The 100 Year Thinkers: Long-Term Compounding in a Short-Term World

The Last Moat | Chris Mayer and Ian Cassel on the Stock Picking Edge AI Can’t Replicate

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May 4, 2026

Chris Mayer, long-term investor and author focused on business quality, and Ian Cassel, microcap specialist and founder of MicrocapClub, discuss stock picking in the age of AI. They explore why meeting management and owner-operators matters, how microcaps differ, AI as table stakes not a moat, and why conviction, position sizing, and holding winners define the investor edge.

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ANECDOTE

How A College Meeting Sparked A Microcap Career

Ian Cassel’s first management meeting was with XM Satellite Radio when he was a college sophomore and he bought shares at $1.78 before it rallied to $34 over 14 months.
The experience hooked him on microcaps because a 20-year-old could sit across from a CEO and feel like they gained meaningful insight by being present in person.

INSIGHT

Management Meetings Build Conviction Not Secrets

Talking to management deepens your understanding of how a business actually operates and makes it easier to hold through downturns.
Chris Mayer: management meetings rarely reveal secrets; they mainly teach operational details that build conviction to stay invested when tested.

INSIGHT

Vertical Market Software Holds A Different Risk Profile

Vertical market software tied to mission-critical systems is more defensible against AI disruption because it holds systems of record and industry-specific data.
Chris Mayer still saw large drawdowns but expects the market to sort winners from losers as investors separate horizontal from vertical software.

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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.

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-Odyssey-Resisting-Sirens-Playing/dp/B0GJ3G6F2S

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

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 mislead
14:32 Chris Mayer on the real edge in long-term investing
18:40 Mission-critical software, systems of record and AI disruption
22:45 How microcap companies are using AI in real businesses
27:02 AI as table stakes and when disruption creates opportunity
31:29 Why most microcaps have short shelf lives
35:51 Finding Tom Brady before the market knows he is Tom Brady
40:53 Why owner-operators and intelligent fanatics matter
45:03 Second-in-command leaders, repeat winners and chips on shoulders
49:27 Analyst vs investor and the missing skills of stock picking
54:00 Using data to identify investor strengths, weaknesses and decision errors
58:14 Position sizing and letting small positions earn the right to grow
01:03:00 Peter Lynch, stocks as businesses and learning to think like an owner
01:07:00 AI, human judgment and the limits of automation
01:11:00 Why not every small business can become the next Facebook
01:15:00 Where to follow Bogumil and the 100 Year Thinkers series