary ideas. On the other hand, for the S-tier founders, the wealth is undeniably nice, but it is not the end goal; it is a mechanism for accelerating the increase in quality and/or quantity of either the existing product or the product that naturally proceeds the existing one.

In other words, the true builders don’t simply take the cash from their previous exit and call it a day; they move on to the next goal / mission because the urge to expand is in their DNA. For VCs, being able to determine which companies are headed by these individuals is the game itself.

After all, the founders with the lust for wealth and status as their end goal know they must conceal their true motivations, just as the precocious 20-year-old Ivy League Economics student must refrain from telling the Goldman VP interviewing him that he simply wants to leave after two years before exiting to private equity. Thus, these type B founders put on the type A mask, and it is the VC’s job to discern who is who because the wrong selection could be the difference between life and death.

The easiest way to determine who is who is of course to use a retrospective lens to see who continued to build even after having the opportunity to kick back and relax into perpetuity.

Many examples of repeat founders building multiple impressive companies exist.

Jack Dorsey. Peter Thiel. Evan Wiliams.

But the most notable of them all is of course Elon Musk.

Rather than sell his companies for a payout, he is essentially doing the opposite with the continuous merging of his companies, attempting to pull off one the most ambitious vertical integration schemes of the modern era through the acquisition of xAI by SpaceX just 10 months after xAI’s acquisition of X, formerly known as Twitter.

The strategic consolidation is impressive:

• X feeds one of the richest human language data sources (save Reddit) into xAI, the large language model company

• SpaceX is poised to be the leader of “datacenters in space,” where artificial intelligence infrastructure is relegated to orbit amidst growing backlash and externalities on Earth; this provides a structural competitive advantage for xAI’s compute efficiency

• xAI provides the software infrastructure to help optimize SpaceX operations, from predicting mechanical failures to analyzing sensor data, ultimately reducing launch delays and technical issues

The two mergers within the past year have also converged three different groups of investor blocks to create possibly the most fascinating cap table a private company has ever composed.

Arguably the two most notable VCs in Sequoia and a16z both see their private Elon holdings consolidated into one entity after investing in all three ventures at previous stages. Other notable mentions include Founders Fund investing in SpaceX, Larry Ellison’s and Qatar’s stake in X, and Lightspeed and Nvidia backing xAI.

The SpaceX conglomerate is reportedly valued at $1.25T, qualifying for the largest merger of all time, and if an IPO materializes, it will be cinematic to a fault, likely sucking the air out of the room for OpenAI and Anthropic.

No matter how you slice it, Musk’s run post-PayPal has been generational. His empire is now being brought under one roof, and the pieces fit together quite smugly. An IPO of this size would put him on the Mount Rushmore of founders, right next to Ford, Carnegie, and Rockefeller. This is Kobe against Boston in 2010. One last embrace of victory, oh how she shines when the night falls!

All the greatest kings and emperors throughout history are connected to each other in some fashion.

Swinging back to Napoleon, he was exiled to the island of Saint Helena, as previously mentioned.

Who is Saint Helena exactly? None other than the virtuous mother of Constantine, the Roman emperor famous for legalizing Christianity with the Edict of Milan in 312 AD.

This type of connection is a rare case. The connection is usually that of inspiration.

Caesar wept before the statue of Alexander the Great because the latter had conquered the known world at the same age Caesar had achieved little politically. Vowing to follow in his footsteps, he became the first Roman emperor.

Charlemagne was crowned the new “King of the Romans” in 800 AD by Pope Leo III, resurrecting the line of emperors created by Caesar himself.

Napoleon, crowning himself as previously mentioned, visited Charlemagne’s tomb in Aachen, doing his best to mold the French empire into something akin to the Holy Roman Empire.

So who is the King of Kings, the head of the everlasting empire?

It is neither Alexander, Caesar, Charlemagne, Napoleon, nor Elon.

Yet, Napoleon knew who it was.

He explains:

“Alexander, Caesar, Charlemagne, and myself founded great empires; but upon what did these creations of our genius depend? Upon force. [The King of Kings] alone founded His Empire upon love, and to this day millions would die for Him.”

$5,000.

That was Alex Bars’ signing bonus with the Chicago Bears.

No ESPN headline. No champagne-soaked celebration. Just an undrafted rookie signing a contract that barely covered rent.

Back at Notre Dame, he was the captain, an All-American, the kind of player scouts circled in their notebooks. Then, just before the draft, a devastating knee injury, a torn ACL and MCL, almost ended everything before it even began.

Nine months later, he was back on the field - limping, aching, chasing a dream most assumed came with millions on day one.

It didn’t.

For Alex, the physical grind was tough, but the financial uncertainty was tougher. “People see the jersey and think you’re making millions,” he says. “They don’t realize most guys aren’t making that kind of money.”

In the public eye, he’d “made it.” In reality, he was clinging to a roster spot.

“I still remember the coach telling me, ‘If you’re not on the field, I can’t keep you on the roster,’” he recalls.

In the NFL, hardship is often hidden behind highlight reels. Fans see the stars, the fame, the money. What they don’t see are the players fighting to last another week, earning far less than the headlines suggest.

Some mornings, he’d sit in the locker room after practice, tape still wrapped around his knees, wondering how long his body would hold up.

Looking back, he realizes that the $5,000 signing bonus taught him a harsh truth: making it to the league and making it in life are two completely different games.

One demands talent, training, and toughness. The other demands knowledge the league doesn’t teach.

“By the time most players realize it,” he says, “it’s already too late.”

The Illusion

In the NFL, financial security is an illusion. Most players think they have it once the contracts are signed, until one roster move proves otherwise.

For Alex, the reality hit sooner than he expected. He’d seen teammates get cut before, but now he was living it - one clause in the contract fine print had erased seven figures overnight.

During his fourth year with the Las Vegas Raiders, Alex had signed a contract with incentives worth around a million dollars. Then they cut him, only to re-sign him to the practice squad a few days later - a roster maneuver that wiped out his incentives entirely.

“I hit all of the milestones in the original contract,” Alex explains. “I had a pretty solid season, starting 15 out of 17 games, playing 87% of snaps… But I didn’t get the million because they had cut me and signed me back.”

Just like that, a million dollars evaporated.

Beyond that, Alex learned that most NFL careers last around three years - just long enough for players to think they’re secure, but rarely long enough to qualify for benefits like health insurance or a 401(k). He barely qualified himself.

Four seasons in, Alex had already beaten the odds. But the longer he stayed, the clearer it became: the league rewarded what players produced on the field, not how well they prepared for life off it.

The Education

In the NFL, financial education is often treated like offseason conditioning. Everyone knows it’s important, but few take it seriously.

Alex sat through countless presentations, the ones the NFL requires and the NFLPA endorses. Almost universally, they missed the mark.

One session stood out. A financial advisor pitched the players on real estate, and recommended they prioritize purchasing a house with a fence for the dog they’d eventually want.

“I’m thinking, this applies to maybe two or three guys on the team and no one else,” Alex recalls. “These sessions weren’t about real financial education. It felt like they were just checking a box.”

To make matters worse, most of these sessions were scheduled after practices or midweek during game prep. “Guys were too tired to focus, let alone absorb anything,” he says.

No one covered tax strategies designed for careers with short earning windows. No one explained the fundamentals of investing in the stock market. No one broke down how to evaluate equity stakes in companies. And most importantly, no one taught them how to spot predatory pitches disguised as opportunity.

For Alex, the real education came from watching teammates make costly mistakes.

A teammate invested $100K into a fund to buy a professional sports team. The pitch? He was “first in line” when it went up for sale.

“Are they selling?” Alex asked.

“No. But when they do, we’re first in line.”

Alex walked him through the reality: capital locked up indefinitely, management fees compounding annually, and no timeline for deployment.

“If you don’t make another dime in the NFL, you might need that money,” he told him.

And the pitches just kept coming - cannabis drinks, sports beverages, the next breakthrough supplement. Flashy, tempting, and all aimed at players who had no way of doing proper due diligence.

“Without knowledge of how to evaluate a deal or understand if it fits your financial goals, guys were investing just so they could tell people they were invested,” Alex recalls.

He’d seen too many cautionary tales in the locker room to ignore the pattern.

“You see stories about former athletes suing their advisors because they got scammed? That stereotype… the suits with greasy hair and their feet up on the table, just trying to squeeze every dollar out of athletes? It’s real.”

He knew there had to be a better way. And he knew he and his teammates deserved better.

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The Transition

At 28, Alex faced the question every athlete wrestles with at some point: one more year?

Jacksonville, Miami, Denver, Arizona. Four teams. Four practice squad offers.

“I told my agent, ‘Hey, I’m not sure I want to keep doing this,’” Alex says.

It wasn’t just about the paycheck anymore. It was about passion.

“I was starting to lose love for the game,” he admits. “And I knew that it was time to find something else I was passionate about.”

That something turned out to be wealth management.

For Alex, the decision had been quietly forming for years. His studies in finance at Notre Dame planted the seeds, but it wasn’t until he saw teammates make costly mistakes that the purpose became clear: he wanted to help others make smarter financial decisions.

And when it came to finding a place to start, the choice was personal.

His brother Brad had left Merrill Lynch to start Creative Investment Group, a boutique wealth management firm built on independence from banks and complete transparency for clients.

“When I saw how Brad was doing things, it just clicked,” Alex says. “It was everything I wanted the advisors from the league to be - honest, transparent, and client-centric.”

Those weren’t just slogans on a website. They became the foundation of how he approaches every client today.

Alex refuses to sell products or push opportunities just to boost commissions. Every financial plan he builds is tailored to the client’s specific goals.

“We’re not lazy. It would be easy to pop everybody’s money into mutual funds or ETFs. But that’s not who we are,” he says. “We build each portfolio from scratch. It’s more work, but it’s better for the client.”

And education isn’t optional. Many of Alex’s clients are NFL players planning for life after retirement. Others are young professionals and business owners planning for major life events. No matter who they are, his goal is the same: he wants them to understand the why behind the what.

“If you’re trusting me with your money, you’re going to understand every move we make,” he explains. “You’re going to know what you’re in, why you’re in it, how it’s doing.”

Alex approaches every client meeting like a coach reviewing game tape with his players - breaking down risks, mapping out opportunities, and making sure his clients understand the rationale behind every move he makes.

Because for him, success isn’t just about returns. It’s about helping clients understand their choices and feel in control of their financial future.

The Mission

For Alex, wealth management isn’t just about beating the market. “We obviously want to be the number one firm in the country, but we want to do it the right way,” he says. The litmus test for success, he adds, isn’t rankings or press - it’s the feedback he gets from his clients.

One client recently told him the firm had delivered better returns in a single year than his previous advisor had in four or five. “Hearing my clients happy that they made the switch is incredibly fulfilling,” he says. Another client, a doctor, offered to look out for Alex’s family’s health needs - a gesture that speaks to the kind of trust he builds.

Drawing on lessons from his playing days, Alex’s advice to athletes is simple: spend thoughtfully, budget early according to your lifestyle, and never assume the next contract will always be there.

$5,000 taught him patience. Injuries taught him urgency. A million-dollar loss taught him resilience.

Two years removed from the league, Alex doesn’t miss the roar of the crowd. What drives him now is quieter but far more lasting. Whether it’s teaching players about investing, helping young professionals access off-market opportunities, or guiding business owners through retirement, he’s not just helping his clients grow wealth - he’s empowering others with knowledge and confidence.

“Football gave me a platform,” he says. “Finance gave me a purpose.”

Want to see how Alex brings the lessons he’s learned from the NFL to investing? Follow him on LinkedIn or Instagram, or visit his firm’s website to learn more.

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The older brother-younger brother rivalry is an archetype as old as time.

Cain and Abel.

Mufasa and Scar.

The Prodigal son and his obedient brother.

Despite the shared kinship, history highlights that the younger brother’s success often sparks jealousy in the older brother.

But this isn’t always the case.

The older brother can sometimes pave the way for the younger brother to chase greatness through leading by example.

Think Obi-Wan and Luke Skywalker.

This latter archetype has been the story of sports as an asset class.

The number of emerging leagues, and thus capital flowing into them, has exponentially increased in recent years.

Major League Pickleball. Tomorrow’s Golf League. Unrivaled. Premier Lacrosse League. United Football League.

And many more.

Even youth sports is seeing an unprecedented level of commercialization due to a surge of investor interest.

But one cannot discuss the younger emerging leagues without first giving respect to the older brother: the Fantastic Four of American sports.

The growth these four leagues have experienced over the past few decades is the main reason why the aforementioned emerging leagues can even exist in the first place.

Institutional capital has bankrolled these emerging leagues but had long been prohibited from ever getting involved with the industry titans.

Until a fortuitous day in October of 2019.

One man in particular had been patiently waiting for this moment.

