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Invest Like the Best

How to bet on yourself (without venture capital)

William Hockey, co-founder of Plaid and founder of Column, joins the show to discuss building the global operating system for the US dollar.

Patrick O'ShaughnessyhostWilliam Hockeyguest

Mar 17, 20261h 17mWatch on YouTube ↗

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

CHAPTERS

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Chapter summaries

What Column is: a software company that owns a bank
William Hockey explains Column’s core concept: owning a regulated bank as a moat while building software infrastructure other companies can’t easily replicate without a bank charter. He outlines how Column provides banking and payments “primitives” via APIs to fintechs and software companies, emphasizing that most of Column’s revenue comes from software rather than traditional bank economics.
- •Column is positioned as a software company that also owns a bank, using regulation as a moat
- •It powers payments, deposits, and credit for fintech and software companies through APIs
- •Customers run on Column’s software plus its regulated banking rails
- •Column makes the vast majority of its money from software-style pricing (per API call)
- •The business also targets global use cases centered on transacting and holding dollars
How it works in practice: the ‘Issued by Column’ customer example
To make the model concrete, William walks through how Column supports a recognizable customer, handling the regulated and network-facing parts of money movement while the customer owns the consumer experience. He explains where Column sits in the stack (networks, settlement rails, routing/account infrastructure) and how it monetizes like SaaS.
- •A customer card can show “Issued by Column,” reflecting Column’s regulated role
- •Column connects to card networks and handles complexity involving major rails (e.g., Fed, network rails, Swift)
- •The customer builds the app, marketing, and user experience; Column runs the backend money movement
- •Revenue is primarily software-based pricing rather than traditional bank spread
- •Column passes much of the bank-side economics down to customers
Why travel matters: escaping Silicon Valley consensus and learning from constraints
Patrick asks why William is often in unusual global locations, and William ties it to avoiding consensus thinking and studying how constrained environments drive different innovation. He contrasts Silicon Valley’s consensus culture with emerging markets, where constraints force more creative approaches and reveal different needs—especially around dollar usage.
- •William describes Silicon Valley as highly consensus-driven and potentially isolating
- •Traveling provides exposure to different biases and daily realities than those in San Francisco
- •Emerging markets’ constraints can breed different creativity and innovation
- •William links travel directly to product ideation and market discovery
- •He notes that dollarized places often need U.S. financial services more acutely
Kinshasa as a case study: market scale, low penetration, and leapfrogging
Using Kinshasa and the DRC as an example, William describes large underlying economic activity alongside low mobile and banking penetration. He argues that leapfrogging in financial services often happens fastest in “worse” or more constrained systems, and that emerging markets can produce surprisingly sophisticated financial products and talent allocation patterns.
- •DRC has major exports and investment flows alongside heavy constraints
- •William cites very low mobile phone penetration and even lower banking penetration
- •He argues financial services innovation can be most advanced in highly constrained countries
- •He highlights mobile payments and early innovation in parts of Africa relative to U.S. fintech timelines
- •He discusses how talent in some markets concentrates in banks and other money centers
Emerging-market financial super-apps and what they reveal about distribution
William describes examples of banks and platforms outside the U.S. that bundle many services, enabled by different market structures and distribution advantages. He explains how in some markets financial services serve as an anchor for cross-selling and expansion in ways that don’t map neatly onto the U.S. ecosystem.
- •He describes a Kazakhstan example where a bank expanded into many adjacent services
- •He cites an example in Congo where a bank app offers features that would feel implausible for U.S. banks
- •He argues these markets can be more open to category disruption and rapid product expansion
- •He notes differing “land and expand” dynamics where banking distribution is a powerful wedge
- •He ties this back to dollar usage and opportunities for collaboration and innovation
Silicon Valley’s elite consensus problem and building for people unlike yourself
William expands on the idea that Silicon Valley is elite-dominated and tends to build products for elites. He argues that while this consensus environment can be powerful for research and frontier ideas, it can also reduce relevance to broader populations and harm credibility outside the tech bubble.
- •William characterizes Silicon Valley as elite-dominated and increasingly insular
- •He argues the ecosystem can over-index on building for itself instead of broader markets
- •He distinguishes research strength from real-world applicability to everyday lives
- •He claims Silicon Valley’s broader popularity and approval is low and that there are reasons for that
- •He emphasizes the need to build products that work outside San Francisco and New York
Rejecting the VC hamster wheel: staying ambitious while self-funding growth
Patrick asks why William chose not to raise venture capital for Column, and William contrasts the standard fundraising treadmill with a profit-funded model. He argues venture dynamics can force companies to optimize for the next round and chase trends, while profitability gives Column freedom to invest on longer horizons and maintain cultural alignment.
- •William contrasts the typical venture fundraising path with Column’s profit-funded approach
- •He argues VC-driven burn often forces optimization for the next fundraise and trend-chasing
- •He believes companies can be highly ambitious without being dependent on venture money
- •Profitability provides flexibility to accept slower growth in exchange for better long-term decisions
- •He frames repeated venture fundraising as hard to stop once started
Equity and liquidity by design: buybacks, employee housing support, and retention
William details how Column uses profitability to create employee-friendly structures that venture-backed companies often can’t justify. He explains annual share buybacks for employee liquidity, targeted perks like housing stipends, and how reduced dilution and a simpler cap table change the employee value proposition.
