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

Karen Karniol-Tambour - Macro Headwinds vs. Tech Tailwinds - [Invest Like the Best, EP.329]

Today’s conversation was recorded during last week’s Sohn Conference. I sat down with Karen Karniol-Tambour, Co-CIO at Bridgewater Associates. I hosted Karen on this show two years ago and if you listened to that, you’ll remember she has a rare skill for distilling and analysing complex macro topics. Today’s environment is strikingly different to the summer of 2021 so this is a timely conversation on the big macro variables that are on investors’ minds today. Please enjoy my conversation with Ka...

May 16, 202338 minEp. 329

Fidji Simo - Creating Delightful Consumer Experiences - [Invest Like the Best, EP.328]

My guest this week is Fidji Simo, the CEO of Instacart. Fidji grew up in a small town in the South of France and was the first person in her family to graduate from high school. Since then, she has had a dazzling career with stops at France’s leading university, eBay, and Facebook. Fidji spent the better part of a decade at Facebook where she led the Facebook App before joining the online grocery platform, Instacart, in mid 2021. We talk about Fidji’s consumer product experiences, Instacart’s ro...

May 09, 20231 hr 13 minEp. 328

Bessemer Venture Partners - Building a VC Firm that Lasts Centuries - [Invest Like the Best, EP.327]

My guests this week are Jeremy Levine, Kent Bennett, and Brian Feinstein. They are partners at one of the oldest and most storied venture firms in the world, Bessemer Venture Partners. Our conversation is split into two parts. First, we explore Bessemer itself. It’s over 100 years old and has a unique operating model with lessons for every investment firm in the market. We then discuss Jeremy, Kent, and Brian’s investing styles and outlook. What they look for in businesses, their thoughts on var...

May 02, 20231 hr 18 minEp. 327

Alexis Rivas - A New Blueprint for Homebuilding - [Invest Like the Best, EP.326]

My guest this week is Alexis Rivas. Alexis is the co-founder and CEO of Cover, which is pioneering a new way of building homes. It’s no surprise to anyone that aspects of our housing market is broken. The market is undersupplied and littered with regulatory issues. The homebuilding process has also not changed for the better part of a century. Alexis is attacking the problem and has taken a leaf out of the car industry’s learnings to create a similar production process for home building. In our ...

Apr 25, 202351 minEp. 326

Dr. Peter Attia - The Portfolio to Live Longer - [Invest Like the Best, EP.325]

My guest this week is Dr. Peter Attia. I’ve had Peter on the show twice before but it’s been over 5 years since his last appearance. In that period, his work has exploded and today he’s one of the clear leaders on the topic and practice of longevity and health span. He has a new book out called Outlive, which I heartily recommend. You’ll hear us refer to the last chapter of his book early in our conversation but we chose not to reveal the whole story live so you can read and enjoy it. We highlig...

Apr 18, 20231 hr 25 minEp. 325

Scott Davis & Rob Wertheimer - Lessons from the Industrial Titans - [Invest Like the Best, EP.324]

My guests today are Scott Davis and Rob Wertheimer. Scott and Rob head up Melius Research and are the authors of a great book called Lessons from the Titans. The book explains what the industrial giants of old can teach the new generation of high-growth businesses about how to survive and deliver shareholder value over multiple decades. Drawing on their experience as industrial analysts, they present case studies on businesses like Danaher, Roper, Honeywell, Boeing and GE to reveal both what doe...

Apr 11, 20231 hr 11 minEp. 324

Sam Hinkie, Boyd Varty, Charlie Songhurst - Trail Magic - [Invest Like the Best, EP.323]

Today’s episode is a little different. Rather than share a new conversation, I have put together a few of my favourites from the past six and a half years of doing this show. I often listen back to these for inspiration, energy, and their timeless ideas on life and investing. Each of these is a significantly shortened version of the original episode. The first conversation you’ll hear is with Sam Hinkie, the second discussion is with Boyd Varty, and the last conversation you’ll hear is with Char...