Ian Charles did not come from the world of sports and in fact didn’t even watch sports growing up. He sometimes references being accosted for mispronouncing well known sports players or franchises.

Rather, his background was in private markets.

He initially wanted to be a physics professor and began studying the hard sciences at Texas Christian. This would change after he saw his friend’s finance homework and teased him about how easy the math was.

His friend agreed and shot back, “Yeah, and I’m still going to make more money than you.”

So Charles left behind the physics pursuit and shifted his eyes towards markets. He dove in headfirst by founding a software business and beginning the famous 0 to 1 journey. He’d seen the typical process founders go through: come up with an idea, pitch investors, raise money, and deploy the capital to chase growth at all costs.

But unfortunately for him, the “raise money” part wasn’t exactly successful.

To figure out where he went wrong, he began a deep dive into private markets, specifically private equity and venture capital. He figured if he spent time learning the intricacies of the market, he would understand why he wasn’t able to raise money and thus fix his errors. In addition to scouring every information platform possible, he began interviewing anyone in the VC and PE industry he could get in contact with and began building meaningful connections.

Interestingly enough, the company he started didn’t dissolve after failing to raise outside capital; he eventually moved on to other pursuits while the two people he brought on bootstrapped the company for many years and are still in business today.

This network enabled him to land a private equity job right after graduating from TCU before moving on to work at Cogent, a firm specializing in secondary advisory work. The company was founded in 2002 and quickly built the reputation as the go-to platform for secondary transactions, executing 55 deals valued at $11B in 2014 before being acquired by Greenhill Partners the following year.

“If you wanted to sell secondaries in an intelligent way, we were literally the only firm to hire…we changed the cost of liquidity forever because the secondary market wasn’t that deep at the time but we helped increase the perception of liquidity that has greatly aided in the allocation to private markets.”

After all, as a prospective LP in a notoriously illiquid asset class, the more confident you are that you can access liquidity at some point, the more likely you are to allocate capital.

Charles then moved to Landmark Partners, another secondaries firm that was also later acquired by a larger company, this time Ares Management in 2021.

During these stops, Charles acquired an expertise of private markets and alternative assets, specifically in deal origination and data analysis. He had begun to understand all of the alternative assets, but there was one in particular that was unlike the other.

Sports.

Specifically the major four sports leagues.

He didn’t work with sports assets much during his stints at the secondaries firms, but the more he looked into it on his own time, the more he realized how unique it was.

He quickly realized its most distinctive attribute was its anti-cyclical nature, as its performance is essentially uncorrelated with the broader macro environment. This is a trait that venture capital, private equity, real estate, nor any other major alternative asset could boast of. In fact, along with education and healthcare, it is the only industry / asset class that has experienced a compounded 3-year revenue growth of more than 6% over the past few decades.

In addition to expanding margins and comparable returns to both private and public assets in expansionary times, sports franchises easily outperforms these assets in contractionary periods. For instance, during 2008 and 2009, each major sports league experienced notable growth in ticket revenue, contradicting the theory that lower discretionary spending from consumers due to a recession would naturally lead to decreased ticket sales.

Another unique aspect of sports assets is that the franchises own a proportional amount of equity in its respective league that has its own revenue channels outside of the teams that includes domestic and international media rights deals, data sales, partnerships, and more. These deals are typically long-term contracts with escalators, thus, according to Charles, giving sports LPs access to something of “an investment-grade bond with growth” that is theoretically independent of the asset itself.

But as we know, sports franchises were institutional investors’ forbidden fruit in the garden of private markets up until 2019. The MLB ruled that these institutions could now own a minority stake in teams, and the other leagues slowly followed suit. Charles quickly captured the opportunity and established Arctos in the same year.

Charles brought his expertise in private markets, capital formation, and data to the table and brought on a few people who specialized in sports management and operations. The S-tier team, promising asset class, and opportune timing seemed to be a home-run formula for fundraising, but the company inevitably ran into friction. Many were hesitant to commit, as the MLB was the only league to open up access and it wasn’t exactly obvious as to when / if the others would do the same.

Because of this, many prospective LPs chose to sit on the sidelines. But a select few saw the opportunity and jumped at it, allowing the firm to raise $2B for their first fund.

When analyzing why leagues had historically prevented institutions from being investors, it mainly came down to two words: control and leverage.

Private equity firms are the most likely suitors for these franchises because of their size due to their high debt to equity ratio. They also notoriously aim to control their assets so that they have an active role in their “value creation methods.” Leagues understand this and thus wanted to exclude them from ownership, as the last thing they want is these institutions saddling teams with debt and usurping the decision making power. Taking on a significant load of debt is heavily discouraged by the major leagues, as a team’s financial insolvency due to inability to make interest payments can have a cascading effect on the rest of the league. Because of this, the average maximum allowable LTV hovers around 15%.

With this in mind, it almost seems like a private equity firm like Arctos wouldn’t mesh well with the criteria. However, Charles’s background isn’t executing the textbook leveraged buyouts but rather helping investors access liquidity. This means he would not seek to alter the company’s foundations because his background was in minority stakes not in control stakes.

Keeping his secondaries hat on, he saw a very similar situation he identified a decade or so at Cogent in which there were a lot of existing investors that wanted access to liquidity but had no well to draw from.

Combining the opportunity to invest in a unique asset class, teams’ inability to take on debt, and a lack of liquidity for sports investments, Arctos kills three birds with one stone, specializing in deploying LP’s capital to sports assets, providing teams with no-strings-attached growth capital, and offering liquidity to current franchise investors.

The powerful three-in-one.

It became very obvious very quickly that Arctos was building something special.

KKR took notice and recently acquired the firm for $1B.

When did everyone start using the phrase “barbell strategy”? Was it purely Nassim Taleb’s doing? Taleb is an investor famous for making truckloads of money as a trader at First Boston during the 1987 crash, also known as Black Monday. On Black Monday, Taleb took out a long position on the Eurodollar through call options, which cost pennies on the dollar, and later that same day, he sold the options for a dollar each, pocketing more than a pretty penny in the process, around $35 million to be exact. Taleb went on to found a hedge fund, Empirica, that did well for a short period of time, but closed due to periods of low volatility. His strategy was dependent on large, black swan events that others were not pricing in. Like Black Monday or, more recently, COVID-19. Therefore, extended periods of low volatility were no fun for his fund. Taleb described his investment framework, detailed in one of his famous books, Fooled by Randomness, as barbell strategy, where most of the portfolio is in high quality, safe assets with low-risk returns, and a smaller sleeve of capital, think 10-20%, is in ultra high-risk, high-reward ventures, like out of the money call options trading for pennies on the dollar. Taleb likely used the name barbell because of his love for weightlifting.

Today, the phrase is abused by far too many people.

A New York socialite uses barbell strategy to explain why she eats kale caesar salad six days of the week before binging on eggs benedict and mimosas on the seventh.

An NBA data analyst uses barbell strategy to justify his recommendation that players only shoot three pointers and layups.

A venture capitalist in Menlo Park uses barbell strategy to rationalize only investing in serial entrepreneurs or college dropouts.

And today, I will shamelessly clothe myself in the comforting linens of hypocrisy, and use barbell strategy to push my agenda on sports investing forward.

The Arctos investment mandate was strict and unforgiving: blue-chip or die. Golden State Warriors, Sacramento Kings, Philadelphia Sixers, Washington Wizards, Boston Red Sox, LA Dodgers, Aston Martin F1, the list continues. Even within the “Big Four” landscape, the firm selected for teams that were either built for scale, or mistakenly undervalued. Eventually, the firm made a number of “emerging league” investments, but let’s set that aside for now.

If the Arctos way represents the conservative stack of plates on the left side of our sports investment barbell, what is the aggressive, singular plate on the right?

One might say Major League Pickleball. Another Unrivaled, the new women’s basketball league. Yet another, Major League Cricket, or Premier Padel, or Baller League, which features creators instead of professional athletes.

Not enough.

These leagues were created with institutional adoption in mind. Investors, ranging from venture capitalists to buyout moguls, have backed these leagues from day one, in hopes of cashing out amidst record levels of capital interest in sports.

To find out where the real emerging leagues live, we must look beyond what the mainstream media puts on our plates. We must look in the cracks and crevices where investors are scared to visit.

If you walked into the wrong basketball gym in New York on November 8th you would have seen it.

What looked like a sold-out high school basketball game in the city was actually something far more nefarious.

In one section of the gym, you would spot one of Canada’s most famous rappers, Nav, checking one of his two phones waiting for the festivities to start. Red Bull in the other hand.

In another section, you would see Terance Mann, the Brooklyn Nets wing most known for his previous role as an NBA starter for the LA Clippers.

Local celebrities and corner boys alike packed the gym like sardines as the crowd waited in anticipation. Left and right, everyone was putting their money down on who would come out alive. Thousands of dollars at a time. This was the modern equivalent of Casanova’s underground fight rings in Brooklyn.

Finally, the two fighters walked to the center of the court.

And they started playing basketball.

Nasir Core, a 29-year-old guard in Ice Cube’s Big3 league, squared off against Isaiah Briscoe, a 29-year-old guard who previously played at Kentucky alongside De’Aaron Fox and Bam Adebayo, before bouncing back and forth between the NBA’s G-League and overseas basketball. The event was structured like a UFC fightcard, with Nasir versus Isaiah as the main event, and players like Jahvon Quinerly and Ty Lawson hopping into the one-on-one arena to fight for their lives.

One-on-one basketball is not a replacement for traditional hoops, it’s a flavorful supplement. It’s my ego versus yours. Just three, four dribbles to create separation and score. Nowhere to hide. At its best, it brings the thrilling ups and downs of fighting sports in a basketball format. At its worst, it can turn into an unpalatable sport, a violent evening, you name it.

There is no real infrastructure around this; different platforms exist on YouTube, namely Ballislife, The Next Chapter, and Off the Dribble, but there is no official league to capitalize on the moment. The space is messy and fragmented. Events like the NYC card got compromised by hotheaded fans with too much money on the line. Figuring out the right business model will also take some tinkering. Right now, the channels charge viewers to watch the highest demand matchups (like Isaiah vs. Nasir) on a pay-per-view basis. Keeping the best players locked in for the long term will be a struggle. Attracting marquee NBA talent won’t happen anytime soon. There are many question marks that must be addressed.

Nonetheless, one-on-one basketball is where the highest-risk, highest reward emerging sports opportunity lies. If someone can create the “UFC for basketball”, that’s a sports platform worth buying into at the earliest stage. The pull is already there: at a Detroit event hosted by Off The Dribble, breakout rapper Babyface Ray made an appearance; at a Charlotte event hosted by The Next Chapter, Hornets standout Miles Bridges showed up; at an Indiana event hosted by The Next Chapter, Pacers player Obi Toppin and former NBA player Marquis Teague both joined. This is where the culture is headed. It’s much riskier than pickleball or padel. But I’ll put my money down and see who comes out on top.

On the topic of basketball, keep an eye out for Project B.

Project B is a new global basketball league formed by former Facebook executive Grady Burnett and Skype co-founder Geoff Prentice, with the goal of introducing an F1 style international tour concept to professional basketball.

At first glance, it seemed as if Project B was positioning itself as an Unrivaled competitor. Unrivaled is a 3v3 women’s basketball league founded to provide an alternative to WNBA players playing overseas in the offseason; they raised funding from a number of venture capitalists and celebrities, gave players equity in the league, and paid out higher average salaries than the WNBA, roughly $222,000 versus the WNBA’s $120,000.

Project B, however, is reportedly handing out Birkin bags with $2,000,000 inside, nearly 10x Unrivaled’s average salary.

The aggressive compensation structure has attracted a number of WNBA all-stars and former MVPs, including Nneka Ogwumike (10x all-star, 1x MVP, 1x champion), Alyssa Thomas (6x all-star), Jewell Lloyd (6x all-star, 3x champion), Jonquel Jones (5x all-star, 1x MVP, 1x Finals MVP, 1x champion), and a handful of other all-star level players.

But disrupting the WNBA isn’t enough for these guys.

Project B is trying to poach current high level NBA players as well. No announcements have been made as to which players they are signing on the men’s side. But be on the lookout for something later this year. Project B is an attempt to disrupt the NBA’s chokehold on basketball, backed by some of the largest technology companies in the world. The CEO of Google Ventures invested, a Managing Partner at CapitalG (Google’s growth equity fund) invested, a founding partner at Lightspeed invested, to name a few.

We have to take a step back and look at the broader landscape to understand what’s happening.

Technology companies are playing a bigger role in sports media rights packages. Amazon, YouTube, Apple. In the next cycle, more tech companies will join the fun, pricing out traditional media. At some point in the distant future, only tech companies will be able to afford media rights for the NBA/NFL.

