Invest Like the Best with Patrick O'Shaughnessy

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 tende...

This coming weekend is the annual Berkshire Hathaway shareholder meeting in Omaha. That means this week is the perfect opportunity to discuss a topic which will likely figure prominently at Berkshire this weekend: Ted Seides’s famous bet with Buffett. Ted and I discuss the origins of the bet, the nuances beneath the headlines, and whether he’d make the bet again for the next ten years. Along the w...

My guest this week is Danny Moses, who was directly in the middle of the biggest trades in market history, chronicled by Michael Lewis in his book the Big Short. Danny was the head trader on the Frontpoint team led by Steve Eisman, which was one of a small group of firms that figured out, in real time, the dire situation with mortgage-backed securities during the financial crisis, and how to build...

In this episode, I continue to pull on one of the most interesting threads that I have uncovered while producing this podcast: the world of permanent equity. My guests today are Royce Yudkoff and Rick Ruback, two Harvard Business School professors who have partnered to create a popular class that teaches students how to search for, acquire, and run a small business directly after graduation. I app...

SPECIAL EPISODE: Introducing Capital Allocators Podcast with Host Ted Seides This is a special episode to premiere a new podcast from my friend, Ted Seides. In this show, Capital Allocators, Ted will feature a broad range of people that control the flow of money through the capital markets.  Ted is in a unique position to this; he knows this world as well as anyone having spent with both allocator...

This week’s episode is the most unique to date. My guest is Boyd Varty, who grew up in the South African Bush, living among and tracking wild leopards. The main theme of our conversation is tracking, and how the same strategy for pursuing animals in the wild can be applied to all aspects of our lives. Boyd’s family has been tracking animals for four generations, and he is bringing what they have l...

My guest this week is Khe Hy. Khe has a very interesting, two-part story. We start with Khe's career at Blackrock, where he rose to be one of the youngest MDs at the firm, specializing in quantitative hedge funds. Khe shares his perspective on how the hedge fund landscape has changed and what investors should look for in hedge fund managers in the future.   The second part of the story is about Kh...

This week, my good friends Ted Seides and Brent Beshore join me to discuss the future of asset management and a ton of fun side topics. While we are all passionate about investing, we’ve had very different careers: Ted in alternatives, hedge funds and fund of funds, Brent in lower middle market private equity, and my own in quantitative equities. What we share is a passion for investing in general...

My guest this week is my father, Jim O’Shaughnessy. He was a pioneer in quantitative equity research, part of an early group of explorers who combed through data to find factors which predicted future stock returns. While we’ve both written extensively on factor investing, we chose to mostly avoid that topic for this conversation. Instead, we discuss what has been a fascinating and colorful career...

My guests this week are Trish and James Higgins, who run Chenmark Capital Management.  In this episode we continue to explore a style of investing I call Permanent Equity.  Returns in permanent equity come first from the ongoing cash flows of portfolio companies, not from reselling businesses down the line.  The partners are Chenmark are pioneering this style of small business investing and share...

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 we explore in detail. We spend a lot of time on mind, body, spirit and performance as it relates to living a better life. Of particular i...

My guest this week is John Rogers, founder, CEO and CIO of Ariel investments, one of the longest standing asset management businesses still in existence.  John has a very impressive resume.  In addition to his success at Ariel, he was the captain of the Princeton University men’s basketball team, he was the co-chair of Barack Obama’s Presidential Inauguration, he sits on the board of McDonald’s, a...

My guest this week is Alex Moazed, the co-author of 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 is since grown into a huge enterprise that helps startups and Fortune 500 innovate with platforms.  Alex and I talk...

My guest this week is Ian Cassel, a microcap investor who is always on the lookout for small companies which are run by men and women who are what he calls intelligent fanatics. Ian’s livelihood is based on the success or failure of a small group of companies that you have never heard of—he takes the idea of “skin in the game” to another level. We explore what Ian looks for in managers, why invest...

My guest this week is Joe Mansueto, the founder, longtime CEO and current executive chairman of Morningstar, Inc.  Joe is an entrepreneur at heart. He has the gene for spotting good business ideas and building them out with the customer in mind, so it is no surprise that the story behind Morningstar’s birth and growth is both entertaining and enlightening. While there are many business lessons in...

Brent Beshore and I spoke for 10 hours about all things investing and business, and decided to record a 2-hour chunk of our conversation. We start by discussing private equity, venture capital, and the importance of brand. We then explore the difference between public and private company valuation, and the potent idea of peer mentorship.  The conversation wraps up with Brent’s recent experience wi...

My guest this week is writer, director, producer, and podcast host Brian Koppelman, who’s film credits include ‘Rounders’, ‘Oceans 13’, and ‘Solitary Man’. More recently he co-created the Showtime show, ‘Billions’, which allowed us to have some fun talking about the world of hedge funds and investing.  Brian’s method for chasing curiosity is something that everyone can learn apply in their own liv...

Jeremiah Lowin is probably the smartest guy I know, and that is saying something. He is an expert in the fields of statistics, artificial intelligence, and risk management—among many other things.  He is currently the Director of Risk Management for a private investment firm in the New York area, but has spent years working with machine learning and AI.  This conversation is broken up into two par...

This week’s episode features the partners of the Collaborative Fund, a venture-capital firm based in New York City.  This is a unique, group interview with Lauren Loktev, Kanyi Maqubela, and Craig Shapiro that explores all aspects of their search and investing process, including how they identify thematic change in the world and then build a portfolio around those themes.  The quality of a team is...

My guest today is Dan Egan, who is the managing director of Behavioral Finance and Investing at Betterment.  In this wide-ranging role, Dan has his hands is most of the ways that Betterment interacts with its clients and how it invests their money. This is one very interested and smart guy who is clearly passionate about helping investors make better decisions.  In this conversation, we explore ev...

My guest this week is Shane Parrish, who created the extremely popular Farnam Street—a website dedicated to understanding the world by mastering the best of what others have already figured out.  More than 100,000 people subscribe to the Farnam Street Newsletter which summarizes what Shane and his team learned and wrote that week. I read it every Sunday. Shane and I cover a lot of ground including...

Joining me on the podcast this week is Jeff Ptak, head of global manager research at Morningstar.  Jeff’s role puts him in the unique position to discuss the state of active management because he gets to see mutual funds from both the bottom-up, through deep diligence on investment strategies and firms, and top-down, using Morningstar’s data to assess industry-wide trends.  Jeff is one of my favor...

This week we explore a rare and underappreciated skill through the lens of an incredible story. My guest is Eric Maddox, whose name you probably don’t know but won’t soon forget. Just trust me that you need to listen to this entire episode, and listen carefully—because that is what the episode is ultimately all about: how to listen to others, with care and empathy, in the age of distraction. Somet...

My guest this week is one of the reasons that this podcast exists.  Josh Brown is a financial advisor and the CEO of Ritholtz Wealth Management. He is also the creator of TheReformedBroker.com, a blog about markets, politics, economics, media, culture, and finance that has become one of the most widely-read sites on the financial web.  He is the author of Backstage Wall Street and Clash of the Fin...

My guest this week is Christopher Cole, founder and managing partner at Artemis Capital Management. Chris’s specialty is in long volatility strategies, setting up portfolios that will benefit from significant change and volatility in markets.  We discuss how a series of small bets can lead to disproportionally large nonlinear payoffs, in both life and in markets.  We also discuss the kind of watch...