We Study Billionaires - The Investor’s Podcast Network

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

98 snips
Mar 23, 2025
Guest
Harris Kupperman
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.
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INSIGHT

Macro Success

  • Harris Kupperman prioritizes letting winning trades run while minimizing losses on incorrect trades.
  • His strategy involves low valuations and high-growth targets, aiming for substantial returns when correct.
ADVICE

Balancing Event-Driven and Core Strategies

  • Use event-driven trades to generate cash flow, especially during market volatility.
  • This allows for averaging down on core positions and exploiting special situations.
INSIGHT

Absolute vs. Relative Returns

  • Most hedge funds prioritize smooth returns to attract institutional investors.
  • Harris Kupperman focuses on absolute returns, treating his fund like a personal account.
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