**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. OpenAI, Cursor, Anthropic, Perplexity, and Vercell 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. 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 system 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.
Hello and welcome everyone. I'm Patrick O'Shaughnessy 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 O'Shaughnessy 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 Dan Sundheim. Dan is the founder and CIO of D1 Capital Partners. I've wanted to do this conversation for a long time. Dan is one of those investors who thinks about markets and business constantly and has built a career entirely around that obsession. What makes him unique is that he operates at full intensity across both public and private markets simultaneously, with major stakes in some of the most important private companies in the world like SpaceX, OpenAI and Anthropic, while running a global public equity portfolio that spans nearly every industry and doesn't concentrate in the consensus names. We start at the beginning of his career with the story I've never heard him talk about publicly before, how a shortcase he wrote on Orthodontic Centers of America and posted on Value Investors Club crashed the stock and helped him land his first job. He shares why he backed Anthropic at a moment when many people told him it was the lift to OpenAI's Uber, what reading Dario Amodei's essays reminded him of Bezos' letters to shareholders, and how he thinks about LLM business models through the lens of Netflix and Spotify. We spend time on the extraordinarily stressful moment in early 2021 when GameStop hit the firm and what Dan believes is the single biggest tail risk facing the global economy right now. It's hard to spend time with Dan and not come away struck by how much he genuinely loves his work. I hope you enjoy this great conversation with Dan Sundheim.
I want to spend a bunch of time talking about public versus private. You do both. You started investing in privates more than 10 years ago. You were kind of one of the pioneers of this. You've got some amazing, huge private positions. Draw the contrast today in 2026 of the difference in how the two markets feel. I'm curious about a lot of things here, like how you think about valuation differences, what one tells you about the other, the business of privates versus a public equity hedge fund. I want to go into kind of all of it. At a high level, what is your feeling on the difference between the two markets?
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