Invest Like the Best with Patrick O'Shaughnessy - podcast cover

Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcastsjoincolossus.com
Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com

Episodes

Mike Zapata – The Darkest Night: Lessons from Battle and Value Investing - [Invest Like the Best, EP.89]

My guest this week is remarkable. He now applies his talents on Wall Street, searching for smaller cap companies trading at huge discounts in an effort to compound wealth for his investors. He is classically trained, having earned his graduate degree from Colombia, a school known for producing value investors. But his method also reflects what he learned across more than a decade of active duty in the U.S. military. Mike Zapata served us all as a Navy SEAL in the aftermath of 9/11 and ultimately...

May 29, 201859 minEp. 89

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 recently as the President and GM of the Philadelphia 76ers. He helped launch basketball's analytics movement when he joined the Houston Rockets in 2005, and is known for unique trade structuring and a keen focus on acquiring undervalued players. Today, he is also an inv...

May 22, 20181 hr 8 minEp. 88

Tren Griffin – Pulling the Thread - [Invest Like the Best, EP.87]

My guest this week is a bundle of curiosity, and that is one of the nicest things I could say about someone. For several years, Tren Griffin has been writing a weekly blog post that highlights things he has learned from various investors, businesspeople, musicians, comedians, and more. Lately, he has also been tackling individual businesses, and broad topics like scaling, competitive forces, and product market fit. Tren’s full time job is serving as a director at Microsoft. He’s also worked with...

May 15, 20181 hr 15 minEp. 87

Jason Karp – Opportunities in Public and Private Markets - [Invest Like the Best, EP.86]

I believe that any investment strategy that will deliver strong returns in the future must evolve. Any strategy should rest on rock solid foundational principles, which change rarely if ever—things like price discipline, or business growth. But the features of the strategy must keep getting better, because the marketplace is incredibly competitive. That evolution is the topic of today’s conversation with Jason Karp. Jason is the founder and CIO of Tourbillon Capital Partners, a multi-billion dol...

May 08, 20181 hr 15 minEp. 86

Chris Douvos – A Value Investor Lost in the Valley - [Invest Like the Best, EP.85]

My guest this week is Chris Douvos, a managing partner at Venture Investment Associates, which allocates 1.6B in behalf of investors. Chris is the first professional allocator I’ve spoken with who focuses specifically on venture capital funds, so I had a ton of questions for him on how to build a portfolio in an asset class known for uncertain, but often enormous, outcomes. We discuss the major recent changes in the asset class and where things might be going. I sought Chris out because while th...

May 01, 20181 hr 8 minEp. 85

Arianna Simpson – The Crypto Landscape - [Invest Like the Best, EP.84]

My guest today is Arianna Simpson, who has spent her career in an around the world of technology working at startups, Facebook, and now in venture capital as an investor focused on the world of cryptocurrencies. I met Arianna when I hosted a panel at a big investing conference in New York City and she was one of the panelists. On the panel, I found her style to be very straightforward and compelling. It is clear that she loves to learn and that the best manifestation of her style of learning is ...

Apr 24, 201853 minEp. 84

Shark Tank with Thatcher Bell and Taylor Greene - [Invest Like the Best, EP.83]

We’ve always found that even in public equities, you learn more once you have a live portfolio. One of the best ways to learn is to put some capital at risk. For this episode, I asked two VCs to sit down with me and Brett and treat the conversation as they would a normal pitch meeting, so that we, the audience, can get a peek into their world and the types of questions they ask. The venture capitalists in question are Thatcher Bell, of CoVenture, and Taylor Greene, of Collaborative Fund. The fir...

Apr 17, 20182 hr 32 minEp. 83

Nikhil Kalghatgi – Moonshot Investing - [Invest Like the Best, EP.82]

My guest this week helps me complete the first trilogy of guests on the podcast. His name is Nikhil Kalghatgi. Along with past guests Ali Hamed and Savneet Singh, Nikhil is a partner at the asset management firm CoVenture. If you liked those two conversations, you will love this one—it is somehow even more wide-ranging than the first two. Nikhil is the CEO of CoVenture Crypto, but he ended up there because of an overarching investing style that he calls moonshot investing, which we explore right...