Burnett and Prentice, both tech executives who were early at Facebook and Skype, understand this perfectly. If they can dilute the NBA’s monopoly and build a product that appeals to their network of tech executives, the dividends will be endless. And if they succeed with basketball, it will not stop there. Every sport is up for grabs.

The hardest part will be the product itself. Will fans care to watch after the novelty wears off? Certainly an international audience helps. But there’s a reason people tune in to the NBA Finals every year even if their team isn’t playing. There’s a reason the Super Bowl does the numbers it does. You can’t engineer that.

Previously:

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The bulls were everywhere.

To say it was out of style to be a bear was a massive understatement. A few brave contrarians stepped forward and expressed their concern with the state of the market.

Barton Biggs, chairman of Morgan Stanley Asset Management at the time, knew the market was grossly overvalued and completely divorced from stock fundamentals.

“You’ve got stocks selling at absolutely unbelievable multiples of earnings and revenue. You’ve got companies going public that don’t even have any earnings. You’ve got people setting up Internet pages to reinforce each other’s convictions in these highly speculative stocks. This is wild stuff out of the past. In every market where it has happened, it always ends in the same way…worthless brother-in-laws are starting hedge funds…I know a guy who is fifty and he’s never done anything [and] he’s starting a hedge fund.”

Barton Biggs

While every brother-in-law wasn’t necessarily starting hedge funds, they were definitely trading online.

In July of 1983, a doctor from Michigan made history when he was the first person to execute a trade virtually using E*TRADE. It wasn’t until 1992 that the company would officially take on its name and a few years later, it would start to see serious traction. By the end of 1995, it had 40K users and was executing 4K trades a day. By the summer of 1996, the number of users had swelled to 800K. The Motley Fool, founded by brothers David and Tom Gardner, also became extremely popular, as people began to devour the latest analysis on their target stocks. E*TRADE and The Motley Fool soon went hand in hand like PB&J for online retail investors.

Thus an interesting loop was created: the Internet begins, Internet stocks boom, and people use the Internet invest in said Internet stocks.

More specifically, many people not only began trading stocks, but also began day trading. Marc Friedfertig, founder of Broadway Trading, describes the art / science of day trading at one of his conferences:

“The first goal is not to lose money…if you make $500 a day, that’s $125K a year…if you make $200 a day, that’s $50K a year. That’s not too bad.”

Seemed easy enough. But the thing is, the guys at the conference didn’t want to be the guy who walked away with $50K. They wanted to be Serge Milman, who grossed $1.4M and pocketed $800K after commission.

The obvious reality with making $50K or $800K day trading is that there is a high level of risk involved. Many more people lose money day trading compared to those who make money. And for those who lose money, the end result isn’t always pretty.

Take Mark Orrin Barton for example. His life was pretty normal on the outside looking in: he lived in the suburbs of Atlanta, was on his second marriage, and had two kids. He began trading in 1998, but by April of 1999, he’d racked up a decent chunk of losses. By early June, his account got shut down. He shifted to a different platform called Momentum Securities where he claimed to be worth $750K and wrote a check for $87,500 to open his account. He quickly lost $105K after borrowing even more capital on margin. He inevitably got slapped with a margin call and his account was closed after he couldn’t come up with any more money. After hearing the check he wrote bounced, he went home and brutally murdered his wife and two children. Soon after, he drove to the Momentum Securities office and killed four people and wounded several others before taking his own life.

Although this was undeniably a one-off event with poor timing of the market, many people bought into the idea that day trading during this time was as easy as printing money right off the press.

The media played a massive role in this.

In general, the media’s role is to discuss topics by presenting both sides of the coin so that the public can make an independent and rational decision with the information. During this time, the financial media space did the opposite, as those critical of the market’s valuation were either ignored, slowly deplatformed, or simply drowned out by the ubiquity of the bulls. When watching CNBC, for instance, during this era, the only conclusion one could logically conclude was that if you weren’t invested in tech stocks, you were missing out.

“Seeing such price gains, you may have two questions. Is the Internet based on anything more than hype and is it too late to get in on the action? The answer is reassuring: yes, the Internet boom is for real and second you are not too late. It’s true that investors have bid many Internet stocks to astonishing prices, but the Internet potential is so great that even today’s rich prices will likely be justified for many companies in the long run.”

Money Magazine

No one had a larger influence on financial media than the one and only James Joseph Cramer.

Jim Cramer was raised in the suburbs of Philly and attended Harvard. One day, a professor named Marty Peretz asked Cramer to write a book review on markets, and eventually began taking some of Cramer’s stock tips. After seeing some of his ideas materialize, he cut him a check for $500,000 and told Cramer to make something happen.

Two years later, Cramer came back with $1.5M.

After briefly trading equities at Goldman, he quit his job and cofounded a hedge fund that returned 22% between 1988 and 1996. During this time, he wore the hat of both an investor and journalist, contributing regularly to publications like GQ and The New Yorker.

For those wondering: yes, one can argue this presents a conflict of interest.

For instance, he publicly recommended four stocks when writing for Smart Money without disclosing that his fund owned significant stakes in the companies. Once the piece was released, his fund’s stake in the companies increased by $2M. After an investigation, he beat the case.

When it came to tech stocks, no one was a bigger advocate than Mr. Cramer. In his eyes, the only problem with Internet stocks was that “we simply don’t have enough pieces of paper that represent the right to own future profits from the ‘net.”

Cramer, along with the rest of the media, continued to blow the FOMO horn and capital continually poured into the market.

The New York Times began to report that it was common for UPS and taxi drivers to be trading tech stocks their laptops and portable quotation machines.

Alan Greenspan, the Fed chair, saw this and knew the market was officially a bubble. He’d had the feeling for a while but wasn’t sure what to do exactly. If the overall economy was overheated and inflation was picking up, then everyone would be on the same page: increase rates, burst the bubble, and bring everyone back down to Earth.

But that wasn’t the case.

Everything was going a little too well. Inflation was low, the labor market was strong, GDP growth was north of 4%, and the market was outperforming all three. Although it was clearly a bubble, was it Greenspan’s responsibility to single-handedly cut the music and end the party? His laissez faire instincts whispered that it in fact was not.

Greenspan seemed to relish in the idea that he seemingly held the global financial world in his hands. The duties and responsibilities of the Fed chair had not materially changed relative to previous decades, but many identify him as the catalyst for the Fed chair becoming more of a public figure.

After speaking with mainstreet media, John Murfee, a financial services expert with 40+ years of banking and trading experience, agrees wholeheartedly:

“When I was first getting started in the business, I couldn’t even tell you who the Fed chair was because that’s how little he mattered…Greenspan was the first Fed chair to become a nationwide public figure. He is the main culprit of the phenomenon we see of everyone in the finance world hanging on to every last word the Fed chair says because people used to call him ‘The Maestro’ and he loved it.”

John Murfee to mainstreet media.

Greenspan had decided that the fiesta must draw on; for everyone except the contrarians of course. Bears went from being few and far between to essentially extinct, especially those with a financial manager or investor role. Not only did their credibility suffer as stocks continually climbed higher, but their performance severely lagged behind relative to the herd.

There were many stories like Charles Clough, a Merrill Lynch stock strategist, who, after pleading with his investors to keep their money in cash and bonds because equity valuations were too high, saw his performance at the bottom of a Wall Street Journal survey performance. He made the decision to spend more time with his family and become a deacon full time for his local Catholic church.

As more bears went extinct, more people began to flood the startup scene, as the incentive to join or found a startup was at an all-time high.

An anonymous HBS grad that founded an Internet company in the fall of 1999 describes the process of entering the founder space:

“It was absurdly easy…you would walk into the offices in New York and people would immediately offer you money if they thought you were smart. We didn’t have any data or even a market. We didn’t even have a product demo. We had a business plan and that was it.”

Tom Gardner, co-founder of the Motley Fool, echoes a similar sentiment. In an exclusive sit-down with mainstreet media, Gardner explains just how hungry VCs were for up-and-coming businesses.

“After getting the company up and running on AOL in 1993, from the investor side it was pretty quiet, but after a few years we had nearly every VC knocking at our door. In a short span, roughly 150 VCs reached out to us, wanting to invest. We ended up raising $55M in total, giving away 20% of the company. At the time we had $10M in sales that mainly came from discount brokerages like Fidelity and Schwab that would advertise on our site. All of these discount brokerages would go to VCs, raise capital, and then spend it on us. It was a great time…we really saw our popularity start to take off after we would make appearances in our patented bell hats.”

Tom Gardner, CEO of the Motley Fool, to mainstreet media

Being a founder was now the hottest job on the market. Michigan’s business school had just started a new course called “From Idea to IPO in 14 weeks,” and HBS’s survey indicated that more students (343) were planning to join a tech startup than management consulting or finance (308).

VCs were willing to throw money at whoever as long as “they thought you were smart” because of how easy it was for companies to go public. The entire ecosystem incentivized a reckless bombardment of cash in every direction because founders knew VCs wanted to deploy at a fast rate, as bankers would underwrite the IPOs without even thinking twice—as long as it operated on the web. Even better, once the company would go public, the stock would pop on the first day as investors’ demand for internet stocks seemed to be insatiable.

Founders were worth millions in the blink of an eye. VCs realized unbelievable gains. Bankers were raking in cash from underwriting fees hand over fist. Public market investors were living the dream.

Again, all of these companies had minimal revenue, excessive losses, and no concrete guidance for investors as to when they would become profitable. Most companies explained this away, loosely conveying a plan similar to Amazon’s “winner-take-all” model in which they would aggressively spend to offer below equilibrium prices and eventually worry about profits down the line.

On December 31st, 1999, Muhammad Ali rang the opening bell on the NYSE, and when it closed, the Dow was up 25% and the NASDAQ was up 86%, surpassing the Dow’s 81% performance in 1915 as the highest major index performance of all time.

Don’t let that slip through - NASDAQ did hedge fund numbers… 86% from an index is unheard of.

What a time to be alive.

But as we know, good times can’t last forever. As Isaac Newton famously proclaimed, “What goes up, must come down.”

The come-down wasn’t as simple as raising rates and watching the economy and market slow down. By the time 2000 rolled around, there were whispers that Greenspan was indeed thinking about raising rates not to interfere with the market’s unsustainable run but to get ahead of potential inflation. Like mentioned previously, inflation was under control but Greenspan was nervous, as demand was rising much faster than supply and guessed it was only a matter of time before inflationary pressure manifested.

By the time March rolled around, rates had increased from 5.5% to 6%, and investors mainly shrugged it off.

But other than the rates, the overall sentiment was beginning to shift just a bit.

Sometimes, that all it takes.

Jack Willoughby wrote a piece questioning whether the bubble would burst soon, and teamed up with a notable research firm called Pegasus Research International to examine the financial statements of more than 200 internet companies. After some basic analysis, he concluded that over a quarter of them would have no cash in the next year based on their current burn rate.

Around the same time, Business Week ran a piece accusing Wall Street of peddling high risk investment strategies to the public.

Another writer named Mark Mobius at Templeton Mutual Fund Group suggested that the mania for Internet stocks is coming to an end. Simply put, “if you look closely enough, it’s beginning.”

By the turn of the next month, the market continuously trickled downwards. The drop was large enough that many investors faced margin calls and needed to sell some of their stocks to combat this.

The NASDAQ would soon drop 600 points.

At this point, it wasn’t clear whether the beginning of the end had truly arrived or if it was just a minor dip that could be capitalized on.

On April 10th, the NASDAQ dropped 6%, and just two days later, after Rick Sherland–a well-respected Goldman Sachs equity analyst–lowered Microsoft’s revenue expectation, the exchange dropped 7%.

It was at this point that Cramer, along with the rest of the investing world, knew the party was officially over.

“It’s a sobering and humbling experience. I feel like I went from being at the top of my game to being pretty humiliated…yeah it’s over; the gold rush is over.”

Jim Cramer

By the end of the year, the NASDAQ was down 40% for the year with Microsoft losing 63%, Amazon losing 77%, Yahoo losing 86%, and Priceline losing 97%.

Gardner gave us an inside look on how the crash affected The Motley Fool:

“After raising $55M during the latter half of the 1990s, our valuation sank to $1M. All of the discount brokerages ran out of cash and we were left exposed. We had to get creative and we eventually pivoted to a newsletter subscription model that has served us well ever since. It was actually one of our least interesting ideas out of the 12 we came up with…but the early days of the crash were brutal…we had to let go of over 80% of our staff.”

The Motley Fool managed to stay alive, but many of its dot com counterparts were dead upon the arrival of the crash.

Webvan was the most notable, as the online grocery store that raised $800M, went bankrupt in the summer of 2001.

By Q2 of 2001, the effects began to spill over into the real economy, as the it expanded by just 0.2%. By September, the exchange was sitting at $1687, down from its peak of over $5100.

