Invest Like the Best

By Patrick O'Shaughnessy

Business Investing Careers

What's Invest Like the Best about?

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at InvestorFieldGuide.com

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Kevin Systrom and Mike Krie...

11.19.2019

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 ...

Invest Like the Best episodes:

11.19.2019 Kevin Systrom and Mike Krieger – How to Build a Great Product 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 ...
11.12.2019 Daniel Ek – The Future of Audio - [Invest Like the Best, EP.147] 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 ...
11.05.2019 George Rzepecki – Investing in Africa - [Invest Like the Best, EP.146 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 ...
10.29.2019 Chad Cascarilla – The Future of Blockchain and Financial Services - [Invest Like the Best, EP.145] 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, ...
09.24.2019 Bill Gurley – Direct Listing vs. IPO - [Invest Like the Best, EP.144] 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 ...
09.17.2019 [REPLAY] Albert Wenger - World After Capital - [Invest Like the Best, EP.80] 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 ...
09.11.2019 [REPLAY] Deep Basin – Earning Alpha in Energy - [Invest Like the Best, EP.81] 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 ...
08.27.2019 [REPLAY] Pat Dorsey - Buying Companies With Economic Moats - [Invest Like the Best, EP.51] 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 ...
08.20.2019 Joe McLean – How to be a Pro’s Pro - [Invest Like the Best, EP.143] 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 ...
08.13.2019 Zack Kanter – All Things Business - [Invest Like the Best, EP.142] 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 ...
08.06.2019 Chris Bloomstran – What Makes a Quality Company - [Invest Like the Best, EP.141] 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 ...
07.30.2019 Brian Christian – How to Live with Computers - [Invest Like the Best, EP.140] 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. ...
07.23.2019 Eric Sorensen - How Quant Evolves - [Invest Like the Best, EP.139] 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 ...
07.16.2019 Jane McGonigal – How Games Make Life Better - [Invest Like the Best, EP.138] 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 ...
07.02.2019 Bill Gurley – All Things Business and Investing - [Invest Like the Best, EP.137] 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 ...
06.25.2019 Jesse Livermore – The Search for the Truth with the Anonymous Master - [Invest Like the Best, EP.136] 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 ...
06.18.2019 Chuck Akre – The Three-Legged Stool - [Invest Like the Best, EP.135] 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 ...
06.11.2019 Jerry Neumann – Why Venture is Hard - [Invest Like the Best, EP.134] 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 ...
06.04.2019 [REPLAY] Sam Hinkie – Data, Decisions, and Basketball - [Invest Like the Best, EP.88] 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 ...
05.28.2019 David Epstein – Wide or Deep? - [Invest Like the Best, EP.133] 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 ...
05.21.2019 Priya Parker – The Art of Gathering - [Invest Like the Best, EP.132] 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 ...
05.14.2019 [REPLAY] Tim Urban - Grand Theft Life - [Invest Like the Best, EP.59] 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 ...
05.07.2019 Stephanie Cohen – The Evolution of M&A and Corporate Strategy - [Invest Like the Best, EP.131] 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 ...
04.30.2019 [REPLAY] Will Thorndike - How Skilled Capital Allocators Compound Capital - [Invest Like the Best, EP.36] 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 ...
04.23.2019 Josh Wolfe – The Tech Imperative - [Invest Like the Best, EP.130] 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 ...
04.16.2019 Katherine Collins – Impact and ESG Investing - [Invest Like the Best, EP.129] 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 ...
04.09.2019 Geoffrey Batt – The Nature of Transformational Returns - [Invest Like the Best, EP.128] 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 ...
04.02.2019 Brian Singerman – Investing in the Best Founders - [Invest Like the Best, EP.127] 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 ...
03.26.2019 Michael Mauboussin – The Four Sources of Alpha - [Invest Like the Best, EP.126] 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 ...
03.19.2019 Annie Duke – Wanna Bet? - [Invest Like the Best, EP.125] 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 ...
03.12.2019 Michael Mayer – Pseudonymous Social Capital and Bottomless Coffee - [Invest Like the Best, EP.124] 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 ...
03.05.2019 Peter Zeihan – The Future of Geopolitics - [Invest Like the Best, EP.123] Peter is a geopolitical strategist who combines expertise in demography, economics, energy, politics, technology, and security to assess an uncertain future. Before founding his own strategy firm, Peter helped develop the analytical models for Stratfor, one of the world’s premier ...
02.26.2019 Michael Kitces – The Past, Present & Future of Financial Advice - [Invest Like the Best, EP.122] My guest this week is Michael Kitces, who is one of our industries go-to experts on all things financial advise and financial planning. We discuss the past, present, and future of financial advise, financial technology, and investing. If you are ...
