Freedom to Make Non-Scalable Bets

William Hockey is the co-founder of Plaid and the founder and CEO of Column, a software company that owns a bank and powers Ramp, Wise, Bilt, Mercury, and others. He funded Column by borrowing against his Plaid shares and has never raised outside capital. 

William talks about what owning 100% of his company allows him to do that other venture-backed founder cannot and the personal risk he took to do so. He shares how Silicon Valley's consensus culture produces consensus founders, and why becoming a founder has become too safe. He believes the best builders are specialists and explains with unusual clarity what it takes to become the best in the world at one specific thing.

William also spends a lot of time in emerging markets which has given him a unique perspective of the power of the US dollar.

For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. 

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Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠).

Timestamps:

(00:00:00) Welcome to Invest Like the Best

(00:02:43) Intro: William Hockey

(00:03:49) Column: A Software Company That Owns a Bank

(00:06:46) Finding Ideas in Emerging Markets

(00:11:58) Why Constrained Societies Are More Innovative

(00:16:02) What’s Wrong With Silicon Valley

(00:19:28) Building a Business Without Raising Money

(00:22:48) What Venture-Backed Companies Can't Do

(00:28:39) Getting Margin Called

(00:31:41) Starting Companies Has Become Too Safe

(00:34:23) Why Employees Take More Risks Than Founders

(00:37:09) A Maniacal Commitment to Research

(00:39:09) Finding Boring Problems to Solve

(00:41:45) Why Building a Second Company is Easier

(00:42:36) Missionary vs. Mercenary

(00:45:49) Funding a Company with Cash Flows

(00:50:04) Perspective on the Venture Ecosystem

(00:52:48) The Dominance of the US Dollar

(00:58:37) The Future of Financial Services

(01:02:06) Why Big, Inefficient Brands Win From AI

(01:06:29) The Opportunity for Non-Consensus Founders

(01:08:03) The Kindest Thing