William Hockey on Plaid, Column and Building Financial Infrastructure

William Hockey tells Harry Stebbings that growing up on a farm in central California made him a builder: he welded with his grandfather and worked on buildings with his father. In college, programming became another way to make things. He and his friend Zach founded Plaid while Hockey was still a student.

Working with financial institutions through Plaid, Hockey saw an opportunity to build inside the regulatory perimeter rather than add software outside it. He and his co-founders bought a regulated bank to create Column. He says the venture required time and resources he did not have when he first started Plaid.

Hockey argues that regulated banking is a difficult fit for the usual fast-starting venture model: buying a bank, building infrastructure and obtaining expertise require substantial upfront work. At the time of the interview, he says, the team had already spent almost three years building and expected a long ramp.

He describes his upbringing as pragmatic and work-oriented. Rather than focus exclusively on distant theoretical futures, he is drawn to solving tangible problems in the world as it exists. He acknowledges that the distinction between idealism and pragmatism is not absolute.

For Hockey, high performance includes doing difficult work quietly for a long time without depending on recognition. He thinks valuable companies take years to build. He admits that he too wants external validation, but tries to admire people whose less visible work makes a lasting difference.

Hockey says a long-standing circle of friends helps him separate identity from company status and take risks. Stebbings points out that wealth also makes risk easier. Hockey agrees: the success of his first company gave him the financial room to spend time on a longer-term, uncertain second venture.

He sees leadership development as gradual rather than a series of sudden transformations. Column, which he describes as self-funded and employee-owned, operates with more constrained resources than Plaid did in a boom. That requires more pragmatic prioritization and delegation, he says.

Hockey describes Plaid, Stripe and Twilio as businesses that make complex systems easier to use through software abstractions. With Column, his ambition is to work deeper in the system by operating a bank and building infrastructure from the bottom up. He does not claim the latter is necessarily the better business model.

He credits Plaid co-founder Zach with a high hiring bar and says the company was willing to endure short-term pain while waiting for the right person. He has tried to carry that patience into Column. The approach is his experience and preference, not a guarantee that every company can wait.

Stebbings questions whether a company can fill hundreds of roles with only the very best candidates. Hockey replies that many companies may not need to grow as large as they assume, but concedes that different roles require different people: a highly ambitious hire can be a poor fit for a role that calls for long-term stability.

For founders with dwindling runway and investor pressure, Hockey acknowledges that the tradeoff is difficult. His preference for slower building is shaped by financial infrastructure, where customers depend on reliability. In a fast-moving consumer application facing immediate competition, a different pace may be appropriate.

Stebbings argues that a capital-intensive, long-duration business like Column is precisely what venture capital should fund. Hockey agrees in principle but says risk management and regulatory expertise take time and cannot simply be bought faster with more capital. His long-term value ambitions are forecasts, not results.

On personal portfolio construction, Hockey says most of his wealth is concentrated in Plaid and Column, with smaller investments elsewhere. He describes himself as a company builder rather than a professional asset manager and acknowledges that investing in his own venture carries substantial risk.

He doubts that the best technology CEOs are always the best financial allocators: founders may be unusually willing to take risks to build. To cultivate patience at Column, he says the company attracts people who value careful, long-term work, while recognizing that the culture will not suit everyone.

Column, Hockey explains, is a bank offering APIs to developers and enterprises to move, hold and lend money. He says teams previously had to work through multiple providers and banks to build financial products. This description is also a sales proposition for the bank he co-leads.

His analogy is a physical supply chain: many intermediaries help turn raw materials into a shirt, and a financial transaction can likewise pass through several providers. Column’s stated approach is to own more of the banking infrastructure and reduce those layers. His numerical estimates of intermediaries are illustrative, not a verified count for every transaction.

When Stebbings asks what problem consumers actually experience, Hockey focuses on the developers building financial services. He says long, expensive bank integrations can limit what they launch, and argues that better infrastructure can lower barriers and eventually create more consumer choice. Those claimed effects are his hypothesis.

Column does not directly serve consumers in the model he describes; its customers build products such as payments, lending or new banking services. Hockey does not claim to know the next winning consumer product. He wants to provide the regulated plumbing on which others can build.

Hockey argues that complaints about the US financial system often conflate underlying payment infrastructure with the way individual banks implement it. He believes rebuilding that implementation can address many problems associated with older bank technology without replacing the entire financial system.

He suggests traditional infrastructure could provide many features associated with crypto, including faster payments, and attributes some limits to bank implementation. His specific claims about availability and capabilities of Federal Reserve payment services are his views in 2022; the interview does not verify the operating hours or technical details.

Asked which country has the best system, he cites the US dollar as a major advantage while saying China has moved quickly on payment technology. He also rejects authoritarian decision-making as a model for the US and argues that slow, multi-party processes have both benefits and costs.

On regulation, Hockey advocates a balance that lets companies innovate within a protective framework. He argues that restrictive rules can push activity offshore or into less regulated markets, while no regulation would create its own dangers. This is a policy argument from a regulated-bank founder, not a legal conclusion.

He hopes the FTX collapse will lead to a better balance but admits the outcome is uncertain and that regulators could instead move in a direction he considers too restrictive. He says he hopes Coinbase succeeds because, in his view, it has sought to work with regulators. His characterization of companies and rules reflects his perspective at the time.

Looking ahead ten years, Hockey predicts that specialist software companies with strong customer relationships will increasingly offer financial services to their audiences. In his view, some banks may operate more behind the scenes. Column would benefit from that model, so his forecast is also aligned with its business.

He argues that knowing a particular customer can be more valuable than assembling a broad portfolio of products for many audiences, especially if software and financial services become cheaper to provide. He expects more companies to build services internally and thinks acquisitions may become harder under competition scrutiny; these are predictions.

Hockey calls Apple a kind of consumer-focused specialist operating in a very large market. Asked about future financial leaders, he expects software companies to own customer relationships while regulated banks supply underlying functions. He says Column aims to be part of that infrastructure.

In quick-fire questions, Hockey recommends Merchants of Grain and The World for Sale. He advocates direct cold emails and follow-ups, recalling that Jack Dorsey responded when he wrote as a teenager. He sees optimism and tolerance for difficult detail as strengths, and describes social anxiety as a weakness.

Hockey co-leads Column with his wife. He values the alignment of incentives but says working together can blur personal and professional life. He also recalls the abandoned Visa–Plaid acquisition as painful and disagrees with the regulatory outcome; that is his own assessment of the antitrust process.

He wants his children to enjoy reading, be pragmatic and have confidence to bet on themselves. As an investor, he recalls missing an early opportunity in Deel and investing later at a higher price; the lesson for him is to acknowledge a miss rather than refuse a later opportunity solely because the price rose.

Hockey says boards can add value depending on the company’s stage and individual directors, but a great board alone cannot make a company successful. He places particular weight on aligned incentives. On venture capital, he argues that investors should recognize their role as allocators of capital.

Looking toward 2027, he jokes that he may have more gray hair and still be doing the same work. Startups are hard but, for him, unusually enjoyable; progress may be slower than people expect. Stebbings thanks him and ends the conversation.