My guest this week is Brian Christian, the author of two of my favorite recent books: Algorithms to Live By and The Most Human Human. Our conversation covers the present and future of how humans interact with and use computers. Brian’s thoughts on the nature of intelligence and what it means to be human continue to make me think about what works, and life, will be like in the future. I hope you 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 1:11 - (First Question) – Summarizing his collection of interests that led to his three books 2:59 – Biggest questions in AI 3:43 – Defining AGI (Artificial General Intelligence) and its history             5:18 – Computing Machinery and Intelligence 7:54 – The idea of the most human human 9:59 – Tactics that have changed the most in learning to be the most human human 16:10 –Tests for measuring AGI and updates made to them 20:12 – Concerns for once we have AGI 26:06 – Self-awareness as a threshold for AGI 31:58 – Skeptics’ take on AGI 37:14 – Advice for people building careers and how AGI will impact work 38:16 – Explore/Exploit trade-off 44:57 – How to explore/exploit applies to business concepts 49:16 – Impacts of AGI on the economy 52:40 – Highlights from his second book 57:39 – Kindest thing anyone has done for Brian   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

My guest this week is Eric Sorensen, the CEO of Panagora asset management, which manages more than $46B for clients across a variety of strategies. Eric began his career serving in the Air Force as both a pilot and instructor in high-performance jet aircraft. He then accumulated 40 years of quantitative research and investment experience, with a Ph.D. along the way. Please enjoy our conversation on the changing landscape of quantitative investment strategies. 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) – His background in the Air Force             1:23 – Boyd: The Fighter Pilot Who Changed the Art of War 3:18 – Training people on high-performance machines 4:47 – Traits that made for better pilots 5:51 – The evolution of quantitative equity research and its stages 7:56 – How his research led to becoming a practitioner 9:10 - The early feature sets in his research 10:44 – Tradeoffs in the spectrum of interpretability 12:08 – Early days of his practitioner career 13:24 – Risk Premia and the 5 C’s 14:28 – Quantitative Equity Portfolio Management: Modern Techniques and Applications 17:13 – Applying the 5 C’s to value investing 18:38 – Knowing when a strategy/signal is broken 21:24 – What does this strategy plan mean for his firm today 24:56 – Mixing expert systems and portfolio construction 30:07 – Natural language processing 32:00 – The cultivating the power and creativity to ask good questions 35:13 – The concept of a research graveyard 37:45 – State of risk premia today 40:04 – Active equity process 46:37 – Frontiers of research that he’s excited about 48:53 – Safe havens for non-quantitative investors 52:16– Advice for young quants 54:36 – Quants on the buy-side that he admires 55:41 – 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

Jane McGonigal, PhD is a world-renowned designer of alternate reality games — or, games that are designed to improve real lives and solve real problems. She is the Author of Reality is Broken: Why Games Make Us Better and How They Can Change the World and is the inventor and co-founder of SuperBetter, a game that has helped nearly a million players tackle real-life health challenges such as depression, anxiety, chronic pain, and traumatic brain injury. Our conversation is about how to design useful games, how games effect us and our kids, and what the future might hold. Please enjoy. 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) – Her take on the history of gaming and studying the players themselves 3:44 – Where her passion for gaming really started 4:55 – Her take on flow states 7:47 – Kids and gaming 10:32 – Advice for parents when it comes to the role of games             11:06 – SuperBetter: A Revolutionary Approach to Getting Stronger, Happier, Braver and More Resilient--Powered by the Science of Games 13:53 – Types of games that develop the right skills for kids 16:20 – Four things all games share in common             16:23 – Reality Is Broken: Why Games Make Us Better and How They Can Change the World    20:50 – Her take on Carse’s theory about infinite gaming             21:04 – Finite and Infinite Games 26:28 – How to understand gaming culture if you’ve never played a game before 28:28 – Amazon and gaming 31:18 – How fun makes anything more enjoyable 34:55 – How game designers calibrate feedback loops 39:14 – The good and bad of gamifying life 45:01 – What is the superbetter app 52:43 - Why powerups and bad guys are so important in games 57:03 – Secret identity 59:04 – Playing with boundaries 1:00:36 – Most worried about in the gaming world, and most exited about 1:07:32 – Kindest thing anyone has done for Jane   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

