How I Invest with David Weisburd
E163: How Thiel Fellows Build Billion-Dollar Startups w/Zaid Rahman
13 May 2025
Zaid Rahman is the founder and CEO of Flex, a breakout fintech startup that’s reinventing credit and payments for the middle market. Backed by the Thiel Fellowship and known for his “Delta 4” product philosophy, Zaid is building a multi-product platform that’s helping profitable, owner-operated businesses unlock capital and scale faster. In this conversation, Zaid breaks down how Flex is using AI to radically reduce underwriting time, why he’s obsessed with hiring 10x talent, and how “taste” and first principles thinking guide everything from product design to risk management. If you’re building in fintech, hiring in tech, or just obsessed with the craft of company-building, this episode is full of tactical insight.
Full Episode
Something like 10% of TL followers have started billion-dollar-plus companies. A third of them have started companies valued over $100 million. Some of the best companies in the last 10 years have come out of the fellowship, including things like Figma, Loom, Luminar, OERooms, Ethereum.
Today, I'm excited to welcome Zaid Rahman, founder and CEO of Flex, the fintech super app transforming financial management for small businesses. A serial entrepreneur and Teal Fellow, Zade has recently raised capital at a $225 million valuation in order to build an all-in-one platform that bundles credit, banking, payments, and expense automation for business owners.
Without further ado, here's my conversation with Zade. You were part of this very elite fellowship, Peter Thiel's fellowship, which is over 10 times more difficult to get into YC, which itself is elite. Tell me about that program and tell me about your experience.
Peter Thiel started the Thiel Fellowship now 12 years ago or so. The idea was that, you know, he would select 20 people every single year and give them 100 grand with no conditions except one that he had to drop out of college. At the time, it sort of started as a kind of like a social experiment. Over time, it sort of scaled into this much bigger thing.
Something like 10% of TL followers have started billion-dollar-plus companies. A third of them have started companies valued over $100 million. And so the program itself is doing fantastically well. Some of the best companies in the last 10 years have come out of the fellowship, including things like Figma, Loom, Luminar, OERooms, Ethereum, and so on and so forth.
And so it was sort of an awesome experience just being part of that. And from my kind of vantage point, I like to sort of joke that I'm the least sort of qualified person in the room when I'm around these guys, because to me, it's sort of been just about surrounding myself with the right kind of peers. And the fellowship just comes in with this amazingly elite group of people that
kind of all very driven to be extremely ambitious and kind of really change the way things are done. And so it's been an awesome sort of experience being part of that. Last time you were talking about this very specific way that you use the fellowship in order to scale Flex and to solve problems. Tell me about how you benefit from the fellowship today.
The TL Fellowship has this amazing group of 285 people. And so, you know, a couple of years ago, I thought it was crazy that we were not all in a WhatsApp group together. And so I created a little group chat and that became pretty successful. I think the group chat is like 250 of the 300 or so fellows now.
And in that context, you know, if you go on the group chat, I mean, even right now I can see it on the side. There are people talking about all sorts of problems that they're running across. Just yesterday, someone mentioned that, you know, they're going through an M&A and there's a difficult investor and, you know, they're giving them a hard time, you know, in the M&A process.
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