William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Technology, Business, Investing

4.7 • 2.5K Ratings

🗓️ 17 March 2026

⏱️ 72 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- 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

Transcript

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0:00.0	Most software companies try to maximize your time on their app to juice engagement.
0:03.8	Ramp does the exact opposite.
0:05.6	Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports,
0:10.0	and checking for policy violations.
0:12.0	So they built their tools to give that time back, using AI to automate 85% of expense
0:17.1	reviews with 99% accuracy.
0:19.3	And since Ramp saves companies 5%,
0:21.5	it's no wonder that Shopify runs on Ramp,
0:23.8	Stripe runs on Ramp, and my business does too.
0:26.1	To see what happens when you eliminate the busy work,
0:28.2	check out ramp.com slash invest.
0:30.5	Every investor should know about Rogo,
0:32.4	because Rogo AI's platform is not just another generic chatbot.
0:36.1	Instead, it was designed to support how Wall Street
0:38.1	bankers and investors actually work, from sourcing diligence and modeling to turning analysis
0:42.7	into deliverables. For me, three key things differentiate Rogo. First, it connects directly to your
0:48.1	systems so it can work with your actual data. Second, it understands your workflows, how work really
0:52.7	happens across a deal or an investment.
0:54.9	And third, it runs end to end and produces real outputs the way the best people do, auditable spreadsheets, investment memos, diligence materials, and slide decks that match your standards.
1:03.6	This all comes from the fact that Rogo is built by finance professionals for finance professionals, and it's already being adopted by some of the most demanding institutions
1:11.0	in the world. To learn more, visit rogo.a.i slash invest. OpenAI, cursor, anthropic, perplexity, and
1:17.7	Versel all have something in common. They all use WorkOS. And here's why. To achieve enterprise
	...

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