On episode 240 of The Compound and Friends, Downtown Josh Brown and Michael Batnick sit down with Neeraj Khemlani ⁠and⁠ Matt Ankrum to discuss The Coffee Can Investor, the search for 100-bagger stocks, and what it really takes to build generational wealth through long-term investing. Matt shares the investing philosophy behind his concentrated “coffee can” portfolio for his three daughters: 20 stocks, $250,000 each, held with the goal of compounding over decades. The conversation covers the psychology of holding through massive drawdowns, why high-quality companies can outperform with lower volatility, and how investors can improve their odds by eliminating the 96% of companies unlikely to create lasting wealth. They also dig into Charlie Munger’s “invert, always invert” framework, Hendrik Bessembinder’s research on wealth creation in the stock market, the role of AI in disrupting software companies, and why some incumbents may be more resilient than Wall Street thinks. This episode is sponsored by Victory Capital. To learn more about Victory Capital, visit: https://advisor.vcm.com/products-fa/victoryshares-etfs ►00:00 - Cold Open ►04:43 - Intro ►08:03 - The Coffee Can Investor ►12:17 - The Magic of Compounding ►16:38 - The Fastenal Example ►23:18 - Picking 100 Baggers ►41:52 - The Philosophy and Origin Story ►46:19 - The Amazon Example ►52:23 - 100 Baggers from The Study ►59:44 - The Reality of AI's Disruption ►01:16:41 - Motivation for The Next Generation Check out the The Coffee Can Investor at: https://cup.columbia.edu/book/the-coffee-can-investor/9780231563529/ 👕 Check out The Compound shop: https://www.idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.thecompoundnews.com/show/TCAF/ Animal Spirits: https://podcasts.thecompoundnews.com/show/animalspirits/ Ask The Compound: https://podcasts.thecompoundnews.com/show/ATC/ The Compound Newsletter: https://www.thecompoundnews.com/subscribe Linkedin: https://www.linkedin.com/company/the-compound-media/ Instagram: https://instagram.com/thecompoundnews Twitter: https://twitter.com/thecompoundnews Tik Tok: https://www.tiktok.com/@thecompoundnews Investing involves the risk of loss. This podcast is for informational purposes only and should not be or regarded as personalized investment advice or relied upon for investment decisions. Josh Brown and Michael Batnick are employees of Ritholtz Wealth Management and may maintain positions in the securities discussed in this video. All opinions expressed by them are solely their own opinion and do not reflect the opinion of Ritholtz Wealth Management. See our disclosures here: https://ritholtzwealth.com/podcast-youtube-disclosures/ The Compound Media, Incorporated, an affiliate of Ritholtz Wealth Management, receives payment from various entities for advertisements in affiliated podcasts, blogs and emails. Inclusion of such advertisements does not constitute or imply endorsement, sponsorship or recommendation thereof, or any affiliation therewith, by the Content Creator or by Ritholtz Wealth Management or any of its employees. For additional advertisement disclaimers see here https://ritholtzwealth.com/advertising-disclaimers. #Investing #StockMarket #TheCompoundAndFriends