Software and AI: which moats survive?

This episode of 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.

Matt Zeigler and I had the privilege of hosting Ian Cassel and Chris Mayer for a special 100-Year Thinkers Edition of the Excess Returns Podcast.

Available now on Excess Returns Podcast and Talking Billions. 🎧

I’m excited to share this episode with you—it’s reposted here with permission and blessing from the Excess Returns team. Don’t miss it! And follow their work, links below.
Resources Discussed
The Last Moat
https://microcapclub.com/the-last-moat/
Stock Picker by Ian Cassel
https://microcapclub.com/stock-picker/
The Investor’s Odyssey by Chris Mayer
https://www.amazon.com/Investors-Odys...
Follow Chris Mayer on Twitter
https://x.com/chriswmayer
Follow Ian Cassel on Twitter
https://x.com/iancassel
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

Podcast Program – Disclosure Statement

Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.

Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.

Information expressed does not take into account your specific situation or objectives, and is not intended as recommendations appropriate for any individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment adviser to determine whether any information presented may be suitable for their specific situation. Past performance is not indicative of future performance.