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Colossus | Investing & Business Podcasts · Investment

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

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Fidji Simo - Creating Delightful Consumer Experiences - [Invest Like the Best, CLASSICS]

30 May 2025
1h 12m
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In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Fidji Simo, the CEO of Instacart, about her career journey from Facebook to Instacart, her leadership philosophy, and the future of Instacart within the evolving grocery and technology landscape. They discuss the importance of data and AI in enha...

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Graham Weaver - Building Alpine - [Invest Like the Best, EP.425]

27 May 2025
1h 30m
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In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Graham Weaver, the founder of Alpine Investors, about his unique approach to private equity. Weaver discusses Alpine's focus on acquiring smaller businesses with retiring owners and installing young, talented CEOs to drive growth. He emphasizes t...

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Gustav Söderström - How Spotify Thinks - [Invest Like the Best, EP.424]

20 May 2025
1h 24m
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In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Gustav Söderström, Co-President, CPO, and CTO of Spotify, about Spotify's approach to innovation, particularly regarding AI, and its business strategies. Gustav discusses how Spotify is adapting to the age of generative AI by focusing on creating...

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Asurion: The Early Days (‘95-‘01) with Kevin Taweel - [50X, S2 EP.1]

16 May 2025
1h 9m
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This episode explores the history and evolution of Asurion, a company that achieved exceptional investment returns, through an interview with its co-founder and chairman, Kevin Taweel. Taweel recounts his early entrepreneurial experiences and the pivotal decision to pursue a search fund, leading to the acquisition of R...

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Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

13 May 2025
1h 28m
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This episode explores entrepreneurship through acquisition, focusing on the evolving landscape of search funds and small business acquisitions. It highlights a bifurcation in the market, with funded searchers targeting larger companies and self-funded entrepreneurs finding success with smaller businesses, often leverag...

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David Senra - The Focused Few - [Invest Like the Best, EP.422]

06 May 2025
1h 21m
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This episode explores the critical importance of focus for entrepreneurs, drawing on David Senra's extensive study of over 400 biographies. Senra argues that exceptional builders achieve success through decades-long dedication to simple ideas, such as Todd Graves' obsession with perfecting chicken fingers, while reject...

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Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

29 Apr 2025
2h 1m
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This episode explores the investment philosophy of Cliff Sosin, founder of CAS Investment Partners, and delves into a detailed case study of his significant investment in Carvana. Against the backdrop of Sosin's long-term investment approach focused on identifying "contained" businesses with durable competitive advant...

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Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]

25 Apr 2025
1h 25m
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This episode explores the intersection of spirituality, venture capitalism, and contrarian investing strategies, featuring angel investor Cyan Banister. Against the backdrop of Banister's remarkable life journey, including periods of homelessness and a rare stroke, the discussion delves into her unique investment phil...

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Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]

22 Apr 2025
1h 33m
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This episode explores the life and career of Matt Huang, co-founder of Paradigm, a leading crypto investment firm, and his unique approach to identifying exceptional investment opportunities. Against the backdrop of his early success with ByteDance, Huang details his framework for navigating the complexities of the cr...

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Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]

15 Apr 2025
1h 35m
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This episode explores the investment philosophy and strategies of Neil Mehta, founder of Greenoaks Capital, a remarkably successful venture capital firm. Against the backdrop of Mehta's grandfather's gun shop in India, which instilled in him an appreciation for craftsmanship, the discussion delves into his unique appr...

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Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]

08 Apr 2025
1h 43m
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This episode explores the identification and cultivation of exceptional talent, and the subsequent building of enduring institutions. Against the backdrop of Michael Ovitz's extensive career, the discussion delves into his unique approach to spotting talent early, exemplified by his involvement with individuals like A...

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Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]

01 Apr 2025
1h 15m
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This episode explores the evolving landscape of defense investing and the future of warfare. Against the backdrop of shifting global dynamics and a reevaluation of the U.S.'s role in global defense, the conversation delves into the complexities of defense budgeting and the challenges of adapting to a rapidly changing ...

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Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]

28 Mar 2025
1h 47m
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This episode explores the investment philosophy and strategies of Josh Kushner, founder and managing partner of Thrive Capital, a venture capital firm managing $15 billion. Against the backdrop of Kushner's relatively low public profile, the interview delves into his approach to identifying and investing in companies,...

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Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]

25 Mar 2025
56m
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This episode explores the rapidly evolving cybersecurity landscape and the unique investment strategy of Cyberstarts, a venture capital firm focused on the sector. Against the backdrop of escalating global conflicts and the transformative impact of AI, Gili Raanan, founder of Cyberstarts, describes the current cyberse...

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Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]

18 Mar 2025
1h 4m
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This Invest Like the Best podcast episode features an interview with Alex Wiltschko, founder and CEO of Osmo, a company digitizing the sense of smell. The conversation covers Osmo's technology, which involves "reading" and "writing" scents using AI and advanced chemistry, and its first commercial application, Generati...

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Kelly Granat - Investing At Lone Pine - [Invest Like the Best, EP.414]

11 Mar 2025
1h 28m
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This Invest Like the Best podcast episode features an interview with Kelly Granat, Co-Chief Investment Officer at Lone Pine Capital. The conversation explores the evolution of investing, focusing on market structure changes, the rise of passive investing and algorithmic trading, and the impact of readily available dat...

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Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]

04 Mar 2025
1h 17m
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This Invest Like the Best podcast episode features an interview with Devon Zuegel, founder of the Esmerelda Institute, about her project to build a new town, Esmerelda, in California wine country. The conversation explores the impact of environment on human behavior, the role of space and cost in shaping creativity, a...

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Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

28 Feb 2025
1h 9m
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This Invest Like the Best podcast episode features an interview with Doug Leone, former Sequoia Capital leader, discussing his long career in venture capital. The conversation covers his relationship with Sequoia's founder, Don Valentine, Leone's approach to identifying promising founders (emphasizing the importance ...

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Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]

25 Feb 2025
1h 1m
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This Invest Like the Best episode features Patrick O'Shaughnessy interviewing Chris Pedregal, founder of Granola, an AI-powered note-taking app. The conversation centers on "tools for thought," exploring how technology has historically enhanced human cognitive abilities and how AI represents the next frontier. Pedreg...

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Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]

18 Feb 2025
59m
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This Invest Like the Best podcast episode features Patrick O'Shaughnessy interviewing Ravi Gupta, a Sequoia Capital partner, about Gupta's essay "AI or Die." The conversation explores the transformative impact of AI on businesses, emphasizing the need for rapid adaptation and agility. Gupta argues that traditional me...

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