Apr 04, 20231 hr 41 minEp. 323

David Senra - Passion & Pain - [Invest Like the Best, Forever Episode]

Hello everyone. A few days ago, we discussed what we call forever episodes, which are the few episodes of our show that we think will be as popular a decade from now as they are today. When I re-listened to this episode with David Senra, I left wildly energized and wanting to share that feeling. So we are re-releasing it today for anyone who missed it the first time or hadn't yet discovered Invest Like the Best. Please share with your friends and loved ones as I think anyone will benefit from Da...

Mar 31, 20231 hr 25 min

David Einhorn - The Long and Short of Investing - [Invest Like the Best, EP.322]

My guest today is David Einhorn. David is the President of Greenlight Capital, a long-short hedge fund that he co-founded in 1996. He is a prominent value investor with a reputation for rigorous security analysis. In 2002, he revealed a short position in Allied Capital, which was ultimately proven correct and similarly in early 2008, he told the Sohn Conference he was short Lehman Brothers. Over his near three decades managing money at Greenlight, he has delivered impressive returns but it has n...

Mar 28, 20231 hr 12 minEp. 322

Avi Goldfarb - The Economic Impact of AI - [Invest Like the Best, EP.321]

My guest today is Avi Goldfarb. Avi is a Professor at the University of Toronto’s Rotman School of Management, the Rotman Chair in Artificial Intelligence and Healthcare, as well as the co-author of two bestselling books on AI and its economic impact. His most recent book, Power and Prediction, is probably the best piece of content I have read in explaining how AI may reshape business models, systems, and products. We recorded this before GPT-4’s release last week which, if anything, makes Avi’s...

Mar 21, 202359 minEp. 321

Auren Hoffman - A Deep Dive on Data - [Invest Like the Best, EP.320]

My guest this week is Auren Hoffman. Auren is the CEO of Safegraph, which curates data on physical locations. He also founded LiveRamp, a public data connectivity business. Auren knows more about data businesses than almost anyone I know and that is the topic of today’s discussion. We look at the business of data from every angle and finish with a fun masterclass on how to host a dinner party. Please enjoy my conversation with Auren Hoffman. For the full show notes, transcript, and links to ment...

Mar 14, 20231 hr 11 minEp. 320

Trae Stephens - Find Good Quests - [Invest Like the Best, EP.319]

My guest this week is Trae Stephens. Trae is a partner at Founders Fund and co-founder and Executive Chairman of Anduril. Trae’s philosophy can be boiled down to finding good quests, which has led him to investing in businesses that work closely with the government on societally important issues. Clearly, that extends to co-founding Anduril and I would highly recommend listening to my Business Breakdowns episode on Anduril if you haven’t already. In this conversation, we discuss the importance o...

Mar 07, 20231 hr 8 minEp. 319

Doug Leone - Lessons from a Titan - [Invest Like the Best, EP.318]

My guest this week is Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, a...

Feb 28, 20231 hr 11 minEp. 318

Tim Urban - Idea Labs and High-Rung Thinking - [Invest Like the Best, EP.317]

I’m excited to share this conversation with Tim Urban. Tim is, in my opinion, one of the best and most engaging writers of our era. He’s tackled many of the most interesting topics in the world from AI to procrastination. I interviewed him in 2017 in an episode we called “Grand Theft Life”, and it remains one of my favorite episodes ever. In the 6 years since that episode, he hasn’t published almost anything. That’s because he’s been writing the book we discuss in this episode. The book is calle...

Feb 21, 20231 hr 30 minEp. 317

Dan Rose - How Stunning Founders Operate - [Invest Like the Best, EP.316]

My guest today is Dan Rose. Dan is the chairman of Coatue Ventures and has one of the most interesting collections of experiences of anyone I’ve talked to. He spent 20 years at Amazon and Facebook in their early days, working closely with Jeff Bezos, Andy Jassy, Mark Zuckerberg, and Sheryl Sandberg. He’s had a front-row seat to the defining products and founders of our era and his lessons from those experiences do not disappoint. Please enjoy this great discussion with Dan Rose. For the full sho...

