Invest Like the Best with Patrick O'Shaughnessy

My guests today are Ben Gilbert and David Rosenthal. Ben and David are investors but also the duo behind the Acquired podcast, which is one of my favorite podcasts that dives deep into business history and famous acquisitions. I recommend you check it out. In this conversation, we review of some of the greatest corporate acquisitions of all time and also discuss investing lessons Ben and David hav...

My guest today is Leore Avidar. Leore is the co-founder and CEO of Lob, a company which makes it easy to send direct mail programmatically. He’s also the founder of a new company focusing on sports card collectibles, Alt, which is how we originally connected. Our conversation ranges from building Lob, buying a Lebron James rookie card, starting a 2nd business while operating his first and how Leor...

My guest today is Jacqueline Novogratz. Jacqueline is the founder and CEO of Acumen, a non-profit global venture fund that uses entrepreneurial approaches to solve the problems of poverty.  Our conversation touches on how Jacqueline left Wall Street and ended up starting a micro finance bank in Rwanda, how she thinks about investing in character, how creating dignity plays such a major role in her...

My guest today is Justin Singer, the founder and CEO of Caliper Foods and Stillwater Brands, two leading companies in the cannabis industry. We start our conversation with a fascinating discussion on how regulation creates or destroys business and investing opportunities, and then go on to discuss the ins and outs of the cannabis industry in detail. You’ll be able to tell quickly how high-quality...

My guest today is Jesse Livermore. I’ve worked with Jesse as part of our research partners program at O’Shaughnessy Asset Management for years now. Whenever there is a huge, important, and complex issue to be studied, I believe he’s among the best minds in the world to tackle it. He did that recently on the topic of what he calls “upside down markets,” which is the topic of this conversation. We s...

Today’s episode represents a new chapter for Invest Like the Best, so requires a longer introduction than normal. Starting today, I’ll be bringing you two episodes per week on the same feed. On Tuesday’s, I’ll focus on investors, and on Thursday’s, I’ll host builders—founders, CEOs, and operators from all different fields. We call this new Thursday series Founder’s Field Guide. There’s nothing mor...

Before getting to this week’s guest, an announcement: starting Thursday we will be introducing a new series of interviews. Be sure to check this same podcast feed in two days to learn more. My guest this week goes by the pseudonym Modest Proposal. He’s both a close friend, and one of the most respected thinkers on financial twitter. I field more inbound questions about him than just about anyone,...

My guest this week is Lauren Taylor Wolfe. Lauren is the co-founder and Managing Partner of Impactive Capital. Prior to founding Impactive she spent 10 years at Blue Harbour Group, a $3 billion activist investment firm. Our conversation is on the modernization of the activist investor playbook—how investors engage with companies to make them better and improve long term outcomes. We discuss the en...

My guest today is Rory Sutherland. Rory is the Vice Chairman of Ogilvy & Mather Group, which is one of the largest and most renowned advertising agencies in the world. He’s also the author of one of my favorite recent books called Alchemy: The surprising power of ideas that don’t make sense. In this conversation, we explore many of his counterintuitive ideas about business. Rory makes you think as...

My guest this week is Michael Seibel. Michael is a Partner at Y Combinator, and the CEO of YC's startup accelerator. He was the cofounder and CEO Justin.tv, which eventually became Twitch, and Socialcam. In this conversation, we discuss all Michael has learned reviewing thousands of applications to YC, interviewing countless new entrepreneurs, and watch young companies begin to grow and, occasiona...

My guest this week is Michael Mauboussin, the head of consilient research at Counterpoint Global. Michael is an all-time favorite guest here on the show, and this is his fourth appearance. We discuss one of the biggest topics in the world of investing: the shift from public to private markets that has taken place over the last several decades. We explore the reasons for this shift, the biggest ove...

My guests this week are Jeremiah Lowin and Chetan Puttagunta. Jeremiah is the founder of Prefect.io, an open-source software company where my family and I are investors, and Chetan is a partner at Benchmark Capital. Both are past guests and good friends. I asked them on to help the audience understand the open source software business model. I’ve been fascinated with this model in which companies...

