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William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy

2026-03-17 - 72 min - source - Read full transcript

Patrick O'Shaughnessy (host)William Hockey

Key insights

Column treats its annual profit as its funding round, splitting earnings between an employee share buyback, growth, and a capital reserve instead of raising venture capital.

Hockey runs a tender every year, buying back roughly 25% of earnings in employee shares, which gives staff yearly liquidity and zero dilution or preference-stack risk in exchange for growing more slowly than a fully venture-funded peer would. He says this produces near-zero regretted attrition because employees get both near-term financial stability and long-term upside.

bootstrapped-company-building

The venture model only works past a specific growth-and-scale threshold, and most founders never honestly test whether their business clears it.

Hockey argues that growing 100% off a $10-30 million revenue base is comparatively easy, but sustaining above 30% growth off a $1-2 billion base is roughly 99 times harder; venture capital is built for companies that can productively absorb hundreds of millions to billions of dollars and still compound, and founders should assess their margin and revenue profile against that bar before raising rather than defaulting to it.

bootstrapped-company-building

Hockey funded Column's initial bank acquisition by pledging over $1 billion of Plaid stock for a $70 million loan, and was margin-called three times before nearly going bankrupt.

After a $5 billion Visa acquisition of Plaid was blocked by the DOJ, Hockey was paper-rich but cash-poor. He borrowed against his Plaid shares at SOFR-plus-10% and low loan-to-value to buy a regulated bank for $70 million, then spent multiple years unable to generate revenue while regulatory buildout continued, describing the period as the most intense of his life and repeatedly recalling the Keynes line that markets can stay irrational longer than you can stay solvent.

founder-risk-and-skin-in-the-game

Silicon Valley has systematically de-risked founders while leaving early-stage employees to carry disproportionately more real financial risk.

Hockey contrasts a 24-year-old giving up a $400-500K total-comp job at a large tech company for 1% equity in a startup (a genuine multi-year sacrifice) against a founder who can typically raise again, take secondary liquidity, or fall back on a 'founder' resume credit even if the company fails. He argues this asymmetry, not a lack of ambition, is why so many startups end up building safe, consensus bets like AI wrappers instead of taking real risk.

founder-risk-and-skin-in-the-game

About 75% of global trade is still denominated in dollars, even between countries that actively dislike the US and each other, which functions as an underappreciated form of American power.

Hockey cites Qatar-to-Switzerland gas trade and China's oil imports from Russia as examples: neither pair of counterparties wants the other's currency or particularly likes the US, yet the transactions clear through dollar-denominated, US-linked financial rails. He frames this as a form of soft and hard power that lets the US enforce its will through sanctions before ever deploying the military.

dollar-as-geopolitical-weapon

Financial sanctions functioned as a precondition for the US intervention in Venezuela, not just a parallel tactic.

Hockey argues that years of sanctions had already collapsed Venezuela's ability to export oil and trade internationally, which softened the population's willingness to resist once the US acted militarily. He frames financial services broadly as 'the first line of war,' with sanctions and dollar-clearing control preceding boots on the ground.

dollar-as-geopolitical-weapon

Hockey deliberately spends significant time in overlooked emerging markets like Kinshasa because he considers San Francisco and Beijing the two most consensus-driven societies he knows.

He says roughly 90% of his best product ideas come from walking around unfamiliar, constrained markets rather than from Silicon Valley's own AI-saturated discourse, and that operating far from the Bay Area's bias helps him see product opportunities the rest of the industry is structurally blind to.

silicon-valley-consensus-bias

Y Combinator's public 'Request for Startups' list should be read as a signal of what not to build, not what to build.

Hockey argues that by the time an area becomes consensus-interesting enough to appear on such a list, capital and talent have already flooded in, making it one of the most crowded and competitive places to compete. He'd rather work in an unfashionable niche with less competition, even if it is less exciting to talk about.

silicon-valley-consensus-bias

Outsized value in a niche business can come from one obscure insight buried deep in exhaustive primary-source reading that almost no competitor will bother to do.

Hockey describes reading a roughly 2,000-page history of banking in 19th-century China, most of which was useless, purely to extract a single idea that fed directly into a Column product. He says this kind of study is inefficient unless you already own the business positioned to exploit the insight, but when it pays off it can create hundreds of millions of dollars of value precisely because the reading itself is a deterrent to competitors.

specialist-depth-and-niche-focus

The best founders find the single most boring possible problem endlessly interesting over a multi-decade horizon, rather than chasing broadly fascinating, generalist topics.

Hockey contrasts topics like AI and geopolitics, which make compelling podcast content because almost anyone can hold an informed-sounding opinion, with the genuinely defensible niches, which tend to be narrow and tedious. He argues the willingness to 'suffer in silence' studying an unglamorous area for years is a better predictor of company-building success than general intelligence or breadth.

specialist-depth-and-niche-focus

Legacy US financial infrastructure (the Fed's clearing systems) is technically capable of instant, 24/7 money movement today; the friction that remains is a business-model and implementation choice, not a technology gap.

Hockey argues the Fed 'is a pretty good tech team' whose systems already clear money faster than stablecoins or crypto, but small community banks can't staff 24/7 operations the way JPMorgan or Stripe can. Much of the remaining friction in consumer payments is also intentional: making transfers instant and frictionless increases exposure to fraud and elder-abuse scams, and he expects AI-driven fraud detection to let banks safely remove that friction over time.

bootstrapped-company-building

Books referenced

unnamed 19th-century history of banking in China - A roughly 2,000-page book Hockey read cover to cover; he says almost none of it was useful but the single idea buried inside was worth building leverage on.

Media referenced

Dan Wang's letter on China - article - Cited for the observation that San Francisco and Beijing are the two most consensus-driven societies Wang has encountered, a framing Hockey agrees with and extends to Silicon Valley's product blind spots.

