Mar 17, 2026 · 1h 17m · invest-like-the-best
How to bet on yourself (without venture capital) · Invest Like The Best
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In this episode of Invest Like The Best, host Patrick O'Shaughnessy interviews William Hockey, founder of Column and co-founder of Plaid, discussing how to build an enduring financial technology company without traditional venture capital. Hockey shares contrarian insights on self-funding, global U.S. dollar infrastructure, avoiding Silicon Valley consensus, and finding massive operational leverage in obscure, highly regulated industries.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Patrick holds 18.2% of the talking time here. How this is scored →
Patrick as informed peer 4.3 Guest teaching 6.4 Guest disagreement 3.0 Patrick pushing back 0.1
speaking balance: gold is Patrick, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 34:45 Scathing take on founder risklessness
William forcefully challenges prevailing Silicon Valley norms, asserting that starting companies has become far too safe and early-stage founders take negligible personal risk compared to their employees.
Hardest push from Patrick ▶ 27:59 Challenging the self-funding narrativePatrick directly pushes back on William's bootstrapping thesis by questioning whether self-funding Column was only feasible because William was already extremely wealthy from Plaid.
Biggest teaching moment ▶ 1:03:15 Dismantling legacy banking tech mythsWilliam educates listeners by dispelling the popular tech talking point that Fed systems are slow or obsolete COBOL mainframes, proving that the infrastructure already handles instant 24/7 settlement.
Patrick holds their own ▶ 37:30 Economic framing of employee compoundingPatrick builds on William's thesis with a precise financial analysis, noting that building what you own is inherently the highest-leverage investment due to the friction and taxation of capital withdrawal.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Patrick as informed peer | Guest teaching | Guest disagreement | Patrick pushing back | Why |
|---|---|---|---|---|---|---|
| Understanding Column: Software Company with a Bank | 4 | 5 | 1 | 0 | Patrick sets the stage by asking William to break down Column's unique hybrid model of software and banking infrastructure. William explains Column's core mechanics and revenue structure clearly. | |
| Emerging Markets and Escaping Silicon Valley Consensus | 3 | 6 | 3 | 0 | Patrick asks about William's unconventional travel habits to places like Kinshasa. William contrasts the intense constraints of emerging markets with the consensus-driven bubble of Silicon Valley. | |
| Financial Services Leapfrogging & Global Dollar Demand | 5 | 7 | 2 | 0 | Patrick engages on leapfrogging in emerging markets and mentions Kaspi. William explains how international banks in constrained environments out-innovate Western banks due to talent allocation and verticalization. | |
| The Elite Bubble and Consensus Culture of Silicon Valley | 4 | 6 | 4 | 0 | Patrick prompts William to expand on Silicon Valley being as consensus-oriented as Beijing. William delivers a critical critique of elite echo chambers building exclusively for other elites. | |
| Sponsor Advertisements: Ramp, Rogo, and WorkOS | 5 | 5 | 3 | 1 | Patrick reads mid-roll sponsor spots and then kicks off the discussion on self-funding and avoiding venture capital. William explains how avoiding the VC hamster wheel enables true long-term decisions and employee share buybacks. | |
| The Hidden Truth: Debt, Margin Calls, and Extreme Risk | 4 | 7 | 2 | 1 | Patrick challenges the narrative by asking if self-funding was only feasible because William was already rich. William dispels this misconception, revealing he financed Column with debt, pledging over a billion in illiquid stock and nearly getting margin called multiple times. | |
| The Safety Trap of Modern Startup Culture | 4 | 7 | 6 | 0 | Patrick asks about the psychological impact of surviving near-bankruptcy. William delivers a scathing critique of modern startup culture, arguing that early-stage founders take virtually no real risk while asking employees to sacrifice significantly. | |
| High Concentration, Self-Betting, and Becoming a Specialist | 5 | 6 | 3 | 0 | Patrick observes that building what you own is often the most compounding investment. William explains his extreme portfolio concentration and how being a deep specialist in unsexy domains yields unfair advantages. | |
| Finding Leverage in Boring Niches | 5 | 7 | 3 | 0 | Patrick explores the challenge of maintaining focus amidst hype. William explains how deep value is generated by tolerating tedious, obscure research that cannot simply be summarized by AI tools. | |
| Value of Founder Experience and Failing Forward | 4 | 6 | 2 | 0 | Patrick asks about differences between first-time and second-time company building. William discusses how learning on someone else's dime saves years of costly dilution and outlines how he evaluates talent archetypes. | |
| The Role and Misconceptions of Company Mission | 5 | 7 | 4 | 0 | Patrick asks about the importance of mission and margins in tech businesses. William downplays corporate mission hype, stating customers only care about product value, and explains why high margins and cash reserves ensure corporate survival. | |
| Sponsor Advertisements for Vanta and Ridgeline | 4 | 6 | 2 | 0 | Following sponsor advertisements, Patrick asks what advice William would give founders regarding venture investors. William explains the mathematical mismatch between standard venture fund return requirements and sustainable multi-billion-dollar revenue growth. | |
| The Global Dollar System and U.S. Economic Dominance | 4 | 7 | 3 | 0 | Patrick asks for non-obvious insights gained from operating within the global dollar ecosystem. William details how global trade routes, even between geopolitical rivals like China and Russia, remain deeply reliant on U.S. dollar clearing rails. | |
| Financial Services as a Tool of National Security | 5 | 7 | 3 | 0 | Patrick inquires whether national security is explicitly part of Column's internal ethos. William articulates how financial sanctions act as America's non-kinetic weapon and why financial infrastructure is as vital as traditional defense contractors. | |
| The Future of Financial Infrastructure and Federal Reserve Technology | 4 | 8 | 4 | 0 | Patrick asks about the future evolution of financial infrastructure. William debunks the myth that Federal Reserve systems are outdated, explaining that instant settlement already exists and operational bank constraints are the true bottlenecks. | |
| Value Accrual in the Age of AI and Distribution Moats | 5 | 7 | 3 | 0 | Patrick explores the broader landscape of AI and financial services. William argues that value will accrue to entities with massive distribution and fat cost structures, comparing AI's economic dynamic to Standard Oil benefiting from the railroads. | |
| Entrepreneurship Today and Non-Consensus Opportunities | 4 | 7 | 5 | 0 | Patrick asks whether now is a favorable time for new entrepreneurs. William suggests contrarian founders should avoid crowded AI requests-for-startups lists and instead target lucrative, uncompetitive industries. | |
| Resilience, Risk-Taking, and Lessons from Parents | 4 | 5 | 1 | 0 | Patrick closes with his traditional question regarding kindness. William reflects on how his parents allowed him to experience hardship and failure, giving him the resilience necessary to endure extreme entrepreneurial risk. |
Statements from this episode (37)
Column generates over 90% of its revenue from software, not banking
“We are technically a bank, but unlike banks, we make 90 plus percent of our money off of software. And so similar to a, any kind of SaaS company, it's a per API call. It's a, Pure play tech business. And then we pass most of the economics and the actual banks …”
San Francisco's hyper-consensus culture creates a safe environment for outlandish bets
“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 because you can go and you can ha…”
Kinshasa will probably be the world's largest city in 5–10 years
“Kinshasa, which is the capital democratic Republic of Congo, It's gonna be the largest city in the world then in probably five to 10 years.”
The DRC has under 25% mobile penetration and under 5% banking penetration
“Like, take DRC, like, mobile phone penetration is still less than 25%. You know, banking penetration is, like, still less than five percent.”
Financial services are most innovative in the world's worst-off countries
“Financial services tend to be most innovative and most progressive in like their worst countries.”
Emerging market bank executives are vastly superior to their Western counterparts
“I'd say you take your like emerging markets, bank executive team, they're hands down is way better than I think probably what you see in the Western world.”
AI will cause domestic fintech and enterprise software to collapse
“One of our theses is like fintech is probably going to be like the last area that is somewhat maybe disrupted by AI. I think what you'll see is you'll see a collapse in like domestic fintech and enterprise software.”
Silicon Valley resembles 1990s Wall Street more than a 1950s research lab
“SF and Silicon Valley, like it's an elite dominated society, whether we like it or not. It's probably more akin to Wall Street in the 19 nineties than it is to what we want it to be, which is like, you know, a research lab in Cambridge in like the 19 fifties.”
Silicon Valley will dominate AI because research requires an insular, concentrated consensus
“If you look at AI, like, our research labs are doing fantastic. Because that's like a consensus oriented problem. If you take a bunch of people that are super smart and you like pretty much like blind off everything from the you and you can all talk and you ca…”
Silicon Valley's ability to build resonant software is at a historic low
“And so our ability to actually build software or have ideas or perspectives that really resonate is probably at the low point in the entire time I've been here.”
The venture capital hamster wheel prevents startups from being genuinely long-term oriented
“The hamster wheel of VC doesn't actually allow us to be long-term. Because if you are having to spend a lot of money for employees and you're burning a rate of you have to raise every, like, year, year and a half, you end up optimizing for that next fundraise.”
Column pays employees a $2,000 monthly subsidy to live near the office
“We pay employees like you, here's 2000 dollars a month to go to a rent or mortgage if you live two miles with the office.”
Column allocates 25% of annual earnings to buy back employee equity
“What we do every single year, we take 25% of our earnings and we just buy back our shares with employees. So we just run our own tender every single year.”
Early-stage founders typically lose 50% to 75% of their equity to dilution
“If you're an early stage founder, like you're going to lose probably 50 to 75% of your equity value due to dilution alone. You may lose 10 to 80% of your upside Buy the preference stack.”
