Over the years, I have gotten to know Jim through one-on-one conversations and by listening to Infinite Loops and other podcasts where he was a guest.My goal with this podcast is to help you get to know Jim better, from his origin story to his early career in finance and quantitative investing, the writing of his influential book, all the way to the seeds of the idea that became O’Shaughnessy Ventures (OSV) where I now work (more on that below) and how we see the past and future of the Media space.I hope that you will enjoy our conversation and learn a few things even if you’ve been following Jim for years. If this is your introduction to him, I hope you’ll come out on the other side feeling like you have a good understanding of who he is, what his North Star is, and what he’s building. 🏗️🛠️For more context about my joining OSV, see this piece that I wrote about it:* Why I took the job of Head of Infinite Media at O'Shaughnessy Ventures! (OSV) 💡Also, make sure to add Infinite Loops to your podcast player and subscribe to the Infinite Loops substack to keep track of what comes next! This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

I had the great pleasure of talking with someone I admire a lot: Kevin Kelly!He not only influenced my life directly through his works & ideas but he’s also cited as an inspiration and influence by many of the people that I admire, so I’m sure there’s an indirect influence too!Among other things, we discuss his new book (order your copy today!), creativity, the impact of AI, how to create family traditions and rites of passage, Universal Personal Interns (UPIs), what is scarce in the universe, making friends with older and younger people, and more.Please enjoy my wide-ranging conversation with the inimitable K.K.! 💚 🥃 This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

🚨 SPOILERS SPOILERS SPOILERS 🚨 If you haven’t seen the show, bookmark this and come back after you’ve seen it. It’s a show worth seeing without spoilers!I’m very pleased that my friends Matt Reustle (🎧🎙️) and Tinkered Thinking (✍️📚) joined me to discuss what may very well turn out to be my favorite TV shows of the year.Above is one of my fave shots. I’m mad that I forgot to mention it in the podcast!Context: Joel wakes up in a panic because he fell asleep during his night watch. He turns around and Ellie is watching over him with the rifle.🎧 Listen on Spotify 🍄If you prefer to listen on Spotify, here’s the feed:* Liberty’s Highlights podcast feed on Spotify🎧 Listen on Apple Podcasts 🍄Here’s the podcast feed on Apple Podcasts:* Liberty’s Highlights podcast on Apple📺 Watch on Youtube 🍄💚 🥃 For more, please subscribe:🗄 More from the Archives 🍄* 🎧 David Senra and Jimmy Soni: 'The Founders' Book Club on the PayPal Mafia 📖* 🎧 Big Tech Compensation: Going Deep with MBI* 🎧 'Severance' Season 1: Going Deep with Mostly Borrowed Ideas (MBI)* 🎧 David Senra on Deadwood (also: founders, entrepreneurs, civilization, Henry Singleton, Walt Disney, David Ogilvy, etc)* 🎧 Interview with David Kim a.k.a. Scuttleblurb (2023 Edition: Exploration as a Service)* 🎧 Going Deep on the Energy Crisis and Nuclear Power with Mark Nelson (Part 1 of 2) 🔌⚡️💡* 🎧 Claude Shannon fan club with Jimmy Soni and David Senra 📖* 🎧 Podcast #6: Jimmy Soni on the PayPal Mafia (Musk, Thiel, Levchin, etc), startups, tech, the research process, and much more* 🎧 David Senra of Founders Podcast (Podcast #11)* 🎧 Cedric Chin: What Operators can Teach Investors, the Study of Expertise, Knowledge Shields, and More (Podcast #10)* 🎧 Going deep on Constellation Software with Mostly Borrowed Ideas (MBI)🐕🎠🕹️🌳🦒🦒 This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

I’m very happy to share with you this conversation with my two very good friends, Jimmy Soni (📚✍️) and David Senra (🎙📚).We discuss Jimmy’s excellent book The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley, while taking 57 different tangents and detours into things that we find interesting or that are indirectly connected to the main story.I hope you enjoy this special Book Club edition!📃 Full transcript (human-corrected and everything!)* Transcript: David Senra and Jimmy Soni: 'The Founders' Book Club on the PayPal Mafia 📖🎙 Previous Book Club on Claude Shannon 📘📗📕🐁* 🎧 Claude Shannon fan club with Jimmy Soni and David Senra 📖💚 🥃 Enjoyed this? Want more? 👇You can become a paid supporter to get 2x additional editions/week + access to the private Discord + support the recording of more podcasts:Subscribe to Liberty’s Highlights This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

