This week I have a very special guest years in the making. Like another favorite episode, with anonymous guest Modest Proposal, this conversation is with one of the stars of the financial twitter universe who writes anonymously and goes by the pseudonym Jesse Livermore. I met Jesse 6 years ago after reading his unbelievably unique investing research, which tackled all the big and interesting issues in markets. He now also works with me as a research partner at OSAM, where’s he’s used our data to continue to his search for truth in markets. Despite being one of the brightest minds I’ve encountered he is also as humble and unassuming as they come. I’m at least a slightly better person because of trying to emulate how he conducts himself. I get to have many conversations with him that go from 0-100 fast, and I’m thrilled to be able to share one of those with you. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 1:33 - (First Question) – Jesse’s origin story for investing 4:37 – Exploring his ways of problem solving starting with intuitive             7:53 – David Epstein Podcast Episode 11:46 – Looking at the analytical way of problem solving 15:42 – Statistical inference 24:45 – Should we opt for simplicity in the investment process 25:26 – Does his own investing include all three, intuition, analysis, and statistics 26:09 – The evolution of his research, process, and thinking on various investment factors. 31:38 – Thoughts on inflation and its impact on market valuation 40:05 – The Earnings Mirage 46:25 – Free Cash flow and valuations 50:51 – What should investors take away from this research 53:01 – Thoughts on trend as an interesting market signal 59:00 – The problems with trend 1:00:34 – Post on “The Single Greatest Predictor of Future Stock Market Returns” 1:11:15 – His work into understanding factors 1:15:36 – Looking at momentum 1:18:16 – His curiosity into the current market cycle 1:20:04 – Lessons learned from his time in the military, an effective way to create an environment where people can safely disagree with their co-workers 1:30:10 – The concept of progress in meaningful work 1:33:08 – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

In this episode, Chuck Akre, founder of Akre Capital Management and a seasoned investor managing $10 billion, unveils his unique 'three-legged stool' framework for evaluating companies. He emphasizes the importance of imagination over mere knowledge in investing. Chuck shares insights on identifying extraordinary businesses, effective leadership traits, and the critical role of capital allocation. He also illustrates his investment philosophy with real-world examples like Bandag and shares thoughts on the significance of reinvestment in long-term success.

In this engaging discussion, Jerry Neumann, a thoughtful early-stage investor known for his structured insights on venture capital, shares his views on the pitfalls of gut-based investing. He delves into the risk misalignment in the VC space, the diminishing returns on popular edges like network effects, and emphasizes the importance of understanding value chains and IP protection. Jerry also critiques the influx of new VC firms and the implications of short-term thinking. His data-driven approach offers listeners a fresh perspective on navigating the complex landscape of venture investments.

In this engaging discussion, Sam Hinkie, the former President and GM of the Philadelphia 76ers, delves into his innovative, data-driven approach to basketball management. He shares how adopting a long-term perspective can minimize competitive pressure and foster success. Hinkie also highlights the thrilling early days of basketball analytics at the Houston Rockets and the importance of courage in navigating asymmetric outcomes. With insights on decision-making and team building, he explores the challenges and triumphs of integrating data in sports.

David Epstein, renowned writer and researcher behind "The Sports Gene" and "Range," dives into the fascinating debate of specialization versus generalization. He discusses how individualized training can lead to elite athletic performance, challenging conventional wisdom like the 10,000-hour rule. Epstein also shares insights from his research on effective learning strategies and the need for cognitive diversity in innovation. The conversation touches on educational systems and the importance of embracing varied perspectives for problem-solving.

This week I’m hosting an investor retreat and so thought it fitting to release this conversation with Priya Parker on the art of gathering. I’ve been interested in the topic of community and gathering for some time and along with the book The Art of Community, Priya’s book on the art of gathering is by far the best I’ve read. It is both conceptually interesting and extremely practical. In the book there is literally a table for how big a gathering space should be per person, sorted by the type of vibe you are after. We had a time constraint but I could have talked to Priya for much longer. I hope you enjoy our conversation as much as I did, and that it inspires you to do something new and different with friends, family, or colleagues. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 1:23 - (First Question) – Overview on what she does as a conflict resolution facilitator             1:38 – The Art of Gathering: How We Meet and Why It Matters 4:45 – Lessons about structuring a gathering from her early very difficult work and the idea of sustained dialogue 7:43 – First event she facilitated 9:38 – Importance of a good opening for any gathering 12:30 – Identifying a good purpose for a gathering 15:06 – Why being specific on rules/code of conduct leads to more success 18:54 – Do rules help facilitate more creativity in groups 21:22 – Segregating a good from bad purpose 24:34 – Identity and good/bad gatherings 26:50 – Purpose and the guest list for a gathering 31:03 – Community building is line drawing             32:27 – Dreams from My Father: A Story of Race and Inheritance 34:29 – Importance of well crafted invitations 35:17 – Making the middle of gatherings interesting 39:21 – Exploring risk at gatherings             41:28 – Patterns of Transformation 41:43 – The hero’s journey 46:54 – Making a meaningful transition out of these gatherings 52:39 – Kindest thing anyone has done for Priya   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

