Jeremy Giffon - The Billion Dollar PDF

**Patrick O'Shaughnessy** (0:00)
Ramp is the only platform built to make your finance team leaner, faster and better, saving businesses 5% annually on average, so you can stay focused on growth. Ramp customers grew revenue 3.2 times faster than the average American business. Visa, Vercel, Cursor, Stripe, Notion, 11Lab, Shopify, and 70,000 other businesses all run on Ramp. Mine does too, and so should yours. Learn more at ramp.com/invest.
Felix by Rogo is a personal finance agent that turns a single prompt into finished, client-ready work using your firm's own templates, context, and standards. Send Felix an email like take these comments and turn them for me, or update my tracker with the context of these emails, or run the ability to pay math on this buyer, and Felix sends back finished PowerPoint decks, Excel models, and sourced research. Felix works the way your team already does, delivering work quickly and accurately around the clock. Learn more at rogo.ai/felix.
OpenAI, Cursor, Anthropic, Perplexity, and Vercel 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 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** (1:53)
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** (2:21)
My guest today is Jeremy Giffon. Jeremy has been on the show before as one of our most popular guests and this conversation is every bit as enjoyable as the first. Over the last 18 months, Jeremy has had hundreds of conversations with founders and the capital behind those companies. I don't know many investors with such a high rep count in the most interesting corners of private markets, so I asked him about everything that he has learned. We talk about what those lessons mean for founders and investors, why everyone has become subservient to the poster class, the hidden intellectual history behind Silicon Valley and much more. Please enjoy my conversation with my friend, Jeremy Giffon.
So we're going to have the chance to talk about, as we do on a daily basis, you and I, 57 different ideas. But I'm always interested to begin with you, a couple of questions about investing. I sit near you, we share an office, so I get to hear a lot of these stories every day. I think it would be really fun for you to turn your observations from all those, God knows how many hundreds of conversations with founders of these companies and the capital that has backed them in the past, to share what you've learned from that frontier over the last 18 months, framed as advice for founders and advice for capital. I just don't know very many investors that are looking at situations like you are with such a high rep count.
What have you learned in the first 18 months of doing this?

**Jeremy Giffon** (3:36)
You really realize in, let's say, long-term private markets that the great filter for funds is their storytelling ability, fundamentally, because their product, which is realized cash returns, take a decade. The thing that you're selling in the interim, whether it's through a quarterly update or your event or just your one-on-one conversations with your LPs, is really just a narrative. A particular situation that's very interesting that we've seen a lot of is companies wear twofold. One is that the business is kind of old, but it has started to do well recently. That's an interesting scenario because it's one of these instances where merely because the company, the story, again, the narrative of the company is that it's seven years old.