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Invest Like the Best with Patrick O'Shaughnessy

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Invest Like the Best with Patrick O'Shaughnessy
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  • Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, CLASSICS]
    Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Sean Feeney makes you want to be a better person, friend, and leader. Sean is the co-founder of Grove House Hospitality Group and the owner of Lilia and Misi, two of New York City’s most sought-after restaurants. He left his job in Trading to chase down a dream with Michelin star chef Missy Robbins. Sean leveraged his finance background to write his own rulebook for the restaurant industry, crafting several establishments that now boast several thousand people on the waitlist any given night. His story is as entertaining as it is inspiring. As we go step by step through his business endeavors, he points out all of the times he was told “it’s just always been done this way” and how that revealed to him where he could innovate. Sean’s restaurants are the perfect example of building a business into the fabric of a community, collaborating with other brands in authentic ways, and staying true to yourself along the way. Please enjoy this awesome conversation with Sean Feeney.  For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠⁠⁠⁠⁠WorkOS⁠⁠⁠⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠⁠⁠⁠WorkOS.com⁠⁠⁠⁠⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. 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 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 (00:03:58) A Chance Encounter with a Michelin-Starred Chef (00:08:52) The Birth of a Culinary Partnership (00:12:49 Embracing the Genius Within (00:16:41) Innovative Approaches to the Restaurant Business (00:24:53) Creating Demand: The Art of Exclusivity (00:28:49) Learning from the Best: Insights from Kith's Success (00:34:21) Defining Exceptional Hospitality (00:44:20) The Power of Customer Relationships in Hospitality (00:52:31) Unlocking Team Potential  (00:53:33) The Philosophy of the Perfect Turn (00:54:05) Balancing Art, Commerce, and Satisfaction (00:56:13) The Impact of Authentic Experiences and Brands (01:03:24) The Evolution of a Hospitality Brand (01:06:38) Community Engagement and the Power of Simplicity (01:24:40) Creative Responses and Business Lessons Learned (01:36:05) Lessons From Working In The Restaurant Industry  (01:43:01) The Kindest Thing Anyone Has Ever Done For Sean
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  • Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY]
    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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  • Joe Liemandt  - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]
    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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  • Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]
    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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  • Peter Lacaillade - Backing The Best Managers In Private Markets - [Invest Like the Best, EP.437]
    My guest today is Peter Lacaillade. Peter is the Chief Investment Officer for Private Investments at SCS Financial and has built a notable private equity allocation platform within the wealth management industry. He shares his insights on how SCS's pooled vehicle structure has enabled them to compete with institutional giants, avoiding the adverse selection that plagues most wealth platforms. Peter shares his investment philosophy across lower middle market buyouts, emerging independent sponsors, and investing with what he believes to be category-defining managers. We discuss what separates high-quality private equity managers, the evolution of the industry toward AI-powered strategies, and private markets going mainstream. Please enjoy this conversation with Peter Lacaillade. 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. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). -- The views expressed reflect personal views of participants at the time of recording and not necessarily any third party and are subject to change.  The information provided is for informational and illustrative purposes only and does not constitute investment advice or an offer to buy or sell any securities. Assets under management is an estimate that reflects total assets managed and advised on. This recording contains certain forward-looking statements that reflect the participants’ current views. These statements are subject to many risks, uncertainties and factors which may cause future events to be materially different from these statements. Statements that reference past trends or activities should not be taken as a representation that such trends or activities will necessarily continue in the future. The investment strategies and any performance discussed are strictly intended to be for illustrative purposes only and are not meant to be representative of any entire investment program. Investments risk loss of capital and there is no guarantee that an investment will achieve its investment objective. Private investments in particular involve significant risks and are intended for experienced and sophisticated investors. -- Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:31) Advantages of Private Equity Over Public Markets (00:08:59) Talent Acquisition and Growth at SCS (00:10:28) SCS's Wealth Management Strategy (00:12:42) Trends in Private Equity (00:20:14) Challenges and Risks in Private Equity (00:26:06) The State of the Wealth Management Industry (00:35:07) Lower Middle Market Buyouts and Independent Sponsors (00:49:38) Introduction to Long Lake and Its Innovative Approach (00:54:26) The Rise of Holding Companies (00:57:03) Emerging Trends in Venture Capital 01:05:44) The Role of Endowments and Liquidity Solutions (01:10:40) Jake and Frank's Partnership (01:13:57) The Kindest Thing Anyone Has Ever Done For Peter
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    1:30:27

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About 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.joincolossus.com
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