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

Rebecca Kaden – Thesis Driven Investing - [Invest Like the Best, EP.155]

My guest today is Rebecca Kaden, a partner at famed venture firm union square ventures. USV is known for thesis-driven investing, which is the topic of our conversation. Rebecca walks us through the evolution of USV’s thesis into its third generation, and from there we explore many of the most interesting and exciting areas of business, technology, and learning. Please enjoy our conversation For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a ful...

Jan 21, 202056 minEp. 155

Matt Clifford – Investing Pre-Company - [Invest Like the Best, EP.154]

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 ...

Jan 14, 20201 hr 16 minEp. 154

Peter Buffett – Finding Your Note - [Invest Like the Best, EP.153]

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...

Jan 07, 20201 hr 11 minEp. 153

Ben Savage – All Things Fintech Investing - [Invest Like the Best, EP.152]

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 f...

Dec 17, 20191 hr 7 minEp. 152

Jeff Ma – Making Decisions with Data - [Invest Like the Best, EP.151]

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 bus...

Dec 10, 201955 minEp. 151

Vaughn Tan – Quality and Innovation - [Invest Like the Best, EP.150]

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...

Dec 03, 20191 hr 24 minEp. 150

Gavin Baker – Tech and Consumer Growth Investing - [Invest Like the Best, EP.149]

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 m...

Nov 26, 20191 hr 6 minEp. 149

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 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...

Nov 19, 20191 hr 35 minEp. 148

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 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 wa...

Nov 12, 201958 minEp. 147

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 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...

Nov 05, 201948 minEp. 146

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, 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...

Oct 29, 20191 hr 9 minEp. 145

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 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 sur...

Sep 24, 201949 minEp. 144

[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 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...

Sep 17, 20191 hr 8 min

[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 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, th...

Sep 11, 201956 min

[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 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 ...

Aug 27, 201952 min

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 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 ...

Aug 20, 201954 minEp. 143

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 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 interc...

Aug 13, 20191 hr 24 minEp. 142

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 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 w...

Aug 06, 20191 hr 19 minEp. 141

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. 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 c...

Jul 30, 20191 hr 2 minEp. 140

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 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 InvestorFiel...

Jul 23, 201959 minEp. 139

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 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 use...

Jul 16, 20191 hr 12 minEp. 138

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 might discuss past glories, I’ve been incredibly impressed with how both Bill and his partners emphasize the current portfolio and market landscape. I’m thankful to have had the chance to speak with him in this format. I hope you enjoy our conversation. ...

Jul 02, 20191 hr 10 minEp. 137

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 the pseudonym Jesse Livermore. I met Jesse 6 years ago after reading his unbelievably unique investing research, which tackled all the big and interesting issues in markets. He now also works with me as a research partner at OSAM, where’s he’s used our data to...

Jun 25, 20191 hr 39 minEp. 136

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 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 ...

Jun 18, 201949 minEp. 135

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 a notoriously mysterious investment category. This is our second conversation, in which we cover why investing with one’s gut is a bad idea and why some of the popular edges in startups, like network effects, may be picked over. Please enjoy our conversation...

Jun 11, 20191 hr 2 minEp. 134

[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 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...

Jun 04, 20191 hr 8 min

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 the generalist and specialist mindsets in detail and go down many interesting trails along the way. 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 e...

May 28, 20191 hr 25 minEp. 133

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 the book The Art of Community, Priya’s book on the art of gathering is by far the best I’ve read. It is both conceptually interesting and extremely practical. In the book there is literally a table for how big a gathering space should be per person, sorted by the type o...

May 21, 201958 minEp. 132

[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 cook. My guest is Tim Urban, along with his business partner Andrew Finn. Tim is the most entertaining writer I’ve come across in years, who explains complicated and interesting topics to his millions of dedicated readers on the website “Wait,...

May 14, 20191 hr 22 min

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 M&A divisions at Goldman. We discuss lessons learned from her career in M&A and the many initiatives she now leads at the firm. I really enjoyed her perspective on how a big, established firm like Goldman can balance innovation with improving existing businesses....

May 07, 201957 minEp. 131
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