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
April 29, 2025 • 120 mins
My guest today is Cliff Sosin. Cliff is the founder of CAS Investment Partners, a fund he started with $5 million in 2012 and has grown to $1.7 billion as of the last reported numbers at the end of 2024. At the time, CAS had only four positions.
This conversation is different to our typical episodes. We start by talking about Cliff's investing philosophy but the bulk of this long discussion is a case study into his remarkable inve...
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April 25, 2025 • 86 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. There aren't many people like Cyan Banister. Her 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 ...
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April 22, 2025 • 92 mins
My guest today is Matt Huang, co-founder of Paradigm, a leading crypto investment firm with over $12 billion in assets under management. Before launching Paradigm in 2018 with Coinbase co-founder Fred Ehrsam, Matt was a partner at Sequoia Capital, where he led many of the firm's crypto investments. It’s widely reported that Michael Moritz called Matt “the only regrettable loss in Sequoia’s history.”
In our conversation, Matt shares...
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April 15, 2025 • 94 mins
Today's guest is Neil Mehta, founder of Greenoaks Capital. In 2012, aged 27, Neil left D.E. Shaw to start Greenoaks with his friend Benny Peretz. One of their first investments was in Coupang, a South Korean e-commerce company led by founder Bom Kim. Neil was so convinced of Coupang's potential that he invested 40% of their initial $50 million fund into the company—a bet that eventually returned about $8 billion.
Over its first 13 ...
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April 8, 2025 • 102 mins
My guest today is Michael Ovitz. Michael is the legendary talent agent and Co-Founder of CAA or Creative Artists Agency and he is joining me on Invest Like the Best for a second time. Michael started CAA in 1975 and over the next 20 years, he built it into the world's most formidable talent agency, changing Hollywood forever. He shares insights into how he identifies exceptional people across diverse fields - from Hollywood directo...
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April 1, 2025 • 74 mins
My guest today is Darren Farber. Darren is a Managing Partner of Albion River, a private direct investment firm focused on acquiring companies that produce highly technical Defense Products & Services. He is a Former special advisor to the Deputy Under Secretary of Defense, a Former member of U.S. Department of Defense Task Force for Business and Stability Operations, and the list goes on and on. Darren is a wealth of knowledge in ...
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March 28, 2025 • 109 mins
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. This is a rare opportunity to hear from one of the best investors of the past decade—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 ...
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March 25, 2025 • 55 mins
My guest today is Gili Raanan. Gili is the founder of Cyberstarts, a VC firm focused on cybersecurity and the world’s first VC that is majorly backed by cyber entrepreneurs. Cyberstarts’ $50 million dollar first fund exploded to close to $2 billion in just three years. Gili describes cybersecurity today as "the perfect storm" where global conflicts and AI advancements are creating unprecedented threats. He talks about Cyberstarts' ...
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March 18, 2025 • 63 mins
My guest today is Alex Wiltschko. Alex is the founder and CEO of Osmo, a science and technology company giving computers a sense of smell. He set out on a mission to digitize our sense of smell and he describes how Osmo is teaching computers to both read and write scent. Alex was kind enough to walk me through the laboratory which you can watch in the video version of this interview on Youtube and Spotify, where he demonstrates the...
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March 11, 2025 • 87 mins
My guest today is Kelly Granat. Kelly is the Co-Chief Investment Officer and Managing Director at Lone Pine Capital, one of the most storied and successful hedge fund and investment firms of the last several decades. We explore how investing has evolved since Kelly joined the industry and she shares insights into Lone Pine maintaining its edge through deep fundamental research and a collaborative culture. We discuss what makes grea...
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March 4, 2025 • 76 mins
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
My guest today is Devon Zuegel. Devon is the founder and president of the Esmerelda Institute, and she is creating a new town called Esmerelda in California wine country. Learning of Devon and her plan, I couldn’t help but wonder why there aren’t more people building new towns. She shares the origin story of her project Esmeralda, a modern reinvention of the Ch...
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February 28, 2025 • 71 mins
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. There's nobody I've met quite like 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 ex...
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February 25, 2025 • 60 mins
My guest today is Chris Pedregal. Chris is the founder and CEO of Granola, an AI-powered notepad that transcribes your meetings and enhances your meeting notes. Chris shares fascinating insights on how humans have historically developed tools to extend our cognitive capabilities - from writing and mathematical notation to data visualization - and how AI represents the next frontier in this evolution. We explore competitive dynamics...
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February 18, 2025 • 58 mins
My guest today is Ravi Gupta. Ravi is a Partner at Sequoia Capital and a host on Glue Guys, a podcast on the Colossus network that intersects business and sports. I wanted to have him back on Invest Like the Best to discuss his recent most recent blog post titled “AI or Die.” As both an investor and former Instacart operator and CFO, Ravi believes we're entering an era where the constraints that historically limited small teams are...
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February 11, 2025 • 83 mins
My guest today is Marc Andreessen. Marc is a co-founder of Andreessen Horowitz and one of Silicon Valley's most influential figures. He combines deep technical knowledge from his engineering background with broad historical understanding and strategic thinking about societal patterns. He last joined me on Invest Like the Best in 2021, and the playing field looks a lot different today. Marc goes deep on the seismic shifts reshaping ...
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February 4, 2025 • 137 mins
My guest today is Graham Duncan. This conversation will make you think about your life in new ways. This is a two-hour segment of a 4.5-hour interview I did with Graham last year. It stands alone as remarkable, but those who subscribe to Colossus Review will gain access to the full conversation. This will be true in future issues, too.
In 2006, in his early 30s, Graham convinced Stuart Miller, CEO of home construction company Lenn...
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January 28, 2025 • 93 mins
My guest today is Blake Hall. Blake is the co-founder and CEO of ID.me, a secure digital identity network with over 100 million members. He was an officer in the United States Army and served our country for four years as a a rifle platoon leader, the battalion reconnaissance platoon leader, and as the battalion logistics officer. We explore his formative years in the military and transition into entrepreneurship. Blake shares powe...
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January 21, 2025 • 45 mins
My guest today is Dylan Field. Dylan is the co-founder and CEO of Figma and last joined me on Invest Like the Best in 2020. A lot has changed since then and we explore the evolving landscape of design and how Figma has been navigating AI while staying true to its founding vision of eliminating the gap between imagination and reality. Despite Figma's incredible success in becoming the default design platform, Dylan remains deeply mo...
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January 14, 2025 • 81 mins
My guest today is Tal Zaks. Tal is a physician-scientist turned biotech executive and investor who served as Moderna's Chief Medical Officer during their COVID-19 vaccine development, giving him an extraordinary perspective on one of modern medicine's pivotal moments. His combination of medical expertise, platform innovation experience, and investing acumen allows us to explore the interconnected challenges of turning scientific br...
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January 7, 2025 • 65 mins
My guests today are Dwight Churchill and Gaurav Misra, co-founders of Captions, which uses AI to generate and edit talking videos and has grown to significant scale at remarkable speed. We explore a key distinction in AI: tackling bounded problems like video generation versus unbounded problems like general intelligence and what this means for building sustainable businesses. We also explore their unique data flywheel, why video ge...
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