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Invest Like the BestHow to bet on yourself (without venture capital)
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Episode Details
EPISODE INFO
- Released
- March 17, 2026
- Duration
- 1h 17m
- Channel
- Invest Like the Best
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
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
SPEAKERS
Patrick O'Shaughnessy
hostFounder of the Invest Like the Best podcast and an investor who interviews founders and business leaders.
William Hockey
guestFounder of Column and co-founder of Plaid, focused on banking and financial infrastructure.
EPISODE SUMMARY
In this episode of Invest Like the Best, featuring Patrick O'Shaughnessy and William Hockey, How to bet on yourself (without venture capital) explores William Hockey on building Column by owning a bank, self-funded 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.
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