Dec 3, 2022 · 1h 0m · news
William Hockey: How I Founded Plaid; The Ultimate Cold Email Tip; Hiring Lessons | 20VC #955 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this engaging interview, Plaid co-founder and Column co-CEO William Hockey shares his gritty, pragmatic approach to startup leadership, the necessity of building inside the financial regulatory perimeter, and his vision for the future of embedded finance.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 23% of the talking time here. How this is scored →
Harry as informed peer 4.3 Guest teaching 4.6 Guest disagreement 2.7 Harry pushing back 4.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:07 William rejects premise on scaling headcount
William explicitly rejects Harry's framing that scaling a business mandates expanding headcount to 500+ employees and accepting lower hiring bars.
Hardest push from Harry ▶ 20:35 Harry directly disagrees on Venture Capital fitHarry directly challenges William's claim that venture capital is ill-suited for infrastructure banks, forcefully asserting what VC was originally created to fund.
Biggest teaching moment ▶ 36:00 William demystifies protocol vs bank implementation layersWilliam educates Harry by dissecting how modern Fed protocols are obscured by legacy banks running outdated COBOL wrappers.
Harry holds his own ▶ 46:44 Harry calls out contradiction in guest's exampleHarry sharply highlights a logical contradiction in William's narrative by demonstrating that Salesforce represents product bundling rather than niche specialization.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Inside vs. Outside the Regulatory Perimeter | 3 | 5 | 1 | 3 | Harry asks a direct, blunt question regarding why founders avoid building inside the regulatory perimeter. William explains the structural friction and high upfront capital required to acquire and run an OCC-regulated bank. | |
| Debating Silicon Valley's Ambition and Intellectual Elitism | 6 | 3 | 3 | 6 | Harry challenges William's premise about Silicon Valley's multi-decade vision, citing Peter Thiel and arguing that most current tech innovation is incremental. William acknowledges the nuance while defending the valley's culture of pragmatism. | |
| Managing Ego and Embracing Boring Work | 2 | 3 | 1 | 2 | Harry steers into a personal, reflective discussion on ego, identity, and detachment. William shares candid insights about stepping back from Plaid and avoiding vanity metrics. | |
| Wealth, Risk Appetite, and Building with Long-Term Time Horizons | 4 | 4 | 2 | 3 | Harry probes the relationship between personal wealth, risk appetite, and long-term execution horizons. William contrasts Plaid's venture-funded boom-era growth with Column's self-funded, constrained model. | |
| The Philosophy of Patient Hiring and Team Scaling | 5 | 5 | 5 | 6 | Harry pushes back on William's patient hiring philosophy, asserting that mathematical distribution makes maintaining top 1% talent impossible at 500+ employee scale. William directly rejects Harry's premise, arguing that most software companies shouldn't scale headcount that high. | |
| The Speed of Execution Debate | 5 | 6 | 4 | 6 | Harry states a core startup belief that 'speed of execution is everything' and asks William to prove him wrong. William educates Harry on why thoughtful, deliberate infrastructure building beats rapid daily feature releases in financial services. | |
| Venture Capital's Fit for Long-Duration Infrastructure | 7 | 6 | 5 | 7 | Harry explicitly disagrees with William's view that Column isn't a fit for traditional VC, arguing VC was originally intended for high-cap capital-intensive infrastructure. William counters with pragmatic reality, explaining VC pressure for immediate 100M ARR metrics. | |
| Personal Asset Allocation and Betting on Yourself | 3 | 4 | 3 | 3 | Harry asks about personal asset allocation and whether top founders are ideal resource allocators. William shares that 99.9% of his wealth is tied up in his own ventures. | |
| Imbuing Patience and Retaining Ambitious Talent | 3 | 6 | 2 | 4 | Harry calls out William's term 'money supply chain problem', noting he searched it online and found nothing. William uses a detailed t-shirt supply chain metaphor to educate Harry on the banking middleware stack. | |
| Why Middlemen and Legacy Systems Stifle Financial Innovation | 4 | 6 | 3 | 6 | Harry presses William on what actual problem Column solves for end consumers, claiming money movement works fine for him. William clarifies that the bottleneck exists at the developer and regulatory integration layer. | |
| Lowering the Barrier to Entry to Protect and Empower Consumers | 4 | 6 | 4 | 5 | Harry teases William for sounding like a buzzword-heavy VC when describing financial systems as protocols. William explains the distinction between modern Fed protocol capabilities and archaic legacy bank implementations. | |
| Comparing Financial System Architectures: US vs. China | 5 | 5 | 2 | 4 | Harry brings up user-facing payments like UK contactless vs signing checks in the US. William reinforces that these quirks stem from legacy bank operating hours rather than Fed protocol limitations. | |
| Centralized Adaptability: Lessons from China's Financial System | 4 | 5 | 2 | 3 | Harry asks how the US can adopt the rapid adaptability of China's centralized financial system. William discusses finding a regulatory middle ground to keep crypto and fintech innovation onshore. | |
