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Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcasts

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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
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My guest today is Sean Feeney. Sean is the co-founder of Grovehouse Hospitality Group and the owner of Lilia and Misi, two of New York City’s most sought-after restaurants. He left his job in Trading to chase down a dream with Michelin star chef Missy Robbins. Sean leveraged his finance background to write his own rulebook for the restaurant indust…
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My guest today is Dave Fontenot, founder of HF0. Born out of Dave’s experiences in monasteries across the world, HF0 is a twelve-week residency for repeat founders to supercharge their next venture. For 12 weeks, 10 teams of engineers relocate to HF0’s house in San Francisco. During the residency, everything is taken care of so their sole focus is …
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My guest today is Anne-Marie Peterson. Anne-Marie is an equity portfolio manager at Capital Group, a storied investment firm managing 2.5 trillion dollars and getting ready to celebrate its centennial anniversary. Anne-Marie is a seasoned investor, approaching three decades in the industry, with nearly 20 of those years being with Capital. She has …
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My guest today is Aravind Srinivas. He is the founder and CEO of Perplexity, a startup that he describes as an “answer engine” built from scratch with AI. Aravind has set out for perplexity to become the most powerful answer engine backed by up-to-date sources. He helps me pick the technology apart, describing the behind the scenes of what it takes…
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My guest today is Ali Hamed. Ali was first on Invest Like the Best six years ago. He was 26 at the time and four years into building his investing firm, CoVenture. Both then and now, Ali is an example of what’s possible when you think creatively. Six years later, CoVenture now manages two-and-a-half billion dollars, and Ali continues to find alpha …
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My guest today is Cyan Banister. Cyan’s life story is remarkable. She was homeless at a young age, dropped out of high school, and five years ago she suffered an extremely rare stroke. Yet, in spite of everything, she is one of the most optimistic and curious people you can hope to meet. Cyan is also one of the great angel investors of this era, ha…
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Today, we're replaying my conversation with Danny Meyer. He is the founder and CEO of Union Square Hospitality Group, which comprises some of the most acclaimed restaurants in New York, like Gramercy Tavern and Union Square Café. Danny is also the founder and chairman of Shake Shack, which began in NYC but is now a publicly traded company with hund…
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Today, we're running a replay of my 2019 conversation with legendary investor Chuck Akre. Chuck founded Akre Capital Management in 1989, which now manages approximately $14B dollars. We discuss his investing style and his “three-legged stool” for evaluating companies. Please enjoy this great conversation. Listen to Founders Podcast For the full sho…
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My guest today is Alex Telford. Alex is the founder of Convoke, a software platform to help streamline drug development and commercialization. He also has been writing frequent blog posts on the biotech industry since 2019, keeping a pulse on the direction of innovation. He joined me today to talk about the history of the pharmaceutical industry an…
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My guest today is Madhavan Ramanujam. Madhavan quite literally wrote the book on how to price products. It’s called “Monetizing Innovations” and his concepts have been used by companies across the world like Porsche, Uber, LinkedIn, and SuperHuman. Our conversation is a masterclass on pricing. We discuss common mistakes when pricing products, why y…
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This week, we are running a replay of my conversation with Daryl Morey from last year. Daryl is the President of basketball operations for the Philadelphia 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 n…
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My guest today is Michael Ovitz. Michael is the legendary talent agent and co-founder of CAA, or Creative Artists Agency. Michael started CAA in 1975 and over the next twenty years, he built it into the world’s most formidable talent agency, changing Hollywood forever. The list of stars he’s worked with is endless, from Meryl Streep to Steven Spiel…
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My guest today is Erik Serrano. Erik is the CEO of Stable Asset Management, which he started 14 years ago in his early 20s and has scaled to over $3 billion in AUM. Unusually, Stable’s strategy focuses on other investing firms. They look to back the Blackstone's of tomorrow and provide those founders with capital and support so their time is spent …
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This week we are replaying our episode with 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 pow…
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My guest today is Justin Ishbia. Justin is the Founding Partner of Shore Capital. Shore is a private equity firm that invests in microcap businesses within industry niches. With $7 billion in capital deployed but an average transaction size of just $12 million, Justin has worked to build a system to drive success for hundreds of businesses through …
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Today, my guest is 21-year-old Gavin Uberti, who dropped out of Harvard to build Etched, which is one of the most fascinating companies I’ve seen. The topic of our conversation is the ongoing revolution in artificial intelligence, and more specifically the chips and technology that powers these incredible models. To date, general-purpose AI chips l…