My guest this week is Bill Gurley, a general partner at Benchmark Capital and one my favorite investment thinkers. As you’ll hear, despite enormous success through his career, Bill is clearly still in love with business and investing. Where many might discuss past glories, I’ve been incredibly impressed with how both Bill and his partners emphasize the current portfolio and market landscape. I’m thankful to have had the chance to speak with him in this format. I hope you 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 1:13 - (First Question) – The idea of increasing returns             1:21 – Competiting Technologies, Increasing Returns, and Lock-in By Historical Events             2:07 – Complex Systems Theory – Santa Fe Institute 4:35 – Markers that could be a sign of network effect in a company 6:27 – The opportunities for companies to capture network effect 8:46 – Are there certain teams/leaders that are more conducive to leading a network effect company 11:55 – Liquidity quality 13:35 – How important is the revenue model at the beginning 15:59 – Fascination with Nextdoor             17:56 – Paradox of Choice 18:39 – Finding opportunities 20:17 – Potential marketplaces and assets that could be commoditized             20:20 – All Markets Are Not Created Equal: 10 Factors To Consider When Evaluating Digital Marketplaces 21:39 – Usage yield on the world’s assets 23:50 – Has technology changed the world of value investing 26:28 – Hyper niche marketplaces 27:52 – Challenges of labor marketplaces 30:12 – User generated content businesses 32:44 – People who are capable of building UGC businesses 33:16 – His interest in Discord 34:31 – Factors of a healthy marketplace 37:57 – Fools’ gold in marketplace businesses 39:04 – How influx of cash is impacting the marketplace business landscape             40:43 – All Revenue is Not Created Equal: The Keys to the 10X Revenue Club 43:20 – How does the influx of money into the space impact him 46:44 – Spending money to attack top brands 50:32 – Regulatory capture 53:36 – His thoughts on the IPO market 57:49 – How did he realize this was his passion 1:00:42 – Qualifying his passion 1:01:52 – Favorite thing about working with entrepreneurs 102:48 – Honing your craft 1:04:33 – Making yourself a good mentor 1:05:56 – 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  

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

My guest today is Chuck Akre, a now widely famous investor who founded Akre Capital Management in 1989, which now manages approximately $10B dollars. We discuss his investing style and his “three-legged stool” for evaluating companies. Please enjoy this great 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 1:06 - (First Question) – Advantage of being in Middleburg, Virginia 2:11 – What a day looks like for Chuck 3:06 – Why imagination is more important than knowledge 3:38 – Difference between curiosity and imagination 4:38 – The origins of the Nirvana Three-Legged Stool concept 10:14 – First leg of the stool, Extraordinary business and ROE’s with a focus on Bandag. 14:36 – How his evaluations of value has changed over the last 10-15 years 16:10 – A look at recent businesses that he’s bought and why they are interesting 19:56 – Why they keep things simple 21:35 – Second leg of the stool, the people involved and characteristics of managers he has invested in 23:20 – Role of capital allocation in the people he focuses on 28:03 – Favorite biographies             28:22 – 100 to 1 in the Stock Market: A Distinguished Security Analyst Tells How to Make More of Your Investment Opportunities 29:34 – Third leg of the stool, reinvestment 21:09 – How does he think about diversifying across an investment area 33:32 – Great businesses wrapped in a bad balance sheet 37:35 – What would cause him to sell 38:52 – What does he look for in people 43:27 – How curiosity has impacted his interest in land conservation 43:51 – Advice for investors, especially younger ones 46:14 – 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

My guest this week is Jerry Neumann. Jerry is one of the most thoughtful early stage investors that I’ve encountered, and his writings at reactionwheel.net are my favorite on this topic. He applies an incredibly structured way of thinking to a notoriously mysterious investment category. This is our second conversation, in which we cover why investing with one’s gut is a bad idea and why some of the popular edges in startups, like network effects, may be picked over. 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 1:17 - (First Question) – His take on the venture landscape and the type of investments new VC’s are making vs what they should be making 3:44 – Most important implications of excess VC firms 5:32 – Misalignment of incentives in the VC space 8:19 – What he does differently from angel investors or VC’s 10:11 – The notion of risk and the types of risk the people he invests in takes 14:33 – Protections that he thinks about when it comes to the ideas he invests in 19:37 – Is there an area of expertise that provides an edge for startups 20:11 – Network effects are picked over 21:35 – IP protection 23:08 – One of the two most interesting things for VC’s to go after, brands 25:13 – The other most important thing, the value chain 27:42 – A current example of a disruptive value chain 29:14 – Innovation as the source of profit             29:16 – Schumpeter on Strategy 31:50 – Efficiency innovation vs value innovation             31:52 – Energy and Civilization: A History 35:50 – Efficiency investments he’s made 37:13 – Investment in Unsupervised and the machine learning landscape 41:25 – Investment in Sila 43:14 – Investment in Edmit 44:44 – investing on gut 50:32 – Black boxes and their value in investments 53:23 – Metrics about the predictive level of whether people are going to succeed 54:45 – What defines good people worth backing 57:50 – Advice for LP investors in this space and how they should evaluate VC’s in this space   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