02.12.2019 Alex Danco – Scarcity, Abundance and Bubbles - [Invest Like the Best, EP.121] My guest this week is Alex Danco. Alex is a member of the Discover Team at Social Capital, has a background in biology, and has written about all things tech and business. While Alex is only 30, it seems like ...
02.05.2019 Keith Wasserman – Real Estate Investing - [Invest Like the Best, EP.120] My guest this week is Keith Wasserman, co-founder of the real estate investment firm Gelt. This was my first fully dedicated conversation on direct real estate investing, so we cover many different topics, including the pros and cons of different ...
01.29.2019 Alex Mittal – Early Stage Investing - [Invest Like the Best, EP.119] My guest this week is Alex Mittal, co-founder of Funders Club. Following past guest Jeremiah Lowin, Alex is my second elementary school friend to appear on the podcast—a trend I hope continues. Funders club is a unique venture firm, because ...
01.22.2019 Eugene Wei – Tech, Media, and Culture - [Invest Like the Best, EP.117] My guest this week, Eugene Wei, has one of the most interesting backgrounds of anyone I’ve had on the podcast. He worked at Amazon early in its life, was the head of product at Hulu and Flipboard, and head of ...
01.15.2019 Michael Duda – Investing In Brands - [Invest Like the Best, EP.117] My guest this week is Michael Duda, and the topic of our conversation is the role that brand plays in business and investing. Michael has worked on and invested in a wide-range of brands including Birchbox, Casper, Harry's, Citibank, DirecTV, ...
01.08.2019 Abby Johnson – Future of Finance - [Invest Like the Best, EP.116] Over the summer. I spent time with Abby Johnson, who is the chairman and CEO of Fidelity Investments and several other business leads at Fidelity to understand how a very large firm like theirs is navigating change in our industry. ...
12.18.2018 Keith Rabois - If You Can’t Sell Them, Compete with Them - [Invest Like the Best, EP.115] My guest this week is Keith Rabois. Keith is currently an investment partner at Khosla Ventures, but has a storied and diverse background as an investor, entrepreneur, and executive. He has worked in senior positions at Paypal, LinkedIn, and Square; ...
12.11.2018 Bryan Krug – High Yield Credit Investing - [Invest Like the Best, EP.114] My guest today is Bryan Krug, who manages the Artisan Partners Credit Team and overseas more than $3B in high yield credit investments for the firm. This was my first conversation on high yield, so I took it as an ...
12.04.2018 Maureen Chiquet – Leadership Through Hard Conversations - [Invest Like the Best, EP.113] My guest this week is Maureen Chiquet, the former longtime CEO of Chanel. Maureen also spent much of her career at the Gap, growing Old Navy from scratch, and serving as the president of Banana Republic. The topic of discussion ...
11.27.2018 Hunter Walk – Building Picks and Shovels - [Invest Like the Best, EP.112] My guest this week is Hunter Walk, the co-founder of Homebrew, a unique venture capital firm. Hunter is a tool builder, having spent his career before venture at companies like Google and YouTube. The topic of our conversation is the ...
11.20.2018 [REPLAY] Alex Moazed – Building Modern Monopolies - [Invest Like the Best, EP.25] [REPLAY] Modern Monopolies: What It Takes to Dominate the 21st Century Economy, which explores the platform business model (Uber, Airbnb, Github). Alex is also the founder and CEO of Applico, a company that he started in his dorm room that ...
11.13.2018 Cliff Asness – The Past, The Present & Future of Quant [Invest Like the Best, EP.111] My guest this week is Cliff Asness, the managing and founding principal at AQR Capital Management. 20 years after its founding in 1998, AQR manages $226 Billion dollars across a number of quantitatively based investing strategies. Cliff was an original ...
11.06.2018 [REPLAY] Peter Attia, M.D. - How to Live a Longer, Higher Quality Life - [Invest Like the Best, EP.27] [REPLAY] My guest this week is Peter Attia, M.D., whose mission is to understand and improve human lifespan and healthspan (or quality of life). Reading Peter’s research, you find that there are many similarities between health and investing—ideas like compounding—which ...
10.30.2018 Ryan Caldbeck – Quant in Private Markets - [Invest Like the Best, EP.110] My guest this week is Ryan Caldbeck, a private equity investor who wants to bring quantitative rigor to the private markets. Ryan is the CEO of Circle Up, which uses a system it calls Helio to identify attractive investments in ...
10.23.2018 Howard Lindzon – Fintech and Trend Following - [Invest Like the Best, EP.109] My guest this week aspires to be the Larry David of investing, and we discuss why. Howard Lindzon is hard to categorize. He’s primarily an early stage investor right now, but he’s participated in all types of investing. He describes ...
10.16.2018 CoVenture Credit - Esoteric Credit with Ail Hamed, Brian Harwitt, and Marc Porzecanski - [Invest Like the Best, EP.108] My guests this week are Ali Hamed, Brian Harwitt and Marc Porzecanski who work together at CoVenture Credit. When I first had Ali on as a podcast guest, we discussed the many aspects of what his firm does, ranging from ...
10.09.2018 Saifedean Ammous – The Bitcoin Standard - [Invest Like the Best, EP.107] My guest this week is Saifedean Ammous, author of the book the Bitcoin Standard. This was one of the more interesting conversations I’ve had in the world of cryptocurrency, primarily because we don’t talk about Bitcoin or Crypto until 25 ...

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