Companies

Column - Hockey's current company: a software company that owns a regulated bank charter and monetizes almost entirely through per-API-call software fees rather than net interest margin, serving fintechs and global-dollar customers.
Plaid - Hockey's first company, co-founded with Zach Perret; he pledged over $1 billion of his Plaid stock as loan collateral to fund Column's bank purchase after a $5 billion Visa acquisition of Plaid was blocked by the DOJ.
Visa - Attempted to acquire Plaid for $5 billion; the deal was blocked by the DOJ, leaving Hockey with paper wealth but little liquidity when he started Column.
Ramp / Brex / Mercury / Wise / Bill - Named as fintech companies that run their payments, deposits, and credit infrastructure on Column's bank charter and software rails.
Built - Used as a concrete walkthrough example of a Column customer: a consumer-facing rent-payment product whose account and routing numbers are actually issued by Column behind the scenes.
Caspi (Kazakhstan) - Cited as a model of extreme vertical integration in an emerging market: started as a bank acquisition and expanded into the country's largest e-commerce platform, tax payments, and driver's license renewals.
Rawbank (DRC) - Referenced as the largest bank in Congo, whose mobile app Hockey says is more capable than typical US bank apps (e.g., letting users upgrade a TV subscription in-app), illustrating emerging-market cross-sell advantages.

Techniques and frameworks

Earnings-as-funding-round model - Column treats each year's profit as its de facto funding round, splitting it between an employee share buyback, growth investment, and a capital reserve, instead of raising external venture capital.
Annual employee equity tender - Column buys back roughly 25% of earnings in employee shares every year, giving staff yearly liquidity and undiluted equity in place of the multi-year illiquid vesting typical of venture-backed startups.
Missionary / mercenary / hybrid hiring framework - Hockey's mental model for evaluating candidates: mercenaries chase optionality across a portfolio of companies, missionaries follow inspiration regardless of near-term pay, and a third hybrid type wants both stability and upside; matching the type to the company's stage matters more than pedigree.
Deep primary-source research for single high-leverage insights - Hockey reads exhaustive, unglamorous primary material (e.g., centuries-old banking history) on the premise that one idea buried in thousands of pages can be worth hundreds of millions of dollars precisely because almost no competitor will do the reading.

Summary

William Hockey, founder of Column and co-founder of Plaid, joins Patrick O'Shaughnessy to describe a startup he has built almost entirely without venture capital and almost entirely outside the Silicon Valley playbook. Column pairs a regulated bank charter with software, letting fintechs like Ramp, Brex, Mercury, Wise, and Bill run their payments, deposits, and credit infrastructure on Column's rails while Column earns SaaS-like, per-API-call economics rather than traditional banking spread. Hockey funded the company's initial bank acquisition by pledging over $1 billion of his Plaid stock (paper wealth left over after a $5 billion Visa acquisition of Plaid was blocked by the DOJ) for a $70 million loan, was margin-called three times, and describes the ensuing years of unprofitable regulatory buildout as the most intense period of his life.

The conversation's throughline is Hockey's contrarian operating model. Instead of raising venture rounds, Column treats its annual profit as a de facto funding round: roughly a quarter of earnings buys back employee shares every year, giving staff undiluted equity and yearly liquidity in place of the multi-year illiquid vesting typical of venture-backed startups, which he credits with near-zero regretted attrition. He argues the venture model itself only makes sense above a specific scale threshold, since sustaining 30%+ growth off a billion-dollar-plus revenue base is vastly harder than early hypergrowth off a small base, and most founders never honestly test whether their business clears that bar before defaulting to fundraising. He also argues Silicon Valley has quietly de-risked founders (safe seed rounds, a YC playbook, a resume-boosting founder credit even after failure) while leaving early-stage employees to carry the real financial risk, an asymmetry he thinks is producing safer, more consensus-driven companies.

Hockey extends this contrarian instinct to where he spends his time and attention. He deliberately travels to overlooked emerging markets like Kinshasa, arguing that San Francisco and Beijing are the two most consensus-driven societies he knows and that most of his product ideas come from walking around constrained, dollarized markets rather than from Silicon Valley's own AI-saturated discourse. He treats Y Combinator's public "Request for Startups" list as a signal of where not to build, since consensus interest means capital and talent have already flooded in, and he credits much of Column's edge to exhaustive, unglamorous primary-source research, including a roughly 2,000-page history of 19th-century Chinese banking, on the theory that a single obscure insight can generate outsized value precisely because almost no competitor will do the reading.

The back half of the conversation turns to the dollar's geopolitical role, a subject Hockey says he has a unique vantage on given Column's global-dollar business. He argues roughly 75% of global trade remains dollar-denominated even between counterparties that dislike the US and each other, such as Qatar-to-Switzerland gas trade or Russia-to-China oil, and frames this as an underappreciated form of American soft and hard power, with sanctions functioning as a first line of war before military force. He credits years of financial sanctions, more than the eventual military action itself, for weakening Venezuela's capacity to resist US intervention. He closes by arguing that legacy US financial infrastructure is already technically capable of instant, always-on money movement; the remaining friction is a deliberate business-model and fraud-prevention choice by individual institutions rather than a genuine technology gap, and he expects AI-driven fraud detection to let banks strip that friction away over time.

Notable Quotes

"I sometimes make this joke, like VC money is kind of heroin. It feels good. It's amazing. But like you got to keep shooting up." - William Hockey

"The value in railroads accrued to the oil companies... what is the equivalent area for AI?" - William Hockey

"We should still have the nuclear weapons of financial services, which is we control the world's trade." - William Hockey

"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?" - William Hockey

"The problem isn't in the fundamental infrastructure. It's in our implementation of it." - William Hockey