The Financial Samurai Podcast

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Mezzi: The AI Investment Advisor That Saved Me Over $20,000

September 09, 2026

This summer, my new AI wealth advisor, Mezzi, discovered roughly $300,000 of Google exposure I didn't know I had. It sounds a little absurd, given the amount. But I've been investing in Google for over 15 years, and with a complicated net worth it's hard to track everything accurately when your mind anchors to old price points. Weeks after I trimmed the position, Google sold off about 10%. I sidestepped over $20,000 in losses. Then I did something I'd never done in 17 years of writing about m...

Nobody Is Ever Truly Independent: Caring for Parents, Raising Kids, and the 37-Year-Olds Still Cashing Dad's Checks

August 04, 2026

Being an adult is hard, and nobody is ever truly independent. In this episode, my wife and I talk about spending 30 days in Honolulu with my parents and what it's like to slowly shift from being cared for to being the caretaker. We also get into a bizarre encounter with two park rangers on an empty public tennis court while I was teaching my own kids, and a discussion about what a real adult actually is when a 37-year-old still depends on her father for money. Three generations, one uncomfort...

From Startup To Acquisition by Symantec: The Entrepreneur's Journey With Domingo Guerra

June 23, 2026

In this episode, I sit down with my friend and fellow school dad Domingo Guerra to trace his entrepreneurial journey: from growing up in Mexico, to studying engineering at UT Austin, to co-founding the mobile cybersecurity company Appthority with my poker and softball buddy Kevin, to selling it to Symantec in 2018. Today, Domingo runs his own seed-stage venture fund focused on cybersecurity, called Chispa VC. It always fascinates me how people become entrepreneurs, given that most of us just...