Is Claude a Boglehead? A Conversation With AI Revealed Surprisingly Familiar Investing Principles

I’ve been using artificial intelligence for some time now, mainly to take large amounts of data and turn it into useful information. I’ve seen it do many brilliant things, and I’ve seen it hallucinate and give false answers, though it’s doing fewer and fewer of the latter.

I think AI will change the way investing advice is delivered, but AI by itself can be dangerous and hazardous to your wealth. There are many risks, from its hallucinations to models wanting to please users by giving answers based on their past use of AI.

For example, I think the analysis and advice I find on the Bogleheads forum are typically spot-on. The Bogleheads is a group of more than 152,000 individuals who invest based on principles inspired by the late Vanguard founder, John C. Bogle. Morningstar’s director of Personal Finance, Christine Benz, leads the planning of the annual Bogleheads conference. (This year’s conference is being held Nov. 13-15.)

Based on my past use of AI, it knows that I’m a Bogleheads fan.

Is Claude Really a Boglehead?

To illustrate, here are some excerpts from a recent chat I had with Claude, Anthropic’s large language model.

Me: Claude, give me some principles of investing.

Claude:

1. Start with clear goals.

2. Diversify across asset classes.

3. Minimize costs.

4. Favor broad, low-cost index funds over trying to beat the market.

5. Stay disciplined and ignore the noise.

6. Be tax-aware.

7. Match risk to both tolerance and capacity.

8. Rebalance periodically.

9. Keep it simple.

Me: But I have a friend who made millions trading in the market.

Claude: You hear from the winners, not the losers. A great outcome doesn’t prove a great strategy. Your friend may have been skilled, lucky, or taken big risks that happened to pay off. The typical individual investor loses ground.

Me: So, I should hire an expert to beat the market since individuals don’t?

Claude: Not quite. Hiring an expert “to beat the market” mostly runs into the same problem, just with higher fees. But hiring an advisor for other reasons can be worth it.

Me: What are those other reasons?

Claude: Tax planning, withdrawal strategies, Social Security and pension decisions, and insurance and risk reviews, among others.

Me: Can’t you do these for me?

Claude: I can do a lot: I can run the numbers, analyze your portfolio, explain your options, and prepare you to decide. But I’m not a licensed advisor; I only know what you tell me, I don’t remember to check in, I can’t act for you, and I’m not great as an emotional circuit breaker.

Me: Claude, are you a Boglehead?

Claude: Not in the literal sense. I don’t have money, a portfolio, or a seat at the Bogleheads forum, so I have no skin in the game.

But if you’re asking whether my answer leaned that way: Yes, and I’d own it. The evidence on costs, diversification, and the long-run odds of active funds beating their benchmarks points pretty consistently toward the core Bogle ideas: Own the whole market cheaply, stay the course, and don’t let fees, taxes, or your own behavior eat your returns. That’s less ideology than following the data.

Allan: Thank you, Claude

Claude: You’re welcome. Enjoyed the conversation and good luck staying the course.

Was Claude Giving Me Answers I Wanted to Hear?

The principles Claude gave me were similar to the Bogleheads principles of investing. It did skip living below your means, which is critical because if you don’t invest early and often, you will never reach financial independence.

The most enlightening answer in this so-called interview was the answer that Claude gave me as to why it was a Boglehead. Claude stated that “it was less of an ideology than following the data.” I was a bit concerned that Claude was giving me answers I wanted to hear, since I use Claude frequently. I tested other AI LLMs and got similar logical and fact-based responses.

Lessons Learned About Using AI

None of the advice given by AI goes through a vetting process by other investors, whether it’s the Bogleheads, the experts at Morningstar, or the financial media. Following AI advice blindly is exactly how not to use it.

A recent Vanguard paper titled The AI advice frontier states: “Personalized financial support has long felt like a luxury, with a price tag that gives investors pause. AI changes that math, putting a no-pressure, no-cost, personalized option at your fingertips any time of day.”

The paper suggests using AI as a starting point rather than the last word.

I agree. Always run AI’s advice by people such as those in the Bogleheads forum. Anyone can post a question in the forum, and I’ve found no shortage of investors willing to give their thoughts on any advice or topics. Most importantly, these are people wanting to help and get nothing in return.

Remember that money is more than math. Money is emotional. When it comes to investing, we are often irrational. AI can be a fantastic starting place because it presumably has no emotions and isn’t trying to sell you anything. But check its advice with real people who do have emotions and can relate to how you might be feeling after the next dramatic market plunge.