| The Aftermath of FTX: Optimism for Regulatory Evolution | 5 | 4 | 3 | 6 | Harry challenges William's optimism regarding post-FTX regulatory evolution, arguing collapse usually triggers increased bureaucracy and stifling rules. William admits his stance is optimistic but maintains good players need clear pathways. | |
| The Future of Fintech: Embedded Finance and Vertical Software | 6 | 4 | 3 | 6 | Harry catches a logical flaw in William's vertical software explanation, pointing out that using Salesforce contradicts the unbundling argument. William quickly pivots to Procore as a clearer vertical example. | |
| Audience Lock-in, M&A Restrictions, and In-House Building | 5 | 5 | 2 | 4 | Harry asks whether tightening regulatory scrutiny will prevent future M&A rollups. William agrees, suggesting platforms will build embedded financial capabilities in-house rather than acquire. | |
| Apple's Financial Strategy and the Future of Banking Giants | 3 | 3 | 1 | 2 | Harry transitions into a rapid-fire round covering Apple's financial strategy, favorite books, and cold emailing. William shares a key tip about skipping warm intros in favor of multi-touch cold outreach. | |
| The Co-CEO Dynamic: Co-Founding Column with His Wife | 2 | 3 | 1 | 2 | Harry asks about working with his wife as co-CEO and the painful lesson of the blocked Visa acquisition. William reflects on viewing government regulatory decisions as static realities when designing business models. | |
| Do Boards Add Value and How to Fix Venture Capital | 5 | 4 | 4 | 3 | Harry asks about board value and fixing VC. William criticizes tech founders and investors as 'sycophants' who treat capital as something more than financial allocation, with Harry agreeing that VC is selling money. |
Statements from this episode (33)
Hockey: Almost every US fintech company works with Plaid
“Pretty much anybody building in financial services in the U.S. Is some way associated with Plaid.”
Hockey: 99.9% of Silicon Valley builds outside financial regulatory perimeters
“What I was doing in a lot, like what, 99.9% of Silicon Valley is doing is building outside that regulatory perimeter.”
Hockey: Building a regulated bank from scratch creates massive value
“What I realized actually is you can drive a huge amount of value if you actually jump in Be a regulated bank and actually build it from scratch.”
Hockey: Silicon Valley is not structurally set up for regulated businesses
“I think Silicon Valley really isn't set up. To build regulated businesses.”
Hockey: Column founders personally purchased an OCC-regulated bank in California
“So what we had to do is we actually went out and we personally bought a financial institution. We bought an OCC regulated bank out here in California.”
Hockey: Silicon Valley disguises mundane practical products with grandiose, world-changing language
“I think we definitely celebrate intellectual elitism for sure, right? I think we celebrate couching what is probably a pretty boring practical problem in like large language, gonna go change the world, but like, I don't know, maybe like building like an API fo…”
Hockey: True high performance is grinding in the shadows without public validation
“Being able to be quiet, grinding and building in the shadows and be okay, not being recognized, I think is the highest sort of high performance.”
Hockey: Everyone craves external recognition, and anyone claiming otherwise is lying
“Everybody's vain, right? And so anybody that tells you that they don't need that, myself or otherwise, they're lying to your face, right? Everybody, everybody craves that.”
Hockey: Grounded personal relationships enable founders to take bigger risks
“What they also do is if you're so focused on keeping that, you're never going to take the big risks. But if you have a base that you can really fall back on and that kind of loves you and your friends with you hang out with, Irrespective of kind of who you are…”
Hockey: Fintech startup Column is completely self-funded and employee-owned
“And I think we're in a different world right now, and we're completely self-funded and employee-owned.”
Hockey: Most 1,000-person tech companies could achieve the same with 100
“I think as we're learning and have learned that most companies that are over a thousand people, you can probably do the same damn thing with a hundred people.”
Hockey: B-players are often better long-term fits than A-players
“Not every role needs that a plus player. Sometimes it's actually the opposite, right? If you get an a plus player and they're in a role, they're not going to be super happy. They want to move quickly. You can have attrition risk or they want new responsibiliti…”
Hockey: Fast hiring and execution speed are false goals for startups
“I do generally think that this desire for speed and this desire to, like, move quickly and hire a lot is a little bit of a false lie. I think companies can be built much more slowly than people think. As you look at value creation over a five to 10 year period…”
Hockey: Column will slowly reach $100M ARR but can hit $10B-$100B long-term
“It's not gonna happen in my space. I'm a bit the slowest company to like ever get to a hundred million dollars an hour ever. But I think if we look at it from a 20, 30 year perspective, the ability for us to generate 10, fifty, hundred billion dollars, I think…”
Hockey: 99.9% of my wealth is concentrated in Plaid and Column
“99.9% of my wealth is in platinum column.”
