This week’s conversation is about artificial intelligence and interplanetary travel. Its about content creation, thinking from first principles, and death progress units. Its about brain machine interfaces and why it is crucial that you be a chef and not a cook.  My guest is Tim Urban, along with his business partner Andrew Finn. Tim is the most entertaining writer I’ve come across in years, who explains complicated and interesting topics to his millions of dedicated readers on the website “Wait, But Why.” As an example, Tim’s last post on Elon Musk’s neurlink venture is 40,000 words long, roughly the length of a short book. It explains almost all of human progress and our potential future using drawings and cartoons. Its impossible to stop reading. While this conversation is wildly entertaining, it is also chock full of metaphors and lessons that will be useful to anyone doing creative work or building a company. I hope this leaves you as energized as it left me. I called this episode Grand Theft Life because that is the name that Tim and Andrew give to their worldview, which I think will change the way you behave, too. Please enjoy my conversation with Tim Urban.   For comprehensive show notes on this episode go to http://investorfieldguide.com/urban For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. 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   Books Referenced Superintelligence: Paths, Dangers, Strategies   Links Referenced The Cook and the Chef: Musk’s Secret Sauce Wait But Why Neuralink and the Brain’s Magical Future Wait But Hi YouTube Channel  Kurzgesagt – In a Nutshell   Show Notes 1:50 – (First question) –  Explaining his concept of planets 1, 2, 3 and 4 and understanding the human colossus 5:46 – Tim’s favorite idea of the human knowledge compounding 7:52 – Die Progress Units (DPU) 9:45 – Different stages of AI and the positives and negatives of each stage 14;04 – What happens when AI gains breadth and general intelligence 16:23 – The idea of a cook vs a chef and how Tim had the chance to interview Elon Musk 17:48 – Why you should reason from first principles instead of reasoning by analogies 25:19 – Why it’s possible to turn a cook into a chef 30:08 – Why being a chef is the safer route in a world with AI and what Tim has changed in himself as to why. 31:22 – Looking at the discovery process             34:39 – Superintelligence: Paths, Dangers, Strategies\ 40:01 – Being the person who creates the metaphor vs being the people who simply using them             43:41 – YouTube Channel  Kurzgesagt – In a Nutshell 44:54 – Most fun that Tim has had researching a topic 46:08 – Musk model for attaining your goals 53:43 – Why not caring what people think is one of the world’s best superpowers, grand theft life 56:50 – Neuralink – what is it and how did Tim come to research it 1:02:38 – Elon Musk’s concerns about AI 1:14:28 – What then if the Neuralink concept works out 1:18:02 – Kindest thing anyone has done for Tim   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 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

My guest this week is Katherine Collins, who is the head of sustainable investing at Putnam Investments, a portfolio manager on two of Putnam’s sustainable investing funds, and the author of the book The Nature of Investing: Resilient Investment Strategies through Biomimicry. Our conversation is on the ins and outs of ESG and impact investing, a young but increasingly common topic in the investing world. This is challenging ground for me as a quant, because the data available is so new and limited—so Katherine’s perspective was very helpful as we continue to learn. Given the importance of this topic, I’m also searching for more guests with both positive and negative views on the role of ESG in an investing framework, and welcome suggestions for future guests. Please enjoy my conversation with Katherine Collins.   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 1:29 - (First Question) –Mechanical vs human judgement processes 4:21 – ESG, and the non-utility portion of it. 7:11 – Data behind the objective function that is different from returns 12:34 – What are the most interesting data sets 16:04 – How does she determine what factors to target 19:31 – Why do we know that diversity of experience/opinion/background is good for a company 21:30 – The social vertical and how it plays into her investing system and better returns             25:51 – Corporate Sustainability: First Evidence on Materiality 27:00 – Environmental factors and the issues that jump to mind 29:48 – Importance of signing the UNPRI and is it just box checking 32:33 – Data for companies on the solution oriented companies 34:53 – Why doesn’t the market recognize the Alpha 36:17 – LP interest in ESG investing 38:25 – How other groups of investors approach ESG 40:03 – Best practices at business making an impact in ESG 44:01 – Unique or interesting tactics in environmental 46:33 – Who is the biggest opponent or position in opposition of ESG 47:37 – Most interesting edge 48:20 – Playbook for business managers thinking about social for the first time 49:59 – Measurements vs principles/values 51:21 – Advice to quants trying to use ESG in how they gather data 53:04 – Most memorable encounter with a company through the lens of ESG 53:53 – Where to learn more about ESG 54:50 – How much role regulation plays in the future of business sustainability 56:30 – Any more lessons from her research into natural systems 57:05 – Kindest thing anyone has done for her   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 Geoffrey Batt and the topic of our conversation is how to earn transformational returns in very hard markets. In his case, that means Iraqi equities which we cover in detail. He now runs a large pool of capital in Iraqi stocks through his firm Euphrates, but the journey was arduous to say the least. This is one of my favorite boots on the ground contrarian investments stories thus far on the podcast. I hope you enjoy the story and the lessons that Geoff has to offer.  