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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Kyle is joined by the Founder and Chief Investment Officer of Praetorian Capital Management LLC, Harris Kupperman. Here, they discuss Harris’ investing strategy based on concentrated macro and events bets.

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