William Hockey: Column avoids new grads, average employee age over 30
“We don't hire a lot of new grads. Like, I think the youngest people on our team are like, 26, 27, and the average age is over 30.”
Hockey: Building on traditional banks takes 9-18 months and limits features by 90%
“However, anytime you build in financial services, you have to build on top of the bank. And to do this right now, it takes nine, 1218 months. It's extremely painful. It's extremely expensive. And you can only probably ship 10% of the products that you want, ri…”
Hockey: Legacy bank implementation, not base protocol, flaws US finance
“What's broken is the implementation of the US financial system that's flawed, not the underlying protocols and product.”
Hockey: US banking protocols can accomplish 95% of crypto's goals
“You can actually accomplish, I'd say, kind of, 90, 95% of what crypto wants and what people want by actually building this from scratch, by actually looking at the protocol layer and not getting distracted by how it's been implemented.”
Hockey: Bank wire cutoffs stem from bank implementation, not the Fed
“A lot of this, like, hey, I can't send a wire past four p.m., that has nothing to do with when you can actually send a wire at the Fed. It's all about when the bank is open for you to send that wire.”
Hockey: US dollar strength makes America's financial system the world's best
“The US has a massive, like the US has the dollar, right? Which is probably the strongest implement. And so that probably inherently bar none makes the US the best financial system, but it's really because of our currency.”
Hockey: 95% of Crypto Trading Occurs Overseas Outside US Regulation
“95% of trading actually just goes overseas outside of kind of that protective umbrella and ends up blowing up.”
Hockey: Restricting legit crypto companies drives consumers to harmful black markets
“I'm probably a hopeless optimist, but I think what it shows is actually, if we don't allow the good players, like a Coinbase, et cetera, to move quickly and actually be able to innovate, those people, like those people are gonna go somewhere, right? People wan…”
Hockey: Coinbase was punished for following regulations while competitors like FTX cheated
“I hope they do really well, because I think what they have tried to do very well is they've tried to embrace regulation and they've tried to do things the right way. They've tried to do things that are right by the regulators and they're right by consumers. An…”
Hockey: Non-financial software companies will dominate financial brands within ten years
“Over the next 10 years, the new financial brands that will win over time and that will be that dominant player are already probably brands today. They just aren't financial services brands. I think what will happen is these large banks that you and I have hear…”
William Hockey: Stricter regulation will make M&A harder, driving in-house software development
“Acquiring is probably gonna be much more challenging over the next 10 years. And so I think you'll probably see these people just build more in-house, right?”
Hockey: Traditional banks offering cradle-to-grave direct services are dead on arrival
“I think the banks that kind of view themselves as still like, hey, we know our consumers and we know our businesses. We're going to offer you cradle to grave. I think they're I think they're dead on arrival.”
Hockey: Persistent cold emails are far more effective than warm introductions
“Cold emails save lives. I think kind of, you know, no matter how powerful, rich or famous you are, I think just skipping the warm intro and going straight to a cold email and following up three times is like the most valuable skills that you have. I've kind of…”
Hockey: Co-founding a company with a spouse creates perfectly aligned incentives
“I think the best thing is, or you have aligned incentives. I think incentives, you know, they, it's the kind of the cause for most of our decision-making framework. And when you start it with a spouse, you have perfectly aligned incentives. And I think that's …”
Hockey: Founders must view government regulation as a static entity when building
“As you have to view, I think government and stuff like this as a static entity, that's probably not going to change. And I think you need to build with that knowledge in the back of your head.”
Hockey: DOJ blocking Visa's acquisition of Plaid was unfair and incorrect
“Is I don't think it was fair. I don't think it was correct, but it doesn't, my opinion doesn't matter is, you know, the government is a decision maker at the end of the day.”
Plaid raised at triple valuation nine months after acquisition was blocked
“You know, you raise a triple evaluation nine months later.”
Hockey: Venture capital is just mutual fund management, not operating
“I think everyone should just admit that venture is just capital allocation and private tech and, you know, It's more like being a mutual fund manager than an operator maybe present company excluded, but I think pretending otherwise is probably anything but a d…”
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▶ POV: The US Govt blocks your $5BN payday 😠 #shorts · 20VC w (@55:40)
▶ Billionaire's Life Hack 🥶📪 #shorts · 20VC with Harry Stebb (@53:31)
▶ 30-year-old Billionaire Gives Secret To Success 🤫💰 #shorts (@6:49)