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The Twenty Minute VCWilliam Hockey: How I Founded Plaid; The Ultimate Cold Email Tip; Hiring Lessons | 20VC #955
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At a glance
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 ideasTrue 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 quotesBeing 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
High quality AI-generated summary created from speaker-labeled transcript.