What could be more exciting than carefully reading through Big Tech proxy statements to look at management incentives, comparing them across companies to see what’s similar and different, what we like and don’t like, and how they rank from best to worst..?If this is not your bag, you’re in luck! MBI did this work for you and shared his findings in a post.But that’s just a starting point: In today’s episode, we go deep into Big Tech compensation, and MBI shares additional thoughts and analysis based on feedback he received after publishing his work. We discuss Apple, Google/Alphabet, Microsoft, Amazon, and Meta.For a lot more good stuff from Mostly Borrowed Ideas (💎🐕), sign up for MBI Deep Dives (now is the best time to sign up, because prices are going up on March 1st, 2023).🎧 Listen on SpotifyIf you prefer to listen on Spotify, here’s the feed:* Liberty’s Highlights podcast feed on Spotify🎧 Listen on Apple PodcastsHere’s the podcast feed on Apple Podcasts:* Liberty’s Highlights podcast on Apple📺 Watch on Youtube📃 Full transcript of the podcast* Transcript: Big Tech Compensation: Going Deep with MBI🎙 More podcasts with MBI:* 🎧 Going Deep on Cloudflare and Datadog with Mostly Borrowed Ideas (MBI)* 🎧 'Severance' Season 1: Going Deep with Mostly Borrowed Ideas (MBI)* 🎧 Going deep on Payments with Mostly Borrowed Ideas (MBI): Adyen, PayPal, Stripe, Square, Amazon, Apple Pay, Google Pay, Visa, Mastercard!* 🎧 Going deep on Constellation Software with Mostly Borrowed Ideas (MBI)🗄 More Podcasts from the Archives* 🎧 Interview with David Kim a.k.a. Scuttleblurb (2023 Edition: Exploration as a Service)* 🎧 Going Deep on the Energy Crisis and Nuclear Power with Mark Nelson (Part 1 of 2) 🔌⚡️💡* 🎧 Claude Shannon fan club with Jimmy Soni and David Senra 📖* 🎧 Podcast #6: Jimmy Soni on the PayPal Mafia (Musk, Thiel, Levchin, etc), startups, tech, the research process, and much more* 🎧 David Senra of Founders Podcast (Podcast #11)* 🎧 Cedric Chin: What Operators can Teach Investors, the Study of Expertise, Knowledge Shields, and More (Podcast #10)💚 🥃 Enjoyed this? Want more? 👇You can become a paid supporter to get 2 additional editions/week + access to the private Discord + support the recording of more podcasts: This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

David Kim is the author of Scuttleblurb (now also on Substack! More on that new development in the podcast).This is the third time I have interviewed David — he’s that interesting! For more context, you can find the previous two interviews linked below.In this one, David shares his journey as an investor, talks about how Scuttleblurb started and how it’s doing these days, and who inspired him to get started (if Scuttleblurb is the grand-daddy of a lot of current ‘deep dive’ newsletters, who’s the great-grand-daddy?).It’s a two-way conversation, so we also talk about what I’m doing.We also touch on some businesses: Carvana (😬), Texas Instruments (🐜), Sherwin-Williams (🎨), and Transdigm (🛩️).David has a great riff about the various approaches to investing and the trade-offs inherent to each. He also discusses the EQ aspects of investing, which can sometimes be overlooked in favor of the IQ side of things (where there’s also a fluid vs crystalized intelligence dynamic at play over time).David also talks about the two kinds of errors in investing, with examples for each (Twitter & Coinbase!), and when more information can help and when more information can potentially hurt you.📃 Full transcript of the podcast* Transcript: Interview with David Kim a.k.a. Scuttleblurb (2023 Edition)🗣️ More interviews with David Kim* 📄 Interview with David Kim a.k.a. Scuttleblurb (2020)* 📄 Interview with David Kim a.k.a. Scuttleblurb (2022 Edition) This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

