Invest Like the Best with Patrick O'Shaughnessy

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 replicable operating procedures and championing yo...

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 like Nvidia GPUs have powered the revolution, but G...

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 consulted with those close to him, everyone agreed t...

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 companies in the world. Peter has been a board member at W...

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 the terror attacks of October 7 and the path forwar...

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 2011 and has grown into one of the largest logistics...

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 contentious book called "Founder vs Investor" tha...

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 reality business that he sold to Facebook for $2 bil...

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 from macro risks to Nvidia and the process of craft...

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 attracts ambition, why the returns to sweating the d...

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 strong and fast into the industry as he worked his way...

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 allocators. A few years ago, they also set up a clas...

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 already serves over 5,000 organizations. In our di...

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 opportunity to take advantage of a compelling the...

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 from studying the lives of not just entrepreneurs,...

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 discuss the operational complexity behind the model, w...

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 my favorite recent episode of David's. Please enjo...

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 what it takes to build an enduring investment busi...

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 and bars in America - Alinea, Next, and The Aviar...

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. Our conversation is roughly split in half. First, we...

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 history and his work has led him to some fascinati...

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 value swaps to business model product fit and the s...

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 Oscar. Thrive has gone from strength to strength since...

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 internet and technology focused businesses. Prior to t...

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 guest to deliver a primer on VMS, which is exactly w...