Tim Urban, writer and creator of "Wait But Why," joins his business partner Andrew Finn for a vibrant conversation that spans artificial intelligence and interplanetary travel. They dive into the idea of treating life like a game, emphasizing creativity and first principles thinking for personal growth. The duo discusses AI's evolution, the significance of brain-machine interfaces, and how content creators can authentically connect with audiences. Packed with metaphors and engaging insights, this talk will energize anyone striving for innovation.

My guest this week is Stephanie Cohen, who is the chief strategy officer for Goldman Sachs and a member of their management committee. Prior to her current role, she spent the majority of her career in the investment banking and M&A divisions at Goldman.  We discuss lessons learned from her career in M&A and the many initiatives she now leads at the firm. I really enjoyed her perspective on how a big, established firm like Goldman can balance innovation with improving existing businesses. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 1:15 - (First Question) –  Motives on both sides for doing M&A 3:26 – Most difficult deal she worked on 4:50 – Biggest value add she brought from her seat on the Fiat deal 5:59 – Biggest changes since she started to today 8:31 – Smartest ways for companies who want to be acquired to be prepared 10:14 – Best M&A banker she’s seen 11:13 – What should businesses looking to make an acquisition be thinking about 15:16 – What does a strategy from her perspective mean 17:16 – Tension between innovation and change 19:46 – Difference between bottom-up and top-down components of strategy 22:15 – Exploration vs exploitation 26:28 – Submission process within accelerate 29:37 – Next step after you see a good idea 31:05 – Her take on FinTech and Industrials and their collision 35:15 – Lessons from elite early stage investors 37:21 – The origins of the LAUNCH program 40:06 – Important pieces beyond just the capital 42:42 – How they market to women starting business 44:56 – Lessons that she has learned about narrative and communications 47:07 – How she handles developing talent internally 49:28 – Managing her time 59:28 – Biggest concerns about OKR’s? 52:09 – Kindest thing anyone has done for Stephanie 53:07 – Kids in the area of competing   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week’s guest is Will Thorndike, an author and investor whose book The Outsiders is an all-time favorite of mine. Our conversation is in two parts. First, we dive deep into the lessons of his 8-year research project studying CEOs who were master capital allocators. These CEOs include Henry Singleton, John Malone, Tom Murphy, Katherine Graham, and Warren Buffett. We discuss how these CEOs tended to be contrarians on topics like dividends, buybacks, acquisitions, and the use of debt. As we go through each of the tools in the capital allocators toolkit, you’ll hear several useful lessons for running or evaluating a business. In the second part, we cover Will’s career in private equity. Will founded and continues to run Housatonic Partners, investing in buyouts, recaps, and search funds. Will has been one of the most active search fund investors for decades, and given how much time I’ve spent in past episodes on the searchers or operators in the micro-cap, permanent equity space, it was great to get the perspective of an experienced LP. As always, we also take time to survey the dangers and opportunities in today’s private equity market. For comprehensive show notes on this episode go to http://investorfieldguide.com/thorndike For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Josh Wolfe, co-founder and managing partner at Lux Capital. I had Josh on the podcast last year which was one of the most popular episodes in the shows history. This is a continuation of our ongoing conversation about investing in the frontiers of technology. My favorite thing about Josh and the way that he invests is the mosaic that he and his team at Lux are constantly building to understand the world and where new companies may fit in. We cover a crazy variety of topics from business model innovation, roles of a CEO, the military, the death of privacy, and arrows of human progress. Please enjoy round two with Josh Wolfe. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:22 - (First Question) –Ability to tackle massive scale problems 4:05 – Key roles of leaders and his checklist for evaluating them 5:55 – Common traits among founders that make them incredible storytellers and leaders 10:22 – The concept of ill-liquidity 14:53 – Thoughts on the types of companies going public 16:41 – Most innovative business models 19:14 - Advice for LP’s 23:51 – Common devil             24:01 – The True Believer: Thoughts on the Nature of Mass Movements 25:09 – Big internal debates at his firm, starting with price discipline 28:45 – The value debate internally 33:34 – CRISPR from an investment standpoint 36:50 – Edge cases they are looking at 46:52 – How they target ideas in a single concept             50:01 – The Coast of Utopia: Voyage, Shipwreck, Salvage 51:04 – New theses that they chase 56:31 – Recent adventure with special operations guys Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag