# Who Should You Trust With Your Money? (Friends, Family, Experts, AI, and Bad Advice) SB1869

Page: https://stenobird.com/podcast/the-stacking-benjamins-show-745268/who-should-you-trust-with-your-money-friends-family-experts-ai-and-bad-advice-sb1869
Text version: https://stenobird.com/podcast/the-stacking-benjamins-show-745268/who-should-you-trust-with-your-money-friends-family-experts-ai-and-bad-advice-sb1869.md
Podcast: [The Stacking Benjamins Show](https://stenobird.com/podcast/the-stacking-benjamins-show-745268)
Published: 2026-07-17T08:01:00+00:00
Episode link: https://pscrb.fm/rss/p/mgln.ai/e/345/rss.art19.com/episodes/1db4bd55-9d1f-4658-9985-f626c0abb12a.mp3?rss_browser=BAhJIg90cmFuc2NyaWJyBjoGRVQ%3D--952c5701c84ad333c69d5faa668f8177091704f0
Audio file: https://pscrb.fm/rss/p/mgln.ai/e/345/rss.art19.com/episodes/1db4bd55-9d1f-4658-9985-f626c0abb12a.mp3?rss_browser=BAhJIg90cmFuc2NyaWJyBjoGRVQ%3D--952c5701c84ad333c69d5faa668f8177091704f0
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JSON: https://stenobird.com/v1/public/podcasts/the-stacking-benjamins-show-745268/episodes/who-should-you-trust-with-your-money-friends-family-experts-ai-and-bad-advice-sb1869
Duration seconds: 4309

## Resource

A Wall Street Journal story about a 17-year-old helping his family with financial decisions kicks off a much bigger Stacking Benjamins question: who should you actually trust with your money? Joe, Doug, Paula Pant, Jesse Cramer, and special guest Roger Whitney dig into where great advice comes from, why bad advice often comes from people who love you, and how to build a better filter before you act. Along the way, they talk books, podcasts, family advice, AI, confirmation bias, homebuying myths, index funds, retirement plans, and why "smart" isn't enough. What You'll Walk Away With Why Roger says "advice" has a high bar: real advice should apply to your specific life, not just sound smart in public The difference between information and advice -- and why confusing the two can lead you into trouble Why books often beat random internet advice: they usually have more vetting, structure, and accountability How well-meaning friends and family can still give terrible money advice when they speak confidently about things they don't really understand Paula's advice pyramid: avoid people who profit from outrage, be skeptical of people with no accountability, and seek sources with both expertise and vetting Why AI can be useful as a sparring partner, but not as a substitute for your own thinking or fact-checking The danger of "always" and "never" advice: always buy a house, always max your 401(k), never finance a car, always buy index funds Why renting isn't automatically throwing money away -- and how the price-to-rent ratio can help you think more clearly Why maxing out your workplace retirement plan may not always be the right move, especially when tax flexibility, business investment, or other goals matter more How confirmation bias, present bias, and absolute certainty can…

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## Transcript

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