Episode summary
Five Practices That Have Shaped My Career
Money For The Rest Of Us
· · 32 min · Hosts: David
Summary
The host lays out five career practices that have helped him through market cycles, business pivots, and the rise of AI: take notes, keep getting input, experiment on the leading edge of the present, understand probabilities, and get out and move. He frames these as a personal “script” or rules of thumb, borrowing from the idea of panarchy: persistent structures create enough stability to guide action, while the edges of change are where new opportunities appear.
He argues that durable note-taking and regular reading create a searchable corpus of ideas over decades, while curated sources and selective experimentation help surface better opportunities than passively following consensus. He also stresses that AI is powerful but biased, sometimes overly homogeneous, and still requires judgment because it can be wrong or incomplete. That leads into his fourth lesson: investors and builders need to think in medians, averages, and skewness, not just upside anecdotes, because many creative activities have low odds of big financial payoff.
Finally, he emphasizes physical movement and stepping away from constant input so the subconscious can process information. The host presents that rhythm of input, experimentation, probability thinking, and reflection as the practical framework that has shaped his career and net worth.
Key takeaways
- The host says his first rule is to take notes continuously and keep them in a format that can be exported and searched later.
- He prefers the Financial Times as his top periodical for finance, with The Economist second, because he wants broad and international input.
- The host says experimentation on the “leading edge of the present” created many of his opportunities, including URLs, blogs, podcasts, and software products.
- He argues that AI should be used with judgment because large language models are biased toward common web-trained advice and can be wrong.
- The host says most creative careers are skewed: a book, podcast, or YouTube channel is unlikely to produce outsized income unless you are a major outlier.
- His fifth practice is to walk or exercise regularly so new ideas can surface after periods of focused input.
Notable quotes
“I've narrowed it down to five practices”
“the best periodical, if you're in finance or you're interested in investing, I prefer to get a broader, more international exposure, so the Financial Times is is my top choice”
“We want to see where where there's some momentum, some some trends and use our curiosity”
“The median podcast gets 125 listens per episode”
“the wisdom of the crowds depends on the errors of individual investors canceling each other out”
How the episode opens
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. 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?
But I I even asked the 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 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 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 probably with Moleskine is yeah, you can kind of go back and and review, but you can't really search that.
And so when technology came along where you could record online in in somewhat of a a wiki format, that's what I did. Starting with Socialtext 2005, I used Backpack by Basecamp, now known as formerly 37 Signals, that was in 2007. 2008, I started using Evernote, and 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 continue to use Basecamp.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- ai rise
- prediction markets
- probabilities
- idea generation
- note-taking practices
Companies and tickers mentioned
- NYT
- The New York Times
- Harvard Business Review
- Livewire Labs
- Libsyn
- Cold Eye Earth
Watch the episode
Watch “Five Practices That Have Shaped My Career” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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Money For The Rest Of Us, this episode and its artwork belong to J. David Stein. Octagon is not affiliated with the show; this page is an independent summary.
