How to bet on yourself (without venture capital)

William Hockey, the co-founder of Plaid and founder of Column, offers a provocative look into building a modern financial infrastructure company. Column is a hybrid entity—a software company that also owns a bank—providing the regulatory and technical backbone for major fintechs like Brex, Ramp, and Wise. Unlike traditional banks, Column generates over 90% of its revenue from software API calls, passing the underlying banking economics directly down to its customers. Hockey’s approach to building Column is rooted in a rejection of "consensus" thinking. He argues that Silicon Valley has become an elite-dominated society that builds for itself, losing touch with the rest of the world. To counter this, Hockey frequently travels to emerging markets like Kinshasa in the Democratic Republic of Congo. He observes that constrained environments breed a unique type of creativity. While the West lives in a world of abundance, emerging markets often "leapfrog" technologies—moving straight to mobile payments or social commerce because they are not tied to legacy systems. For Column, these markets are vital because the US dollar remains the world’s primary operating system, especially in countries where local central banks are untrusted or inflation is high. One of the most striking aspects of Column’s story is Hockey’s decision to avoid venture capital. Having used the standard VC playbook with Plaid, he now views venture money as "heroin"—addictive and forcing founders to optimize for the next fundraise rather than long-term stability. Instead, Column is funded entirely by its own earnings. This independence allowed Hockey to make massive 10-year investments, such as the multi-year process of acquiring and integrating a regulated bank during a difficult political climate. He notes that venture capitalists likely would have rejected such a move in favor of chasing shorter-term trends like AI or stablecoins. This self-funding model extends to employee ownership. Column is 100% owned by Hockey and his staff. To solve the problem of illiquidity that plagues many startups, the company uses 25% of its annual earnings to buy back shares from employees. Hockey finds this is a powerful retention tool for senior talent—experienced professionals who have seen previous startups fail and now prioritize real-world financial needs like mortgages over paper wealth. By avoiding dilution and preference stacks, Hockey offers his team a transparent and stable path to wealth that mirrors the growth of the business. Hockey’s personal journey with Column involved extreme risk. He funded the initial $70 million bank acquisition with debt, pledging over $1 billion in Plaid stock as collateral. During the first three years, he faced multiple margin calls and nearly went bankrupt. He believes this "raw" fear is missing from modern entrepreneurship. In his view, Silicon Valley has made starting a company too safe for founders, which results in uninspired businesses. He argues that founders should "bet on themselves" more aggressively, noting that early-stage employees often take more relative life-risk than founders who have "CEO" on their resumes regardless of success. Success, according to Hockey, comes from being a specialist in "boring" fields. He describes himself as the best in the world at a few niche, unglamorous topics. He spent years studying the history of banking, even reading obscure 2,000-page books on 19th-century Japanese and Chinese finance to find single ideas that could create millions in value. He advises founders to find the "most boring thing humanly possible" and remain fascinated by it for decades. He suggests that the "Request for Startups" lists published by incubators are often lists of what not to start, as those areas are already too crowded with smart people and intense competition. Regarding the global stage, Hockey views the US dollar as a critical pillar of national security. It acts as a "nuclear weapon" of soft power, allowing the US to enforce its will via sanctions rather than military force. Even "enemy" nations like China and Russia still denominate much of their trade in dollars because they lack trust in