Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcasts
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491 snips
Nov 4, 2025 • 1h 21min

Luca Ferrari - Building Bending Spoons - [Invest Like the Best, EP.446]

Luca Ferrari, co-founder and CEO of Bending Spoons, shares insights from his tech and private equity model. He dives into their acquisition strategies and how they rebuild companies like Evernote. Luca discusses the challenges of operating in Europe, emphasizing the importance of local talent. His obsession with excellence drives Bending Spoons' culture, while a commitment to unique employer branding sets them apart. The conversation also touches on leveraging AI for efficiency and the importance of long-term investor relationships.
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674 snips
Oct 31, 2025 • 1h 8min

Kevin Kelly - Be Generous and Unique - [Invest Like the Best, CLASSICS]

Kevin Kelly, a renowned writer and co-founder of Wired magazine, dives into the importance of embracing uniqueness and generosity. He discusses the idea of defining personal success rather than imitating others, the necessity of prototyping one's life, and how mastery can lead to authenticity. Kelly emphasizes that money should be seen as a tool rather than a goal and shares how imagination can be cultivated. He also reflects on the role of family rituals in strengthening identity and marriage, creating a rich tapestry of insights for living fully.
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41 snips
Oct 30, 2025 • 49min

Ken Langone - The American Dream - [Invest Like the Best, REPLAY]

Ken Langone, a seasoned businessman and co-founder of Home Depot, shares his extraordinary journey and thoughts on loyalty, culture, and leadership. He recounts his early work with Ross Perot, highlighting the value of trust and integrity in negotiations. Ken emphasizes the importance of prioritizing employees in company culture and discusses how Home Depot’s unique upside-down hierarchy fosters loyalty and success. He also reflects on the essence of capitalism in creating opportunities, demonstrating that people are the key to investment success.
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633 snips
Oct 21, 2025 • 1h 45min

Karim Atiyeh - Building Ramp - [Invest Like the Best, EP.445]

Karim Atiyeh, Co-founder and CTO of Ramp, shares his innovative approach to finance automation, emphasizing 'self-driving finance' through AI agents. He discusses how these agents automate expenses and enhance policy context with ongoing improvements. Karim elaborates on his 'divinely discontent' philosophy, focusing on long-term impact while maintaining a startup-like agility. He also touches on the advantages of consumer-grade UX over competitors and the crucial role of technical founders in transforming industries. Dive into his journey from engineering pragmatism to building a groundbreaking finance platform.
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676 snips
Oct 16, 2025 • 1h 35min

Dan Wang - The US vs China In The 21st Century - [Invest Like the Best, EP.444]

In this discussion, technology analyst Dan Wang, an authority on U.S.–China dynamics and author of *Breakneck*, shares insights from his six years in China. He reveals the stark realities of U.S. manufacturing versus China’s rapid innovation, emphasizing that the latter’s societal structure allows for swift execution of large-scale projects. Dan also addresses the 'ByteDance problem,' explaining why Chinese firms are undervalued in global markets due to political risks. Throughout, he explores the cultural and operational differences that define both superpowers.
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381 snips
Oct 6, 2025 • 1h 21min

Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]

Jesse Zhang, co-founder and CEO of Decagon, delves into the world of AI customer service. He discusses the importance of understanding customer willingness to pay, revealing insights that shaped Decagon's direction. The conversation highlights the intense competition in AI, the need for continuous improvement loops in product development, and the critical nature of data as a competitive edge. Jesse also shares his thoughts on the dynamics of fundraising in the AI space and the importance of hiring the right talent in a competitive market.
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2,288 snips
Sep 30, 2025 • 1h 58min

Dylan Patel - Inside the Trillion-Dollar AI Buildout - [Invest Like the Best, EP.442]

In this discussion, Dylan Patel, founder and CEO of SemiAnalysis, dives into the intricacies of the semiconductor supply chain and AI infrastructure. He analyzes the interconnected strategies among OpenAI, Nvidia, and Oracle, highlighting how compute capacity drives their deals. Dylan shares insights on current high-value AI applications, the significance of reinforcement learning, and the implications of supply chain bottlenecks. He also contrasts US and Chinese approaches to AI, offering a comprehensive view of the industry's landscape and future opportunities.
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436 snips
Sep 26, 2025 • 1h 3min

Rolex: Timeless Excellence - (Invest Like the Best, CLASSICS)

In this engaging discussion, Ben Clymer, founder of Hodinkee and luxury watch expert, shares his passion for Rolex, especially the iconic Daytona. He dives into the watch's motorsport roots and sentimental value. Ben explains the shifting dynamics of the luxury watch market, including Rolex's strategic focus and manufacturing innovations. He also unpacks the impacts of rarity and distribution on customer experiences. Listeners will gain insights into Rolex's meticulous craftsmanship and the brand's enduring legacy in horology.
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382 snips
Sep 23, 2025 • 54min

Barry Diller - Building An Entertainment Empire - [Invest Like the Best, EP.441]

Barry Diller, a veteran media executive and founder of IAC, dives into his transformative career that shaped modern entertainment. He shares his 'creative conflict' philosophy, emphasizing the power of pushing boundaries for innovation. Diller recounts engaging tales of collaboration with icons like Rupert Murdoch and Bill Gates, discusses the risks behind pioneering the Movie of the Week, and explores how personal struggles can empower professional success. Get insights into his experience with 150 internet deals and his current media portfolio strategies.
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1,043 snips
Sep 16, 2025 • 1h 31min

Jeff Horing - Building Insight Partners - [Invest Like the Best, EP.440]

Jeff Horing, Cofounder and Managing Director of Insight Partners, dives into the inner workings of one of the largest tech investment firms with over $100 billion in assets. He shares insights on their unique sourcing strategy involving 60-80 global analysts and the advantages of a contrarian ‘one fund’ approach. Horing discusses the evolution of investment strategies, the transformative role of AI in accelerating growth, and the importance of strong relationships with founders. This conversation offers a fascinating glimpse into the world of tech investing and mentorship.

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