I came across this week’s guest thanks to the overlap of three passions of mine: data informed investing, value creation, and basketball. Sam Hinkie worked for more than a decade in the NBA with the Houston Rockets, and then most recently as the President and GM of the Philadelphia 76ers. He helped launch basketball's analytics movement when he joined the Houston Rockets in 2005, and is known for unique trade structuring and a keen focus on acquiring undervalued players. Today, he is also an investor and advisor to a limited number of young companies in which he feels his experience can improve outcomes. Please enjoy this unique episode with Sam Hinkie. Show Notes3:24 – (First Question) Advantages of having a long view and how to structurally harness one6:08 – Using technology to foster an innovative culture           6:18– Empire of the Summer Moon: Quanah Parker and the Rise and Fall of the Comanches, the Most Powerful Indian Tribe in American History10:16 – Favorite example of applied innovation from Sam’s career11:34 - Most fun aspect of doing data analytics early on the Houston Rockets13:38 - Is there anything more important than courage in asymmetric outcomes14:29 – How does Sam know when to let the art of decision making finish where the data started16:29 - Pros and cons of a contrarian mindset17:26 – Where he wanted to apply his knowledge in sports when first getting out of school and how his thinking is best applied in the current sports landscape21:39 – How does he think about trying to find the equivalent of mispriced assets in the NBA23:12 – Where tradition can be an impediment to innovation25:07 – What did the team and workflow of the team look like in the front office27:03 - The measure of truth in a sports complex29:10 – What were the early factors coming out of the data that helped to shape NBA teams30:42 – Best tactics for hiring33:59 – Process of recruiting spectacular people35:39 – Thoughts on fostering a good marriage37:57 – Picking your kids traits in your spouse           38:02 – Selfish Reasons to Have More Kids: Why Being a Great Parent is Less Work and More Fun Than You Think40:45 – What kind of markers does he look for when evaluating long term investment ideas42:44 – His interest in machine learning45:55 – What’s more exciting, the actual advances in machine learning or the applications that can be imagined as a result           47:15– International Justice Mission48:11 – How he got started teaching negotiations and some of the points he makes in that class49:16 – Effective techniques for negotiating50:03 – Is negotiating contentious, do you need empathy50:41 – A Rorschach test of Sam based on his reading of Lessons of History (book)53:01 – Biggest risk Sam took in his career54:37 – Biggest risks Sam took while with the 76ers58:09 – Do people undervalue asymmetric outcomes in the NBA 1:00:11 – The players Sam has enjoyed watching over the years1:02:45 – Why Robert Caro is a favorite author of his1:04:30 – Kindest thing anyone has done for Sam

My guest this week is David Epstein. David is a writer and researcher extraordinaire and the author of two great books. His second, Range, is out today and I highly recommend it. We discuss the pros and cons of both the generalist and specialist mindsets in detail and go down many interesting trails along the way. 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 1:12 - (First Question) – What he uncovered in “The Sports Gene: Inside the Science of Extraordinary Athletic Performance” that led him to his latest book             2:38 – Debate with Malcolm Gladwell (YouTube) 4:12 – What did the public pay most attention to and what did they gloss over 7:56 – How his views on nature vs nurture shifted during the process of writing The Sports Gene 10:05 – Blending practice with your nature 13:04 – His process of reading 10 journal articles a day as part of his research 19:06 – Exploring his new book “Range: Why Generalists Triumph in a Specialized World”, and his idea of Martian tennis 23:03 – Idea of the cult of the head start and how we set up our own feedback loops 28:58 – What does his research say about the nations education system 30:42 – The Flynn Effect chapter 33:54 – Hacks for learning 37:52 – The concept of struggle and harnessing the power of it 46:31 – Personality changes and how to drive those changes in a positive way 52:00 – Using the outside perspective in businesses for more productive outcomes and how it applied to Nintendo             52:59 – Josh Wolfe Podcast Episode 1:04:45 – Other examples of using withered technologies, 3M 1:09:00 – The arc of his work and how it has evolved 1:13:54 – Taking a different view on problems             1:17:52 – Ending Medical Reversal: Improving Outcomes, Saving Lives 1:18:04– Anyway to change these bad trends with new strategies   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 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