Let’s go deep into season 1 of Severance (2022, Apple TV+), a thriller with science fiction elements created by Dan Erickson and directed by Ben Stiller and Aoife McArdle. It was nominated for 14 Emmys!🤫 🚨NOTE ON SPOILERS 🚨🤐This podcast has a SPOILER-FREE INTRO.The spoilers only start after the “spoiler horn” about 11 minutes into it (you can’t miss it 📢).So even if you haven’t seen the show, you can listen to the first part — I hope it piques your curiosity and convinces you to check it out!For more of my thoughts on Severance, I also wrote about it in edition #354 (with both a spoiler-free intro and then spoilers).I hope you enjoy it.Covering a TV show is a bit different (David Senra and I discussed Deadwood). But MBI and I still end up talking about Google, Warren Buffett, technological disruption, capital allocation, value creation vs value capture, and workplace productivity. So it’s still us. ¯\_(ツ)_/¯We also run a few thought experiments: Would we ever consider getting severed ourselves? Can we imagine scenarios where that would be convincing? If this were offered, what percentage of the population would do it?What about you?The podcast even has some trivia near the end with a Claude Shannon connection! This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

First, something to keep in mind: This is a conversation about these companies not an interview of MBI. We both talk about equally and ask each other questions. I want to mention it upfront just so you don’t expect a different format going in.I had a great time discussing these two very interesting companies with my friend MBI (💎🐕).When I saw on his 2022 deep dive calendar that he was going to write about Cloudflare and Datadog, I knew we had to find time to talk about them at some point, since I had independently studied both and had a few things to say.We discuss the businesses, technology, products, and management.We also analyze the rise and fall of cloud software stocks over the past few years, issues with stock-based compensation, competition for engineers from Big Tech, how profitable can these companies be at maturity, and a bunch of other related topics and companies.📃 Full transcript* Going Deep on Cloudflare and Datadog with Mostly Borrowed Ideas (Transcript)🎙 More podcasts with MBI:* 🎧 Going deep on Payments with Mostly Borrowed Ideas (MBI): Adyen, PayPal, Stripe, Square, Amazon, Apple Pay, Google Pay, Visa, Mastercard!* 🎧 Going deep on Constellation Software with Mostly Borrowed Ideas (MBI) This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

I’m very happy to share with you this conversation I had with my two very good friends, Jimmy Soni (✍️) and David Senra (🎙📚).We got together for a very special occasion. To talk about this man:Claude Shannon was both a genius and a very authentic human being, and I think more people should learn from him — understanding his masterwork, Information Theory, helps to understand the digital world, but I also strongly believe that reading about how he lived his life can help steer us to a deeper, more satisfying life for ourselves.Jimmy Soni and Rob Goodman wrote an excellent biography of Shannon, and this book is the starting point for today’s episode.But in our usual fashion, we don’t stop there and make all kinds of connections to all kinds of other things and people (Ed Thorp, Henry Singleton, Warren Buffett, Vannevar Bush, Dee Hock, Benjamin Franklin, John von Neumann, Alan Turing, Albert Einstein, etc).💚 🥃 Enjoyed this? Want more? 👇If you enjoyed this and would like more, you can become a paid supporter to get 2x extra editions/week + access to the private Discord + support the recording of more podcasts. This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe

🤬 First a warning: This podcast includes a few swear words. It’s impossible — or at least not as fun — to talk about Deadwood without them. It is what it is. 🤬The main topic is Deadwood (HBO, 2004-2006) and what can be learned from the show, but of course, this being David & I, we also talk about:* founders,* entrepreneurs,* obsessive creators,* the power of focus,* the power of strategy,* how civilization emerges,* intelligence as a currency,* violence as humanity’s fatal flaw,* sanitized origin stories,* addiction & abuse,* Andrew Carnegie,* Henry J. Kaiser,* Henry Singleton,* David Ogilvy,* Walt Disney,* Warren Buffett,* planting seeds,* optionality from future technology,* the lessons of history about violence and corruption,* and all kinds of other interesting things.We also talk about Tombstone (1993), which I hadn’t seen at the time, but watched soon after we recorded. I shared some thoughts on it here in edition #338.If you liked the pod and want more, please consider becoming a paid supporter (💚 🥃). This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.libertyrpf.com/subscribe