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Today, we’re releasing a conversation between John Collison and Charlie Munger. We've had this interview with Charlie scheduled to air for a while, coinciding with Stripe Press's launch of the amazing reprint of Poor Charlie's Almanack, which is released today. We were all stunned last week when we heard the news of Charlie's passing, but having co…
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My guests this week are Peter Fenton and Victor Lazarte. Peter and Victor are both General Partners at Benchmark. Of the six equal partners at the storied venture firm, Peter is the longest serving and Victor is the newest, having spent the past decade founding and building Wildlife Studios into one of the biggest independent mobile gaming companie…
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Today's episode is a conversation with Lior Susan, the Founder of Eclipse Ventures, whose mission is to unlock solutions to age-old physical industry problems through the intersection of bits and atoms. Lior is Israeli, and served in Israel's special forces before founding Ecplise. The topic of conversation is one fellow investor's perspective of t…
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My guest today is Brad Jacobs. Brad’s resumé is remarkable. He has founded seven companies, all of which are billion-dollar or multibillion-dollar businesses. He has done 500 M&A transactions and raised $30 billion dollars of debt and equity capital. Currently, he is the Executive Chairman of XPO, a commercial trucking company that he started in 20…
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My guests this week are Elizabeth Zalman and Jerry Neumann. Jerry has been on this show two times before. He’s an early-stage Venture Capitalist, an adjunct professor of entrepreneurship, and an excellent writer. Liz is a two-time founder, most recently co-founding StrongDM, in which Jerry was a seed investor. Together, they have written a somewhat…
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My guest today is Palmer Luckey. Palmer is the founder of Defense company Anduril Industries, which makes next-generation military technology for the US and its allies. Since bringing the company to life in 2017, Palmer and Anduril have disrupted the established order in the Defense industry. Prior to Anduril, Palmer founded Oculus VR, a virtual re…
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Today’s guest is Aswath Damodaran, who is joining us for a second time on Invest Like the Best. Aswath is a Professor of Finance at NYU’s Stern School of Business and is often referred to as the Dean of Valuation for his clarity of thought on the subject. This conversation picks up where we left off 18 months ago and covers a wide range of topics f…
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My guests this week are the co-founders of Stripe, Patrick and John Collison. My conversation with John in 2020 is still one of our most popular. A key theme that emerged from that first discussion was John’s boundless curiosity for all things business and this conversation continues that thread. We talk about setting a strategy and culture that at…
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My guest this week is Strauss Zelnick, the CEO of leading game publisher Take-Two Interactive. Maybe most well-known for its hugely successful Grand Theft Auto game, Take-Two is a sophisticated, top-tier developer, publisher, and marketer of interactive entertainment that owns Rockstar Games and 2K. Strauss’s passion for entertainment led him stron…
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My guests this week are Rick Buhrman and Paul Buser. Rick and Paul spent over a decade managing the public equity portfolio at Notre Dame’s Endowment before leaving in 2020 to set up a permanent capital vehicle called Sator Grove. As you’ll hear in this conversation, they know, have studied, or have invested with most of the world’s best capital al…
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My guests today are Jack Altman and Miles Grimshaw. Jack is the co-founder and CEO of Lattice, an HR software platform. Miles is a General Partner at Benchmark, an early investor and Board Director at Lattice, as well as a former guest on Invest Like the Best. Jack started Lattice in 2015 and has scaled it into a multi-billion-dollar business that …
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My guest today is Michael Simanovsky. Mike is the Managing Partner of Conversant Capital, a real estate investment firm he founded in early 2020. Conversant aims to be the most flexible capital provider in real estate, investing across public and private markets as well as equities and credit. The firm will also incubate platforms where they see an…
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My guest today is David Senra, the creator and host of Founders Podcast. With an incredible appetite for biographies, David has delved into the lives of over three hundred entrepreneurs, extracting invaluable wisdom that he shares with his audience each week. Throughout the conversation, we discuss David’s love of podcasts, and what can be gained f…
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My guest today is Will England, the CEO and Co-CIO of Walleye Capital. Walleye is a multi-strategy hedge fund headquartered in Minnesota that manages around $5 billion. Our conversation is a primer on multi-strategy hedge funds, which have become a force in markets through the success of firms like Millenium, Citadel, Point72, and Balyasny. We disc…
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Almost exactly a year ago, Colossus entered into a partnership with David Senra and the Founders podcast to join the Colossus network. The show has since exploded with more devoted fans than any podcast that I've encountered. With that in mind, we are excited to share an example episode from his show here today on the director, James Cameron. It's …
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My guest today is Lee Ainslie, the founder of Maverick Capital. Lee started his investing career at Tiger Management where he worked for Julian Robertson. In 1993, he left to start Maverick and has built the firm into one of the top-performing hedge funds of the last 30 years. Lee doesn’t speak in public often so this is a fascinating insight into …
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Today, we are running a special episode from our show Founder's Field Guide. In this conversation, Nick Kokonas shares his experience of bringing a business mindset to the restaurant industry. It is one of our favorites at Colossus and there is something for everyone in this timeless conversation. Nick is the co-founder of 3 of the best restaurants…
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My guest today is Des Traynor. Des is the co-founder and Chief Strategy Officer of Intercom - a customer service solution that helps businesses answer product questions, offer instant support, and automate sales. The business was founded in 2011 and its products operate within 25,000 businesses, including the likes of Amazon, Lyft and Atlassian. Ou…
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My guest today is Samo Burja. Samo is the founder of consulting firm, Bismark Analysis, and has dedicated his life’s work to understanding why there has never been an immortal society. His research focuses on institutions, the founders behind them, how they rise and why they always fall in the end. As you’ll hear, Samo has an encyclopedic grasp of …
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My guest today is Chris Paik, who is a General Partner at early-stage venture firm, Pace Capital. Before Pace, Chris spent eight years building and investing alongside last week’s guest, Josh Kushner, at his firm Thrive Capital. During that time, he sat on the board of Twitch. Our conversation explores Chris’ frameworks for investing, from atomic v…
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My guest today is Josh Kushner, founder and managing partner of venture firm, Thrive Capital. Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Osca…
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My guest today is Jeremy Giffon. I spend all my time trying to find people who have some “singularity” to them. People who seem like they can do an N of 1 something. Having spent many days with Jeremy recently, he strikes me as one of those people. He was the first employee and general partner at private equity firm, Tiny, which buys and holds inte…
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My guest today is Dave Yuan. Dave is the Founder and Partner of Tidemark Capital, which he started in 2021 after 15 years as a General Partner at Technology Crossover Ventures. Dave has been investing in vertical market software as long as anyone I know and he currently sits on the board of two VMS businesses, Toast and Karbon. He is the perfect gu…
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My guest today is Kevin Kelly. Kevin co-founded Wired magazine and has published a number of seminal books and essays on technology over the past three decades. I have devoured everything Kevin has put out into the world and many of his ideas shape the way I live today. Our conversation explores media, family, money, his concept of the Technium, AI…
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My guest this week is Justin Mares. Justin is the founder of TrueMed and has previously founded three different health food brands that collectively do $100M+ in annual revenue. Every time I speak with him, he makes me reflect on my own health and the state of our health more broadly. This conversation is no different. As Justin puts it, we're in a…
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My guest this week is Scott Goodwin. Scott is the co-founder and managing partner of Diameter Capital Partners, which he started as a credit hedge fund in 2017 and has expanded into a $13 billion investment firm that covers all credit markets. Scott spent the first 8 years of his career at Citi where he rose to head of High Yield Trading before mov…
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Today, we are running a special episode from our show Business Breakdowns. In this conversation, Ben Clymer does an incredible job breaking down what makes Rolex so special. If you enjoy this episode, follow Business Breakdowns for more discussions like this. Founded in the UK in 1905 under the name Wilsdorf & Davis, Rolex has become the leading na…
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My guest today is Kieran Goodwin. Kieran spent over two decades at the frontier of credit investing. During the global financial crisis, he was a Partner and Head of Trading at King Street Capital, which grew from $4 billion to $20 billion while he was there. He then left to start his own credit hedge fund, Panning Capital Management. In our discus…
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My guest today is Henry Schuck, the founder and CEO of ZoomInfo. I’ve gotten to know Henry over the past year by virtue of him being on the board of Tegus, where I’m a board observer. I meet a lot of people and Henry is one of my favorites. His energy is unmatched and he knows his business down to the tiniest details. He has tenacity and curiosity …
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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 t…
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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 t…
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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 investme…
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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. Alex…
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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 re…
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