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

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. BOOKS AND RESOURCES Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here. Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Read Harris' articles here. Follow Kyle on Twitter and LinkedIn. Check out all the books mentioned and discussed in our podcast episodes here. Enjoy ad-free episodes when you subscribe to our Premium Feed. NEW TO THE SHOW? Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter. Check out our We Study Billionaires Starter Packs. Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Learn how to better start, manage, and grow your business with the best business podcasts. SPONSORS Support our free podcast by supporting our sponsors: Hardblock SimpleMining CFI Education Netsuite Vanta Found The Bitcoin Way Shopify Fintool Unchained Onramp TurboTax Fundrise HELP US OUT! Help us reach new listeners by leaving us a rating and review on Spotify! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm