The Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211
Apr 29, 2026
What if the biggest shift in your FI journey isn't hitting the number—but finally realizing you need a life plan, a tax plan, and maybe even a fiduciary teammate to help you spend it? Bill steps into the guest chair with Morningstar's Christine Benz for a thoughtful, surprisingly candid conversation about going...
Hot Takes & Money Debates: Social Security at 62, New Trump Accounts, & more! | Bill & Jackie | 210
Apr 26, 2026
What happens when the two co-hosts stop being polite, start being honest, and publicly debate the money moves they still don't agree on? We throw open the doors on four of our favorite friction points:
- Simple index-fund investing versus "modest complexity"
- Whether high school personal finance classes are...
Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209
Apr 19, 2026
What if the real reason family wealth disappears by the third generation has almost nothing to do with investing, and everything to do with what parents fail to teach at home? We sit down with Dr. Julia Myers, founder of Generational Wisdom, for a conversation that goes way past trusts, spreadsheets, and "someday"...
20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208
Apr 12, 2026
APRIL IS FINANCIAL LITERACY MONTH! What do you get when two late starters hand the mic to two twenty-somethings and let the money questions fly? In this unusually fun follow-up to the University of Tennessee classroom visit, we bring Dr. Karen DeLong and two of her students, Emilie and Britton, onto the podcast to...
Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207
Apr 8, 2026
APRIL IS FINANCIAL LITERACY MONTH! What happens when you hand a room full of almost-graduates a microphone, a few $2 bills, and permission to ask the money questions most adults still avoid? In this special on-the-road episode, we take you inside the financial literacy presentation at the University of Tennessee to...