Jeremy Giffon - The Billion Dollar PDF - [Invest Like the Best, EP.481]
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What key lessons did Jeremy learn from 18 months of founder conversations?
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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.
Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions 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.
My guest today is Jeremy Giffen. 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 Giffen. So we're gonna 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 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 with the capital that has backed them in the past to sort of 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. So what have you learned in the first 18 months of doing this? 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.
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Chapters
8 chapters
1
What key lessons did Jeremy learn from 18 months of founder conversations?
0:01–9:48
2
How does the “Billion‑Dollar PDF” concept shape capital formation?
9:48–19:37
3
Why are founders and investors now sub‑servient to the poster class?
19:37–27:43
4
How are AI algorithms changing the creation and impact of content on the timeline?
27:43–36:51
5
What does the power‑law breakout content look like in today’s markets?
36:51–46:39
6
Why is the billionaire class losing influence and what class is replacing it?
46:39–55:37
7
What is the next wave of finance and how do equity‑first firms differ from traditional models?
55:37–1:05:45
8
How can firms attract differentiated talent and hire the right people for the future?
1:05:45–1:15:34
Speakers
1 identifiedMore from Invest Like the Best with Patrick O'Shaughnessy
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Sarah Guo - Funding the Frontier - [Invest Like the Best, EP.489]
Neil Movva - Making AI 10x Cheaper - [Invest Like the Best, EP.488]
Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487]