We Study Billionaires - The Investor’s Podcast Network
TIP708: Why Wall Street’s Playbook Is Broken w/ Harris Kupperman
Mar 23, 2025
In a captivating discussion, Harris Kupperman, founder and CIO of Praetorian Capital Management, shares his investment strategies shaped by macro trends and events. He reveals the secrets to effective macro investing and the importance of solid capital allocation. Kupperman argues against overhyped stocks while advocating for asset-heavy investments during inflation. He underscores the value of patience and adaptability in an ever-changing market, and explores the pros and cons of hedging as a strategy. This conversation is a goldmine for investors eager to rethink traditional approaches.
01:19:13
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Quick takeaways
- Harris Kupperman's investment strategy revolves around macroeconomic trends and event-driven opportunities, particularly focusing on undervalued hard assets like shipping and real estate.
- He emphasizes the importance of making concentrated bets on high-conviction trades while prioritizing absolute returns over relative performance metrics to maximize profits.
Deep dives
Unique Investing Philosophy
Harris Kupperman adopts a distinctive investment strategy that combines macroeconomic trends with event-driven opportunities. His focus is on hard assets and asset-rich businesses, which he believes are undervalued by the market, particularly as inflation drives up replacement costs. This approach contrasts with many investors who favor capital-light businesses. By investing in industries like shipping, energy, and real estate, he capitalizes on limited supply and strong cash flows, positioning himself for significant returns.
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