Invest Like The Best

My guest today is Matt Clifford. He’s the co-founder of Entrepreneur First, the world’s leading talent investor. They invest “pre-company” by helping the best people in cities around the world find a co-founder, develop an idea, and start a company. So far, they’ve helped 1000 people start 200 companies worth a combined $1.5B. This conversation covers their entire ecosystem and holds lessons for anyone building a business. I especially loved Matt’s ideas on the history of ambition.   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 1:20 – (First Question) – An overview on talent investing 4:37 – The history of ambition 10:08 – How do they search for ambitious people 12:21 – What happens early on for these formed teams 17:43 – Assigning an idea to a talented te

My guest today is Peter Buffett. Peter is a musician, composer, author, and philanthropist. Peter is an Emmy Award winner, New York Times best-selling author and co-chair of the NoVo Foundation. We discuss music, community, philanthropy, and finding one's note in life. This is a very different episode much more about life in general, with no business or investing discussed. Like his father Warren, Peter has the gene for phrasing ideas in memorable ways, and I think you’ll find many great phrases in this chat that will stick with you. I’ve been thinking about Peter's idea making sure those in your life are safe, seen, and celebrated ever since our chat. 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 1:27 - (First Question) – Welcome and small talk 1:35 – Why Peter is in Kingston and h

My guest today is Ben Savage, a partner at Clocktower ventures. Ben is focused on financial technology, fintech, investing which is the topic of our conversation. I’ve been making the fintech is rounds of late, and plan on making a few of these conversations public. Ben is the first in what may be a mini-series because of the sheer amount I learned in our discussion. We cover all aspects of the fintech ecosystem. 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 Notes 1:15 (First Question) – The market portfolio and how technology will move us away from liquid markets 7:24 – Businesses that are making assets that weren’t investable, investable             9:11 – Ryan Caldbeck Podcast Episode 12:03 – Most interesting places where technology is creating investment opportunities 18:33 –

My guest this week is Jeff Ma. Jeff was on the famous MIT Blackjack team from the book Bringing Down the House but has spent his career in an around fields of analytics and data science. He’s studied sports betting and analytics, built companies for analyzing human capital, and ran the data science and analytics group at Twitter. Here are links to his book, blog, and podcast. Our discussion is about a number of fascinating ways data is being used to make decisions in the worlds of sports and business. 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 1:20 - (First Question) – How quantitative analytics have evolved in sports and how they’re being used 4:26 – Best role of humans in the analysis process 8:38 – Sports that are most interesting to observe through analytics 10:26 – How d

My guest today is Vaughn Tan, who studies quality, innovation, and organizational behavior. His resume is bonkers. He’s a PhD from Harvard, Was an infantry signals logistician in the Republic of Singapore Army, then worked at Google on advertising, Earth, Maps, spaceflight, and Fusion Tables. He’s also been a wood sculptor. But the topic of our conversation is how to foster quality and innovation in ourselves and inside of companies—lessons he learned in part by studying inside some of the world’s best restaurants. If you enjoy this conversation, I recommend you also check out his new book, The Uncertainty Mindset Innovation Insights from the Frontiers of Food. Please enjoy my conversation with Vaughn Tan.   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) – Interesting wa

My guest this week is Gavin Baker, the founder, and manager of Atreides Management. I met Gavin in the same way I meet many of the most interesting people, on twitter. His focus is on consumer and technology growth investing, which is the topic of our conversation. We discuss many of the largest trends in these sectors, several fascinating investment cases, and also explore the videogame industry in detail—which I found especially interesting. Please enjoy my conversation with Gavin Baker. 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 1:16 – (first question) – His unique view on the markets 4:00 – Distilling Apple as a growth investment 6:44 – What is the most important lever for Apple looking forward 9:01 – His view on Intel 11:03 – Most important technological changes that may dictate his i

