William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy

**Patrick O'Shaughnessy** (0:00)
Most software companies try to maximize your time on their app to juice engagement. Ramp does the exact opposite. Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports, and checking for policy violations. So they built their tools to give that time back, using AI to automate 85% of expense reviews with 99% accuracy. And since Ramp saves companies 5%, it's no wonder that Shopify runs on Ramp, Stripe runs on Ramp, and my business does too. To see what happens when you eliminate the busy work, check out ramp.com/invest. Every investor should know about Rogo, because Rogo AI's platform is not just another generic chatbot. Instead, it was designed to support how Wall Street bankers and investors actually work, from sourcing diligence and modeling to turning analysis into deliverables. For me, three key things differentiate Rogo. First, it connects directly to your systems, so it can work with your actual data. Second, it understands your workflows, how work really happens across a deal or an investment. 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. 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 in the world. To learn more, visit rogo.ai/invest. OpenAI, Cursor, Anthropic, Perplexity and Versel all have something in common. They all use Work OS. And here's why. To achieve enterprise adoption at scale, you have to deliver on core capabilities like SSO, SCIM, RBAC and Audit Logs. That's where Work OS comes in. Instead of spending months building these mission critical capabilities yourself, you can just use Work OS APIs to gain all of them on day zero. That's why so many of the top AI teams you hear about already run on Work OS. Work OS is the fastest way to become enterprise ready and stay focused on what matters most, your product. Visit workos.com to get started.
Hello and welcome everyone. I'm Patrick OShaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus along with all of our podcasts at colossus.com.

**SPEAKER_2** (2:15)
Patrick OShaughnessy is the CEO of PositiveSum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit PSUMVC.

**Patrick O'Shaughnessy** (2:43)
My guest today is William Hockey, the founder of Column. William was also the co-founder of Plat, one of the more famous fintech businesses from the last decade. Column is his second business which he's built from scratch and funding it entirely himself and building it his way. I think you will find this conversation utterly fascinating, not just because of the incredible quality of the business that he's built, but how maniacal he is about studying and implementing ideas in this specific field. This is a great example of a founder that is winning because he is willing to do everything. My favorite example from our conversation today is that he went and found some obscure book about some ancient bank and found one idea buried in the 2,000 pages that gave him a simple idea for his product. He's willing to do that over and over again and he explains his very different, maybe even heretical views on a lot of what's happening in the world of startups and technology today. He offers a very different way of building that I think will be inspiring and interesting to those that want to build a company. Please enjoy my conversation with William Hockey.
Usually, I don't start with a description of the company that someone's building. But in your case, one, I don't think a lot of people are yet familiar with Column, and I want to fix that. It's such an interesting beast in and of itself, that it will be our excuse to talk about many fascinating things in the world. Can you just start by explaining what the business is and does?

**William Hockey** (4:10)
At a high level, we are a software company that also owns a bank. What we do is we say, okay, we have this interesting regulatory mode, we have a bank that most other people don't have, and we're going to build this incredible software behind it that nobody else can build because they're not a bank. We started out by serving a lot of software companies that want to get into financial services in the US. So with a backend infrastructure that powers the payments, deposits, credit of amazing companies like Bilt, Wise, Ramp, Brex, Mercury, these types of companies, they run on our software than our regulatory rails. Then we also expand that to anybody who want to do things with the global dollar. So that could be international fintechs, that could be a lot of times global banks or banks in emerging markets that need to transact holdings in the dollar. So in the US, you have vertical software, people building business software.