I am drawn to a group of investors that I call practitioner philosophers. These are people who have gotten their hands dirty in their respective fields, but despite being doers, they still often sit back and ponder the big questions in business and life. My guest this week is one such practitioner philosopher, NYC based venture capitalist Jerry Neumann. I came across Jerry's essays a year ago, and he is on a very short list of writers whose work I read without fail and almost always more than on...
Jul 11, 2017•1 hr 30 min•Ep. 45
A future guest just told me, every band has a song about being in a band, so today I give you my version. I won’t do this often, and only do it this week in case listenership drops due to the holiday—I didn’t want any guest to have a smaller than normal audience. I have now been doing this for almost one year, and have learned a tremendous amount. Since the whole idea behind the show is to learn in public, I am going to share a few of the lessons I’ve learned with you today. I’ll shape it as a t...
Jul 05, 2017•21 min•Ep. 44
If you told me a year ago that I’d be learning critical life and business lessons from the founder of a ketchup company, and that thirty to fifty thousand people would listen to our conversation, well, I’d have told you that’s impossible. But the fact that it is true proves many of the points laid out by this week’s guest Scott Norton, co-founder of Sir Kensington’s which was recently acquired by Uni-Lever. Sir Kensington’s, which makes “condiments with character” is no ordinary Ketchup company,...
Jun 27, 2017•1 hr 7 min•Ep. 43
My guest this week is Andy Rachleff, who is the CEO of the automated investing platform Wealthfront. Andy was also a co-founder and long-time partner at Benchmark capital--one of the most interesting and successful venture capital firms in the world. We spend most of our conversation discussing venture capital investing and entrepreneurship. Andy coined the now ubiquitous term “product/market fit,” and has great insight into how investors and entrepreneurs should think about business. In that ve...
Jun 20, 2017•48 min•Ep. 42
I’ve often joked that this show should be called “this is who you are up against,” because I am so often having conversations with brilliant people across the investment landscape who are effectively my competition and yours. This week’s conversation fits that description because it gives you an inside view into how things work among some of Wall Street’s most competitive investment firms. My guest is Leigh Drogen, who has worked as a statistical arbitrage portfolio manager and who founded and n...
Jun 13, 2017•1 hr 18 min•Ep. 41
This week’s episode is very unique. It is the first episode devoted to bonds, just not the kind of bonds you are used to. My guest is Ira Judelson, who is the leading bail bondsman in New York City. I met Ira through my friend and former podcast guest Danny Moses, who is also a part of this conversation. I have always had a passion for understanding how different businesses work. In this case, this week we are exploring a different business, but also a different world. Ira’s story is larger than...
Jun 06, 2017•1 hr 17 min•Ep. 40
This week's conversation was especially fun. I have a long history with my guest, Dave Chilton, but this was the first time we'd met in person. I'd heard stories about him from people I work with for twenty years, so getting to finally spend time with him was a real treat. I'll let him reveal the connection. This episode will also be fun for listeners in the US, as Dave is one of the best-known people in Canada because of his famous book the wealthy barber and his more recent stint as a dragon o...
May 30, 2017•1 hr 38 min•Ep. 39
My guest this week is David Salem. David was the founding president and CIO for The Investment Fund for Foundations, which served 800 endowed charities under David’s 18-year tenure. He's now the CIO of the Windhorse Group, which focuses on long-term, value oriented investing. This conversation wanders into and explores many different areas of investing and life. The theme is how to think about asset allocation and investing holistically--from first principles--but we talk a lot about motivation,...
May 23, 2017•1 hr 28 min•Ep. 38
My guest today is Michael Mauboussin, who is the head of global financial strategies at Credit Suisse and is on my short list of must read writers on all things investing. If you read his entire catalogue, Howard Marks's memos, and Buffett's shareholder letters, you be sitting pretty. Michael was also a big reason for the early success of this show appearing as my second guest and now my 37th. He and his team have been prolific in the last six months, publishing several long research reports on ...
May 16, 2017•1 hr 31 min•Ep. 37
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 ...
May 09, 2017•1 hr 11 min•Ep. 36
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 way, we cover many hot topics like hedge funds, alternatives, fees, and indexing. Please enjoy! For c...
May 02, 2017•1 hr 11 min•Ep. 35
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 a portfolio to bet against the U.S. housing market. We cover his part in the Big Short story, but a...
Apr 25, 2017•1 hr 12 min•Ep. 34
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 approach this conversation from an investors standpoint. LP investors usually partner with these search...
Apr 18, 2017•1 hr 24 min•Ep. 33
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 allocators and the money managers who invest on their behalf. Below is the information about this first episod...
Apr 13, 2017•1 hr 14 min
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 learned to a larger audience around the world. The episode includes the best answer I’ve ever heard (...
Apr 11, 2017•1 hr 24 min•Ep. 32
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 Khe's attempt to understand himself. We get into fear, joy, and all that he has learned across several y...
Apr 04, 2017•1 hr 46 min•Ep. 31
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, and a deep interest in where the asset management business and profession is going. This conversat...
Mar 28, 2017•1 hr 33 min•Ep. 30
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 on Wall Street. We talk about the power of premeditation, formative books, and his crazy experience...
Mar 21, 2017•1 hr 7 min•Ep. 29
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 their experience with us thus far. For comprehensive show notes on this episode go to http://investorfi...
Mar 14, 2017•1 hr 4 min•Ep. 28
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 interest is the strategic problem that we face when studying longevity. As Peter puts it in our conver...
Mar 07, 2017•1 hr 29 min•Ep. 27
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, and he has given back to his community more than I can list here. John and I discuss Ariel’s investment...
Feb 28, 2017•1 hr 4 min•Ep. 26
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 about history and future of businesses and different types of business models. There’s a lot in here f...
Feb 21, 2017•1 hr 15 min•Ep. 25
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 investors might want to invest in microcap companies, and the benefits of a frugal approach to life. Buyin...
Feb 14, 2017•1 hr 7 min•Ep. 24
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 this episode, there is just as much to be learned from the way Joe conducts himself. He was kind, wel...
Feb 07, 2017•1 hr 11 min•Ep. 23
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 with one of the greatest investors and thinkers of all time. Above all, this is a conversation about wh...
Jan 31, 2017•2 hr 1 min•Ep. 22
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 lives. In this chat, we discuss creativity, the importance of storytelling and why we are all so intrigu...
Jan 24, 2017•1 hr 3 min•Ep. 21
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 parts. In the first part, we explore artificial intelligence, machine learning, and models. Then we shift...
Jan 17, 2017•1 hr 25 min•Ep. 20
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 crucial to success in investing and this is a great example of a team with chemistry on a singular mi...
Jan 10, 2017•1 hr 11 min•Ep. 19
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 everything from science fiction, automation, investor behavior and how Betterment tries to solve problem...
Jan 03, 2017•1 hr 9 min•Ep. 18
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 the future of work, automation, mental models, and reading. Shane is a voracious reader and offers u...
Dec 27, 2016•55 min•Ep. 17
