How to bet on yourself (without venture capital)
William Hockey, founder of Column (a software company that owns a bank), shares how he built a massive fintech business without raising venture capital. His key insight: constraint breeds creativity. He travels to emerging markets like Kinshasa to escape Silicon Valley's consensus thinking, discover
1h 17mKey Takeaway
William Hockey, founder of Column (a software company that owns a bank), shares how he built a massive fintech business without raising venture capital. His key insight: constraint breeds creativity. He travels to emerging markets like Kinshasa to escape Silicon Valley's consensus thinking, discovering that the most innovative financial services often emerge in the world's most constrained environments. By owning 100% of his company and growing through earnings, he can make 10-year bets that VC-backed companies can't afford—like buying a regulated bank and investing in it for 2-3 years before taking on clients.
Episode Overview
William Hockey discusses building Column, a software company that owns a bank, serving major fintech companies like Built, Wise, Ramp, and Brex. Unlike typical startups, Column is entirely self-funded and employee-owned, allowing for long-term strategic decisions that VC-backed companies cannot make. Hockey emphasizes the importance of escaping Silicon Valley's consensus thinking by traveling to emerging markets, where constraints drive innovation. He explains how operating profitably while maintaining aggressive growth creates unique advantages in talent retention and product development.
Key Insights
Constraint Breeds Innovation in Emerging Markets
The most innovative financial services often emerge in the world's most constrained environments. In emerging markets like Kinshasa or Iran, necessity drives creative solutions that wouldn't be considered in abundance-focused Silicon Valley. For example, Africa pioneered mobile payments decades before Venmo existed because constraints forced them to leapfrog traditional banking infrastructure.
Silicon Valley's Consensus Problem
San Francisco and Beijing are the two most consensus-driven societies in the world. While this creates safety for building emerging technologies like AI, it also creates dangerous blind spots. Silicon Valley has lost touch with how everyday Americans and the rest of the world operate, building elite software for elites rather than solutions for broader populations.
VC Money as Addiction
Venture capital creates a dependency cycle that prevents long-term thinking. Once you raise $100 million, you're on a hamster wheel of constant fundraising, optimizing for the next round rather than building the straightest path to your goal. Companies end up chasing whatever is 'cool this year' (stablecoins, AI) rather than executing a consistent vision.
The Hidden Costs of Dilution
Early-stage founders typically lose 50-75% of their equity value through dilution alone, plus potentially 10-80% more through preference stacks. Most founders don't understand these economics until 5-10 years in or after an exit. By remaining self-funded, Column employees face zero dilution and can receive liquidity through annual tender offers.
Emerging Markets Offer Differentiated Talent
While developed markets have companies like Anthropic and Google competing for top talent, emerging markets have equally talented people with fewer options. In places like Congo, smart engineers join banks or breweries because there's no local Anthropic to work for. This creates opportunities to access world-class talent that wouldn't be available in Silicon Valley.
Notable Quotes
"VC money is kind of like heroin. It like feels good. It's amazing, but like you got to keep shooting up. Like it's very challenging to get off."
"San Francisco is probably the most consensus place I've ever been to. And I think that is both a huge clutch for us, but it's also probably our most valuable asset because as a founder, if you're building in like, I don't know, like AI or like stable coins or something that San Francisco believes is very consensus, but the world does not believe yet, that's actually a great operating environment."
"If you are having to spend a lot of money for employees and you're you're burning a rate of you have to raise every like year, year and a half, you end up optimizing for that next fund raise and you say, 'Okay, stable coins are like cool this year, so I need a stable coin strategy. Okay, AI is cool this year because like I need an AI strategy.'"
"Financial services tend to be most innovative and most progressive in like their worst countries. You can see this in Argentina. You can see this in Iran."
Action Items
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1
Escape Your Consensus Bubble
Regularly travel to or study environments completely different from your own to identify blind spots in your thinking. Hockey generates 90% of his best ideas either in the shower or walking through emerging market cities because these experiences expand his perspective beyond Silicon Valley consensus.
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2
Evaluate True Equity Value, Not Just Ownership Percentage
When evaluating job offers or equity compensation, calculate the impact of dilution (typically 50-75% for early employees) and preference stacks (10-80% of upside). Smaller ownership in a profitable, non-diluting company may be worth more than larger ownership in a VC-backed company.
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3
Build for Constraints, Not Abundance
Look for problems in constrained environments where traditional solutions don't work. These constraints often force more innovative, efficient solutions than building for abundance-focused markets where every option is available.
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4
Target Second-Time Employees
When building a company with an unconventional structure (like being self-funded), recruit people who have experienced the VC cycle once. They understand the nuances of dilution and preference stacks and can better appreciate alternative models. New grads optimize for consensus signals rather than economic fundamentals.