How to Start a Classifieds Business

The business model of classifieds is that it's essentially a winner take all type dynamic why wouldn't you sell your couch on Craigslist that's where the most eyeballs are. The dominant classifieds business will have three four five up to twenty x the market share of the number two and there's a company out there shibstead in Sweden that's one of the premier owners and operators of classified businesses in the world. Once they've built up that liquidity and you've built up the network it's almost impenetrable.

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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.

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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