TIP708: Why Wall Street’s Playbook Is Broken w/ Harris Kupperman

This podcast interviews Harris Kupperman, founder of Praetorian Capital, about his unique investment strategy. The conversation covers his approach of concentrated bets on macro inflections, balancing short-term event-driven trades with long-term core positions, and his focus on absolute rather than relative returns. Kupperman emphasizes the importance of managing downside risk and letting winners run, illustrating his strategy with examples in hard assets and cyclical industries. He also discusses his preference for asset-rich companies benefiting from inflation and his approach to portfolio concentration and capital allocation. Listeners gain insights into an unconventional, high-return investment strategy focused on identifying and capitalizing on market inefficiencies.