Feb 14, 20231 hr 14 minEp. 316

Jeff Green - Modernizing Advertising - [Invest Like the Best, EP.315]

My guest today is Jeff Green, the CEO and co-founder of advertising platform, The Trade Desk. The Trade Desk is the second advertising exchange Jeff has built, having sold his first venue to Microsoft in 2007. He started The Trade Desk in 2009 and has built it into a $30 billion public business. In our discussion, we talk about the parallels between The Trade Desk and an equity exchange, why Jeff chose to align with ad buyers not sellers, and how he shapes the culture of his firm. Please enjoy m...

Feb 07, 20231 hr 6 minEp. 315

Carl Kawaja - Dealing with Regime Change - [Invest Like the Best, EP.314]

My guest this week is Carl Kawaja. It’s the second time I’ve had Carl on the show and my first conversation with him is one I go back to often. Carl is a portfolio manager at Capital Group, where he’s quietly overseen a huge portfolio for decades. He is one of the top investors operating today as well as one of my favorite people. The investing world has changed quite a bit since Carl and I first spoke in mid-2021 so this was a great chance to use Carl’s curious mind and wide range of experience...

Jan 31, 20231 hr 13 minEp. 314

Daryl Morey - Systems Thinking in Sports - [Invest Like the Best, EP.313]

My guest this week is Daryl Morey, who is President of basketball operations for the Philadelphia 76ers. Daryl is a computer science graduate but has become one of the NBA’s most successful General Managers during his time with the Houston Rockets and the 76ers. Together with my friend and past guest of the show, Sam Hinkie, Daryl pioneered the analytics movement in basketball. He’s been so influential his style has its own name, “Moreyball”, a nod to Michael Lewis’s book about baseball, Moneyba...

Jan 24, 20231 hr 5 minEp. 313

Miles Grimshaw - The DNA of Software Companies - [Invest Like the Best, EP.312]

My guest today is Miles Grimshaw. Miles is in his early thirties and is a General Partner at Benchmark. His experience and success belie his age. He was an early investor in Segment, Benchling, and Airtable, all before they had 30 employees. I have learned a ton from Miles about software investing and that’s why I was excited to have him on the show. We discuss his biological approach to investing, whether pure API companies can be good businesses, and what most has his attention right now. Plea...

Jan 17, 20231 hr 12 minEp. 312

John Fio - Creating Magic for Consumers - [Invest Like the Best, EP.311]

My guest today is John Fiorentino. John is a product inventor and entrepreneur who, in the space of a few years, has bootstrapped four products; Gravity Blanket, Moon Pod, Moon Pals, and Birthdate Candles which have collectively sold hundreds of millions of dollars of revenue. Our conversation is quite different than normal. Alongside his successful brands, John has had a range of life experiences – from starting as a Jazz musician to working for Justin Bieber - that give him an original worldvi...

Jan 10, 20231 hr 23 minEp. 311

Amjad Masad - The Future of Software Creation - [Invest Like the Best, EP.310]

My guest today is Amjad Masad. Amjad is the founder and CEO of Replit, whose mission is to bring the next billion software creators online. Replit has built a browser-based coding environment that makes coding more fun, collaborative, and approachable. We discuss how that is possible and why the way most of us interact with computers today is suboptimal. We then go into the effects of AI on software creation and its broader impacts on technology. Please enjoy my conversation with Amjad Masad. Fo...

Jan 03, 20231 hr 2 minEp. 310

Rebecca Lynn - Finding Your Customers - [Invest Like the Best, EP.309]

My guest this week is Rebecca Lynn. Rebecca co-founded early-stage investor Canvas Ventures in 2013 and is regularly featured as one of the best VCs in the market. She has deep positioning and go-to-market experience, which she honed during her time at Procter & Gamble, and that's the focus of our discussion. We cover the details of great marketing, why you should say no to customers, and how she has built Canvas. Please enjoy my discussion with Rebecca Lynn. For the full show notes, transcr...

Dec 27, 202253 minEp. 309

Michael Mauboussin - Sharpening Investor & Executive Toolkits - [Invest Like the Best, EP.308]

My guest this week is Michael Mauboussin. Many of you will know Michael and his work well. He’s Head of Consilient Research at Counterpoint Global, one of the sharpest investment minds I know, and a frequent guest on this show. In this discussion, we go deep into his recent work on market share, returns on capital, and capital allocation - all of which are coming under increasing scrutiny for different reasons. Please enjoy this great conversation with my friend Michael Mauboussin. Listen to Fou...