Apr 10, 20181 hr 24 minEp. 82

Live EP.01 – Peter Attia, M.D. [Invest Like the Best]

This week’s episode was the first one that I’ve recorded live. It was the second dinner in what I expect to be a long series where I bring together 30 people from a variety of backgrounds to discuss an interesting and emerging topic, whether that be cryptocurrencies, health, cannabis investing, or some other compelling, emergent thing. My guest, for the second time on the podcast, is Peter Attia, who has lead one of the more interesting careers I’ve ever come across and who is focused on underst...

Mar 27, 20181 hr 1 min

[REPLAY] Boyd Varty – The Art of Tracking - [Invest Like the Best, EP.32]

[After talking to the brilliant string of guests the past several weeks, Patrick’s brain needed a rest—oh and a concussion didn’t help matters. To hold you over until next week, here is one of the most interesting but less well known conversations from the invest like the best archives.] 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...

Mar 20, 20181 hr 24 min

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 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 ag...

Mar 13, 20181 hr 8 minEp. 80

Savneet Singh - The Berkshire of Software - [Invest Like the Best, EP.79]

My guest this week is another in a recent series of people that makes me want to work harder, learn more, and do more for others. His name is Savneet Singh, and he has already accomplished a remarkable amount in the worlds of business and investing. He’s preferred to keep a bit of a low profile, but I’m hoping, for everyone’s sake, to change that a little bit. Savneet has invested in unique things like Spanish real estate, famous startups like Uber, cryptocurrencies before they were cool, and ev...

Mar 06, 20181 hr 21 minEp. 79

Dan Rasmussen - Private Equity Returns in Public Markets - [Invest Like the Best, EP.78]

It has been a while since we discussed private equity on the show, so I was excited for this week’s conversation. My guest is Dan Rasmussen, the founder of Verdad advisers. Dan worked in private equity and has spent years studying the entire field. Dan identified several key drivers of private equity’s outsized returns: size, value, and leverage. His firm uses these factors as a starting point to build a portfolio of public equities that behave like their private brethren. We cover a ton of grou...

Feb 27, 20181 hr 23 minEp. 78

Pat Dorsey Returns - The Moat Portfolio - [Invest Like the Best, EP.77]

My guest this week, back for a second conversation, is Pat Dorsey. Pat ran equity research at Morningstar before leaving to start his own asset management company: Dorsey Asset Management. His areas of deep interest are competitive advantage and capital allocation. He believes that capital allocation should be in service of competitive advantage and invests in a concentrated portfolio that he and his team feel embody these ideas. If you have not already, I strongly recommend listening to our fir...

Feb 20, 20181 hr 4 minEp. 77

Josh Wolfe - This is Who You Are Up Against - [Invest Like the Best, EP.76]

Long-time listeners will have heard me joke before that this podcast should really be called “this is who are you up against.” I’ve been waiting for the right episode to deploy the joke as a title, and this week we have it. The joke is meant to convey how incredibly impressive these people are who we get to hear from every week. My guest this week is Josh Wolfe, a founding and managing partner at Lux Capital in New York City. Lux is a venture capital firm, but a highly unique one. They’ve spent ...

Feb 13, 20181 hr 17 minEp. 76

Harvey Sawikin - Emerging Market Opportunities - [Invest Like the Best, EP.75]

My guest this week is Harvey Sawikin, a co-founder and lead portfolio manager at Firebird Management, which manages funds dedicated to investing in emerging market equities. Emerging markets are often a blind spot for investors of all types: most of us have never traveled to the far east or eastern Europe, where many of the thousands of emerging market public equities operate. I’ve been very lucky to travel quite a bit in Asia and the Middle East, but never to eastern Europe, which where Firebir...