It was during this time that the 9/11 attacks occurred and the Twin Towers came crashing down.

The idea of American economic and militaristic invincibility had come crashing down as well.

Fast forward to today, and it is hard to ignore the whispers.

“The AI bubble is bound to pop any day now.”

“P/E ratios are higher now than they were during the Dot Com bubble.”

“History seems to be repeating itself.”

There is some truth to the whispers. It doesn’t take a genius to realize that the equity market is overvalued and has largely been driven by AI hype.

Since January of 2023, the S&P’s gross return is roughly 77%.

Thus, we seem to be in the same situation as the early 1990s: bulls believe that a revolutionary technology has been introduced that will seemingly increase productivity and thus future profits. Because of this, we should be willing to pay a higher price for today’s earnings given their future growth rates will increase. Bears believe that the hype of said new technology is overblown and equities have become too expensive because of this. Similarly, companies’ stocks are being rewarded for simply signaling they are going along with the new trend. Instead of mentioning the incorporation of the Internet into their operations, companies are telling investors they will increase AI expenditure and are receiving rounds of applause in response.

So what’s the difference?

Murfee explains a major one:

“Despite the ‘hype’ being the underlying factor for both run-ups, the main difference is the public market AI companies are actually well capitalized and generating cash.”

Murfree makes an excellent point. But, public market AI companies are still at risk if OpenAI cannot deliver a generational performance. This is because AI capital expenditure, funding data centers and hard infrastructure, has been financed with debt, leading to some of the highest debt-to-equity ratios ever seen in public tech companies.

• Microsoft: 0.2 debt-to-equity ratio (2x higher than D/E ratio in 2000)

• Cisco: 0.3 debt-to-equity ratio (5x higher than D/E ratio in 2000)

• Oracle: 4.75 debt-to-equity ratio (7x higher than D/E ratio in 200)

Furthermore, the debt here is fundamentally riskier than the debt in 2000, considering the high usage rates of private credit and SPVs. There is more synthetic leverage floating around off market than ever before.

All the while, stocks are trading at some of their most expensive levels yet. GPU depreciation accounting practices are questionable at best, multiple forecasts demonstrate the largest AI players on the public markets today would be unprofitable if traditional depreciation schedules were employed. The entire picture is hanging on to the prospects of AI related growth. In the case that OpenAI fails to reach the moon, they cannot cover datacenter commitments, the Magnificent Seven public companies are left holding the bag, and the stock market plunges given the concentration of wealth held in the top tech companies, then we might see the biggest bubble burst of our lifetimes.

Moving to the private market side, AI agents are everywhere.

These companies have no regard for healthy unit economics and are being built purely because it seems like the right timing. The fact that their compute (variable) costs are higher than their revenue per unit is irrelevant because of the idea that these costs become cheaper over time. Most importantly, most of these companies offer no real competitive advantage given their lack of a proprietary model, thus leaving them susceptible to extinction at the snap of an OpenAI finger.

No matter how you slice it, it’s clear that both the public and private markets would suffer greatly at the hands of a pullback in AI optimism.

What exactly could cause this isn’t obvious.

Weakness in economy as a whole doesn’t seem to be the answer. Stock market returns and major economic indicators like inflation, unemployment, wage growth, and GDP growth have seen weak correlations in the past handful of years, so it’s unlikely that changes in any of these factors would cause a correction.

One potential cause could be choppy waters during OpenAI’s IPO.

Both OpenAI and Anthropic are expected to go public this year, and to do so, the books will need to be opened and inspected by America’s finest bankers. An IPO will either slightly increase the market’s confidence in LLM companies or wake the bears up from their hibernation. Things could get bad if OpenAI’s business is worse than the market has been led to believe, particularly if investors start doubting whether they can handle their datacenter commitments or not. More on that here.

Another cause for pullback could be worries about Nvidia’s performance.

It’s no secret the company is at the heart of the AI revolution.

Whether it is geopolitical risks, supply chain issues, or simply a bad earnings miss, a slip in the confidence of Nvidia can serve as the first domino in the AI correction, just as Jack Willoughby’s piece did for the Dot Com correction.

As we saw with the Dot Com bubble, all it takes is a sudden shift in the public consciousness to completely eradicate trillions of dollars of wealth.

When this will happen, or even whether this will happen, is unknown. Despite this obvious fact, many “financial prophets” boast that they know the exact day or hour the market will implode.

This is ludicrous.

After all, we know nothing about tomorrow.

“Come now, you who say, ‘Today or tomorrow we shall go into such and such a town, spend a year there doing business, and make a profit’ — you have no idea what your life will be like tomorrow. You are a puff of smoke that appears briefly and then disappears. Instead you should say, ‘If the Lord wills it, we shall live to do this or that.’”

Remain humble, as pride always precedes the fall.

The largest private technology companies outperformed the public markets by 7x in 2025.

Caplight’s Top 20 Index is a financial index tracking the performance of the largest late-stage, venture-backed, private companies with active secondary markets.

The index is dominated by the largest six companies - OpenAI, SpaceX, Anthropic, xAI, Databricks, Stripe - which account for 86% of the Top 20 Index by valuation. Investors who prioritized access to these names, rather than public market darlings like NVIDIA, Google, Amazon, etc., saw significantly better returns in their portfolios last year.

Ultra-high net worth family offices are showing very high demand for OpenAI, SpaceX, and Anthropic in particular. One investor recently told us a story involving an UHNW family trying to get directly on Anthropic’s cap table with a $140M check. The effort was fruitless, and they ended up investing a smaller amount into an SPV that fed into another SPV. A sign of the times.

According to Caplight’s data, 2025 was the strongest venture capital secondary market since 2021.

• Total VC secondary transaction volume increased 75% year-over-year

• Average secondary trade size increased to $3.6M in Q4 ‘25, up from $2.0M in Q1 ‘23

• The top 10 private AI companies outperformed their top 10 public peers by 5x+

Mercor (+423%), Anthropic (+402%), Skild AI (+368%), Crusoe (+244%), ElevenLabs (+205%), OpenAI (+144%), and Perplexity (+94%) led the way for private AI companies.

On the public side, companies like AMD (+77%), Google (+65%), TSMC (+54%), ASML (+53%), NVIDIA (+39%), Microsoft (+15%), and Meta (+13%) saw very solid returns, but paled in comparison to the private market’s stars.

The delta is multifactorial, but it’s useful to focus on two key drivers. First, the pure-play AI companies are all private due to AI being a recent phenomenon. Every company built from the ground up with a focus on AI was founded in the past ten years. Google, NVIDIA, and AMD are the closest thing you get to pure AI exposure on the public markets. Second, the private markets are less sensitive to macroeconomic pressures. Investors on the public side trim exposure in the face of geopolitical uncertainty, while the private market is much less reactive in the short/medium terms.

The top three private tech companies - SpaceX, OpenAI, and Anthropic - are all aiming to graduate to the public side this year.

These 3 companies combined account for 23% of the entire VC pre-IPO market.

The big three also accounted for 17% of secondary market activity.

Lastly, an interesting shift took place around the end of year mark: investors are now looking to lock in gains as quarter-over-quarter ask volume increased at 4x the rate that buy volume increased.

There are three main storylines to watch going forward:

IPO Games.

Who has the most successful debut? OpenAI, Anthropic, and SpaceX are all three very different companies and it will be peak cinema to watch this blockbuster trio of IPOs pan out in real time. If you are a tech investment banker, get your rest in now.

Anthropic is likely expected to have the lowest valuation, but public investors might like them relative to OpenAI, a much more expensive foundation model name. In addition, Anthropic has been making great in-roads into enterprise adoption while OpenAI is leaning into building a consumer oriented platform (ChatGPT Health is a preview of this, expect similar releases in the future, i.e. ChatGPT for Personal Finance). On the secondary market, Anthropic’s valuation skyrocketed in 2025 as investors saw it as a stable, cheaper alternative for foundation model exposure - the company’s secondary valuation grew 2.8x faster than OpenAI’s. I’d even go as far as saying the smart money’s on Anthropic: earlier this week it was reported that Sequoia Capital is joining a private round for Anthropic despite already investing in rival companies OpenAI and xAI. The round is being led by Coatue and GIC.

Private Delta.

Will private markets go mainstream? The top 10 names are trading at public market valuations, and provided more portfolio growth than the public side. Going forward, the secondary market will need to evolve to support more liquidity, transparency, and ease of access for interested investors. The biggest barrier to a highly liquid secondary market is information asymmetry. Are secondary buyers getting information rights? Where do they sit in the capital stack? How do liquidation preferences affect their exposure? These access barriers are not simple problems. Investors must be cautious.

Money Machines.

The largest venture capital funds are just getting warmed up. Andreessen Horowitz announced their new $15B fundraise two weeks ago. Founders Fund closed on $5B a year ago. You should expect Thrive to announce a new fund in the next six to twelve months, likely between $7B - $10B. More money than ever has been secured in the hopes of crowning the next Sam Altman or Dario Amodei. The amount of capital at the later stages combined with more transparent secondary markets means that early stage venture capital investors will start taking more chips off the table, earlier. The venture capital market will continue to bifurcate into a16z/FF/Thrive/Sequoia/GC/Lightspeed and boutique early stage investors that don’t touch anything at the Series A stage or onwards. The middle market Series A/B firm is dead, save for sector specialists who have carved out their respective niches. It won’t be long before the pre-seed/seed boutiques start exiting positions entirely when the big boys pick up the tab at Series A/B stages. No more holding for an IPO exit ten years down the road; pre-seed funds are exiting at Series A when a16z turns their portfolio company into a unicorn, just a few years after the initial investment. Be on the lookout for signals that this shift is taking place.

Venture capital is now officially two separate asset classes.

At 28, Matt Mooney had already lived the dream most players spend a lifetime chasing - a professional basketball career spanning the NBA, G League, and top international leagues. But the part of his career that matters most never made the highlight reels. It was a borderline obsessive pursuit of becoming the best shooter he could possibly be.

He wasn’t just trying to make shots - he was studying them: the angles, the timing, the mechanics. That fixation followed him everywhere, from practice gyms to hotel rooms to overseas arenas. And over time, it evolved into a simple thesis: the way players learn to shoot is fundamentally broken.

Every player practices shooting, but almost no one train with data, feedback, or repeatable systems. To Matt, it was a massive market hiding in plain sight.

When his playing career ended, he didn’t drift toward coaching, media, or any of the familiar post-retirement paths. Instead, he stepped straight into the startup world with no tech pedigree, no startup network, and no safety net.

In the months since hanging up his jersey, Matt has been channeling the same competitiveness that made him a force on the court into scaling his startup - AthletIQ, an AI-powered training app he’d been quietly building for years while playing professionally.

The journey has been anything but linear. There have been pivots that tested his conviction on the market, setbacks that forced him to rethink his product, and long stretches where he was context-switching between two high-pressure arenas - professional basketball and startups. Few founders operate with that level of constraint, and even fewer find a way through it.

Today, AthletIQ represents the convergence of everything that makes Matt who he is: the discipline of a pro athlete, the curiosity of a lifelong student, and the conviction of a founder willing to empty his bank account and go all in.

In this conversation, he opens up about the psychology behind taking unconventional risks, the identity shift from athlete to founder, and the hard-earned lessons from navigating the 0→1 phase of a startup.

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

If someone’s hearing about AthletIQ for the first time, how would you explain the problem you’re solving, who you’re solving it for, and why it matters to them?

Matt: The origins of AthletIQ go way back. I hit this stretch in my career where I was consumed with perfecting my shot. That obsession pushed me to build something pretty wild: a robotic defender that could contest your jumper and analyze your mechanics in real time. It was my first attempt at solving a problem I lived every day.

That prototype became the earliest version of what would eventually turn into AthletIQ.

The tech worked. The business model didn’t.

Turns out, the product was too expensive for the people who needed it most - high schools, AAU teams, and everyday hoopers who don’t have the luxury of having trainers with them 24/7. There was real demand, but the willingness to pay just wasn’t there at the price point required to make the margins work.

But that experience taught me something important. I realized that the robot itself wasn’t the product. The feedback was.

Today, AthletIQ is that same idea, stripped down to its essence. We built an app with three core modules designed to help anyone become a better shooter:

• Learn: a guided shooting program we co-developed with sports scientists

• Improve: AI-powered analysis on your footwork, follow-through, release time, and other factors that affect your shot

• Compete: gamified scenarios that make training feel like a video game

And the timing finally makes sense. AI can now deliver highly personalized feedback without the need for trainers or expensive equipment. With just a phone, players at every level can now access the type of training that used to be reserved for the pros.

At what point did your obsession with perfecting your shot evolve from a personal edge into a vision to transform how players train?

It really shifted when I realized I could actually change my shot.

