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Invest Like the Best with Patrick O'Shaughnessy

Invest Like the Best with Patrick O'Shaughnessy

De: 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.joincolossus.com Economía Finanzas Personales
Episodios
  • Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY]

    Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY]
    Sep 2 2025
    Today we are replaying my conversation with Justin Ishbia. Justin is the Founding Partner of Shore Capital. Shore is a private equity firm that invests in microcap businesses within industry niches. With $7 billion in capital deployed but an average transaction size of just $12 million, Justin has worked to build a system to drive success for hundreds of businesses through replicable operating procedures and championing young professionals. The firm has created a moat around volume with nearly 600 acquisitions over the last three years, some of the highest numbers in the world. We discuss identifying growth prospects, constructing a meaningful board, and the business mentality behind main street, not wall street, as Justin puts it. Please enjoy my conversation with Justin Ishbia. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes: (00:00:00) Welcome to Invest Like the Best (00:03:07) The Role of Early Career Energy in the System (00:07:47) The Importance of Being Thematic and Process-Driven (00:08:25) The Journey of Building a Business (00:09:50) The Perfect Shore Capital Deal (00:15:44) Building Competitive Advantage through Volume (00:19:02) The Role of Board Members in Investment Success (00:25:10) Choosing Industrial Subsectors Over Software (00:29:37) Identifying Industry Leaders (00:34:15) The Process of Identifying Potential Investments (00:37:35) The Impact of Business Consolidation on Reputation (00:46:33) Exploring the Concept of Unfair Advantages (00:51:03) Building Platforms, Not Buying Them (00:52:16) The Power of Operations and Knowledge Sharing (00:57:36) The Excitement of Sports Franchise Ownership (01:09:48) The Kindest Thing Anyone Has Ever Done For Justin
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    1 h y 14 m
  • Joe Liemandt - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]

    Joe Liemandt - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]
    Aug 26 2025
    My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital. He became the youngest member of the Forbes 400 in the 1990s before vanishing from public view for two decades—only to emerge with a $1 billion bet that he can make kids learn 10x faster using AI. Joe has built an AI tutoring system so effective that students at his Alpha School literally beg not to take summer breaks, achieving 2x learning outcomes in just 2 hours with standardized test results that compete with the best of them. We dive deep into why this could be the most valuable product he's ever built, his contrarian thesis that traditional SaaS is facing AI-driven obsolescence, and how his experience buying 100+ software companies prepared him for this moonshot in a trillion-dollar market that hasn't innovated in 200 years. For investors, this is a masterclass in deploying patient capital to rebuild broken systems from first principles, with insights on everything from regulatory moats to the intersection of AI and human psychology. As your excited skeptic, I push hard on the technology readiness, parental adoption hurdles, and whether this audacious vision can actually scale to a billion kids. Additionally, in a Colossus Profile released last week, our editor-in-chief Jeremy Stern reported, for the first time, Joe as the product guy behind Alpha School in a can’t miss piece of writing. And now please enjoy my conversation with Joe Liemandt. Joe Liemandt’s Colossus Profile by Jeremy Stern. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best(00:06:08) How Alpha School Is Revolutionizing Learning(00:12:47) Personalized Tutoring with AI(00:19:59) Measuring the Impossible: 2x Learning Outcomes(00:25:39) All Educational Content Is Obsolete(00:35:51) Motivating Students: The Key to Success(00:42:06) Life Skills Workshops: Real-World Lessons(00:47:47) The Key to Happiness: High Standards(00:52:33) The Role of Guides and Coaches(00:58:22) Feedback Loops and AI in Education(01:04:20) The AI-Powered Classroom Experience(01:18:06) From Self-Doubt to Limitless Learning(01:28:20) Challenges in Public School Systems(01:41:56) Gamified Learning and Technology(01:49:46) From Trilogy to Trillion-Dollar Markets(01:55:05) Why Software Companies Fail(02:01:21) Trilogy University(02:10:39) Lessons from Mentors(02:17:25) Pushing Limits and Finding Passion(02:27:12) Joe's Kindest Thing
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    2 h y 27 m
  • Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]

    Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]
    Aug 19 2025
    My guest today is Mark Bertolini. Mark is the former CEO of Aetna and the current CEO of Oscar Health. He shares one of the most extraordinary leadership stories I've encountered—surviving a catastrophic skiing accident that left him in chronic pain for 18 years while simultaneously leading one of healthcare's most successful corporate turnarounds. His personal experience navigating his son's life-threatening cancer battle and his own medical challenges fundamentally changed his approach to healthcare, leading to innovations in employee welfare that Wall Street initially questioned but ultimately celebrated. During his tenure at Aetna, Mark generated 652% total shareholder return by implementing revolutionary employee policies and is now applying these lessons at Oscar Health to disrupt the $4 trillion healthcare industry with a technology-first approach. We discuss the power of servant leadership, employer-sponsored insurance vs individual choice-based plans, and the horizons of healthcare. Please enjoy this incredible conversation with Mark Bertolini. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:52) Mark's Ski Accident and Recovery (00:07:54) Early Life and Career Beginnings (00:12:51) Leadership Philosophy and Career Highlights (00:19:03) Healthcare System Insights and Innovations (00:25:31) Oscar Health: Current State and Future Vision (00:42:06) Personal Stories and Eastern Belief System (00:51:57) Discovering the Healing Power of Yoga (00:57:21) Transforming Employee Benefits and Wages (01:02:41) Personal Journey Through Chronic Pain (01:08:10) Reflections on Business Success and Leadership (01:15:54) Joining Bridgewater and Transitioning Leadership (01:22:47) Leading Oscar Health and Future Goals (01:34:12) Enduring Hardships and Finding Purpose (01:32:34) The Kindest Thing Anyone Has Ever Done For Mark
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    1 h y 38 m

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Featured Article The Best Investing Podcasts to Help You Build Your Portfolio
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