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

We Study Billionaires - The Investor’s Podcast Network

On today’s episode, Kyle Grieve chats with Harris Kupperman about his investing strategy based around concentrated bets on macro and events. Harris has decades of market experience and shares his thoughts on why investors have so much difficulty navigating the markets.

Harris Kupperman is Praetorian Capital Management LLC's founder and chief investment officer. He focuses on inflecting trends and event-driven strategies. He’s also the author of Kuppy’s Korner, a widely followed investment blog. In addition to his investing work, he serves as Chairman and CEO of Mongolia Growth Group, giving him firsthand experience as an operator.

IN THIS EPISODE YOU’LL LEARN:

00:00 - Intro

02:57 - Unlocking macro investing secrets that actually work in real markets

15:58 - How Harris shifts between strategies based on market conditions

19:58 - Why cutting low-conviction positions can unlock capital for bigger winners

25:35 - The hidden advantage of focusing on absolute returns over benchmarks

28:18 How averaging up in commodity cycles can multiply your returns

31:13 - Why Harris believes many MAG-20 stocks aren’t worth the hype

42:38 - Why asset-heavy businesses still hold massive value in today’s economy

53:13 - Why stubbornness and patience are key to real investing success

56:54 - Hedging: A smart risk strategy or just a waste of returns?

1:01:32 - The case for moving fast when investing in inflection point businesses

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

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