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You are here: Home / Podcast / 555: Five Practices That Have Shaped My Career

555: Five Practices That Have Shaped My Career

April 29, 2026 by David Stein · Updated May 7, 2026

I share five business practices that have carried me through internet bubbles, financial crises, business pivots, and now the rise of AI.

Building mare of square sections with the caption "Five Practices"

Show Notes

Researchers Asked LLMs for Strategic Advice. They Got “Trendslop” in Return. By Angelo Romasanta, Llewellyn D.W. Thomas and Natalia Levina—Harvard Business Review

Paul Kedrosky

Gregor Macdonald – Cold Eye Earth

Prediction Market Accuracy: Crowd Wisdom or Informed Minority? By Roberto Gomez Cram, Yunhan Guo, Theis Ingerslev Jensen, and Howard Kung

U.S. Soldier Charged With Using Classified Information To Profit From Prediction Market Bets—Office of Public Affairs, U.S. Department of Justice

64% of business books are profitable. That’s the bottom line from our study of Business Book ROI.—Josh Bernoff

Libsyn Statistics, visualized—Livewire Labs

The Big Bang: A.I. Has Created a Code Overload By Mike Isaac and Erin Griffith—The New York Times

High earners race ahead on AI as workplace divide widens By Madhumita Murgia and John Burn-Murdoch—Financial Times

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Transcript

Welcome to Money for the Rest of Us. This is a personal finance show on money, how it works, how to invest it, and how to live without worrying about it. I’m your host, David Stein. Today is episode 555. It’s titled “Five Practices That Have Shaped My Career.”

Taking Notes

Tomorrow I’m speaking to a graduate finance class at the University of Arizona. It’s something that I do about once a year. The professor invited me to share what I’ve learned across a 30-year career as an investment advisor, an author, an entrepreneur. And as I thought about it, I’ve narrowed it down to five practices. 

The first I learned really my first day at university. In high school, the teachers would write all the notes on the board, and I would just copy them down. That first class, the professor just started speaking, and I. “What do I write down?” I even asked the girl sitting next to me, like— well, at least I watched what she was doing, that she was writing some of the stuff down, and so I started taking notes. That’s a practice that I continued, obviously, throughout my undergraduate, my graduate, but I have continued to do that throughout my professional life.

I started by writing down in hardcover Moleskine notebooks, and I would fill one up, I’d write the next one down. But problem with Moleskine is— yeah, you can kind of go back and review, but you can’t really search that. And so when technology came along, where you could record it online in somewhat of a wiki format, that’s what I did. 

Starting with Social Texts, 2005, I used Backpack by Basecamp, formerly 37signals; that was in 2007. In 2008, I started using Evernote, and I used primarily Evernote and Basecamp for our business, as well as Backpack, up until 2019, when I started using Roam Research for most of my notes, with the exception of things that have to do strictly with organizing our business, and we continued to use Basecamp. I also have kept a written journal since the seventh grade. Now, I generally just write a summary post by hand, once a year.

So in thinking about this note-taking—I’ve not used Evernote in a long time, but I have all these notes, and I figured out today how to export them as HTML, and then I used Claude Cowork, that basically formatted the HTML into a Markdown file that I could import into Roam Research. So hey, there’s something AI could do—format an HTML file.

So then I was reviewing the notes—which is why it’s such a helpful practice; I occasionally go back—and I found a note from 2009 on Panarchy. I was in the process— I was reading a book by that topic, Lance Gunderson and C.S. Holling. I was writing our— it would have been our quarterly market commentary, strategy report at FEG Advisors, and I was introduced to this concept of panarchy, and how it describes how complex systems change over time. Everything’s connected, but you have different layers; you have microbes that live and die very quickly, you have trees that live longer.

I was recently visiting where I grew up in Cincinnati, and it felt familiar, my neighborhood—I drove by the house I used to live at—because some of the trees were still there. They’ve been there now 50 years or more; probably close to 100 years, because they were big even when I was small. So they change much more slowly. And so you have these higher-up levels in the panarchy that are persistently there.

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Filed Under: Podcast Tagged With: AI, best practices, prediction markets, rules of thumb

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