Episode summary
How to bet on yourself (without venture capital)
Invest Like the Best
· · 1 hr 17 min · Hosts: Patrick O'Shaughnessy · Guests: William Hockey
Summary
William Hockey argues that Column is a software company that also owns a bank, built to provide the regulated rails behind payments, deposits, credit, and global-dollar services for customers like Built, Ramp, Brex, Wise, and Mercury. He says the company makes most of its money from software, not traditional banking spread, and that financial-services infrastructure matters even more as AI pushes businesses deeper into the money layer.
A major theme is his rejection of the venture-capital playbook. Hockey says he funded Column with debt and retained ownership, which let him buy a bank, delay revenue-driven decisions, and make long-horizon bets without chasing the next fundraising cycle. He argues that VC can create a “hamster wheel” of fashion-driven pivots, while self-funding and profitability keep the company focused on durability, liquidity for employees, and capital efficiency.
He also makes a broader case that Silicon Valley is too consensus-driven and too detached from the rest of the world. Hockey says emerging markets like Kinshasa and Congo reveal constraints, talent, and product opportunities that San Francisco misses, especially in dollarized economies where financial services are underbuilt. Across the conversation, he argues that the best founders go extremely deep, embrace risk, and find leverage in boring, specialized problems rather than broad, fashionable themes.
Key takeaways
- Hockey says Column is built as a software company with a bank underneath, and most revenue comes from software rather than banking economics.
- He argues that self-funding let Column buy a regulated bank early and make long-term bets that venture-backed companies usually cannot.
- Hockey says Silicon Valley is increasingly consensus-driven, so founders should look to emerging markets like Congo for non-consensus ideas and constraints-based innovation.
- He believes the best founders are specialists who can make the most boring problems interesting for a decade or more.
- He says VC funding can distort strategy by pushing founders to chase the latest theme instead of building a durable business.
- Hockey argues that employees at early-stage companies often take more personal risk than founders do, so Column tries to offer real liquidity and stability.
Notable quotes
“We are a software company that also owns a bank”
“we make 90 plus% of our money off of software. And so similar to a any kind of SAS company, it's a per API call”
“I think you can actually be highly ambitious. I think you can hire like the world's best talent”
“VC money is kind of like heroin. It like feels good. It's amazing, but like you got to keep shooting up”
“the good founders bet on themselves and take an extreme amount of risk to do that”
How the episode opens
My guest today is William Hockey, the founder of Column. William was also the co-founder of Plat, one of the more famous fintech businesses from the last decade. Column is his second business, which he's built from scratch and funding it entirely himself and building it his way.
I think you will find this conversation utterly fascinating, not just because of the incredible quality of the business that he's built, but how maniacal he is about studying and implementing ideas in this specific field. This is a great example of a founder that is winning because he is willing to do everything. My favorite example from our conversation today is that he went and found some obscure book about some ancient bank in Japan and found one idea buried in the 2,000 pages that gave him a simple idea for his product.
He's willing to do that over and over again. And he explains his very different, maybe even heretical views on a lot of what's happening in the world of startups and technology today. He offers a very different way of building that I think will be inspiring and interesting to those that want to build a company.
Please enjoy my conversation with William Hockey. Usually I don't start with a description of the company that someone's building, but in your case uh one I don't think a lot of people are yet familiar with column and I want to fix that
And it's such an interesting beast in and of itself that it it'll be our excuse to talk about many fascinating things in the world. — Can you just start by explaining what the business is and does at a high level? We are a software company that also owns a bank. And what we do is we say, okay, we have this interesting regulatory mode.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- bootstrapping vs venture capital
- founder risk
- solving boring problems
- emerging markets
- us dollar as a national security asset
Companies and tickers mentioned
- Plaid
- Column
Watch the episode
Watch “How to bet on yourself (without venture capital)” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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Invest Like the Best, this episode and its artwork belong to Colossus | Investing & Business Podcasts. Octagon is not affiliated with the show; this page is an independent summary.