My guests this week are Kevin Systrom and Mike Krieger, the co-founders of Instagram. I met Kevin and Mike a few months ago over a shared interest in business and investing. I have found them both to be extremely good people who have a rare talent for finding and solving interesting problems. Indeed, problem-solving and jobs-to-be-done is a big part of our conversation. I realized walking into the podcast that Kevin and Mike have a rare set of experiences: having both built and sold an extremely successful product from scratch, but then also operated and scaled inside one of the largest businesses in the world. This means they have unique knowledge to offer just about anyone interested in business and products. We dig into all those lessons here. I am working on hosting more founders and CEOs on the podcast, and can’t think of a better pair to show you why I want to do so. Please enjoy my conversation with Kevin and Mike.  For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club,

My guest this week is Daniel Ek, the founder and CEO of Spotify. In my conversations with Daniel, I’ve found him to be one of the most interesting and thoughtful business leaders in the world. You’ll see what I mean as you listen to our conversation. We talk about Spotify plenty, but what I so enjoy about Daniel is his way of thinking in systems and frameworks. He is committed to evolution, innovation, and growth for both himself and for Spotify and is on my shortlist of CEOs to emulate. This was one of my favorite conversations on the podcast, I hope you enjoy it.   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 1:21 – (first question) – Management lessons from a Dubai chocolate maker 4:54 – Trends shaping the business landscape today: globalization, automation, and digitation 7:51 – How he

My guest this week is George Rzepecki, the found and managing partner Raba, an Africa focused investment firm. George is making investments across Africa in early-stage companies. Africa represents a fascinating opportunity: a huge and diverse population and enormous room for per capita GDP growth. We cover all aspects of investing in the continent, including unique potential rewards and risks. 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 1:18 – (first question) – Interest in emerging markets and the tech landscape in Africa 4:57 – Similarities across all of the different metro markets across Africa 8:05 – Why has the continent lagged behind the rest of the world 10:49 – What is the history and landscape of capital in the African continent 13:32 – The market o

My guest today is Chad Cascarilla, the CEO and co-founder of Paxos, which describes itself as a financial technology company “mobilizing assets at the speed of the internet.“ Thanks to more than 20 years of investing and financial services experience, Chad has a unique perspective on integrating blockchain technology with traditional systems. He also has one of my favorite bitcoin origin stories, which we explore. Before Paxos, Charles co-founded institutional asset management complex Cedar Hill Capital Partners in 2005 and its blockchain-focused venture capital subsidiary, Liberty City Ventures (LCV). Our conversation is less about cryptocurrencies and more about the history, current state, and potential future states of our financial system. 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   Sho

My guest this week is Bill Gurley, general partner at Benchmark Capital. Our conversation is about one specific issue that has popped up as a topic of interest in the investing community in recent months: the comparison between bringing a company public through a traditional IPO vs. what’s known as a direct listing. As a third party observer with no real dog in the hunt (as we don’t buy IPOs at O’Shaughnessy Asset Management), I thought this was a small and nuanced issue. I’ve therefore been surprised by the strength of opinions on both sides of this issue as I’ve explored it behind the scenes this past week. It feels almost like I’ve encountered a political third rail, where one side throws a lot of vitriol towards the other.  To be clear, this episode is very much in favor of direct listings instead of traditional IPOs. For those that want a good discussion of the IPO process and its upsides, check out episode 173 of the Exponent podcast with Ben Thompson.  Now please enjoy my very interesting conversati

My guest this week is Albert Wenger, a managing partner at Union Square Ventures and the author of the book World After Capital. Albert studied economics at Harvard and earned a PhD in information from technology, but if you’d asked me to guess before looking those up, I’d have guessed that he studied philosophy because of how widely he has thought about the world and the impact of technology. Our conversation is about how technology is changing the world from an Industrial Age to a knowledge age. We explore how cryptocurrencies, low cost computing, and regulation will impact our future and why the transition may require delicate care. I loved this conversation because of my obsession with the concept of scarcity. We explore what has been scarce through time and what may be scarce in the future. Albert is one of the most interesting thinkers I’ve come across and was a pleasure to speak with. I hope you enjoy our conversation. Hash Power is presented by Fidelity Investments For more episodes go to Investo

