Starcast Join the waitlist
The Boldin Your Money Podcast

The Boldin Your Money Podcast

Retirement Planning's Hidden Tradeoffs | With Jesse Cramer (Ep. 114)

Oct 1, 2026 · 50m

Coming soon to iPhone. Already have it? “Listen in Starcast” takes you straight there.

About this episode

Building a retirement plan means balancing financial security with the life you want to live. Steve Chen sits down with fee-only fiduciary financial planner Jesse Cramer, host of Personal Finance for Long-Term Investors and writer behind The Best Interest, to explore both the numbers and the human side of retirement. They discuss how Coast FIRE can create flexibility, why retirement requires more than a portfolio adjustment, and how stacking conservative assumptions can keep you working longer than necessary. Along the way, Jesse shares ways to think about retirement income, competing risks, and the trade-offs behind Roth conversions. To learn more about the Boldin Planner, visit boldin.com…