For most of my life, I assumed my form was fixed, and I just had to shoot more and get the reps in. But a few years ago, I got injured and had to rethink everything - the way I trained, the way I moved, the way I shot. It forced me to study biomechanics in a deeper way, and I made real improvements.

That was a big moment for me. I remember thinking, ‘If I’m in my late 20s and I can still fix this, then younger players definitely can.’

How many players out there never get real feedback on what to work on? How many think they’ve peaked because no one taught them the right way?

There’s a huge number of players at every level, all facing the same problem. That’s when I realized this wasn’t just about me. This was a massive opportunity to change how players train. That’s when it all clicked.

You could have pursued more predictable and lower-risk opportunities after your playing career. But you chose the founder path. What pulled you towards that direction?

I think it’s who I am at my core.

First, I love competition and the pressure that comes with it. It’s part of what I love about the game of basketball. It’s how I’m wired - that competitive mindset doesn’t just turn off when you retire.

Second, I’ve always been a risk-taker. I don’t want to live with any regrets. I already carry some from my playing career, and I don’t want to add another. I’d rather go after an opportunity and fail than not take the opportunity in the first place.

And honestly, the founder path spoke to a part of me that’s always been there - the entrepreneurial side that loves solving problems and doing the hard things. It’s definitely the tougher road, but it’s a meaningful one. And my faith in God gives me the confidence that things are going to be okay no matter what, so it feels like the right leap to take.

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Athletes entering tech often feel like outsiders. How did you build the kind of worldview that allowed you to operate on equal footing and compete with the best founders out there?

It starts with knowing my strengths and weaknesses.

I understood the problem better than anyone because I lived it. I could speak to players and coaches in a way no one else could. I knew how to sell the vision, pressure-test ideas, and translate feedback into product decisions.

At the same time, I had to be honest about what I couldn’t do. I lacked expertise in AI, robotics, fundraising etc, so I surrounded myself with people who could fill those gaps. For example, I brought in a team that knows how to build great products. I also have a number of advisors that help me with things like fundraising.

One of the hardest lessons for any founder is learning how to delegate effectively. You can’t do everything yourself. You have to double down on your strengths and trust others to execute on the rest.

But I will say this. Recently, I’ve realized that I could stretch myself farther than I thought. I can learn pretty quickly, figure things out, and grow into certain roles. So I’ve been taking on a lot more these days. Some days it’s messy. But I’ve learned that it’s part of the process.

And that’s the beauty in being a founder - you just start and you figure it out.

Some founders hesitate to go all-in. But not you. You cleared your bank account to get AthletIQ off the ground. What gave you the conviction to take that risk?

That’s true. It was a risky move - clearing my bank account like that. But it didn’t feel reckless at all, because I had conviction: in the problem, in the market, and in myself.

I started the company during COVID, right after being called up to play for the Cleveland Cavaliers on a two-way contract. I remember sitting in my apartment, thinking to myself, ‘I’ll make money in life. I’m still young. I believe in this. So I’m going to do it’

I’d been wrestling with this idea for years. It felt like the thing I was meant to build. I even ran it by my financial advisor. Luckily, he gave me his blessing, though honestly, even if he hadn’t, I still would have gone for it.

I had nothing to my name but the $50k in my bank account. So I went all in.

At the end of the day, I’m a risk-taker. That’s just who I am. I’ll take the shot - because if I don’t, I’ll always wonder, what if? And that doubt, that regret, is far heavier than missing.

There’s a perception that athletes have certain advantages - capital, network, distribution. What do people fundamentally misunderstand about the realities of building a startup as an athlete?

A lot of people don’t understand what it takes to start a company as an athlete. The stress is real, and obviously, it’s self-imposed because I chose this path. But being an athlete-founder is like juggling a hundred variables at once - product, fundraising, team… all while still playing professional basketball.

Truth is, I’m thinking about my company 24/7. It’s always on my mind. But I have to compartmentalize.

When I’m on the court, my focus is entirely on competing at the highest level - every practice and every game matters. When I’m working on my company, it’s a totally different mindset - strategy, team dynamics, sales meetings, product decisions. And at home, it’s about showing up for my wife, making sure she feels appreciated. Switching between those worlds takes effort. Some days it’s messy, and I don’t do a great job. But learning to be fully present in each moment, without letting one world bleed into the other, that’s the challenge.

As for the advantages of being an athlete? They’re not what people think. Discipline, work ethic, competitiveness - those skills definitely translate. But startups is totally different game. You’re basically starting from zero. You have to learn new skills and build new networks. Being an athlete might open doors, but everything else was new to me when I first started. I had to ask a lot of questions, make mistakes, and surround myself with people who knew the game better than I did.

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Every startup has near-death moments where things almost fall apart. What was that moment for AthletIQ? And how did you overcome it?

Oh man, we’ve had some of those moments for sure. The one that really sticks out was our pivot from a robotic defender to a mobile app.

Early on, we were laser-focused on building the best robotic defender imaginable. One of our investors even pushed us to double down. But it became pretty expensive to develop. Only NBA teams could afford it, but they already had real players contesting shots in practice. So they didn’t necessarily need it.

It was a classic lesson in early-stage startups: the hardest part isn’t just building something cool - it’s building something people need and are willing to pay for.

So we pivoted. We started listening to the players we actually wanted to serve. What they cared about most was personalized feedback on their shot. That was the core value in what we had built.

It was a tough situation to navigate internally. My co-founder was really attached to the robotics idea, and we clashed on product vision. And that’s when you feel the pressure - not just from investors, but from the team itself. Misalignment in strategic direction can slow everything down. That tension is part of the grind, but it’s also where you learn who’s committed to the mission and how flexible you need to be as a founder.

Fast forward to today, we’re seeing real signals from the market that the mobile app resonates. Our beta is about to launch in a few weeks, and every step feels like validation that we’re heading towards the right direction.

A huge part of the 0→1 journey is convincing investors to take a bet on you. What have been the most formative lessons there?

Fundraising is incredibly hard. It’s a grind, and it rarely goes exactly the way you expect.

Consistency is everything. You have to keep showing up, lining up calls, following up. That’s how you build momentum and stack wins over time.

You can never be sure how any conversation will play out. Warm investors don’t always convert, and cold ones sometimes surprise you with a yes. I had one investor who was kind of dodging me. I hadn’t heard from him in weeks. And then out of nowhere, I get a text: “Hey, I’m wiring the money tomorrow.”

I’ve learned to embrace that uncertainty. You never know who will invest, who they know, or what doors a conversation might open. That’s why, in every pitch, you have to be fully present. Treat the investor in front of you like they’re the most important person in the world at that moment. That focus, that energy - investors will notice, and it often makes all the difference.

If a young athlete told you they wanted to build a startup, what’s the one piece of advice you’d want them to internalize?

Honestly, it starts with relationships.

It’s the people you know and the relationships you nurture that really matter. Get to know people outside of sports, ask questions, be genuinely curious, and follow up.

I’ve never used LinkedIn that much, but I’d start there. It’s a great place to connect with people.

Being an athlete will also open some doors. Basketball has helped me get into some places because people remember me. So leverage that as well.

My advice to young athletes is to start building your network early. Don’t wait until you need something. If you invest in these relationships now, they’ll pay off when the time comes.

Between prepping for AthletIQ’s beta launch and fielding investor calls, Matt’s hit that inflection point where things are moving faster than he can plan for. Last week he was halfway across the world in Thailand demoing the product; this week he’s back to the usual chaos of product development and investor meetings.

What’s been particularly refreshing? Watching NBA players, coaches, and college athletes explain why they invested. Because when people who’ve lived the problem are willing to bet on a solution, that tells you something.

Want to learn more about what Matt’s building? Connect with him on LinkedIn or Instagram.

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Before we jump into the deep end, a word on Caplight.

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Pride goeth before destruction: and the spirit is lifted up before a fall.

A man, that maketh haste to be rich, and envieth others, is ignorant that poverty shall come upon him.

Wise words from a wise man.

Some would say the wisest man in history.

In 1998, Michael Jordan hit a game-winning jumper in Game 6 against the Utah Jazz, winning his sixth title in six tries. Everyone between the millennial and boomer age agrees that this feat made him the greatest player of all time.

The moment was undeniably an impressive feat.

But arguably not the most impressive of the year.

By the end of 1998, Priceline, the online marketplace for airline ticket sales, had sold $35M worth of tickets. Strangely enough, the cost of those tickets came in at $36.5M, posting a negative gross profit before incorporating their $54M worth of operating expenses. When taking other miscellaneous expenses and the stock options distributed to investors, the company lost $150M.

On March 30th, 1999, Priceline debuted on the public markets, issuing 10 million shares at $60 each. The price peaked at $85 before falling back to $68 by the end of the day, valuing the company north of $10B.

The airline ticket marketplace that couldn’t even turn a gross profit had just reached a valuation that was larger than United Airlines, Continental Airlines, and Northwest Airlines combined.

Now that is the definition of impressive.

However, no one batted an eye.

It was just another day in the late 90s “Dot Com” era.

While everyone was in agreement that the Internet was the next big technological advancement that would increase efficiency and thus future profits, the optimism seemed to be a bit higher than normal.

At the time, the only technological development seemed to be militaristic with the development of the atomic bomb in WWII and the seemingly unending battle that was the Cold War. But eventually, it did end, right as the Internet began to develop.

The first major step was the development of Mosaic, the first web browser that was relatively easy to use, install, and work on a variety of operating systems. Before Marc Andreessen founded Mosaic, non-computer nerds had no chance of figuring out how to use the Internet, as people needed to be familiar with the Unix operating system and the TCP/IP communication protocols. Mosaic instantly made it more user-friendly by inserting scroll bars, pull down menus, the back-and-forth button, and images being displayed alongside text.

There was only one problem: Mosaic wasn’t technically owned by Andreessen. He was still a student at the University of Illinois and was a paid employee at the National Center for Supercomputer Applications at the school while he developed the software. When it became clear that the school had no intention to commercialize it, Andreessen had no choice but to move on, so he got a job at Enterprise Integration Technologies (EIT). It was here where Andreessen would receive an email from Jim Clark that would alter history forever.

Clark was a high school dropout that would eventually make his way to the Navy where he discovered he was something of a math genius. After this realization, he completed his his school degree before receiving a masters in physics at the University of New Orleans and a PhD in computer science at the University of Utah. Once he graduated, he borrowed $25K in 1981 to build Silicon Graphics, a company that provided high quality 3D graphics before most computers had the ability to do so. After a while, Clark shifted to the chairman position and brought on a chief executive named Ed McCracken.

It became apparent quickly that Clark and McCracken did not see eye to eye and Clark would eventually leave.

He needed a new gig.

One of his associates had showed him the new web browser Mosaic and he immediately knew it was special. He contacted Andreessen and made a simple proposal: find a way to rebuild it and he would finance it.

At the time, it wasn’t very obvious how money would be made on the Internet, as everything about it seemed to be free. But he would worry about that later. In his eyes, developing revolutionary technology came first.

The money would eventually come.

Clark, having dealt with VC firms for many years, held a contrarian view on the institutions. Everyone else believed that VCs were the protagonists of the American economy, taking on the role of the benevolent philanthropists that funded the best ideas and powering American ingenuity and prosperity. Clark firmly believed that VCs were nothing more than vultures that swoop in with a “lust for control” and a lack of hesitancy to screw over founders and companies if it means satisfying their investors. Because of this, Clark would only allow VCs to invest in his new company if he maintained 25% ownership and they paid 3x what he paid for the shares.

Most VCs saw this ultimatum and scoffed; how dare a founder try to set the rules in which the game was played. After all, this is traditionally the role of VCs.

They hold the money and thus the power.

John Doerr, however, gave it some thought. The Kleiner Perkins partner had been a part of several successful tech investments in the 1980s like Lotus, Compact, and Sun Microsystems, but the proceeding decade had seen some embarrassing flops. He was yet to hit a home run and he was ready to swing for the fences. His gut was telling him this was gonna be a hit so he acquiesced to Clark’s demands. Doerr invested $5M and Kleiner Perkins became the second largest shareholder behind Clark.

Clark had seemingly done the impossible and set the terms in his favor. He proved that founders could actually have leverage in the twisted game that is venture capital. He walked so Travis Kalanick could run.

Clark began to think even more outside the box.

The company’s business model was beginning to take shape. Mike Homer, the former Apple executive and now head of marketing, wanted to charge $99 for a copy of each browser. Andreessen instinctively knew this was not a good idea. People had been accustomed to using the Internet for free and placing a significant price tag in the early stages was antithetical to growth. The compromise was to allow students and educators to download the browser for free and charge enterprises for their web server.

The beta version was released in October 1994 and by March 1995, they had distributed more than 3 million copies and posted a top line of $7M.

“Why not just go public now?”

This thought from Clark was a bit bizarre. When he began to deliberate this, the company had only been in existence for about a year.

In addition to unlocking a larger pool of capital and giving existing investors liquidity, there was also some external pressure given that their competitors were planning to do an IPO soon. The IPO would not only raise capital but also serve as a marketing campaign to get the company’s name out there, since the company was doing well financially but wasn’t a household name yet.

So Clark called up his boy Frank Quattrone, an investment banker in Morgan Stanley’s SF office, and pitched him on the company. For a long time, there was a large chasm between the blue chip investment banks and Silicon Valley companies wanting to go public, as the investment banks that typically did these deals were Hambrecht & Quist, Montgomery Securities, and Robertson Stephens.

Quattrone wanted to break this mold and helped Morgan Stanley land emerging companies like Cisco Systems and Silicon Graphics, which is how he met Clark. The new chief executive Clark and Andreessen brought in, Jim Barksdale, wasn’t sure that the time was right; Q2 revenue was only $12M and they were losing quite a bit of money. But he would eventually flip on the position after Spyglass went public and gave the green light.

The IPO was set for August 9th and Morgan Stanley originally recommended a price of $31 per share. Barksdale wanted to be more conservative and insisted on $28.

Both were way off.

The demand was so high that the stock didn’t start trading two hours after opening bell. Around 11:30 AM EST, Clark’s secretary told him the stock opened at $71. Clark’s stake was now worth $663M.

Andreessen woke up after a long night of work and logged into to quote.com to check the stock’s price. He quickly calculated that his stake was worth about $70 million and then went back to sleep.

By December, the stock reached $170.

Netscape was on the path to becoming the next revolutionary company.

Bill Gates had other ideas.

As we read in Andreessen Horowitz II, Gates would eventually squash Netscape’s ability to compete after releasing Internet Explorer.

After seeing its market cap rise to nearly $7B, the company would be sold to AOL for $4.2B in 1998.

Andreessen, Clark, and the rest of the crew would have to go their separate ways to solidify their legacy.

Many companies sprung about around the same time and few were able to survive the impending crisis about to happen.

One of them was Amazon.

Many know of Jeff Bezos’s background: exceptional high school student, top of his Princeton class, worked at DE Shaw for a while before using the “regret minimization” framework to decide on quitting his job to build his own company. What some don’t know about his background is that the idea to build an online bookstore didn’t just magically pop into his head after he quit his job—his higher-ups at DE Shaw told him to investigate how to make money using the Internet. After he assessing different options, he landed on an online bookstore. It was only after they told him this wasn’t his brightest idea that he decided to take the venture into his own hands. He initially incorporated the company under the name Cadabra (ordering a book online and receiving it at your door soon after was considered magic at the time) but needed something that started with the letter A, as websites were typically listed alphabetically. He settled on the world’s largest river and attached the “.com” at the end to ensure everyone knew his company was an Internet company and not simply a bookstore. After all, it doesn’t take a genius to realize that an Internet company will have much more attractive multiples than bookstores.

The company hit the ground running and sold $12K worth of books in the first week. By the end of 1995, the company’s top line was $511K. The company’s prospects became much brighter once the Wall Street Journal published a piece in May of 1996 detailing how a young guy from Wall Street was now selling books on the Internet. This was the dagger for Bezos & Co. His business had turned from a modest small business to one answering the call of VCs day and night. Before the article, General Atlantic was interested in investing $1M on a valuation of $10M. After, he had several offers for valuations of $100M.

The power of the press.

It wasn’t strictly hype however. The publicity served as a real shock to the company’s top line and it was seeing serious growth.

After sifting through the suitors, Bezos chose the established Doerr from Kleiner Perkins and received $8M in funding on a $60M valuation. This created a great cycle for Amazon, as the media coverage led to growth which led to more investors which led to more capital which they could then use to buy ads to get even more media exposure. They were soon everywhere: USA Today, WSJ, NYT, The New Yorker, Atlantic, and Wired.

Next came the IPO.

Quattrone had moved on from the Morgan Stanley and now heading the ship was Mary Meeker. Meeker interestingly was not on the equity capital markets team but was rather on the equity research team. That didn’t matter to her. She worked closely with the ECM group and held real sway there. Looking at Amazon, she knew this was Morgan Stanley’s next target.

To Meeker’s frustration, the bank’s top executives overruled her desire to underwrite the offering because of the longstanding relationship between the firm and Barnes & Noble. In fact, she was so angry she nearly resigned. Quattrone had moved to Deutsche Bank and helped the firm secure the offering.

The initial target was to issue about 2.5M shares for $12-$14 each.

Interestingly, in the company’s prospectus, Amazon was extremely clear that it would continue to suffer substantial operating losses for the foreseeable future, and the losses would increase over time given the competitive nature of the online e-commerce market because there are little to no barriers to entry. Those with any semblance of economic knowledge know that, in theory, industries with no barriers to entry likely won’t see any profit, as competitors will be able to enter the market freely and undercut the firms generating profits. So why would anyone invest in Amazon?

Besides the large gap between economic theory and reality, Amazon had a simple roadmap: the winner-take-all model. Their goal was to raise a ton of money from investors to offset the losses suffered due to low prices, build market dominance, and then after achieving this dominance eventually increase prices incrementally and focus towards generating profits.

In hindsight, we can all agree this worked well for them.

At the time, it would have been fair to question how exactly they would survive if it their total cost to ship a book was $25 and the average price was $20.

However, given the frenzy surrounding Internet companies, no one bothered asking these types of questions.

A few days before the IPO, Deutsche increased the share total to 3M and the price to $18. By the end of the day, it had jumped to just under $24, and both Bezos and Kleiner Perkins saw their stake balloon to a nine figure amount.

Again, public market investors really were not necessarily investing in Amazon because they thought Bezos was a once in a lifetime founder, or because they believed it was a generational product, or because they believed in the business model. It was really because Amazon was one of many companies that was connected to the Internet by sheer fate, and the company along with all of the rest were going to ride the miraculous tide of the 90s and the Internet into the sunset of the forever profits, prosperity, and peace that the internet would inevitably create. After all, the Internet brought about the new economy in which the money spent on the web was finally starting to materialize into revenue. More importantly, economics had been solved and the idea of a recession was in the past.

1998 was the year of the Internet.

Scratch that.

1998 was the year of the Internet stock.

AOL increased 593%.

Yahoo increased 584%.

Amazon increased 970%.

While the rest of the world posted average economic numbers, America was flexing its supremacy once again.

The country was invincible. The Internet had solved the classic “boom and bust” economic cycle once and for all.

Or so it seemed.

Pride always precedes the fall.

$200B+ of venture capital gets deployed in the U.S. on an annual basis.

That’s enough money to buy every NBA team and have lunch money leftover.

Despite this, startup media coverage is fragmented and low signal.

Our thesis is that, over time, startup media coverage will start to resemble sports media coverage.

Watchlist is a new mainstreet media vertical that covers the soon to be superstars: early standouts from the Series A stage, with the occasional super senior (Series B) and sensational freshman (seed).

On a monthly basis, we will release our picks on the top 7 to 10 unicorn prospects to keep an eye on.

At the end of the year, we will review the picks.

If you think we missed a startup, reply in the comments or shoot us a note at info@themainstreetfund.com.

You do not know your customer.

You only know yourself.

So build accordingly.

Some variation of this maxim has been regurgitated by countless artists, founders, and creatives.

August Wilson said, “I don’t write for a particular audience… I have to satisfy myself as an artist. So I always say that I write for the same people that Picasso painted for. I think he painted for himself.”

Steve Jobs said, “We think the Mac will sell zillions, but we didn’t build the Mac for anybody else. We built it for ourselves… We just wanted to build the best thing we could build.”

But Paul Graham might have said it best: “‘Make something people want’ includes ‘make something you want.’ In fact, that’s often the best way to start. The most successful startups generally begin by the founders building something they themselves want.”

Building for yourself is the only way to ensure that you are building something that someone will enjoy. You cannot enter into the minds and hearts of other people and experience the emotions they feel when they see a work of art or use a new tech gadget or watch an advertisement. But you can make things you know you like and continue to do so until other people start to like it as well. In some sense, building for yourself is an American ideal; it is a permissionless pursuit that mirrors what the founding fathers did when the British system no longer worked for them. It is wonderfully childish, like a preschooler abandoning his teacher’s instructions and coloring outside the lines to his own delight, yet utterly serious, like Michelangelo striking the chisel with his hammer, steadily carving away into marble until King David emerges from the stone.

Building for yourself is selfless.

At some point in every successful company’s life, the incentives shift to reward building for others instead. But doing so is an extraordinarily difficult task, because it is not enough to know who the audience is or what their desires are. You must know everything about them, a task impossible for mortal man. This is why large companies often seem out of touch with their consumers, delivering products no one asked for and making public statements that disgust their core fans.

What if you could know exactly what your customers want?

Customer research is a $50B+ industry.

Fortune 500 companies spend tens or even hundreds of millions per year on customer research.

Firms like Gartner ($16B+ market cap), Nielsen ($16B acquisition, 2022), Qualtrics ($12.5B acquisition, 2023) and Ipsos ($1.5B+ market cap), make billions of dollars selling quantitative and qualitative insights from focus groups, interviews, and surveys. Even though the process is slow, outdated, and oftentimes, inaccurate, an obvious need for customer insights exists within the global economy. Firms ranging from publicly traded fashion brands to private B2B companies to entire governments pay Gartner, Nielsen, and Ipsos for anything that can help ease the pain of not knowing.

Listen Labs raised $100M to make customer research fun.

The company, founded by Florian Juengermann and Alfred Wahlforss, is an AI-powered customer research platform that automates the process of conducting and analyzing qualitative interviews. Listen uses artificial intelligence to design interviews, source participants from a large pool, conduct video and voice interviews at scale, and then analyze the responses to generate reports, themes, and presentations. The end-to-end automation enables businesses to get customer insights in hours rather than weeks.

The company started when Florian and Alfred teamed up to build an image generating app named BeFake (a play on then viral app BeReal). Florian and Alfred met while doing a Masters program at Harvard. In 2023, BeFake erupted, and the app saw 20,000 downloads in a single day. The founders were caught off guard, and the cost of hosting the app - namely the GPU costs for AI functionality - put a dent in their personal credit card balances. They needed to figure out a way to know what customers wanted, deliver it at a high level, and monetize it. So Florian and Alfred scrambled to conduct customer research as quickly as possible. Midway through the process, it became obvious that traditional user interview methods would not suffice. This is when they had an epiphany: what if we could use LLMs to speak to every single one of our customers and then summarize what they care about? The minimum viable prototype was promising enough for the duo to abandon BeFake and pursue a new dream - Listen Labs - that same year, 2023. Ironically, the startup that makes money from allowing companies to listen to customers came to fruition because the founders built something for themselves; the tool they created to solve their most painful problem ended up being extremely valuable to countless deep pocketed corporations.

Why now? The technology had just caught up. On March 14, 2023, OpenAI released GPT-4, and API availability was released in July 2023. There are a couple of major improvements from GPT-3.5 that allowed GPT-4 to conduct customer interviews efficiently:

• Context Window: GPT-4’s context window is roughly 8x larger than GPT-3.5’s; the newer model could process an entire interview transcript in one take, analyze multiple customer surveys simultaneously, and maintain memory and context throughout longer customer interviews.

• Multimodal Capacity: GPT-4 accepts both text and image prompts, such as charts, graphs, screenshots, etc., which is critical to analyzing customer feedback. GPT-3.5 was primarily a text-to-text model.

• Multilingual Improvements: GPT-4 reads and writes in 26 languages, including low-resource languages like Welsh and Swahili, making global customer feedback a reality.

GPT-4 made Listen Labs possible.

The team has technical talent in their DNA. Florian Juengermann was a national champion in competitive programming in his home country, Germany. Alfred Wahlforss’s brother was a co-founder at Soundcloud. Some of their first hires included three medalists in the International Olympiad in Informatics (top 0.1% of programmers), a chess player with a 2000 ELO rating, and former Jane Street quants. In the past year, Listen has grown from 10 employees to around 24.

As the team has grown, so has the competition.

• In October 2025, Strella AI raised a $14M Series A to expand its AI powered customer research platform. The round was led by Bessemer Venture Partners, and customers include Chobani, Amazon, and Duolingo.

• In June 2025, Outset AI raised a $17M Series A to help enterprises scale customer research led by AI agents. The round was led by 8VC, and customers include WeightWatchers, FanDuel, and Intuit.

• In September 2025, Kepler raised a $3.4M seed round to conduct AI powered customer research interviews. The round was led by Kleiner Perkins, and customers include Clorox and Intercom.

