Watchlist: February 2026 Edition.
this Thiel Fellow just bicep curled $60M without breaking a sweat. five startups to scout this month.
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
