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.colossus.com
Episodes
My guest today is John Arnold. John is probably the most famous energy trader of all time and certainly the most successful. One of the things John talks about is cultivating the best seat in your industry – the seat with the best perspective, the most information, the best systems..
John has been closely watching China's convergence in robotics, AI, and EVs, and shares his perspective from his recent trip to the country. We talk...
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February 24, 2026 • 75 mins
My guest today is Dan Sundheim. Dan is the founder and CIO of D1 Capital Partners.
He thinks about markets and businesses constantly, and has built a career entirely around that obsession. He manages over $30B across both public and private markets, with investments in SpaceX, OpenAI and Anthropic, and a public portfolio of names you may never have heard of.
Dan shares the story of the short case he wrote on Orthodontic Centers o...
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February 18, 2026 • 63 mins
This is my second conversation with Josh Kushner, founder and managing partner of Thrive Capital.
I recorded this conversation in October after publishing the Colossus cover story about him and Thrive. Given the overwhelming response, we created some breathing room before releasing it.
Josh started Thrive in 2011. The firm now manages approximately $50 billion with a very small investment team. What makes Thrive different is how ...
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February 10, 2026 • 95 mins
My guests today are Alex Behring and Daniel Schwartz, Co-Managing Partners of 3G Capital.
3G has built one of the most distinctive firms in investing around a simple idea: there are only a handful of truly great businesses and even fewer great CEOs. Their model is to raise capital with the intention of making just one investment per fund, commit meaningful amounts of their own money alongside their partners, and focus all of their...
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February 3, 2026 • 55 mins
My guest today is Ben Horowitz, the co-founder of Andreessen Horowitz. Since its founding in 2009, a16z has grown into one of the most influential firms in venture capital, reshaping how technology companies are funded and how power and ideas move through Silicon Valley and around the world.
This conversation focuses on sides of Ben’s story you don’t often hear. Ben reflects on the people who shaped him, including Nas, Andy Grove,...
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January 29, 2026 • 76 mins
My guest today is Gokul Rajaram, Founding Partner at Marathon Management. Gokul is one of the most prolific product builders and investors of the last twenty years. He has built the core ad and product businesses at Google, Facebook, Square, and DoorDash, working at each company during its most formative scaling periods.
Alongside his operating career, Gokul has invested in more than 700 companies, giving him an unusually broad ...
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January 20, 2026 • 126 mins
This week is a special episode. Only David Senra could get me to be on the other side of the mic. Because I don’t plan on being interviewed often, I wanted to share this conversation, which I so enjoyed, with our audience.
It went in a very different direction than I expected. We barely talk about investing or interviewing. Instead, we talk about finding an organizing principle for life, undiscovered talent, and the idea that “th...
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January 13, 2026 • 74 mins
My guests today are Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO.
Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I’ve been a part of.
Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR with more than 300,000 paying members. But the path from near death to dominan...
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January 6, 2026 • 62 mins
My guest today is Reed Hastings, the co-founder and former longtime CEO of Netflix.
Netflix is an example of two ideas that everyone talks about, but are extremely hard to do in practice. The first is finding a simple idea and taking it extraordinarily seriously. Reed talks about how even the DVD business was nothing more than a stepping stone toward streaming, which they envisioned from the company’s inception in 1997. The second...
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December 30, 2025 • 77 mins
Today, I am replaying my conversation with Nick Kokonas, one of my favorites from the show.
Nick is the co-founder of 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. He majored in philosophy before becoming a derivatives trader and is now one of the most well-known names in the hospitality industry.
In this co...
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December 23, 2025 • 85 mins
Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS]
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.
Ric Elias is the CEO and co-founder of Red Ventures, which has a portfolio of fast-growing digital businesses like Lonely Planet, The Points Guy, Bankrate, and large investments in a variety of oth...
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December 16, 2025 • 107 mins
My guest today is Henry Ellenbogen, founder and Managing Partner of Durable Capital Partners. Henry built his reputation at T. Rowe Price, where he led the New Horizons Fund and turned it into one of the best-performing small-cap growth portfolios in the country. In 2019, he left to start Durable.
His philosophy is grounded in a simple belief that great investing is about understanding people and change. Henry has spent his career...
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December 9, 2025 • 85 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 • 70 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 • 62 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 • 42 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 • 81 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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