Kyle Grieve speaks with Harris Kupperman about his concentrated investing strategy and the challenges investors face in navigating markets. Harris Kupperman is the founder and CIO of Praetorian Capital and author of Kuppy’s Korner. He’s also Chairman and CEO of Mongolia Growth Group. What you’ll learn here: 00:00:00 - Intro 00:01:03 - Unlocking macro investing secrets that actually work in real markets 00:14:57 - How Harris shifts between strategies based on market conditions 00:19:13 - Why cutting low-conviction positions can unlock capital for bigger winners 00:28:53 - The hidden advantage of focusing on absolute returns over benchmarks 01:06:35 - The case for moving fast when investing in inflection point businesses 00:28:52 - How averaging up in commodity cycles can multiply your returns 00:34:40 - Why Harris believes many MAG-20 stocks aren’t worth the hype 00:46:51 - Why asset-heavy businesses still hold massive value in today’s economy 00:57:53 - Why stubbornness and patience are key to real investing success 01:01:36 - Hedging: A smart risk strategy or just a waste of returns? 01:12:22 - Outro Transcript & Guest Info: https://www.theinvestorspodcast.com/we-study-billionaires/ Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here: https://www.theinvestorspodcast.com/summit/ Join our highly vetted community of value investors: https://www.theinvestorspodcast.com/mastermind/ Our Sponsors: 📊 Add the Fundrise Flagship Fund to your portfolio in just minutes and with as little as $10. http://fundrise.com/wsb ✍️ Get your paper tablet at reMarkable.com today. https://remarkable.com/?utm_source=podcast&utm_medium=paid&utm_campaign=westudybillionaires|remarkableaudio2025&utm_term=a&utm_content=marchread ▶️ Related Episodes: - Current Market Conditions & Poor Charlie's Almanack w/ Stig Brodersen & Clay Finck: https://youtu.be/e1Q-QiQyFNA - How To Hedge Against Inflation w/ Nancy Davis: https://youtu.be/MIlVlUxu6m8 - Macro Investing | Understanding How And Why w/ Cullen Roche: https://youtu.be/BnYibUdBTxE Listen to our episodes here: https://open.spotify.com/show/28RHOkXkuHuotUrkCdvlOP Visit our website: https://www.theinvestorspodcast.com/we-study-billionaires/ Free PDF: Investing for Beginners: 4 Principles of Stock-Picking: https://www.theinvestorspodcast.com/subscribe-youtube/ ⚠️ Disclaimer: This show is for entertainment purposes only. Before making any decisions consult a professional. This show is copyrighted by The Investor’s Podcast Network. Written permission must be granted before syndication or rebroadcasting. #HarrisKupperman #InvestingStrategy #CommodityCycles #PraetorianCapital #Kuppy’sKorner