Feb 06, 20181 hr 1 minEp. 75

Anthony Pompliano - Full Tilt Investing- [Invest Like the Best, EP.74]

My guest this week is Anthony Pompliano. Pomp began his career in the military, and has since been a successful entrepreneur, worked as a head of growth at Facebook, and started Full Tilt Capital, an early stage investing firm in North Carolina. This conversation has three memorable sections. Early on, we discuss the four traits Pomp looks for in founders, which we cover in detail. These double as traits that are important when hiring anyone. Next, we discuss his unique take on cryptocurrencies,...

Jan 30, 201845 minEp. 74

Dr. Ben Hunt - The Three-Body Portfolio - [Invest Like the Best, EP.73]

My guest this week is Dr. Ben Hunt, the chief investment strategist at Salient and the author of the extremely popular epsilon theory. I’ve always enjoyed Ben’s writing style, particularly his use of farm and animal based analogies to describe market phenomenon. In this conversation, we discuss his recent post the three body problem, why growth has been beating value, and why a strategy that he calls profound agnosticism—a take on risk parity—may be the most appropriate investing strategy in wha...

Jan 23, 20181 hr 9 minEp. 73

Preston Byrne - Crypto-pocalypse - [Invest Like the Best, EP.72]

My guest this week is Preston Byrne. Preston is vocal critic of crazy prices and projects in the world cryptocurrencies. His background is in the legal world and also as a founder and former COO of Monax, which made the first open-source permissioned blockchain client. As Preston says, he is a “blockchain without bitcoin” guy, who believes that this crypto mania will end in some sort of apocalypse for token holders and ICO issuers . We tackle several issues, from his broad skepticism of crypto a...

Jan 16, 20181 hr 13 minEp. 72

Ali Hamed – Creative Investing - [Invest Like the Best, EP.71]

I have a special request this week: share this episode with every curious person in your life. The conversation, with a 26-year old investor named Ali Hamed, serves as an example of what’s possible when you think creatively. Ali views the world with a fresh set of eyes, and has already become an expert at identifying new investment opportunities where others have not. As the second prodigy 26 year old in as many weeks on the podcast, these young guns are making me feel like an ancient 32 year ol...

Jan 09, 20181 hr 18 minEp. 71

Sheel Tyle - The Future of Venture Capital - [Invest Like the Best, EP.70]

My guest this week is Sheel Tyle, who at just 26 years old has already had a successful career in venture capital. His most recent stint was as the co-head of the seed investing business at NEA, the largest venture capital firm in the world, where Sheel was also a partner. Now, Sheel has set off on his own, setting up his own firm called Amplo and having recently raised a $100M venture fund where he is the sole general partner. He aims to invest with young, mission driven entrepreneurs with a gl...

Jan 02, 201855 minEp. 70

Chris Dixon – The Future of Tech - [Invest Like the Best, EP.69]

My guest this week is Chris Dixon, who has written some of my favorite essays on technology and venture investing. Chris is a prolific investor and thinker, having been an entrepreneur, angel investor, and now partner at the well-known venture capital firm Andreessen Horowitz. Our conversation focuses on major trends in technology, including cryptocurrencies and the future of autonomous vehicles and drones. Chris has a rule of thumb for technology trends: find out what smart people are working o...

Dec 26, 20171 hrEp. 69

Sorin Capital – Retail Contrarians - [Invest Like the Best, EP.68]

So far I’ve spent no time in the podcast discussing real estate, so I was excited to get the chance to talk to the team at Sorin Capital, a billion dollar hedge fund which specializes in commercial real estate, REITs, and commercial mortgage backed securities. Sorin is lead by Jim Higgins, who founded the firm, and Tom Digan, who coincidentally was a college classmate of mine at Notre Dame. You’ve probably heard me joke that this podcast should be called “This is who you are up against,” and thi...

