We Are All Wayfinders
Money For the Rest of Us
J. David Stein
4.5 • 1.4K Ratings
🗓️ 13 May 2026
⏱️ 27 minutes
🧾️ Download transcript
Summary
Why we have to navigate investing, business, and life with a compass rather than a GPS. David also provides an update on what he has learned from hosting live portfolio cohorts and letting AI analyze his portfolio trades over the past 12 years.
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Show Notes
Almost Reckless by Amy Smilovic—Penguin Random House
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Transcript
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| 0:00.0 | Welcome to Money for the Rest of Us. This is a personal finance show on money, how it works, |
| 0:05.1 | how to invest it, and how to live without worrying about it. I'm your host, David Stein. Today is |
| 0:10.6 | episode 556. It's titled, We Are All Wayfinders. This morning, I hosted our third session of our live |
| 0:20.2 | portfolio cohort. This was a new offering from |
| 0:23.8 | Money for the Rest of us, where we worked with a small group of investors in a live setting |
| 0:29.7 | as they work through some of their portfolio construction challenges. It's not a course, |
| 0:36.2 | nor is it specific investment advice. |
| 0:39.6 | The best descriptor I can think of is it's a workshop, like they have in fiction, when in |
| 0:47.3 | novelist. Way back two decades ago, I was working on a novel, and I attended a weekend workshop in Aspen where we worked with a novelist |
| 0:58.6 | and was a group of us and we talked about our novels, our short stories and it was collaborative. |
| 1:06.7 | That's kind of what this is. We did a launch. We had hundreds of people on our webinar. We had a |
| 1:15.3 | lengthy wait list. We were targeting individual investors with five to 10 years from retirement. |
| 1:21.6 | And at the end of the day, only two people signed up. That's a big signal. That means there was not a good product market fit. |
| 1:31.2 | We've done some follow-up surveys to understand, but at the end of the day, what I think the issue is, |
| 1:37.1 | is the fact that we were targeting individuals with five to ten years from retirement. They don't have a |
| 1:43.0 | sense of urgency. They're not feeling |
| 1:45.0 | tension yet. Because here's the thing. The two people that signed up plan are retiring in the next |
| 1:50.9 | year. They didn't even fit the target of the cohort, which was fine because then we could pivot. |
| 1:57.6 | It's a gift that they joined because now we're piloting a workshop for those |
| 2:03.6 | getting ready to retire. And we're testing the tools that we developed. And it's been absolutely |
| 2:09.2 | fascinating. What they're learning, what we're learning as we kind of navigate. For example, |
| 2:15.2 | we realize smaller groups are going to be better. 25 people would have been too many. We probably could use more than two. But example, we realize smaller groups are going to be better. |
... |
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