Listen’s seed and Series A rounds were led by Sequoia Capital, and more specifically, Bryan Schreier, who was an initial investor in the customer experience platform Qualtrics. Their willingness to double down on the investment in such a short timeframe is a positive signal to say the least.

The company has a number of impressive customers including Robinhood, Nestle, Microsoft, UFC, and Canva. Some of these customers pay Listen $1M a year.

In Q4 2025, Listen quietly raised a $69M Series B led by Ribbit, in an unannounced round of funding to leapfrog over the competition. The company officially announced the raise yesterday.

An investor involved with the round says it got done at a $500M - $600M+ valuation.

Be on the lookout for their unicorn round in due time.

Listen Labs’ early success is an excellent reminder that our biggest problems are simply opportunities in disguise.

sometimes you just need to

shut up and listen.

Full January Watchlist.

Delve

• Company Overview: Delve automates compliance for startups, namely SOC-2, which allows founders to get to revenue faster. The company announced profitability in the summer of 2025 and boasts of customers like Lovable, Bland, and WisprFlow. The platform is designed to get companies audit-ready in a matter of days rather than months.

• Founders: Karun Kaushik - MIT dropout and Y-Combinator W24 founder; Selin Kocalar - MIT dropout and Y-Combinator W24 founder

• Investors: Insight Partners, General Catalyst, Soma Capital, Y-Combinator

• Amount Raised: $35M+ (Series A stage)

• Headquarters: San Francisco, CA

Fundamental Research Labs

• Company Overview: Fundamental Research Labs (fka Altera) is on a mission to build digital human beings. The company has an interesting organizational structure with separate teams building multiple AI applications in different fields: a prosumer team building apps, a core research team, and a platform team. Their most notable product launched so far is Shortcut, an AI agent that creates spreadsheet financial models and beats Goldman Sachs + McKinsey analysts head-to-head 89% of the time, even with the analysts getting 10x as much time to complete tasks.

• Founders: Dr. Robert Yang - an MIT assistant professor that spun Fundamental Research Labs out of an applied research lab at MIT; Nico Christie - a former professional dunker and MIT Sloan MBA dropout; Andrew Ahn - an MIT PhD and former Ivy League professor; Shuying Luo - an ex-Google software engineer

• Investors: Prosus, Patron, First Spark Ventures, a16z speedrun, Patrick Collison (Stripe co-founder)

• Amount Raised: $42M+ (Series A stage)

• Headquarters: Menlo Park, CA

Starcloud

• Company Overview: Starcloud (fka Lumen Orbit) is building datacenters in space to power the artificial intelligence boom, reducing associated electricity costs by 90% and generating 24/7 solar-powered efficiency. In early November the startup launched a satellite with an Nvidia H100 GPU into space, and in December the company’s Starcloud-1 Satellite ran and queried responses from Google’s open source large language model, Gemma.

• Founders: Philip Johnston - CEO of Starcloud, a University of Nottingham grad with a Wharton MBA, former McKinsey consultant and sold his last startup, Opontia, in three years; Ezra Feilden - CTO of Starcloud, an Imperial College London MS + PhD, an aerospace engineer with 7+ years of experience.

• Investors: Nvidia, Y-Combinator, NFX, Sequoia, a16z, In-Q-Tel (CIA)

• Amount Raised: $24M+ (seed stage)

• Headquarters: Redmond, WA

PreDoc

• Company Overview: PreDoc is solving one of the most painful problems that doctors have on a frequent basis: chart-chasing, or the manual retrieval of patient records. The company uses AI to automate medical record management and ultimately give physicians an extra day in the week through time savings, allowing practitioners to actually practice medicine.

• Founders: Nishant Hari - CEO at PreDoc, former derivatives trader at Citi, RBS, and HSBC, Kaushal Kulkarni - Chief Medical Officer at PreDoc, a Columbia BA and Rutgers MD, previously founded an eye-care startup that was acquired in 2024.

• Investors: Base10 Partners, Northzone, Eniac, Remarkable Ventures

• Amount Raised: $30M+

• Headquarters: New York, NY

Multiplier Holdings

• Company Overview: Multiplier Holdings is an AI rollup acquiring small accounting firms and deploying AI to improve margins and scale client growth. Their first acquisition was Citrine International Tax, a 12-person tax accounting firm that provides cross-border accounting services. One of the accountants at Citrine, Emily White claimed that “prior to Multiplier, I sent out 14 tax returns in a 14 hour day. This year I was able to send 24 tax returns in a 10 hour day…”

• Founders: Noah Pepper - CEO and founder of Multiplier Holdings, a Reed College graduate who previously sold his startup, Lucky Sort, to Twitter, before serving as Stripe’s APAC Business Lead.

• Investors: Lightspeed, Ribbit, SV Angel.

• Amount Raised: $28M+ (Series A stage)

• Headquarters: Singapore

OpenRouter

• Company Overview: OpenRouter is the unified interface for large language models - it gives over 2.5M developers a single API to access all the models, 400+ to be precise. Developers love the ability to switch between models, making gametime decisions on whether to optimize cost, latency, or performance. OpenRouter’s public LLM rankings board has now become a staple in the developer community, rivaling LMArena ($1.7B valuation) and other competitors. Menlo Ventures and Andreessen Horowitz led the $40M Series A back in June 2025.

• Founders: Alex Atallah - OpenRouter co-founder and CEO, Stanford BA, founder of OpenSea NFT marketplace; Chris Clark - co-founder and COO, Vanderbilt BS, co-founder and CTO of Grove

• Investors: Menlo Ventures, Andreessen Horowitz, Sequoia

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

• Headquarters: New York, NY

90% of startups fail.

Let that sink in for a second. Nine out of ten people who invest their blood, sweat, and tears into building a startup will eventually watch it collapse into dust.

Most people hear that stat and run the other way. Chase Edmonds looked at those odds and thought: “I’ll take those chances.”

After eight NFL seasons, he could have simply followed the traditional athlete playbook: sign a few endorsement deals, throw some money into index funds, or buy some rental properties. All safe, proven, and predictable ways to grow his wealth.

But instead of stopping there, he decided to build a startup.

Not advise one. Not invest in one. Build one. From the ground up. With his own money. Fully aware that he could lose every dollar he put into it.

Earning the Right to Earn

Ask Chase why he chose the business world’s equivalent of a Hail Mary, and his answer shows why he’s different.

“If you’ve built a startup, you can pretty much do anything after that. There ain’t nothing more difficult than building and competing in tech,” he claims.

Truth is, Chase is playing an entirely different game. While most athletes focus solely on financial returns, he’s optimizing for something he believes to be more valuable at this stage of his life: an education that would pay dividends for the next few decades.

Startups are risky, and he knows the odds are against him. But he’s not just betting on his startup - he’s betting on himself.

Think about it. Convincing investors to write him a seven-figure check? That’s sales at its highest level, the kind of skill that translates to any business. Managing a team through the emotional rollercoaster of building something from nothing? That’s leadership skills he can take to any boardroom.

“The way I see it, this is my investment in myself,” he explains. “Even if it fails, I’ll bring everything I learned to whatever I do next.”

For Chase, building a startup is like earning an MBA. But instead of sitting in a lecture room analyzing decade-old case studies, he’s in the trenches learning from real-world experience where every decision he makes has real consequences.

If his startup succeeds, he’ll earn millions, and maybe even billions. If it fails, he’ll earn the most valuable currency in business: experience.

Finding His Billion-Dollar Problem

The idea for Chase’s startup came from his own travel frustrations. When traveling for games, Chase kept running into the same problem: finding places that match his vibe was unnecessarily complicated.

During away games, Chase often found himself scrolling through endless lists and reviews, wasting hours every time. Every app sucked. Google search results felt generic. Yelp reviews were unreliable. YouTube videos were scattered all over the place. The entire discovery process felt broken.

“In the digital age that we are in right now, I can travel anywhere in the world and my phone should be able to give me personalized recommendations,” he explains. “My phone collects so much data on me, but everything feels so disconnected.”

His solution? Sceene, an app that actually gets him. “It’s TikTok’s content discovery meets OpenTable’s venue booking,” Chase explains. It syncs with your network, remembers your favorite spots, and delivers recommendations that feel hand-picked. It’s like your phone knows your vibe before you do. Instead of drowning in hundreds of random options, he wants to touch down in a new city and have his phone say: “Here are five places you’re absolutely going to love.”

The leap from NFL player to first-time entrepreneur hasn’t been easy. For the past few years, Chase has been juggling two full-time careers: NFL player by day, founder by night. “I built a good team around me, and I approach my startup the way I approach football, with focus and discipline,” he says.

But today, the balance has shifted.

When a season-ending injury sidelined him 2024, it unlocked a new obsession. “I couldn’t stop thinking about solving this travel problem,” he recalls.

Before signing with the Washington Commanders in late 2025, Chase had been channeling the bulk of his energy into building an app in a space dominated by tech giants. Along the way, he’s collected five hard-earned lessons from choosing the toughest path possible - lessons that could give athletes a head start if they decide to step into the world of startups.

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Lesson #1: Let Your Users Call the Plays

Chase was at a business conference in Las Vegas, pitching his app to a potential user. He was walking her through all the features he’d built. But it wasn’t resonating, until he mentioned they were offering Uber vouchers to a specific nightclub for first-time users.

Her eyes lit up: “Oh, so you guys are like a transport company!”

That wasn’t what he wanted to be. But that was the perception at the time. That moment hit Chase hard: it doesn’t matter what you think your product is - what matters is what your users think it is.

He realized that product development isn’t about building the perfect features. It was about putting something real in front of users and watching how they behaved. “I wish I had launched sooner,” he admits. “I had this mindset of, ‘Give me 8 hours to chop a tree, and I’ll spend 7 sharpening my axe.’ That worked in football. But in startups, you can’t be a perfectionist.”

He started with athletes who shared his travel frustrations, then expanded to business travelers. Each group taught him lessons he couldn’t have learned if he’d bought into the fairytale that startups are built in a garage.

Launch fast, get feedback, adapt - that’s his mantra now.

“At the end of the day, you can’t get too emotionally invested in your ideas and ignore what users actually want,” he says. “You’ve got to see things from their point of view.”

Chase learned this lesson by watching his product take on a life of its own in the hands of real users. At times, it meant being called a “transport company” even when he envisioned something entirely different. It was a humbling reminder for him: the product vision may start with the entrepreneur, but it ends with the user.

Lesson #2: Turn Your Brand Into a Distribution Advantage

There’s a saying in the startup world: first-time entrepreneurs obsess over product, second-time entrepreneurs obsess over distribution.

Chase agrees. Even as a first-time entrepreneur, he’s learned quickly that the difference between success and failure isn’t just about the product you build, it’s about how effectively it reaches the people who need it.

After all, Facebook wasn’t the only social network, Uber wasn’t the only ride-sharing app, and ChatGPT wasn’t the only AI tool. What set them apart was superior distribution.

“Distribution can be a moat,” Chase explains. “There are so many apps out there, and if you don’t have a way to stand out from the crowd, you’re going to be just one of the thousands of apps in the app store.”

For Chase, his NFL credentials became his unfair distribution advantage, but not in the obvious way. He didn’t just lean on fame. Instead, he used his understanding of the hospitality industry and his network to strike partnerships with local venues in different cities.

Take his partnership with TAO Group Hospitality in Las Vegas. While most startups were burning cash on Google and Facebook ads, Chase leaned on a simple but clever strategy: “For every person who downloads our app at a conference, we’ll send them an Uber voucher straight to their nightclubs.”

The results were immediate. Conference attendees enjoyed free rides. The nightclubs saw a steady stream of customers without paying for ads. And Chase? Hundreds of app downloads per day - all at a fraction of the cost of traditional advertising.

“Relationships are key,” Chase emphasizes. “My network and influence as an NFL player helped me get strategic partnerships that others couldn’t.”

But what most athletes miss is that they can’t just show up as “the famous guy” and expect deals to happen. Chase spent time learning the ins and outs of Las Vegas nightclubs - traffic patterns, spending behavior, and what owners truly care about. His NFL credentials may have helped open the doors, but it was his business acumen that helped closed the deals.

Lesson #3: Hire Missionaries, Not Mercenaries

“If I could go back in time and do one thing differently, it would be to fire faster and hire slower,” Chase says.

For him, early hires don’t just work for the company - they become the company. They define the culture and set the bar for everyone who comes after. Get it wrong, and the cost isn’t just payroll - it’s momentum, morale, and sometimes years of progress.

At first, Chase focused purely on skills. Logical, right? Hire the best and success will follow. But over time, he learned something counterintuitive: “I’d rather hire someone who’s a 6 out of 10 on skill but 10 out of 10 on heart.”

Why? Because heart drives work ethic. And work ethic shows up when the going gets tough.

