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Invest Like the BestInvest Like the Best

How to bet on yourself (without venture capital)

William Hockey, co-founder of Plaid and founder of Column, joins the show to discuss building the global operating system for the US dollar.

Patrick O'ShaughnessyhostWilliam Hockeyguest
Mar 17, 20261h 17mWatch on YouTube ↗

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At a glance

WHAT IT’S REALLY ABOUT

William Hockey on building Column by owning a bank, self-funded

  1. William Hockey explains Column as a software company that owns a bank, offering API-based banking primitives that power payments, deposits, and credit for fintech and global-dollar use cases.
  2. He argues traveling—especially in emerging markets—breaks Silicon Valley consensus thinking and reveals innovation patterns shaped by constraint, dollarization, and different talent dynamics.
  3. Hockey details why he rejected the venture-capital “hamster wheel,” saying VC fundraising pressures can distort product strategy and shorten time horizons compared with growing from earnings.
  4. He describes funding Column through debt against illiquid Plaid shares, enduring margin calls and intense stress as the tradeoff for keeping ownership with employees and maintaining long-term control.
  5. He lays out a worldview where the US dollar and sanctions are central to global connectivity and national security, and suggests AI value will accrue mainly to players with distribution and large cost structures, including legacy banks.

IDEAS WORTH REMEMBERING

5 ideas

Column pairs a regulated bank charter with a software-first business model.

He describes Column as “a software company that also owns a bank,” using the bank charter as a regulatory moat and building software others can’t because they’re not a bank. Column provides API “primitives” that let customers run deposits, payments, credit, and network connections on Column’s rails.

Customers build the frontend; Column runs the regulated backend and charges like SaaS.

Using Bilt as an example, he explains Column is the issuer behind the card and provides the account/routing numbers, while Bilt builds the consumer experience and marketing. Column handles connections to entities like the Federal Reserve, TCH, card networks, SWIFT, and charges in a SaaS-like per–API call model while passing much of the bank-side economics to customers.

Silicon Valley’s consensus culture can distort what founders build and for whom.

He argues Silicon Valley (like Beijing, per a Dan Wang criticism he cites) can become highly consensus-driven, which is useful for some “outlandish” ideas but also isolates founders from how most Americans and much of the world live. He says this contributes to building “software for elites” and weakens resonance with everyday needs.

Constraint-heavy markets can be disproportionately innovative—especially in finance.

He says emerging markets operate under tighter constraints that force different creativity, and that dollarized places often need US financial services most. He also claims financial services innovation often appears in “the worst countries,” citing examples like mobile payments emerging early in Africa and bespoke systems built under constraints in places like Iran and Argentina.

Avoiding VC can reduce fundraising-driven strategy drift and enable longer bets.

He chose to fund Column without venture capital to avoid optimizing for the next fundraise and the trend-chasing that can follow (his examples: needing a “stablecoin strategy,” then an “AI strategy”). He says self-funding enables investments with 10-year paybacks and a straighter path to the goal.

WORDS WORTH SAVING

5 quotes

VC money's kinda like heroin. It, like, feels good, it's amazing, but, like, you gotta keep shooting up.

— William Hockey

I pledged over a billion dollars of stock to get $70 million.

— William Hockey

I think we need to increase the, the, the risk for founders. I think we need to make failure much more expensive.

— William Hockey

And I think starting companies is just... It's too, it's too fucking safe.

— William Hockey

One of the best determiners for success of founders is can they find the most boring thing humanly possible interesting, and can they find that interesting over a multi-decade period?

— William Hockey

Read the available transcript
Bank charter as regulatory moatBanking APIs and fintech infrastructureEmerging markets, constraints, and dollarizationSilicon Valley consensus and elite-focused productsBootstrapping vs venture capital incentivesFounder risk, debt financing, and margin callsEmployee equity, liquidity, and retention via buybacks/tenders

SPEAKERS

  • Patrick O'Shaughnessy

    host

    Founder of the Invest Like the Best podcast and an investor who interviews founders and business leaders.

  • William Hockey

    guest

    Founder of Column and co-founder of Plaid, focused on banking and financial infrastructure.

High quality AI-generated summary created from speaker-labeled transcript.

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