Invest Like the Best with Patrick O'Shaughnessy

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
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Resumen del episodio

My guest today is Christina Cacioppo, founder and CEO of Vanta, which helps more than 16,000 companies manage security and compliance. Five years after our first conversation, we discuss how Vanta became a category leader, what it takes to reinvent a successful software business in the age of AI, and why Christina is betting on agents to do the work rather than simply assist users. We also explore the changing economics of software, the war for exceptional talent, AI's impact on cybersecurity, and what it takes to build an enduring company in Silicon Valley's rapidly changing environment. Please enjoy my conversation with Christina Cacioppo. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a…

Episodios

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Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]

My guest today is Christina Cacioppo, founder and CEO of Vanta, which helps more than 16,000 companies manage security and compliance. Five years after our first conversation, we discuss how Vanta became a category leader, what it takes to reinvent a successful software business in the age of AI, and why Christina is betting on agents to do the work rather than simply assist users. We also explore the changing economics of software, the war for exceptional talent, AI's impact on cybersecurity, and what it takes to build an enduring company in Silicon Valley's rapidly changing environment. Please enjoy my conversation with Christina Cacioppo. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a…

20 oct. 2026
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David Vélez - Building Nubank and the Future of Global Banking - [Invest Like the Best, EP.495]

David Vélez is the founder and CEO of Nubank, which serves 140 million customers across Latin America. David believes the industry is still in its Blockbuster era, with most of the world's banking still running through branches and incumbent banks, and that AI will make digital banks dramatically more efficient than the incumbents they compete with. He explains how Nubank rebuilt its entire organization around AI after missing the moment the technology started working, and why he is now bringing Nubank to the US, a market he says is still dominated by big incumbent banks. Please enjoy my conversation with David Vélez. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses…

13 oct. 2026
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Andrew Huberman - The Frontier of Neurotechnology - [Invest Like the Best, EP.494]

Andrew Huberman is a neuroscientist and professor at Stanford, the host of the Huberman Lab podcast, and the author of Protocols. Most of our conversation is about where neuroscience goes next. For decades the field has focused on reading from the brain, and Andrew believes the next era is about writing to it with precise control over specific brain states. He explains why he thinks the leading AI companies are really building toward this, and why understanding our waking brain states is the problem he most wants to see solved. Please enjoy my conversation with Andrew Huberman. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time…

06 oct. 2026
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Noah Shinn - Building Instinct: The Personal Agent - [Invest Like the Best, EP.493]

My guest today is Noah Shinn. Noah is the founder of Instinct, a personal assistant that you text, call, or email the same way you would a person. It has its own phone and its own computer, and it can do almost anything on your behalf that you would do yourself online. Instinct is about a year old, still invite-only, and growing roughly 10% day over day without any marketing spend. We discuss the surprising ways people are already using Instinct, the trusted network that lets two people's agents coordinate directly, and what Noah has learned about how long it takes users to trust an agent with their credit card, inbox, and calendar. He explains why he refuses to build an ad model and why he believes a personal agent should never influence users against their own interests. We also cover the take rate model behind the more than $1 billion a year now flowing through the platform, how travel and food delivery businesses should prepare for a world of agents, why he spends 40% of his time thinking about compute,…

28 sep. 2026
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Gabe Stengel - Building Investing Superintelligence - [Invest Like the Best, EP.492]

Gabe Stengel is the co-founder and CEO of Rogo, the AI platform for finance. He believes the best investors will spend the next several years reinventing their firms around AI, and Rogo is trying to build the infrastructure that allows them to do it. We discuss how Rogo evolved alongside the frontier models, why the last mile and the harness around the models matter so much, what happens when every portfolio manager can deploy thousands of agents against a problem, and how AI could transform the way capital is raised, assets are priced, and deals get done. We also cover which investing skills become more valuable as AI improves, the move from seat-based to outcome-based pricing, Rogo’s internal company brain called Shrek, the 40 investor rejections Gabe received before his Series A, why building in applied AI requires extraordinary aggression, and what it takes to become a black hole for talent and capital. Please enjoy my conversation with Gabe Stengel. For the full show notes, transcript, and links to…

22 sep. 2026