BTC184: Q2 Macro w/ Luke Gromen (Bitcoin Podcast)

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 Found SimpleMining CFI Education The Bitcoin Way Unchained Netsuite Fintool Shopify Onramp Vanta 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! Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

In this episode, Clay explores When Genius Failed by Roger Lowenstein, the gripping story of the rise and fall of Long-Term Capital Management (LTCM).  Founded by Wall Street’s brightest minds, including Nobel Prize-winning economists, LTCM generated astronomical returns using complex mathematical models and extreme leverage—until a financial crisis in 1998 exposed its fatal flaws. Clay also discusses the dangers of overconfidence, the illusion of diversification, and why excessive leverage can be a ticking time bomb.  Additionally, he shares details on an exclusive value investing event hosted by TIP in Big Sky, Montana, in September 2025. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:34 - How John Meriwether and a team of Wall Street’s brightest minds, including Nobel laureates, built a hedge fund that seemed invincible, using sophisticated financial models and extreme leverage. 25:55 - LTCM’s reliance on mathematical models that assumed markets behaved rationally, leading them to underestimate the possibility of extreme events. 48:30 - How the Russian debt default triggered widening credit spreads, exposing LTCM’s overleveraged positions and leading to catastrophic losses. 54:49 - Why LTCM’s failure posed systemic risks to the global financial system, forcing the Fed to coordinate a rescue with major Wall Street banks. 01:08:17 - The dangers of excessive leverage, overconfidence in financial models, and the mistaken belief that markets always revert to historical norms. 01:15:09 - How to attend our new value investing event in Big Sky, Montana, bringing together passionate investors for deep discussions and meaningful connections. And so much more! 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. Lowenstein’s book: When Genius Failed. Mentioned book: Big Mistakes. Related Episode: Listen to TIP514: Permanent Supply Chain Disruptions that Will Destroy the Economy w/ Jim Rickards. Email Shawn at [email protected] to attend our free events in Omaha or visit this page. Follow Clay on X. 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 Found SimpleMining CFI Education The Bitcoin Way Unchained Netsuite Fintool Shopify Onramp Vanta 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

In this episode, Preston Pysh, Jeff Ross, American Hodl, and Joe Carlasare explore the implications of dollar weakness, overall liquidity, and the impact of Bitcoin bonds. They break down SBR, SAB 121, and recent legal updates, while also explaining the Supplemental Leverage Ratio (SLR). They also discuss whether tariffs are truly inflationary, MMT’s consequences, and the shift toward re-privatization. Finally, they cover contrarian buy signals for Bitcoin and QQQ, and the broader outlook for the U.S. economy versus global markets. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:06 - Insights into US government spending and economic dependence in 2024. 07:13 - The debate on tariffs and inflation, with a look at Truflation data. 09:27 - Why the dollar’s weakness matters for global markets and liquidity. 10:22 - The role of Bitcoin bonds and what they signal for the crypto market. 11:05 - Why some analysts are bearish on US assets but bullish on global markets. 11:49 - The fiscal challenges facing the US and how they compare to global trends. 17:44 - How the US economy is shifting from MMT-driven policies toward re-privatization. 29:58 - Updates on SAB 121, SBR, and recent regulatory/legal shifts. 35:16 - What the Supplemental Leverage Ratio (SLR) is and why it’s important for banks. 01:03:01 - Major contrarian buy signals for Bitcoin and QQQ based on technical indicators. Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Related Episode: Bitcoin Mastermind 4th Quarter 2024. American Hodl on Nostr. Jeff Ross on Nostr. Joe Carlasare on  X (Twitter), Nostr. 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? Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Follow our official social media accounts: X (Twitter) | LinkedIn | | Instagram | Facebook | TikTok. Check out our Bitcoin Fundamentals Starter Packs. 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. Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter. 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 Found SimpleMining CFI Education The Bitcoin Way Unchained Netsuite Fintool Shopify Onramp Vanta TurboTax Fundrise Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

In this episode, William Green welcomes back Pico Iyer, one of his all-time favorite guests. Pico is a famed author & speaker whose TED talks have been viewed about 12 million times. Here, he discusses his new book, “Aflame,” which explores how to find peace of mind, happiness & clarity amid extreme uncertainty & accelerating change. This episode is a masterclass on creating a richer, wiser, happier life while living by what Warren Buffett calls an inner scorecard. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 04:31 - How to find calm & clarity in the midst of uncertainty & change. 14:39 - How silence helps to “cleanse” our agitated, cluttered minds.  19:09 - Why Pico Iyer has stayed at a monastery more than 100 times. 28:02 - Why the greatest luxury comes from craving less, not more.  31:53 - How he designs his life to maximize freedom & fulfillment. 35:50 - Why he loves Warren Buffett’s idea of living by an inner scorecard. 52:41 - How the greatest investors remind Pico of monks. 01:10:28 - How to create more spaciousness in your own busy life.  01:18:25 - How to achieve more by doing less & taking time to reflect. 01:23:05 - Why it’s helpful to view investing as a game. 01:51:27 - How Leonard Cohen rebounded after losing almost all his money. 01:51:27 - How to maintain hope—& gratitude—in the face of adversity. 01:57:55 - What Pico has learned from his long friendship with the Dalai Lama. Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Pico Iyer’s website. Pico Iyer's book: Aflame: Learning from Silence. Pico Iyer's books: The Open Road: The Global Journey of the 14th Dalai Lama. Henry David Thoreau's book: Walden. Pico Iyer’s TED talk on The Art of Stillness. William’s 2023 podcast interview with Pico Iyer. William’s podcast interview with Daniel Goleman & Tsoknyi Rinpoche. William’s podcast interview with Brad Stulberg. William Green’s book, “Richer, Wiser, Happier” – read the reviews of this book. Follow William Green on X. Email Shawn at [email protected] to attend our free events in Omaha or visit this page. 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 Found SimpleMining CFI Education The Bitcoin Way Unchained Netsuite Fintool Shopify Onramp Vanta 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 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

On today’s episode, Clay is joined by Cristiano Souza to discuss his three primary criteria in identifying an excellent business. Cristiano Souza is the founder of Zeno Equity Partners, a firm he started in 2022 after spending 28 years at Dynamo. From 1994 through 2015, he was on the team that managed the Dynamo Cougar fund, which invested in high-quality equities in Brazil. During that time, the fund compounded at 24% per year in US dollar terms. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:33 - The three things that Cristiano looks for in a business. 13:43 - What the Founder’s Mindset is, and why it is so difficult to find. 18:53 - Why Cristiano believes that LVMH has a significant opportunity to continue to grow. 33:53 - The mistakes Cristiano has made in assessing management teams. 39:57 - Why Linde PLC is a core position in Christiano’s portfolio. 51:17 - Why AppFolio is well-positioned to continue growing in the property management space. And so much more! Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Cristiano’s firm: Zeno Equity Partners. Book mentioned: Mastery by Robert Greene, The Nvidia Way by Tae Kim. Email Shawn at [email protected] to attend our free events in Omaha or visit this page. Follow Cristiano on LinkedIn. Follow Clay on X. 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 Found SimpleMining CFI Education The Bitcoin Way Unchained Netsuite Fintool Shopify Onramp Vanta 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 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