My guest this week are Matt Smith and Ian singer of Deep Basin Capital, a hedge fund specializing in the energy sector. I first met Matt almost 10 years and, in that time, I’ve grown to respect him as much as any investor that I’ve ever met. Now having spent time with Ian, who specializes in oil and gas field exploration companies and the rest of the Deep Basin team, I have similar respect and admiration for all of them. Deep Basin does almost the exact opposite of what us quants do. In fact, their entire goal is to build a portfolio of mostly idiosyncratic or stock specific risk, the very thing us quants mostly remove from portfolios. Deep Basin positions the portfolio to make a series of carefully constructed bets, long and short, without taking market risk, style-factor risk, or even commodity risk. They use a hybrid fundamental and quantitative process which we explore in detail.  This is definitely another good example of who we are all up against in public markets. What makes this story unique is tha

My guest this week is Pat Dorsey, who was the longtime director of equity research at Morningstar, where he specialized in economic moats: sources of sustained competitive advantage that allow a few companies to deliver huge returns over time. Several years ago he left Morningstar to form his own asset management firm, Dorsey asset management, and build a portfolio of companies with wide moats like those he studied at Morningstar. And while moats are critical, equally important is how companies allocate the capital generated--or made possible--by the existence of the moat.   A special thank you to Brian Bares who introduced me to Pat, and to Will Thorndike--an earlier guest on the show. In the vast majority of conversations you hear on this show, I'm meeting the guest for the first time. I mention this to encourage you to connect me with anyone whose story or way of looking at the world might resonate. Always feel free to contact me with ideas.   Pat and I begin our discussion with the key differences betwe

My guest this week is Joe McLean, the founder of Intersect Capital, which provides financial advisory services to a variety of clients, including a number of NBA players and other professional athletes.  What I loved about this conversation was the weaving of sport, coaching, and finance into a cohesive whole. There’s so much to take from this discussion—from the importance of service and low self-orientation to the impact of strict standards for who you work with, to common mistakes we all tend to make with money. Please enjoy my conversation with Joe McLean.   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 1:18 - (First Question) – His backstory and the combination of athleticism and finance 2:43 – His time in Ireland 3:29 – Moving away from basketball and into finance 6:08 – What the Inte

This week’s guest is, Zack Kanter, the founder and CEO of the Stedi.  Zack and I decided not to talk much about his business on this podcast and opted instead to explore more generally, so a bit of an introduction to what they do may be helpful here for some extra context. Stedi is a platform for exchanging and automating 300+ types of business-to-business transactions - transactions like purchase orders, invoices, etc. It’s a modern take on an archaic protocol called EDI - electronic data interchange, something I’d never even heard of until several months ago. Learning about EDI is a bit like finding out about the Matrix - every physical object you come across, from the food you ate for breakfast to the clothes you’re wearing and consumer electronics you use - anything with a barcode on it - was likely touched by EDI, often dozens of times before making it into your hands. Stedi is the first update to this messaging later in decades. Our conversation in this podcast is about business in general, starting wi

My guest this week is Chris Bloomstran, the president and chief investment officer of Semper Augustus Investments Group. He became famous in investing circles a few years back for his incredibly detailed investigations of Berkshire Hathaway. While we do cover Berkshire towards the end of the conversation, we spend most of our time talking about what makes for a quality business. I loved some of his angles on the current landscape, including our discussion of companies like Richemont and Disney which are actively taking distribution back in house. 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 1:18 - (First Question) – Largest investing error 4:52 – Defining quality investor and their investment strategy 11:48 – Incremental return on capital and other themes that th

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 mos

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

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