Episode
The Last Moat | Chris Mayer and Ian Cassel on the Stock Picking Edge AI Can’t Replicate
- Podcast
- Excess Returns
- Published
- May 6, 2026
- Duration seconds
- 4606
- Processing state
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Summary
This episode of our new show The 100 Year Thinkers brings together Chris Mayer and Ian Cassel for a deep discussion on long-term stock picking, microcap investing, business quality, AI disruption, management teams, and the behavioral skills that separate great investors from great analysts. They explore why the edge in investing may increasingly come from judgment, presence, relationships, patience, and the ability to hold the right businesses through uncertainty. Subscribe to the 100 Year Thinkers on Spotify Subscribe to the 100 Year Thinkers on Apple Topics Covered Why being present with management teams may still be an investor edge in the age of AI How microcap investing differs from small-cap, mid-cap and large-cap investing Why talking to management can build conviction but also create bias How Chris Mayer thinks about vertical market software, mission-critical systems and AI disruption Why AI may become table stakes rather than a durable competitive advantage How small companies can use AI to improve workflows, sales, inventory and productivity Why many microcaps have short shelf lives and rarely become true long-term compounders The role of intelligent fanatics, owner-operators and repeat winners in great investments Why management transitions can create powerful microcap opportunities The difference between being a great analyst and being a great investor Why execution, position sizing, selling losers and holding winners matter more than hit rate How Matt and Bogumil apply the lessons to AI, business quality and the limits of small business scalability Timestamps 00:49 Introducing Chris Mayer, Ian Cassel and 100 Year Thinkers 04:59 Ian Cassel’s first management meeting and XM Satellite Radio 09:00 Why management meetings deepen understanding but can also m…