Is AI Better Than Your Financial Advisor?

9 snips

Mar 23, 2026

They test AI against real financial planning using a 25-year-old FIRE scenario and reveal AI's cookie-cutter retirement recommendations. The show digs into limits of relying on historical returns and why averages can mislead. It explores behavioral blind spots where cash or whole life insurance might outperform index strategies. Expect a debate on nuance versus automated advice and when bespoke planning matters.

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INSIGHT

AI Repeats Generic Financial Boilerplate

AI often repeats generic, internet-sourced financial advice without nuance.
Chris Miles tested Google Gemini with a 25-year-old FI scenario and found cookie-cutter recommendations like maxing retirement accounts and index funds.

ADVICE

Validate AI Retirement Assumptions Yourself

Do not rely solely on AI for a retirement plan; check the assumptions it uses.
Gemini told Chris to target $3M (3% withdrawal) then suggested maxing 401(k), Roth IRA, HSA and taxable index funds as the execution plan.

INSIGHT

Big Targets Mask Real-Life Affordability Problems

AI's headline numbers hide affordability and behavioral gaps.
Gemini recommended saving about $5,100/month which equals ~61% of $100k income, implying living on $15k–$19k annually for 20 years.

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Is AI better than a financial advisor? That's the question I've been getting a lot lately and honestly, it's a fair one. With tools like ChatGPT, Gemini, and other AI platforms becoming more popular, people are starting to wonder if they even need financial experts anymore. In this episode, I break down the truth about AI in financial planning, where it works, where it fails, and why relying on it blindly could actually cost you years if not decades of your financial life.

I decided to put AI to the test. I gave it a very common financial independence scenario: a 25-year-old making $100,000 per year who wants to retire by 45 and live on $100,000 annually. What did AI recommend? The same cookie-cutter advice that's been recycled for decades max out your 401(k), invest in index funds like the S&P 500, and save aggressively. Sounds familiar, right? That's because it is.

The problem is, AI doesn't understand nuance. It doesn't understand you. It doesn't understand your behavior, your risk tolerance, your goals, or your real-life situation. It pulls from generalized data and spits out theoretical answers. But as I've seen over the last 20+ years helping people create passive income and become work optional, theory rarely works in real life.

In this episode, I walk through why the traditional FIRE (Financial Independence, Retire Early) model often falls short, especially when you factor in inflation, taxes, market volatility, and human behavior. I also explain why strategies like the 4% rule or even the 3% rule—can be misleading when applied without context. AI might tell you to save millions and live on next to nothing for 20 years, but is that realistic? More importantly, is that the life you actually want?

I also share real-world examples of how I advise clients differently based on who they are. For instance, one person might need to stop investing entirely and build cash reserves, while another needs to take more calculated risks. AI can't make those distinctions but a seasoned financial strategist can.

We also dive into why averages in the stock market can be deceptive, how sequence of returns risk can destroy your retirement plan, and how tools like whole life insurance can be used strategically to stabilize income during market downturns. These are the kinds of nuanced strategies that AI simply cannot replicate.

At the end of the day, AI is a tool not a replacement. It's great for calculations, quick research, and brainstorming. But when it comes to building a real financial strategy that actually works in your life, you need experience, perspective, and customization.

If you've been tempted to rely on AI for your financial future, this episode will open your eyes. My goal is to help you avoid costly mistakes and instead create a path to true financial freedom where you can become work optional and live life on your terms.