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
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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August 19, 2025 • 97 mins
My guest today is Mark Bertolini. Mark is the former CEO of Aetna and the current CEO of Oscar Health. He shares one of the most extraordinary leadership stories I've encountered—surviving a catastrophic skiing accident that left him in chronic pain for 18 years while simultaneously leading one of healthcare's most successful corporate turnarounds. His personal experience navigating his son's life-threatening cancer battle and his ...
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August 12, 2025 • 90 mins
My guest today is Peter Lacaillade. Peter is the Chief Investment Officer for Private Investments at SCS Financial and has built a notable private equity allocation platform within the wealth management industry. He shares his insights on how SCS's pooled vehicle structure has enabled them to compete with institutional giants, avoiding the adverse selection that plagues most wealth platforms. Peter shares his investment philosophy ...
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August 5, 2025 • 93 mins
My guest today is Andrew Milgram. Andrew is the founder of Marblegate Asset Management, an alternative investment firm that invests in credit opportunities and special situations. He joins me to discuss his unique approach to distressed investing in the middle market, revealing how middle market EBITDA has declined 20-25% since 2019, creating what he calls the "K-shaped economy." His investment stories are legendary, particularly h...
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July 29, 2025 • 112 mins
My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's remarkable track record—including early investments in Rippling, Solana, and dozens of unicorns—but also the unconventional path he took to get there.
From running a hedge fund straight out of high school to filing for bankruptcy at 24, ...
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July 25, 2025 • 85 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. Brad Jacob's simple principle of "think big, move fast" is one I think about often.
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...
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July 22, 2025 • 82 mins
My guest today is Zach Dell. Zach is the co-founder and CEO of Base Power Company. Base is a modern power company building a reliable and affordable home energy service powered by distributed batteries. We explore one of the most underappreciated machines in our world: the electrical grid. Zach walks us through the complex world of electricity infrastructure and explains why the 100-year-old grid is woefully unprepared for the expl...
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July 15, 2025 • 73 mins
My guest today is Alan Waxman. Alan is the co-founder and CEO of Sixth Street, one of the most unique investment firms with a "go anywhere, do anything" mandate across asset classes, geographies, and time horizons, and over $110 billion in AUM. He describes his journey from CIO of Goldman Sachs’ Special Situations Group and the frameworks he brought with him to lay the foundation for Sixth Street. Alan details their famous investme...
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July 8, 2025 • 86 mins
My guest today is Caryn Seidman-Becker. Caryn is the Chairman and CEO of Clear. She bought the company out of bankruptcy for $6 million in 2010 and built it into the identity platform millions use in airports and stadiums today. Her Wall Street background investing in Apple, Amazon, and Priceline taught her to recognize when products become platforms, which shaped her vision for Clear as the "definitive secure identity platform" fa...
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July 1, 2025 • 90 mins
My guest today is Jens Grede. Jens is the co-founder and CEO of Skims, the shapewear and clothing brand he co-founded with his wife Emma Grede and Kim Kardashian. Our conversation left my head spinning. Jens has this remarkable ability to be both creative and commercial. He puts brilliant frameworks into plain terms and knows consumer like the back of his hand. Jens explains how pop culture is the only remaining hack to the consume...
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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. Charlie Songhurst is a brilliant strategist, accomplished executive, and prolific angel investor. This episode is one of my all-time favorite conversations, not just on the podcast, but period. Please enjoy this timeless discussion with Charlie Songhurst.
For the...
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June 24, 2025 • 77 mins
My guests today are Alex Pall and Drew Taggart, who you might know as The Chainsmokers. We explore their fascinating evolution from scrappy DJs to global superstars to serious venture capitalists with their fund Mantis. Drew and Alex share how the same high-touch, relationship-driven approach that built their music empire now defines their investment philosophy. Their framework for backing founders mirrors their artistic process: t...
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