Connor Leonard - Capital Light Compounders & Reinvestment Moats - [Invest Like the Best, EP.64]

Connor Leonard - Capital Light Compounders & Reinvestment Moats - [Invest Like the Best, EP.64]

This week’s conversation is an ode to old school, fundamental public market investing. My conversation is with IMC’s Connor Leonard, who spends most waking hours thinking and reading about markets. His mandate is to invest purely as if it was his own money, with no pressure to hug a benchmark, and no pressure to do much of anything other than earn strong long-term returns. The portfolio that results from this approach is highly concentrated and unique. Connor’s strategy is to sort companies into four categories based on their type of sustainable competitive advantage. As you’ll hear, the vast majority fall into the first category, which means they don’t have such an advantage and therefore should be largely set aside. We spend the majority of our conversation talking about the other three categories: 1) companies with a legacy moat, 2) companies with a re-investment moat, and 3) an interesting category Connor calls “capital light compounders,” which we explore in detail. When you step back and think about public markets, you realize how amazing it is that we can, from afar, buy an interest in so many companies around the world. A select few go on to deliver outstanding returns. This conversation highlights how hard that can be, but also how fun and ultimately rewarding. Please enjoy my talk with Connor Leonard. For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Books Referenced Margin of Safety: Risk-Averse Value Investing Strategies for the Thoughtful Investor The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success Links Referenced Pat Dorsey Podcast Episode David Tisch podcast Will Thorndike Podcast episode Show Notes 2:31 - (First Question) – Trends in value investing 2:52 – Margin of Safety: Risk-Averse Value Investing Strategies for the Thoughtful Investor 4:43 – A look at Connor’s backstory and the history of IMC, parent company of Golden Corral 8:01 – Why Connor loves the public markets so much 9:21 – The concept of intrinsic value when looking at companies 12:36 – How Connor categorizes MOATS 13:21 – Pat Dorsey Podcast Episode 14:27 – Legacy MOATS 16:11 – Reinvestment MOATS 17:58 – Capital light compounder MOAT 20:00 – Why classifieds are an interesting business model 25:12 – Looking at platform businesses 26:56 – Looking at companies in the 500 million to 5 billion range and what makes it so enticing 30:34 – What is the process that gets Connor to find investment opportunities 35:53 – David Tisch podcast 36:15 – How Connor looks at industry classifications 41:30 – Connor’s strategy for running his portfolio 46:36 – The circumstances in which Conno would buy a legacy MOAT company 46:49 – Will Thorndike Podcast episode 46:51 – The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success 49:21 – How do you pick managers that will beat the markets 52:21 – Second reason to buy a legacy MOAT 54:48 – Comparing the reinvestment MOAT and Capital A compounder in Connor’s portfolio 58:16 – Connor’s Mt Rushmore of Capital Allocators 1:00:03 – Impactful mentorships for Connor 1:01:52 – kindest thing anyone has done for Connor 103:04 – What in the discussion with founder of IMC got him the job Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

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Sam Hinkie - Find Your People - [Invest Like the Best, REPLAY]

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Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, CLASSICS]

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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...

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Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY]

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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. W...

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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]

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...

26 Elo 20252h 27min

Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]

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 catastrop...

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Peter Lacaillade - Backing The Best Managers In Private Markets - [Invest Like the Best, EP.437]

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 manageme...

12 Elo 20251h 31min

Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]

Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]

My guest today is Andrew Milgram. Andrew is the founder of Marblegate Asset Management, an alternative investment firm that invests in credit opportunities and special situations. He joins me to discu...

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Ramtin Naimi - Building Abstract - [Invest Like the Best, EP.435]

Ramtin Naimi - Building Abstract - [Invest Like the Best, EP.435]

My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's rem...

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