My guest today is Katrina Lake, the co-founder and CEO of Stitch Fix. Stitch Fix is a multi-billion-dollar public company which has brought an entirely new model to retail apparel by combining data science, technology, and personal stylists to create a unique shopping experience tailored to the individual consumer. I first met Katrina through past guest Bill Gurley and have been excited to host he...

My guest this week is Brian Armstrong, the co-founder and CEO of Coinbase. The topic of our conversation is the future of cryptocurrency and decentralized finance. Its been a while since I checked in on the world of crypto and while prices are still below the 2017 highs, there’s been a ton of additional work and infrastructure laid. We discuss the major events of the past decade and what might hap...

My guest today, Matthew Ball, is a long time coming. He’s the former head of strategy at Amazon Studios, an investor, and probably my favorite business essayist writing today. In fact, I can’t think of another author whose work I read as quickly once a new essay drops. Read his latest on the past and future of Nintendo and you’ll see why. Our conversation is all about the past and future of media....

My guest today is Kat Cole, the COO and president of North America for Focus Brands, which owns famous companies like Cinnabon, Carvel, Jamba, and more. Kat’s story and career trajectory are remarkable, as are the lessons she’s picked up along the way which she shares with us all in this conversation. We discuss negotiation, distribution, brand building, brand extension strategies, and leadership....

My guest this week is Eric Vishria, a general partner at Benchmark Capital. Eric joined Benchmark after spending the first part of his career as an operator and CEO. The topic of our conversation is the past, present, and future of software businesses. We begin by explaining why public software companies trade at such incredibly high multiples today. We then explore the several different generatio...

My guest this week is Turner Novak, a partner at Gelt VC. Many of the largest companies in the world today are consumer social companies, so Turner and I discuss the past, present, and future of those businesses. When executed right, they are often the fastest-growing companies in history, and the rise of TikTok and some other companies we discuss makes it clear that there may always be more room...

My guest this week is Charlie Songhurst, the former head of strategy at Microsoft and a prolific investor, having personally invested in nearly 500 companies throughout his career. I met Charlie at an event hosted in New York and you can tell within one minute of meeting him that his mind is sparkling with ideas and curiosity. Its no wonder he’s been among the most commonly requested guests when I...

My guest today is Blake Robbins, a partner at Ludlow Ventures. We talk about all things video games, including the major companies in the industry, how games monetize, how in-game economies work, how e-sports has evolved, and much more. This is a fast-growing segment of consumer attention and interest, I believe we are in the very early days of gaming going mainstream. I also have a favor to ask....

My guest today is Brad Gerstner, the founder and CIO of Altimeter Capital, a multi-billion dollar technology-focused investment firm. Brad and his team are known for a deep expertise in internet-enabled businesses, including Expedia, Facebook, Uber, and many more. We discuss the evolution of opportunity in this style of investing, including the important shift to private investing, where so much o...

My guest today is John Collison, the Co-Founder of the digital payments company Stripe. Stripe’s mission is to increase the GDP of the internet, a lofty and deeply interesting pursuit. John is clearly a voracious learner across business and investing, which you’ll hear instantly. He started Stripe with his brother Patrick when he was just 19 years old, and has grown it to, at last valuation, a $36...

My guest today is Jeremy Grantham. Jeremy is the co-founder and chief investment strategist of Grantham, Mayo, & van Otterloo (aka GMO). GMO, which manages more than $60B for clients, was a firm that helped educate me early in my investing career. They’ve long published thought-provoking research, most of which came from Grantham himself. He is regarded as a highly knowledgeable investor in variou...

My guest today is Ben Thompson. Ben is the author of my favorite business strategy newsletter called Stratechery. He’s also the host of the exponent podcast, and now the Dithering, a podcast he recently launched with John Gruber. I think Ben is among the most interesting business analysts in the world, and I’ve learned from and directly applied many of his ideas. We cover many of the major concept...

My guest today is Shishir Mehrotra and the topic of our conversation is the bundle: offering access to multiple products, services, or providers for a single bundled price. This topic is full of incorrect pre-conceived notions, and as it turns out, the bundle is one of the most powerful ideas in business. Properly harnessed it is good for everyone involved. Shishir explains the ins and outs of bun...