Hockey pledged $1B in Plaid stock to borrow $70M to build Column
“I pretty much funded the entire company with debt. I went to a bunch of banks. And I said, here's a bunch of plaid shares. Like, please give me money. You know, I got like a, the best I got was like a sofa plus 10% loan at like five percent LTV. And so, you kn…”
Hockey nearly went bankrupt funding Column with a massive personal margin loan
“I got to pay off that loan a period of time, but in the process I practically got margin called three times and almost went bankrupt multiple times.”
Margin lending against private company stock is inherently a poor business model
“There's a reason that like margin lending and private companies is not is, is like not a great business because when you want to take collateral that stock, that's usually the exact time when you do not want to hold that private stock.”
Silicon Valley's safety net prevents the creation of truly great founders
“We've created this, like, incredible environment in Silicon Valley that it's really safe to start a company. And there's, like, a playbook, and you go through YC, and assuming you're, like, moderately competent and went to the right high school and college, yo…”
Early-stage startup employees take significantly more personal risk than founders
“Cause the weird thing is an early stage employee takes way more risks than early stage founder.”
The startup ecosystem should make failure much more expensive for wealthy founders
“I just think we need to, I think we need to increase the risk for founders. I think we need to make failure much more expensive. I think we need to say, Hey, you're a second time founding of liquidity, like put all of your money into that.”
Founder success hinges on finding the most boring topic interesting for decades
“So I think one of the best determiners for success of founders is can they find the most boring thing humanly possible interesting? And can they find that interesting over a multi-decade period?”
Value creation comes from dominating obscure niches, not chasing broad AI trends
“These are, like, generalist topics that I can probably find a thousand people that have, like, pretty, like, interesting, compelling ideas and can go pretty deep on that. But you can't create value there. You can create value if you're, like, I am the number o…”
Working at another startup for nine months would have saved Plaid three years
“If we would have just like worked at a company for like Nine months. Like, we probably would have saved, like, three years.”
Benefiting from mercenary employees requires a churn-and-burn startup model
“There's like the mercenary type, which is okay. Super smart, probably super pedigreed. And like, and really what they're doing is they are using your company as a launchpad for something else. They are using, they're using their company to like collect a bunch…”
Most enterprise software companies cannot effectively ingest huge amounts of capital
“And I think a lot of enterprise software companies, they cannot ingest like a huge amount of capital. Like if you give me like a billion dollars right now, I don't know if I grow it like, you know, a thousand times faster than I am right now. And I don't neces…”
The venture model only works with 30% growth on a billion-dollar base
“However, the venture model only works is if you can grow above 30% off of a 1,000,000,002 billion dollar base, and you have to like really look inside yourself and be like, does my model make sense for that?”
Unofficial cross-border trade between neighboring economies is actually closer to 90%
“If you look at the official stats like most economies spend less than 10% of their GDP trading with their neighbors.
and that's like been a big focus point of the OECD over, over, over the while.
But when you actually dig into it, like the unofficial trade th…”
China-Russia oil and gas trade remains overwhelmingly denominated in US dollars
“China's a big importer of Russian gas and oil.
It's kind of crazy to think about.
That trade is still denominated for a vast majority in the US dollar.”
Silicon Valley has shifted to actively embrace its national security role
“One of the best kind of shifts I think Silicon Valley has done is we now are like, Hey, like Silicon Valley, we take an active role in the national security of the country.
I, we didn't six, seven years ago, even though like America, like American society, Ame…”
Financial services and sanctions are the US military's first line of warfare
“Financial services is like, is a key pillar.
Like you can argue that financial services is like the first end to war to our country, right?
Like we start with sanctions.
We start on cutting them off from the US trade.
We start with that before we put boots on …”
The Federal Reserve moves money faster than crypto or stablecoins
“The Fed has a pretty good tech team. Like, their systems are actually pretty good. If you think about it, the U.S. Right now, through the Fed, has the capability to move money and to clear money through all these institutions, 24 seven. Faster than stablecoins…”
Community banks lack 24/7 transfers due to business models, not missing technology
“The reason why community banks can't send money 24 seven isn't because, like, the technology doesn't exist at the Fed. It's because there are constraints in those business models that make it very challenging of them to do.”
Long-term economic value will probably not accrue to standalone AI companies
“I actually don't think like quote unquote AI companies are Very set up for success. That's actually probably not where value is going to accrue.”
Inefficient legacy brands will be the primary beneficiaries of AI
“Like hot take here, I think like the biggest, fattest, most inefficient brands are even the best beneficiary of AI because brands have a massive moat and man, there's a lot of costs to cut there.”
It is currently a great time to found a non-AI startup
“I think it's actually probably a pretty good time to be a founder in a non AI related place right now, because there's like less competition, less smart people.”
Founders should target lucrative industries characterized by low-talent competition
“I think if you want to be successful, you can go look at every single industry and you can say, okay, who is the dumbest people and what makes the most money? And if you go like attack that area, Probably pretty good space.”
Founders should avoid building ideas from YC's Requests for Startups list
“You know, YC puts out this you know, quest for startups. My recommendation is like, that should be a list of startups you should not start. Because by the time that gets so consensus that this is a good area or super interesting, the amount of capital and the …”