- •Column provides certain benefits (e.g., housing support near the office) that don’t “scale” in VC logic
- •The company runs an annual tender/buyback program funded by a portion of earnings
- •Employees receive equity similarly to startups but get predictable liquidity opportunities
- •William emphasizes reduced dilution and no preference stack compared to typical VC structures
- •He attributes strong retention partly to meeting employees’ short- and medium-term needs, not just distant upside
Funding a bank with founder risk: debt financing, margin calls, and near-bankruptcy stress
William addresses whether self-funding was only possible because of prior wealth, clarifying his liquidity constraints and describing how he financed Column largely through debt against Plaid shares. He recounts taking an expensive, low loan-to-value facility, facing margin calls, and experiencing intense stress during the early years while needing to maintain leadership composure.
- •William says he started without the liquidity people assumed after Plaid’s attempted sale failed
- •He describes funding the business largely with debt secured by Plaid shares
- •He recounts obtaining a costly loan with low loan-to-value terms and using it to buy a bank
- •He says he faced multiple margin calls and came close to bankruptcy
- •He describes the pressure of carrying that risk while shielding employees from full stress
The necessity of extreme founder risk—and why founders are now too de-risked
William argues that exceptional founders often bet on themselves with real personal downside, and that modern startup ecosystems can make founding “too safe.” He claims the absence of existential risk reduces intensity and creativity, and criticizes second-time founders who raise huge sums while risking little personal capital.
- •He argues extreme risk can unlock creativity and intensity when there’s ‘only one door’ forward
- •He says modern startup systems make founding relatively safe and playbook-driven
- •He questions why wealthy repeat founders risk little personal capital while asking employees to commit
- •He claims early employees can take more risk than founders under typical startup dynamics
- •He calls for making founder failure more expensive to incentivize bolder company-building
Finding leverage through specialization: loving the ‘boring’ and going deeper than others will
Patrick probes how William becomes “best in the world” in his niche, and William describes deep specialization as the path to leverage. He explains that reading massive, obscure industry history can yield small insights with outsized value—if you’re positioned to apply them.
- •William describes compounding on yourself and focusing where you have unique edge
- •He emphasizes specialization over generalist trend-following, especially in a competitive world
- •He argues value often comes from insights buried in tedious, deep research others avoid
- •He frames leverage as finding small ideas that can generate large product and business value
- •He says success depends on sustaining curiosity about extremely boring topics for decades
Matching capital structure to business reality: investor selection, growth limits, and profitability
William shares what he would teach founders about investors: he’s not anti-VC, but he believes capital structure must fit the business. He argues founders should be realistic about whether they can sustain venture-required growth at massive scale and whether their business can productively absorb large amounts of capital.
- •William credits venture capital as essential to Plaid’s existence while arguing it’s not universal
- •He recommends evaluating investor time horizons and alignment rather than assuming all VCs are the same
- •He urges founders to match capital structure to margin profile and realistic growth dynamics
- •He claims sustaining high growth at very large revenue scale is dramatically harder than early growth
- •He questions whether many enterprise businesses can effectively ‘ingest’ huge capital infusions
The unseen power of the U.S. dollar: trade, connectivity, and financial ‘hard power’
William explains how the dollar connects countries and how reliant global trade remains on dollar-denominated rails. He frames U.S. financial infrastructure and sanctions as central tools of power, arguing financial services plays a direct role in national security and that the U.S. should retain that influence.
- •He discusses how money and trade connect societies in ways the U.S. can overlook due to its market size
- •He claims a large share of global trade remains dollar-denominated even between countries that may not align with the U.S.
- •He frames control of financial rails and sanctions as a key element of U.S. power projection
- •He says Silicon Valley increasingly recognizes its role in national security, and finance is a key pillar
- •He argues the U.S. should remain central to global financial services rather than ceding power elsewhere
How AI will transform legacy banks: cost structures, fraud detection, and better UX
William shares a view that value from AI will accrue less to “AI companies” and more to incumbents with distribution and large cost bases. In banking, he argues the business model has been so profitable that it slowed innovation, but AI could unlock efficiency and improve user experience by reducing fraud and enabling safer, lower-friction transactions.
- •He predicts AI benefits will flow to organizations with massive distribution and high costs to remove
- •He says banks’ profitability made them laggards, but also makes them ripe for AI-driven gains
- •He argues banking inefficiencies are large, and regulation makes takeover-driven restructuring harder
- •He notes much financial friction exists to prevent fraud and protect vulnerable users
- •He suggests AI can improve detection, reduce friction, and enable faster, safer experiences
The kindest thing: resilience learned from his parents and what it means for risk-taking
In the closing question, William reflects on how his parents insulated him from hardship and helped create a stable childhood. He connects that upbringing to resilience and comfort with risk—traits he views as essential for founders—and questions whether modern parenting optimizes too heavily for safety over toughness.
- •William credits his parents with insulating him from difficulties and giving him a good childhood
- •He links childhood security to an adult’s willingness to take risks as a founder
- •He describes learning it’s okay to fall and be ‘punched in the face’ as formative resilience
- •He reflects on raising his own child and concerns about overly ‘perfect’ environments
- •He frames resilience as a major gift that shapes his approach to entrepreneurship

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