AI, Automation & the Doorman Fallacy

What kind of money are we talking about? The why behind the holdings? A podcast production secret --- and so much more! Enjoy!

In this third edition of Unfiltered, I talk about the one question I always start with when someone entrusts me with their capital, what multi-generational wealth really means (and why it's a mindset, not a number), the expensive truth about cheap stocks, why I came for the puzzle but stayed for the people, how AI is reshaping the advisory world — and the doorman fallacy that should make us all pause before we automate too much. I also share what I've been obsessing about lately, from Wittgenstein's family story to the art of giving, and I let you in on a little secret about what happened recently after I stopped a certain recording.

Highlights:

• “What kind of money are we talking about?” — The most important question in investing isn’t about returns or risk tolerance. It’s understanding the story behind the capital — how it was accumulated, what it means emotionally, and what losing or growing it would feel like. Context shapes everything.

• Multi-generational wealth is a mindset, not an amount. A family with $100K who thinks about legacy and stewardship has a multi-generational fortune. A family with billions who doesn’t think beyond their own lifetime does not. More families than ever are entering this mindset.

• “I came for the puzzle, but I stayed for the people.” The intellectual challenge of investing draw me in, but the human dimension — serving families across generations, building something cathedral-like brick by brick — is what keeps me going.

• The expensive truth about cheap stocks. Frugal savers are drawn to what looks cheap, but cheap stocks can create more trouble than seemingly expensive businesses with long runways. Quality is like a 30-year-old Toyota still on the road — it wasn’t the cheapest, but it outlasted everything.

• The doorman fallacy and AI. Borrowed from Rory Sutherland’s doorman analogy — replacing human roles with automation by reducing them to their most visible function misses the invisible value. Applies to advisory work, customer service, and anywhere human presence matters.

• Families who rebuild vs. families who build for the first time. First-generation wealth builders are in foreign territory. Families rebuilding after loss are returning to something remembered. Both are powerful, but the relationship with wealth is fundamentally different.

• Playing the long game means playing forever. Don’t think about how quickly you can win — think about how long you can continue to play. If you can play forever, you can’t really lose unless you stop.

• Truly hearing someone vs. just listening. It’s not improv — it’s a deeper presence where you catch the subtle nuance, the pause, the word choice, and steer the conversation toward what matters.

• The post-recording revelation. Some of the best moments happen after you stop recording. Staying the extra five minutes with a guest can yield the “cherry on the cake” that makes the whole episode come together.

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.