Dec 20, 20221 hr 8 minEp. 308

Jeremiah Lowin: Explaining the New AI Paradigm - [Invest Like the Best, EP.307]

My guest this week is Jeremiah Lowin. Jeremiah has been on the podcast a number of times over the years. He’s one of my oldest friends who has been a sounding board for me throughout my career. Today he is the founder and CEO of Prefect, which helps companies automate and orchestrate their dataflows. In full disclosure, Positive Sum is an investor in Prefect. We didn’t plan this conversation, but when OpenAI released ChatGPT, I called Jeremiah for a primer on what’s happening under the hood and ...

Dec 13, 20221 hr 2 minEp. 307

Bill Lenehan: Investing in Commercial Real Estate - [Invest Like the Best, EP.306]

My guest today is Bill Lenehan. Bill is the CEO of Four Corners Property Trust, a listed REIT and one of the leading owners of restaurant real estate in the US. Their portfolio is made up of 982 properties across 47 states. Real estate is something most of us own, whether as an investment or a home, and Bill’s insight into the asset class at this particular moment in time is fascinating to hear. Please enjoy my conversation with Bill Lenehan. For the full show notes, transcript, and links to men...

Dec 06, 20221 hr 18 minEp. 306

Ron Howard and Brian Grazer - Box Office Business - [Invest Like the Best, EP.305]

Today I’m joined by two Hollywood greats, Ron Howard and Brian Grazer. They have produced, directed, written, and acted in a number of the most popular films and tv shows ever made, including Apollo 13, A Beautiful Mind, 24, and Frost/Nixon. Their partnership is one of the longest running in Hollywood, and the business they founded in 1985, Imagine Entertainment, has won 49 EMMY awards, 11 Golden Globes, and 10 Academy Awards. There are few better storytellers in the world and it was a thrill to...

Nov 29, 202254 minEp. 305

Shane Battier - The No-Stats All-Star - [Invest Like the Best, EP.304]

Today’s episode is a special one, in a format that may turn into a series. It is a conversation between Ravi Gupta and Shane Battier. Ravi is a partner at Sequoia, one of our most popular past guests, and a good friend. Shane is Ravi’s friend, and one of the most successful basketball players ever, having won championships and awards at the high school, college, and NBA levels. I spent 10 years as a purely quantitative investor, so naturally I was obsessed with data in sports. When I was meeting...

Nov 22, 202256 minEp. 304

Parker Conrad - Building a Compound Company - [Invest Like the Best, EP.303]

My guest today is Parker Conrad, co-founder and CEO of Rippling. I wanted to speak to Parker because he is building Rippling in a way that we don’t come across often. Rather than focus narrowly on one product, he is building a suite of interrelated products simultaneously to carry out the functions of HR, Finance, and IT for companies. He calls it a compound company and we discuss the idea, as well as some of his other non-traditional theories, in detail. Please enjoy this conversation with Park...

Nov 15, 20221 hr 2 minEp. 303

Bob Elliott - A Macro Tour - [Invest Like the Best, EP.302]

My guest today is Bob Elliott, the CEO and CIO of Unlimited, which creates low-cost index ETFs for alternative investment strategies. Prior to co-founding Unlimited, Bob was a senior investment executive at Bridgewater Associates where he served on their investment committee and led Ray Dalio’s personal research team for a decade. His breadth and depth of experience makes him a great person to assess the current macro landscape. We discuss the relationship between rates, inflation, and asset cla...

Nov 08, 20221 hr 22 minEp. 302

Kirsten Green - Investing in Consumer Change - [Invest Like the Best, EP.301]

My guest today is Kirsten Green, founder and managing partner at Forerunner Ventures. Kirsten launched Forerunner in 2012 and has built it into a leading consumer-focused venture firm with early investments in consumer brands like Dollar Shave Club, Bonobos, Faire, and Warby Parker. Our conversation is an exploration of consumer behavior and how to invest behind change in our society. We also discuss frameworks for identifying brands early, how to build deal flow, and the shift in power between ...

Nov 01, 20221 hr 11 minEp. 301
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