Invest Like the Best with Patrick O'Shaughnessy
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
December 9, 2025 • 84 mins
My guest this week is Gavin Baker. Gavin is the managing partner and CIO of Atreides Management, and he has been on the show many times before.
I will never forget when I first met Gavin in 2017. I find his interest in markets, his curiosity about the world to be as infectious as any investor that I've ever come across. He's encyclopedic on what is going on in the world of technology today, and I've had the good fortune to host h...
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My guest today is David George. David is a General Partner at Andreessen Horowitz, where he leads the firm’s growth investing business. His team has backed many of the defining companies of this era – including Databricks, Figma, Stripe, SpaceX, Anduril, and OpenAI – and is now investing behind a new generation of AI startups like Cursor, Harvey, and Abridge.
This conversation is a detailed look at how David built and runs the a16...
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November 28, 2025 • 75 mins
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Palmer Luckey is a relentless builder and original thinker. He founded Oculus, bringing virtual reality to the mainstream, and is now reshaping the future of defense and technology with Anduril. I hope you enjoy this conversation.
Palmer is the founder of Anduril, whi...
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November 25, 2025 • 69 mins
My guest today is Martín Escobari. Martín is Co-President and Head of Global Growth Equity at General Atlantic.
We talk about General Atlantic’s unique founding story and how its long-term structure, including permanent capital, a single P&L, and partnership culture, allows it to invest differently than other growth equity firms. We discuss the firm’s global perspective and particularly why the premium on U.S. equities is creating...
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November 19, 2025 • 61 mins
My guest today is Ari Emanuel. Ari runs one of the most influential portfolios in global sports, entertainment, and media. He oversees TKO, which includes the UFC and WWE, serves as the Executive Chairman of WME Group, and recently founded MARI, a new company focused on global events and live experiences.
At the center of this conversation is Ari's anti-AI bet: as AI makes digital content cheaper and everyday work more automated, ...
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November 11, 2025 • 41 mins
My guest today is my friend Wolfgang Hammer. Wolfgang is a successful film producer and executive who helped create House of Cards and ran several major studios, including Lionsgate, CBS Films and Miramax. He’s now building a new kind of film studio with support from Mitch Lasky and Marc Andreessen.
Wolfgang also helps founders and CEOs use storytelling to better understand what they do, and why it matters. In many ways, this conv...
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November 4, 2025 • 80 mins
My guest today is Luca Ferrari. Luca is the co-founder and CEO of Bending Spoons, which he describes as 25 percent private equity and 75 percent technology company. Founded in 2013, Bending Spoons fully acquires and operates digital companies like Evernote, Meetup, Vimeo, and most recently AOL.
Our conversation explores the unique model behind Bending Spoons, and the culture required to scale it. Luca shares exactly how their acq...
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October 31, 2025 • 68 mins
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Kevin Kelly 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 ex...
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October 30, 2025 • 49 mins
Today I am replaying my conversation with Ken Langone. Ken is a legendary American businessman best known for his co-founding of Home Depot. He is also a former director of the New York Stock Exchange and a passionate philanthropist. He shares with us a lifetime worth of wisdom, building Home Depot into a powerhouse and prioritizing his employees above all else. He says he still “bleeds orange” to this day. You’ll hear as he recoun...
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October 21, 2025 • 105 mins
My guest today is Karim Atiyeh. Karim is the co-founder and CTO of Ramp, the fastest-growing finance automation platform in history, reaching over $1 billion in revenue in just over five years. Ramp is, of course, also our presenting sponsor, so I’m obviously very biased in how highly I think about Ramp and about Karim. But, this interview was not part of that sponsorship, I simply view Karim as one of the best operators active tod...
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October 16, 2025 • 95 mins
My guest today is Dan Wang. Dan is a technology analyst and author who spent six years living in China studying its manufacturing ecosystem and tech development, best known for his new book Breakneck. Dan offers the most nuanced framework I've encountered for understanding US-China competition. We explore a critical asymmetry: it's far harder for the US to rebuild manufacturing capacity than for China to improve scientific researc...
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October 6, 2025 • 81 mins
My guest today is Jesse Zhang. Jesse is the co-founder and CEO of Decagon, one of the fastest-growing AI customer service companies. Decagon provides a centralized AI engine to auto-resolve issues at any time, in every language, and across every channel. Jesse shares his systematic approach to finding product-market fit by asking potential customers exactly how much they'd pay for solutions. We explore why customer service and codi...
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September 30, 2025 • 118 mins
My guest today is Dylan Patel. Dylan is the founder and CEO of SemiAnalysis. At SemiAnalysis Dylan tracks the semiconductor supply chain and AI infrastructure buildout with unmatched granularity—literally watching data centers get built through satellite imagery and mapping hundreds of billions in capital flows. Our conversation explores the massive industrial buildout powering AI, from the strategic chess game between OpenAI, Nvid...
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September 26, 2025 • 62 mins
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. This Business Breakdowns on Rolex is a long-time stand out. The founder and executive chairman of Hodinkee, Ben Clymer, was the perfect person to take us through the ins and outs of this legendary brand.
For the full show notes, transcript, and links to the best conte...
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September 23, 2025 • 53 mins
My guest today is Barry Diller. Barry is the former CEO of Paramount Pictures, Fox Broadcasting, and the founder of IAC. He has been at the center of every major media transformation over the past five decades, from creating the Movie of the Week format to building the fourth broadcast network to executing 150 internet-era deals. Barry reveals his "creative conflict" philosophy - pushing smart, opinionated people past their enduran...
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September 16, 2025 • 91 mins
My guest today is Jeff Horing. Jeff cofounded Insight Partners and has been the Managing Director since 1995. This is one of Jeff’s first public conversations about building one of the world’s most successful technology investment firms with over $100 billion in AUM. Jeff reveals the mechanics behind Insight's legendary sourcing machine—60-80 people systematically calling companies worldwide. He explains their contrarian "one fund"...
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September 9, 2025 • 77 mins
Today, we are replaying one of my favorite conversations with Sam Hinkie. Sam worked for more than a decade in the NBA with the Houston Rockets and then as the President and GM of the Philadelphia 76ers. And now, after years of personal investing, he has launched his own venture capital firm, 87 Capital. Every conversation I have with Sam is alive with insight, and this one is no different. We explore the idea of studying the "brea...
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September 5, 2025 • 107 mins
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Sean Feeney makes you want to be a better person, friend, and leader. Sean is the co-founder of Grove House 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 Mi...
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September 2, 2025 • 73 mins
Today we are replaying my conversation with 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 young profe...
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August 26, 2025 • 146 mins
My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital. He became the youngest member of the Forbes 400 in the 1990s before vanishing from public view for two decades—only to emerge with a $1 billion bet that he can make kids learn 10x faster using AI. Joe has built an AI tutoring system so effective that students at his Alpha School literally beg not to take summer...
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