“It’s not the size of the dog, it’s the size of the fight in the dog,” Chase explains, a mantra he’s carried since college football. “Most days are a grind. Heart determines who sticks around when we have setbacks.”

Today, much of Chase’s job is about putting the right players on the field - assembling a team that shares the same mission, can execute under pressure, and adapts to challenges. His hiring framework now focuses on three key questions:

• Do they genuinely believe in what we’re building?

• Can I have open and honest conversations with them?

• Will they have the grit to push through difficult situations?

Everything else can be taught.

Above all, Chase looks for missionaries, not mercenaries - the kind of people who buy into the mission so deeply that they’ll give their all, even when the outcome is uncertain. Because in the early days, a startup lives and dies by its people - and they’re often the difference between landing in the 10% that make it or the 90% that don’t.

Lesson #4: Find Smart Capital

Early on, Chase approached investors with “the perfect pitch deck” - every scenario mapped, every assumption justified, every risk accounted for. He thought he was bulletproof.

Turns out, it was working against him.

“Investors are looking for reasons not to invest,” he realized. “The more information you give them, the more reasons they can find to say no.”

From an investor’s perspective, there are literally millions of ways a startup can fail. That five-year financial projection suddenly looks risky. That detailed competitive analysis now raises doubts about differentiation. Every line meant to impress just gives investors a reason to say no.

So Chase learned to flip the script. He stripped his pitch deck down to what actually mattered: the problem he was solving, why he was uniquely positioned to solve it, and the early signs that people actually wanted what he was building. Clean, focused, compelling.

“Less is more,” he discovered. “Give them just enough to get excited, then let the conversation fill in the details.”

But that was only part of the lesson. Over the years, Chase realized that who writes the check matters more than the check itself. Some investors only offer capital; others become connectors and mentors who help navigate the minefield that trips up first-time entrepreneurs. He calls the latter “smart capital” - funding that comes with boosters that can help accelerate a startup’s growth.

Looking back, those early rejections were gifts in disguise. Each “no” forced him to sharpen his pitch and focus on the investors who could actually help him win. Now, Chase approaches fundraising like free agency: he’s showcasing his skills, experience, and upside while evaluating which investors give him the best chance to succeed.

Lesson #5: Experience is the Greatest Teacher

Here’s what most people don’t realize when they first think about building a startup: you don’t know what you don’t know. And the gap between expectation and reality? It’s massive.

Chase doesn’t sugarcoat it. “Zero-to-one is tough,” he admits. “90% of the things you do aren’t going to go as planned. But you gotta fail to learn, and you just keep your head down and keep grinding.”

It’s the same mindset he carried through the NFL. Hours in the film room, extra reps after practice, conditioning in the offseason that no one sees - those are the things that separate players who make it from players who don’t. The same is true in startups.

In the early days, he read everything he could get his hands on. Peter Thiel’s Zero to One became his blueprint for thinking about competition and distribution. He reached out to mentors, like former teammate Larry Fitzgerald, who connected him with early Google employees to learn from their experience.

But even with all that preparation, Chase quickly realized there’s a world of difference between studying the game and playing it.

That’s where his background as an athlete gave him an edge. Years of performing under pressure, bouncing back from failure, and showing up consistently every day created a quiet advantage - one that translates perfectly to startup life.

Whether on the field or in a startup, Chase knows the rule: studying the game only goes so far. The lessons only stick once you step onto the field and experience it firsthand.

Tying It All Together

Chase’s journey from NFL player to first-time entrepreneur is a case study in embracing uncertainty. In retrospect, he doesn’t know how he had the courage to build a startup, just that he did, and that it’s the hardest game he’s played off the field.

Whether Sceene becomes the next billion-dollar company or simply a valuable learning experience, he’s building the kind of wealth that can’t be measured in dollars, at least not right away. From launching products faster and building distribution advantages, to hiring the right people and finding smart capital - every lesson has been earned through real experience.

Chase is living proof that athletes don’t have to be passive capital allocators watching from the sidelines. They can be builders too.

For athletes considering entrepreneurship, his message is simple: startup life isn’t easy, the odds are stacked against you, and failure is part of the game. But the lessons and the growth? They become the foundation for every opportunity that follows. And sometimes, the hardest game off the field is also the most rewarding.

Want the inside scoop on Chase? Catch him on LinkedIn, Twitter, or Instagram.

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No one knows the business of college sports like Parker Graham.

The former undrafted Baltimore Ravens lineman commands attention when he walks into the room; at 6’8 with an athletic frame, no one looks at Graham and thinks of him as a startup founder.

But for the last seven years, Graham has been in the trenches building fintech products with Silicon Valley whiz kids. First, as the founder and CEO of Finotta, a digital banking startup that raised $3 million from one of his early customers. Now, as the founder and CEO of Vestible, a startup creating an investible asset class out of college athletic departments.

To say Graham is an expert on the current state of college sports business would be irreverence of the highest degree; he is an obsessive student of the game with no other interest. If you ask him about NIL donor sentiment, he will give you the ten year history lesson on how we got here. Drop him a question about how investors can make sports IRR add up and prepare for a masterclass in capital markets calculus. When it comes to the business of college sports, Parker Graham is a fearless competitor consumed with passion for value creation.

Naturally, when we wanted to understand more about the University of Utah deal, Parker was our first call.

Below is the edited transcript.

Utah, quite recently, announced a $500M landmark transaction that broke the seal for college sports deals. What was your reaction to the deal?

Parker Graham: I’ve been very blessed in the sense that I have a lot of insider access on not only the Utah deal, but other deals that are forming right now. The reported numbers for the Utah deal don’t make a whole lot of sense to be fully transparent. Just from a private equity math perspective, I think what’s been reported is a little bit obfuscated and I think that we’re probably going to get some more details around what the actual transaction was. The $500 million number, I don’t know if that’s actually a total number, or if it’s an achievable number like they’re going to scale up to that, or if it’s a combination of the directed capital that’s invested plus the growth that they think they’re going to achieve.

For $500 million they would need to be giving up roughly 45% of their revenue. Even with the seven-year time frame, I don’t know if you can get Utah to the revenue number that you would need to to make the money back and make your IRR with that transaction. Now, what I think they did a really good job of though, is giving donors access to that investment. That was genius. I really think giving donors, those long-term stakeholders, a seat at the table was the smartest move that they did. It’s what we’re doing at Vestible, right? So that’s totally in our ethos.

I think that was really smart because that gets buy-in. Now the donors are excited. Now the board of trustees is excited. I think you’re going to see that transaction get replicated in a lot of different ways. And also, you finally have a group that kind of broke the dam, right? I don’t think it’s an accident that the Big 12 immediately announced that they were going to be doing a deal with Weatherford Capital and Redbird. I would be willing to bet we’ll probably have six college sports deals within the first half of the year. And not just the revenue internally to the institution, but you’re going to see a lot of asset deals as well where stadiums are getting built and renovated through these private and public partnerships.

A lot of NIL discussions lately have been around “donor fatigue”. How real is donor fatigue and how much is it driving the search for alternative capital sources?

Parker Graham: You’re being asked to give more money into your school’s ecosystem, but there are only so many wins to go around. And so if you’re doing that and also Alabama’s doing that and Notre Dame’s doing that, eventually we have 12 teams that go to the playoff and that’s the 12 teams that go to the playoff. Over the last couple of years, that’s just gotten harder and harder because you’re asking not only for the same amount of dollars that that donor gave last year, but now you need more because, well, we didn’t win and we need more so that we can win. We didn’t win in basketball or football or baseball or whatever the sport is that you were trying to raise capital for.

Now that donor is looking at you like, well, I just gave you that money last time and it didn’t get us anything. You know, we didn’t even get to keep the player that I paid for. If you saw the Troy Aikman quote that came out last month, he was talking about the fact that he gave money to UCLA for a player and the player left and it’s like you get nothing in return for that. If you’re a business owner and you think in ROI terms, the ROI on that is zero. That’s really what donors are frustrated about. The donor model at the athletic department level just doesn’t work the same as it has over the last hundred years.

You have to create a new vehicle to generate the revenue that you need to put talent on the field, and it can’t just come from, you know, four check writers at your institution. Now, some schools are very blessed - Michigan State just raised $400 million from one donor. KU had David Booth who gave them $300 million. So, if you have those guys walking around, you’re actually okay. But 95% of schools don’t, and they’re beholden to those donors that they do have, and those donors are tired of not getting ROI. That’s why, moving back to private equity, these deals actually make sense to the donors; they’ve been giving money for really just a tax benefit at the end of the day.

They get a 37% reduction in their taxes for every dollar they donate. But now they’re going to get the 37% discount with their donor dollars, and, when they put investor dollars in, they’re going to be getting their investment returns as well. This is a brand new channel that we’re trying to open up at Vestible and that the Utah deal tried to open up in their transaction. This is an extremely viable path to creating sustainability in college athletics. You have the people who went to school there funding the school and getting returns from their funding. You’re still getting donor dollars because those folks still need donations. They still need the tax deduction, right? They still need the tax benefit. But by incorporating them in the actual investment stack on the equity side of the transaction, it’s incentivizing them to keep giving you more money because they’re getting ROI whether you win or lose.

When you think about ways to make the pie bigger in college sports, do you think tech companies could eventually get active in this media rights space?

Parker Graham: These giant corporations - Amazon, Twitter, Netflix - are looking for attention at all times. Where’s the only place where attention is 100% going to show up? On Sunday night, if you’re a Chiefs fan, you’re watching the game. On a weekday, if you’re a Knicks fan, if you’re not at the Garden, you’re going to watch the game. There’s no other media property in the world where that exists. And so I think it’s a natural next step for any of these attention driven platforms with plenty of cash on hand.

The economies of scale are just so much better there…Think of the younger demographic that the NBA and the NFL are trying to reach and what platforms they’re watching on. When you think about how to generate more value as a conference or as a team, it’s by doing something that nobody’s ever done. I would love to see the entirety of the G5 (AAC, MWC, C-USA, SBC, MAC) throw all of their their media rights together and do a massive deal with a tech company like YouTube where you have like 60 teams that are in a quote unquote conference and you’re just providing something so different than what you know the SEC is doing than what whatever anybody else is doing.

Shifting gears away from college sports, what do you think about the influx of emerging sports leagues?

Parker Graham: Unrivaled is a great example of an emerging league that seems to be a way better option than the WNBA purely because of how that league is constructed versus the WNBA. It’s just a better model. It is what it is. If you put all the players from the WNBA into Unrivaled, the WNBA will die because Unrivaled is clearly a better construct and built for this new century and this new viewership. The USL vs. the MLS is another great juxtaposition between leagues.

The USL is a completely different structure than what MLS is. MLS and NWSL have kind of copied the NBA and WNBA model… On the other hand, it seems like the USL is going to be really interesting over the next 10 years with their relegation and promotion structure, which the MLS doesn’t have.

There are some actual startup leagues that I’m actually weirdly obsessed with like Power Slap from Dana White and RUNIT league, an Australian rugby type deal where it’s literally just two guys sprinting at each other. They take the most viral part of a game and monetize that over and over and over again. Instant eyeballs. You watch any of those videos, it’s like, oh my gosh, I can’t stop because it’s just so jarring. They knock each other out. Very similar concept to what Dana’s doing with Power Slap - capture attention and create unforgettable moments.

Anywhere that you can grab somebody’s attention and monetize that attention the moment that you have them, that’s valuable when done right. Getting back to your question, what you’re going to see is a lot of these a lot of these leagues start to develop and generate revenue because they grab attention way better than a 4-hour long baseball game did or a three-hour football game or, you know, a a regular season NBA game where really, unless you’re watching the Thunder right now, the NBA is not a great watch for three hours on a Tuesday.

What predictions do you have for 2026?

Parker Graham: Like I mentioned earlier, I think we’re definitely going to see six college sports private equity deals done. I hope we’re one of them. Even though we’re not technically private equity, I hope there’s a deal that takes place.

I think what we’ve seen this past year with parity in college athletics, because of revenue sharing, I think you’re going to continue to see teams like Vanderbilt, teams that are non-traditional powers dominate certain sports. Especially with men’s basketball and men’s football. I think you’re going to see a non-traditional power win the national championship next year in football… The parity is going to be at an all-time high.

Number three, there’s a lot happening with the NCAA right now from a public policy standpoint. There are three acts right now in Congress that are going to determine the future of college athletics. It’s the SAFE Act, the Score Act, the Protect Act, and there might be a fourth one now with the Restore Act. You’re going to see a massively impactful piece of legislation come out from Congress in 2026. I don’t know which one it’s going to be. I think all of them have pros and cons… But something’s going to come down from the federal government that’s going to rein in a lot of the chaos.

Keep up with Parker on LinkedIn, Twitter, or visit Vestible’s website to learn more.