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Hey, it’s Jeffrey — back again!
I get it. You see ChatGPT analyzing data, making predictions, crushing complex problems — and you think: "Could this pick the next Amazon for me?"
The short answer: No.
The better question: How should I actually use AI for investing?
Because here's the thing: AI won't beat the market for you. But it can help you execute a simple, boring, wealth-building strategy — faster and with way more clarity.
Here's what I recommend:
📬 In this email:
1️⃣ Use AI to See Why Stock Picking Won't Work
2️⃣ Use AI to Audit Your "Simple" Portfolio
3️⃣ Use AI to Map Your 401(k) to a Bogle Portfolio
4️⃣ Use AI to Model "What's Enough?"
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1️⃣ Use AI to See Why Stock Picking Probably Won't Work for You
Before you ask AI which stocks to buy, ask it to show you the odds.
What percentage of active fund managers beat the S&P 500 over 15 years? And what are the main reasons individual investors underperform the market?Then follow up with:
Let AI show you the math on why most people — including the pros — lose to simple index funds.
💡 Pro Tip: Then ask, "Given this, what's a smarter strategy for someone with a full-time job who wants to build wealth?"
Spoiler: It'll probably point you toward index investing.
2️⃣ Use AI to Audit Your "Simple" Portfolio
Many people think they have a simple portfolio... until AI shows them the overlap.
If you own VTI, VOO, and SCHB, you might think you're diversified. But you're probably just holding three versions of the same thing.
💬 Try This Prompt:
Here’s the result that I got, which already confirms what my financial advisor told me: I'd benefit from simplifying things, which makes adding funds or rebalancing my portfolio much easier.
AI can quickly reveal if you're holding funds that basically do the same thing — adding complexity without any real benefit.
💡 Pro Tip: Ask, "If I wanted a true 2-3 fund portfolio, what would you suggest I consolidate?"
3️⃣ Use AI to Map Your 401(k) to a Boglehead Portfolio
Your 401(k) probably doesn't have VTSAX or VTI. But you can usually build a simple 3-fund equivalent with what's available.
The problem? Figuring out which funds in your plan match a total market strategy is tedious.
💬 Try This Prompt:
AI can match your plan's options to your target allocation in seconds — no spreadsheet required.
I assumed the offerings were all Vanguard, and here's what it gave me.
💡 Pro Tip: Ask it to explain why it chose each fund so you understand the logic.
4️⃣ Use AI to Model "What's Enough?"
If you've read The Simple Path to Wealth, you know the goal isn't to beat the market — it's to hit your number and live your life.
AI won't predict the market. But it can show you how your decisions compound over time.
(I covered this in detail in my Should You Really Save More — or Start Living More? newsletter — check that out for the full walkthrough and real examples.)
💬 Try This Prompt:
It'll show you the power of consistency and time — not market timing or stock picking.
💡 Pro Tip: Follow up with, "At what point could I 'Coast FIRE' and stop contributing?"
💡 One Smart Read
Experts Urge Caution About Using ChatGPT to Pick Stocks // Ars Technica
At least 1 in 10 retail investors now use ChatGPT for stock picks — and experts are sounding the alarm. While some AI portfolios look good now, we're near record market highs where almost any strategy looks smart. AI models can confabulate data and lack real-time market info, making them risky substitutes for sound investment strategy.
🎯What to Do Now
✅ Ask AI to show you why stock picking doesn't work
💬 Run one of the prompts above in ChatGPT this week
📊 Stop trying to beat the market — start using AI to execute your plan better
🚀 Want more prompts like this? Check out AI Playbook to level up your AI skills
📤 Know someone trying to pick stocks? Forward them this email
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One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I'm not a financial advisor — just someone sharing ideas and tools I've found useful. Use what works for you, skip what doesn't, and always do your own research. Some links may be affiliate links or sponsored content for which I may receive compensation.