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) – What does it take to earn transformational returns 4:43 – How he deals with LPs, especially given the volatility of the market he invests in 10:26 – Why LPs have to think about the other investors in a fund 1:17 – How Geoffrey got interested in the Iraqi market 16:15 – Factors he was considering when exploring Iraq             16:53 – Harvey Sawikin Podcast Episode 19:20 – Visiting companies in Iraq 22:30 – Most memorable meeting with a company on his first trip 27:18 – Size and nature of Iraqi market when he first got interested 30:44 – A specific allocator in Iraq 34:37 – Does price reflect the work over there 37:51 - What does he perceive as his role in the changes to Iraq’s equity market 40:12 - How do Iraqi equities look today compared to when he started and is the opportunity still interesting 44:14 – How businesses perceive him now that the market has opened up more 47:28 – Scale of potential return and where it comes from 49:51 – Advice for younger aspiring investors exploring frontier markets 52:16 – Kindest thing anyone has done for Geoffrey   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 Brian Singerman, a partner at the venture capital firm Founders Fund. Founder’s Fund is widely considered one of the top VC firms and its partners are known to have diverse investment strategies. Brian invests across industries and focuses on backing exceptional founders. You’ll hear right off the bat that he cares about moat, market, and strong execution. I love his point that the only way to become a good investor is to do a lot of investing. He describes himself an investor who uses his gut a lot, which took me a while to get used to in our conversation. But I have to say that at the end of this episode I felt refreshed and generally excited to keep putting in reps in my own way, both in the podcast and the quant research settings. I hope you 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 Notesd 1:28 - (First Question) – What Brian looks for when evaluating companies 2:38 – What a moat looks like in investing 3:11 – Most memorable initial moat 4:17 – How he evaluates a potential market 5:28 – Attributes they look for in founders 6:24 – Most significant technological changes and how they have impacted his investment strategy 8:57 – The sourcing of his deals 13:00 – Qualities he likes at various stages of deal sourcing 13:46 – How he evaluates the teams he may fund 15:17 – His take on the pricing landscape for deals 16:13 – How he allocates his time as a board member 17:16 – Thoughts on long term stock exchange 18:26 – How much research does he do on an industry in order to stay on top of his investments 20:10 – Outside information he follows 21:20 -  Other investors he’s learned a lot from 23:12 – What values does Peter Thiel instill in the partners 24:05 – Process of StemCentrics 26:03 – Other places holding his interest today 26:57 – His interest in e-sports 31:44 – Interactions with LP’s 32:51 – What they look for in recruiting new partners 34:32 – How geography impacts the opportunity for new ideas 36:24 – Opportunities in public companies and other investment types 37:57 – Aspects of overseeing a startup venture 39:26 – 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 for the third time is Michael Mauboussin. If there is a major question about markets and investing, Michael has usually written one of the best pieces of research on that topic. Today’s conversation is a mix of several of his research pieces, but focuses on the sources of alpha. The framing of the conversation is the brilliant question “who is on the other side” of a given trade. If you are buying, who is selling, and why? Knowing the answer to this question is one key to understanding where excess return comes from. As is usual with Michael, we also explore tons of other interesting ideas that will serve as food for thought. 