Episode summary
A MFTROU Update, Cognitive Offloading Versus Cognitive Surrender, and Live Portfolio Cohorts
Money For The Rest Of Us
· · 7 min · Hosts: David
Summary
The host says he is skipping a regular episode while he finishes his next book and prepares live portfolio cohorts for next month. He uses the break to explain how AI is changing both his workflow and the broader media environment, citing faster growth in self-published books and new iOS apps as evidence that more content is being produced than anyone can easily absorb. His response is to be more selective, focusing on depth and meaning rather than quantity.
He frames AI as a tool for cognitive offloading, but not surrender. Drawing on Ezra Klein’s recent essay, he argues that some people are oversharing with AI, while he prefers to keep control of the inputs and use judgment on the outputs. He describes using Claude to expand portfolio spreadsheets, categorize brokerage holdings, add new asset classes, and build Monte Carlo simulation prompts that estimate future portfolio values and retirement readiness.
The episode closes with details on the May 5 cohort, limited to 25 investors who are within 10 years of retirement. The host says the sessions will be interactive and practical, helping participants assess diversification, risk, rebalancing, asset location, and whether their portfolio can fund retirement. He says attendees can join the wait list for early access, a $200 discount, and preparatory emails.
Key takeaways
- The host says he is doing fewer podcast episodes this year and shifting toward longer-form work because content volume is exploding.
- He cites a 33% rise in newly published books and a 24% rise in new iOS apps as signs of overwhelming content growth.
- He uses Claude to extend portfolio analysis tools with new asset classes, volatility estimates, and brokerage-statement categorization.
- The host says AI boosts productivity, but he still controls return assumptions and must use judgment to catch mistakes.
- The May 5 live portfolio cohort is limited to 25 investors who are planning to retire in the next 10 years.
Notable quotes
“the number of newly published books increased by 33%. Most of which were self-published with heavy assistance from AI”
“The reality is we are drowning in new content. Video shorts, social media, and even longer content such as self-published books”
“I'm focused on depth and meaning, not quantity”
“These are examples of cognitive offloading. While I use AI as a tool, I'm still in control of the inputs”
“this is the first time in 12 years that I'll be working with a small group of investors in real time, walking them through the process”
How the episode opens
Hi, this is David. We don't have a regular podcast episode this week as I take some time off and I'm also working on my next book and preparing for the live portfolio cohorts we'll be hosting next month. I recently shared my thoughts on the podcast and in our insiders guide newsletter about how AI is affecting me and our business.
For example, in the past year, the number of newly published books increased by 33%. Most of which were self-published with heavy assistance from AI. At least that's what I presume.
That compares to a 2% decline in the number of books published in 2024. Another statistic, the number of new iOS apps is up 24% in the past year compared to 6% increase in the year prior. The reality is we are drowning in new content.
Video shorts, social media, and even longer content such as self-published books. Now, given that volume, I want to be more selective in what I release. I'm focused on depth and meaning, not quantity.
And that's why we're doing fewer podcast episodes this year, and I'm doing more longer form content. Most of us are using AI either regularly or we're experimenting with it. We're navigating brand new terrain and one of those boundaries we're trying to decide on is to what extent do we cognitively offload to AI or surrender to it.
Ezra Klein recently wrote about this in the New York Times. many individuals and he found as he went to San Francisco that they're sharing everything they can about themselves with AI so that the tools becomes more effective in helping them being like them even acting for them in many cases and they also he mentioned they're doing it to sort of kind of train the next generation of AI I would consider it oversharing I'm way more selective in what I share with AI but I have been using it a lot especially this week in preparing for these live portfolio cohorts.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- cognitive offloading
- cognitive surrender
- productivity tools
- investment portfolio analysis
- live portfolio cohorts
Companies and tickers mentioned
- Anthropic
Watch the episode
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.
