Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205
Mar 29, 2026
April is Financial Literacy Month and we're starting a little early! That's because we are so excited to launch a new project called "The Great 401(k) Cleanup." What if the easiest way to boost your retirement odds this year isn't reducing your spending or a side hustle, but cleaning up that messy, confusing 401(k)...
Here's What 6 Years of Early Retirement Life is Really Like | "REAL Retirees: Uncut" Crossover | 204
Mar 25, 2026
What if the best retirement advice didn't come from a spreadsheet—but from a real retiree saying, "I wish I'd done it sooner"? Jackie crosses over to "REAL Retirees: Uncut" for a refreshingly candid, walk through of what six years of early retirement have actually looked like. She also shares her top five reasons to...
I Thought the Stock Market was Gambling, Then I Retired at 44 | Jaylynn | 203
Mar 22, 2026
What if you were already financially independent at 40… and didn’t realize it until a random pension search and a couple of podcasts blew the whole thing open? This was Jaylynn's "Surprise FI" and he joins the show to take us blow by blow. He gives us look back to his childhood of money orders, loving parents, and...
Don't Trust AI with Your Money Until You Listen To This | Jeffrey Trull | 202
Mar 15, 2026
Today we’re putting AI (Artificial Intelligence) to the test with AI money expert Jeffrey Trull. He's founder of the blog and newsletter, Money Meets AI where he shares tested prompts for your money. He joins us to sort the genuinely useful from the wildly overhyped when it comes to AI. We expand our conversation into...
The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201
Mar 8, 2026
What if the guy who literally wrote the book on asset allocation told you your biggest risk isn’t the market…it’s the person in your bathroom mirror? Neurologist-turned-market-historian William (Bill) Bernstein joins us for a fascinating conversation about his unlikely path from photochemistry to medicine to...