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 1:23 - (First Question) – An outline of the syllabus for the course he teaches 4:02 – What are smart people missing when it comes to decision making 5:33 – Why Michael went down the path of defining major investing concepts             7:41 – On the impossibility of informational inefficient markets 9:14 – Beware behavioral finance 12:03 – What are the behavioral errors that people can take advantage of in a trade 15:14 – Timing opportunities             17:25 – Modest Proposal Podcast Episode 17:47 – Where the analytical edge comes from 21:16 – Is there an advantage to exhibit time arbitrage 23:53 – Technical arbitrage 29:34 – What impact do flows into ETFs play on the market 32:25 – Informational edge and how you source that edge 36:39 – Biggest changes that he has seen on the buy side 43:18 -  How would Michael apply this as a sports GM 48:35 – His views on stock buybacks             51:02 – The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success 52:55 – EBIT to EBITDA paper             54:43 – What Does a PE Multiple Mean? 59:28 – The concept of benign myths 1:02:06 – What the future holds of Michael             1:04:17 – The Myth of Capitalism: Monopolies and the Death of Competition   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 with Annie Duke, and the topic of our discussion is how to improve decision making. We break decisions down into their component parts: values, beliefs, decisions, randomness, and outcomes. After diving into each, we discuss how to make better decisions, how to work in group settings, and how to harness power of tribes and identity to improve our behavior. Annie has thought about this as much as anyone, and her various tricks for getting us to think in probabilities and to stop evaluating decisions based on outcomes that have been tainted by randomness will be useful for anyone listening. 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 1:23 - (First Question) – Why people don’t take the best investing advice 2:11 – Investing tribes             4:21 – Jay Van Bavel twitter 6:34 – Rule setting as a way of crafting an investment strategy 11:13 – How much control do we have in choosing our values   15:52 – Anatomy of a decision 19:28 – Her concept of resulting 26:47 -  How beliefs impact your decision making 34:28 – Tact’s for making the best decision 42:40 – Ego and decision making 47:06 – People who are exceptional at changing their decision making 48:18 – How often do people who change their decision making, stick with the rules of the game             50:07 – Finite and Infinite Games 50:28 – Psychology of making decision that involves other people 59:20 -  Never close doors on other people 1:01:57 – Best decision that Annie made 1:04:24 – Kindest thing anyone has done for Annie   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 unique and so requires a short story. I met our guest Michael Mayer because of twitter. I followed and enjoyed one of several pseudonymous accounts that he maintains to experiment with ideas. His various accounts have wide followings. I think many of the best accounts on twitter are anonymous or pseudonymous, and I’ve always made a point to get to know the ones I like best. As it turns out, Michael was also an entrepreneur. He’d been building a new company and was raising a small amount of outside capital. I didn’t invest personally, in part because he raised it so quickly after I spoke with him. Ever since, I’ve gotten to know him better and followed his company, Bottomless, with interest. You know that I am always hyper transparent about any potential conflicts of interest, so it’s worth noting that while I am not an investor in this company, I expect to be at some point in the future. The topic of our conversation is both his social media activity and his company. I am a coffee fanatic, and the problem he is solving is one I live. I order a weekly bag of coffee beans, but I often have too much coffee or run out. Bottomless solves this by shipping you a simple scale which you keep wherever you store your coffee, connect to your Wi-Fi, and set your bag of coffee on. It automatically orders new coffee for you at the right time. Thus the name: Bottomless. If you like the conversation, check out bottomless.com  With this podcast, all I’m really trying to do is find, meet, and learn from interesting people. Michael certainly qualifies. I hope you enjoy this unique episode.   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 2:06 - (First Question) – Why he writes under a pseudonym online 2:58 – Positive impacts of writing this way 3:45 – His background 5:02 – Habits he improved upon 7:03 – Where did his exploration into technology and start-ups come from             7:33 – Algorithms to Live By: The Computer Science of Human Decisions 10:32 – Elements of business that interest him most 13:26 – Building social capital vs the current state of education 17:06 – What information does he like to consume             18:17 – Zero to One: Notes on Startups, or How to Build the Future             18:34 – Jerry Neumann blog Reaction Wheel | Podcast episode             18:39 – Kevin Simler’s blog  Melting Asphalt| Podcast Episode 21:01 – Why the current education system is busted 22:54 – Formation of his business 24:04 – Importance of making things legible 25:54 – On demand delivery vs subscription business models 30:16 – Early day in developing the scale for his business 33:50 – What he learned about coffee roasters 35:29 – thoughts on supplier power 36:17 – The customer relationship 39:50 – Best objections to his business 41:58 – Biggest operational/emotional challenges 42:56 – Best moment 44:39 – Time at Y combinator 46:28 – His unique co-founder story 49:47 – Marketing strategies and acquisition costs 51:37 – The idea of a commercial loop 53:27 – Discarded ideas, such as spaced repetition social networks 57:38 – Having a long-term plan vs reformatting a business into success 1:00:35 – What works on twitter based on his experience 1:03:09 – Most controversial opinion 1:05:59 – Kindest thing anyone has done   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