I Used AI to Grade a Real 16-Fund Portfolio. The Result Surprised Me

A viewer named Robbin wrote in about her husband's financial advisor. They pay a $10,000 flat fee plus a 0.69% AUM fee, which works out to about 1.6% a year. Robbin was the one who had to raise Roth conversions, and when she asked the advisor about the widow's penalty, the advisor said she'd never heard of it. She sent me the actual portfolio, 16 ETFs spread across a traditional IRA and a Roth, and asked a fair question: is all this complexity worth it, and could it be made simpler?

Resources mentioned in the video:

Testfolio (portfolio back-testing tool): https://testfol.io
Claude (the AI I used to analyze the portfolio): https://claude.ai
Gemini (Google's AI, used to double-check the numbers): https://gemini.google.com
Vanguard advisory services (0.30%): https://investor.vanguard.com/advice

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0:00 What we're testing: a 16-fund portfolio vs. a 3-fund portfolio
0:28 The viewer's email: a 1.6% fee and the widow's penalty red flag
2:40 Using AI (Claude) to map the whole portfolio
6:31 Don't trust one AI: double-checking with Gemini
9:41 Collapsing 16 funds into a simple 3-fund portfolio
11:11 The 10-year back-test: the surprising winner
14:32 What a 1.6% fee does to the winner
15:40 Should you fire the advisor? Why I won't push you
17:49 Checking the numbers in Testfolio
20:29 My takeaways: good portfolio, costly fee, what to do instead

ABOUT ME

While still working as a trial attorney in the securities field, I started writing about personal finance and investing In 2007. In 2013 I started the Doughroller Money Podcast, which has been downloaded millions of times. I've since sold my websites, bought them back, and started a new website and this YouTube channel.

I'm also the author of Retire Before Mom and Dad--The Simple Numbers Behind a Lifetime of Financial Freedom (https://amzn.to/3by10EE)

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DISCLAIMER: I am not a financial adviser. These videos are for educational purposes only. Investing of any kind involves risk. Your investment and other financial decisions are solely your responsibility. It is imperative that you conduct your own research and seek professional advice as necessary. I am merely sharing my opinions.

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