William Hockey, co-founder of Plaid and founder of Column, joins the show to discuss building the global operating system for the US dollar. Unlike the typical Silicon Valley playbook, William funded Column entirely with his own to avoid the "hamster wheel" of venture capital. In this conversation, he shares unconventional wisdom on why modern founders take too little risk, the strategic importance of solving boring problems, and why he spends time in emerging markets like Kinshasa. We also cover the US dollar as a national security asset and why distribution will matter more than technology in the AI era.

Timestamps:
0:00 Intro
9:19 Emerging Markets
14:03 Silicon Valley's Elite Consensus Problem
16:03 Rejecting the VC Hamster Wheel
21:45 Equity and Liquidity
26:03 Funding a Bank
29:45 The Necessity of Extreme Founder Risk
37:18 Finding Leverage
45:20 Longevity and Profitability in Banking
48:46 Matching Your Capital Structure to Your Business
51:44 The Unseen Power of the US Dollar
1:02:30 How AI Will Transform Legacy Banks
1:09:23 The Kindest Thing

#investing #business #founder #fintech #banking #startups #siliconvalley #risk #entrepreneurship #finance

Presented by Ramp:
https://ramp.com/invest

Sponsored by Vanta, WorkOS, Rogo, and Ridgeline:
https://www.vanta.com/invest
https://workos.com/
https://rogo.ai/invest
https://www.ridgelineapps.com/

******
Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc