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Invest Like the Best with Patrick O'Shaughnessy

Invest Like the Best with Patrick O'Shaughnessy

By: Colossus | Investing & Business Podcasts
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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 Economics Personal Finance
Episodes
  • Mitchell Green - Lessons from Cold Calling 10,000 Companies - [Invest Like the Best, EP.464]

    Mitchell Green - Lessons from Cold Calling 10,000 Companies - [Invest Like the Best, EP.464]
    Mar 24 2026
    My guest today is Mitchell Green. Mitchell Green is the co-founder and managing partner of Lead Edge Capital, a growth equity firm that has spent 15 years building one of the most disciplined investment machines in the business. Unlike most firms chasing power law outcomes, Lead Edge is designed to deliver consistent returns by talking to thousands of companies a year, applying a rigorous eight-point criteria to filter down to a handful of investments, and leveraging a uniquely constructed LP base of world-class executives and entrepreneurs. In this conversation, Mitchell walks through every component of the machine, from how they source and evaluate companies to how they think about selling, building culture, and staying competitive in a world being reshaped by AI. 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 for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:00:53) Episode Intro: Mitchell Green (00:02:01) Cold Calling 10,000 Companies (00:03:54) Building the Lead Edge Machine (00:06:15) Lead Edge’s LP Profile (00:09:22) Hitting Doubles and Triples (00:11:39) Knowing When to Sell (00:15:08) Lead Edge’s Eight Buying Criteria (00:18:12) The Opportunity in Enterprise Software (00:24:54) Using Criteria for Filtering, Not Prediction (00:27:11) Building Relationships with Entrepreneurs (00:29:16) Improving the Investment Machine at Scale (00:31:59) Lead Edge’s Culture (00:35:08) Mitchell’s Schedule (00:36:37) The Mount Rushmore of Investment Machines (00:38:40) The AI Readiness Score (00:40:50) Overhyped, Frothy Markets (00:42:16 When AI Will be a Good Opportunity (00:44:29) Lessons from Competitive Skiing (00:47:33) Starting a Fund & Keeping Score (00:49:15) The Kindest Thing
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    54 mins
  • William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

    William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]
    Mar 17 2026
    William Hockey is the co-founder of Plaid and the founder and CEO of Column, a software company that owns a bank and powers Ramp, Wise, Bilt, Mercury, and others. He funded Column by borrowing against his Plaid shares and has never raised outside capital. William talks about what owning 100% of his company allows him to do that other venture-backed founder cannot and the personal risk he took to do so. He shares how Silicon Valley's consensus culture produces consensus founders, and why becoming a founder has become too safe. He believes the best builders are specialists and explains with unusual clarity what it takes to become the best in the world at one specific thing. William also spends a lot of time in emerging markets which has given him a unique perspective of the power of the US dollar. 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 for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: William Hockey (00:03:49) Column: A Software Company That Owns a Bank (00:06:46) Finding Ideas in Emerging Markets (00:11:58) Why Constrained Societies Are More Innovative (00:16:02) What’s Wrong With Silicon Valley (00:19:28) Building a Business Without Raising Money (00:22:48) What Venture-Backed Companies Can't Do (00:28:39) Getting Margin Called (00:31:41) Starting Companies Has Become Too Safe (00:34:23) Why Employees Take More Risks Than Founders (00:37:09) A Maniacal Commitment to Research (00:39:09) Finding Boring Problems to Solve (00:41:45) Why Building a Second Company is Easier (00:42:36) Missionary vs. Mercenary (00:45:49) Funding a Company with Cash Flows (00:50:04) Perspective on the Venture Ecosystem (00:52:48) The Dominance of the US Dollar (00:58:37) The Future of Financial Services (01:02:06) Why Big, Inefficient Brands Win From AI (01:06:29) The Opportunity for Non-Consensus Founders (01:08:03) The Kindest Thing
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    1 hr and 11 mins
  • Shyam Sankar - Celebrating Heretics - [Invest Like the Best, EP.462]

    Shyam Sankar - Celebrating Heretics - [Invest Like the Best, EP.462]
    Mar 10 2026
    My guest today is Shyam Sankar, the CTO of Palantir Technologies. In this conversation, we explore the ideas that shape how Shyam thinks about technology, talent, and national power. We discuss the origins of Palantir’s forward-deployed engineering model and the lessons he learned from Alex Karp about identifying people's "superpowers". We also talk about Shyam’s fascination with the "heretics" of American history, the unconventional builders who challenged bureaucracy and created many of the systems that powered America’s military and industrial success. Shyam argues that the United States must reindustrialize after decades of moving production overseas, and explains what we can learn from America’s industrial past. In a new Colossus profile, our Editor in Chief Jeremy Stern tells the story of how Shyam became one of the most important but largely unseen figures behind Palantir, tracing his journey from immigrant roots to employee #13 and the architect of the company's success and distinctive culture. 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 for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit⁠ rogo.ai/invest⁠. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: Shyam Sankar (00:03:24) Defining Heretics in US Military History (00:05:01) The Story of Hyman Rickover (00:09:55) Formative Experiences & Worldview (00:14:50) Components of American Greatness (00:17:56) How to Unlock Talent (00:25:56) Palantir's Distinct Culture (00:28:15) Origin of Forward Deployed Engineering (00:34:24) What Does Palantir Actually Do? (00:36:19) Example: Airbus (00:40:20) State of the US Military Today (00:47:33) The U.S. Needs to Reindustrialize (00:52:19) Perspective of China (00:55:56) Our Key Asymmetric Advantages (01:00:57) Executive Orders for a Day (01:02:37) Negative Aspects of US Culture (01:04:47) Managing Rapid Pivots (01:09:17) Where Will AI Value Accrue? (01:12:37) Undeclared State of Emergency (01:15:45) Surprising Aspects of Palantir (01:17:50) To Do or To Be (01:18:50) Reflecting on Fatherhood (01:19:46) The Kindest Thing
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    1 hr and 22 mins

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