The Twenty Minute VC

William Hockey: How I Founded Plaid; The Ultimate Cold Email Tip; Hiring Lessons | 20VC #955

Will Hockey is the Co-Founder and Co-CEO @ Column, the only nationally chartered bank built to enable developers and builders to create new financial products. Before co-founding Column, Will was the Co-Founder, President, and CTO @ Plaid, a world-leading data network and payments platform. In 2020, Visa attempted to acquire Plaid for $5.3BN, however, this was blocked due to regulatory issues and the company went on to raise at a reported $13.4BN valuation just 9 months later. Additionally, Will is on the board of Scale.ai. Timestamps: 0:00 Journey Into Startups 2:04 Why do many fintech companies work outside the regulatory system? 3:28 What are you running from and towards? 5:04 Do startups still build for the long term? 6:38 What does high performance mean to you? 8:02 Relationship to Ego 11:06 Relationship to Money 12:15 Changes in Leadership Style 13:37 Plaid vs Column 15:40 Lessons on Hiring 19:33 When is building slowly advantageous? 23:45 How did you structure your personal portfolio? 25:14 Are CEOs the best resource allocators? 25:50 How do you imbue patience with your team? 27:17 What does Column do? 35:45 US Financial System as a Protocol 40:20 What country has the best financial system? 42:02 How would you change the US financial system? 44:47 What happens to Coinbase next? 45:50 The Next Ten Years of Fintech 50:49 Apple is the Original Vertical Specialist 52:46 What books do you recommend? 53:18 Cold Emails Work 54:00 Biggest Strength and Weakness 54:48 Founding Company with Wife 58:28 What would you most like to change about venture? 59:33 The Next Five Years for William Hockey In Today’s Episode with Will Hockey We Discuss: 1.) The Founding of $13.4BN Plaid: How did Will make his way into the world of startups and come to found Plaid with Zach? If we are all a function of our histories, what is Will running from? What is he running toward? What does Will know now that he wishes he had known when he started Plaid? 2.) Will Hockey: The Makings of a Decacorn Founder: What does the term “high performance” mean to Will? How has this changed over time? Having had such a successful time building Plaid to $13.4BN, how does Will assess his own relationship to risk and his relationship to money? How does Will approach his own personal portfolio planning? Equity, debt, real-estate? How does Will optimize his own personal wealth? Column is his second time founding a company, what did Will decide to take from Plaid that worked well? What did he decide he would not do having seen it work badly at Plaid? 3.) The Building of Truly Great Teams: Why does Will believe that companies can be built so much slower than people think? How does Will determine the decisions that have to be made fast vs those with time? How does Will ensure the same size of urgency and speed within his team without this time or funding pressure? What have been Will’s single biggest lessons when it comes to people acquisition and retention? 4.) Fintech: The Next 10 Years: How will the next 10 years look different from the last in fintech? What changes will be better? What will be worse? What is Will worried about? What is he excited about? What does Will mean when he says, “the US financial system can function like a protocol”? What does Will believe are some of the core myths of the US financial system? Why does Will believe the current financial system can and will fix a lot of what crypto is trying to solve? What barriers will prevent this from happening? Items Mentioned in Today’s Episode: Will’s Favourite Book: The World for Sale: Money, Power and the Traders Who Barter the Earth’s Resources, Merchants of Grain: The Power and Profits of the Five Giant Companies at the Center of the World’s Food Supply Subscribe to the Podcast: https://www.thetwentyminutevc.com/william-hockey/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Kyle Harrison on Twitter: https://twitter.com/williamhockey Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok #WilliamHockey #fintech #ColumnBank #HarryStebbings #20VC

Harry StebbingshostWilliam Hockeyguest

Dec 2, 20221h 0mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

From Plaid To Column: Rewiring Banking Inside The Regulatory Perimeter

William Hockey, co-founder of Plaid and founder/CEO of Column, explains his journey from a farm tinkerer to building two major financial infrastructure companies. He contrasts Plaid’s “abstraction around complexity” model with Column’s decision to become a fully regulated bank and rebuild core money movement from the bottom up. The conversation dives into founder psychology (ego, identity, risk, wealth), hiring philosophy, and why he believes true innovation in finance must happen inside the regulatory perimeter. He also outlines a future where vertical software companies and consumer brands become the primary financial interfaces while regulated banks increasingly power them from behind the scenes.

IDEAS WORTH REMEMBERING

5 ideas

True financial innovation increasingly requires building inside the regulatory perimeter, not around it.

Hockey argues that most fintech has historically been middleware wrapped around legacy banks, which can’t fix systemic issues. By actually being a regulated bank (Column), you control the protocol, risk, and compliance layers, enabling more fundamental, durable innovation than just abstracting old systems.

High performance is the ability to grind quietly for a decade without recognition.

He reframes performance as long-term, low-ego persistence: working in the shadows on boring, complex problems for 10+ years. The most successful people he’s seen are not the most visible, but those who can sustain deep work without constant external validation.

Be excruciatingly patient on critical hires, especially early; pain now beats mediocrity later.

At Plaid and now Column, Hockey was willing to let the business suffer short-term and endure internal pain to wait 12–24 months for true A-level candidates in key roles. He stresses most companies talk about high bars but cave to urgency and end up paying for it long term.

Founders should consciously separate self-worth from company identity to take bigger risks.

Hockey stepped away from Plaid at its peak to start a smaller, riskier company. He credits a stable base of long-time friends and non-founder relationships for making his identity less tied to status, wealth, or brand, which in turn makes big swings psychologically possible.

The “money supply chain” is bloated with intermediaries that can be collapsed.

To move money today, banks rely on a chain of 5–10+ vendors on each side because they aren’t tech companies. Column’s thesis is to go directly to the Fed rails as a bank and expose clean APIs, collapsing many layers of middleware into one cohesive, programmable layer.

WORDS WORTH SAVING

5 quotes

Being able to be quiet, grinding and building in the shadows, and be okay not being recognized, I think is the highest order of high performance.

— William Hockey

What 99.9% of Silicon Valley is doing is building outside the regulatory perimeter. What I realized is you can drive a huge amount of value if you actually jump in, be a regulated bank, and build it from scratch.

— William Hockey

Any company of value takes at least 10 plus years to realize. It’s all about how long can you do that, and can you do that in the shadows?

— William Hockey

Most companies shouldn’t be 500-person companies. Most companies that are over 1,000 people, you can probably do the same damn thing with 100 people.

— William Hockey

Everyone says the US financial system is built on COBOL and is slow. They’re not talking about the Fed; they’re talking about the outdated implementation by legacy banks.

— William Hockey

William Hockey’s background, Plaid story, and motivation for starting ColumnBuilding inside versus outside the financial regulatory perimeterFounder psychology: ego, identity, risk tolerance, and wealthHigh performance, patience, and hiring A-players under resource constraintsThe “money supply chain” and collapsing financial intermediaries with APIsThe US financial system as a protocol vs. bank implementations and cryptoFuture of fintech: vertical software, embedded finance, and role of big banks

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