Dec 19, 20171 hr 28 minEp. 68

Franklin Foer – World Without Mind - [Invest Like the Best, EP.67]

My guest this week is Franklin Foer, the author the recently published book “World Without Mind.” The topic of our conversation is one that I’ve been thinking through often this past year: the impact that large technology companies have on our minds and behavior. This conversation is only indirectly related to markets, but given that the companies we discuss are now several of the largest by market cap in the global stock market, what happens to them likely impacts all of our portfolios whether ...

Dec 12, 201759 minEp. 67

Adam Ludwin - A Sober View on Crypto - [Invest Like the Best, EP.66]

My guest this week is Adam Ludwin, the founder and CEO of Chain, a blockchain technology company targeted at large enterprises. Before shifting his career to focus solely on crypto, Adam was a venture capitalist focused on FinTech, which is how he came across the Bitcoin whitepaper earlier than most. I called this episode “a Sober View on Crypto” because Adam’s take is so balanced. He is certainly long crypto, both in his portfolio and career, but he is very skeptical of much of what is happenin...

Dec 05, 20171 hr 9 minEp. 66

Joanne Wilson - Angel Investing and Trend Spotting - [Invest Like the Best, EP.65]

My guest today is Joanne Wilson, a New York City based angel investor, writer, podcaster, trend spotter, and self-described “woman around town.” Joanne has had a multifaceted and winding career, and began angel investing a decade ago when she put money into NYC-based media company Curbed media which we discuss in detail. Since then, she’s invested in more than 90 companies and been pitched by countless more. She is an instantly likeable person, you can literally tell in 10 seconds you are going ...

Nov 28, 201759 minEp. 65

Connor Leonard - Capital Light Compounders & Reinvestment Moats - [Invest Like the Best, EP.64]

This week’s conversation is an ode to old school, fundamental public market investing. My conversation is with IMC’s Connor Leonard, who spends most waking hours thinking and reading about markets. His mandate is to invest purely as if it was his own money, with no pressure to hug a benchmark, and no pressure to do much of anything other than earn strong long-term returns. The portfolio that results from this approach is highly concentrated and unique. Connor’s strategy is to sort companies into...

Nov 21, 20171 hr 8 minEp. 64

Dhani Jones - Adventures in Sports, Business, and Investing - [Invest Like the Best, EP.63]

My guest this week is unique. As you will hear early and often, he is programmed to go his own way, to, as he says, go one way when everyone else is going another. His name is Dhani Jones, a name I knew as a Notre Dame football fan, because he won a championship with our arch-rivals, the University of Michigan, in the late 90’s. Dhani went on to a long and successful career in the NFL, but even more interesting has been his many pursuits in business and investing outside of football. Like my con...

Nov 14, 201759 minEp. 63

Chris Burniske - How to Value a Cryptoasset - [Invest Like the Best, EP.62]

This episode is a continuation of the Hash Power series. It is the first of what we will call a Hash Power single—a series of conversations each with a single guest on a specific topic. In this case my guest is Chris Burniske, and the topic is cryptoasset valuation. This conversation is loaded with information, I think you are going to love it. Chris recently released book called Cryptoassets, which is a must read for those interested in this field. Chris was at one point the only tradintional b...

Nov 07, 20171 hr 1 minEp. 62

Brad Katsuyama - What Happens When You Hit “Buy” - [Invest Like the Best, EP.61]

My guest this week is Brad Katsuyama, the founder of the IEX exchange and protagonist of Michael Lewis’s famous book Flash Boys, which chronicled the role of high frequency trading in markets. This conversation was yet another reminder of how complicated markets can be, and that very few participants know all aspects of the process well. Brad and I get deep into the history behind his company, and the ways in which markets and exchanges have evolved, better or worse. One of my favorite parts of ...

Oct 31, 20171 hr 7 minEp. 61