How to Get Health Insurance When You Retire Early | Lyndia Cunningham(Part 1) | 239
Sep 27, 2026
What if the biggest thing standing between you and early retirement isn't your savings... it's your health insurance? Bill and Jackie welcome Lyndia Cunningham of Move Health to tackle the healthcare headache that keeps so many Americans working until 65. From COBRA and short-term medical plans to faith-based...
The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238
Sep 20, 2026
Exposed! We go behind the scenes with industry experts and disrupters in the retail car-buying market, Ray and Zach Shefska. They are the powerful father-son team behind CarEdge, a car-buying platform that’s fighting fiercely for transparency. Ray brings 43 years of dealership experience and Zach brings the modern...
61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237
Sep 13, 2026
What if the biggest retirement risk isn’t running out of money, but being too afraid to spend the money you worked decades to build? Personal finance icon Jean Chatzky joins Bill and Jackie to tackle the psychology and math behind turning a lifetime of savings into a Forever Paycheck. Jean shares her own late-start...
The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236
Sep 9, 2026
What happens when you finally reach financial independence and your brain responds with, “Great, now what?” In this special crossover from ChooseFI, Ginger turns the microphone on Bill and digs into the part of financial independence that spreadsheets rarely prepare us for. He shares how a lawsuit and burnout woke...
How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie’s Real #s | Bill Stecker (Part 2) | 235
Sep 6, 2026
A 72(t) plan is little-known IRS provision which gives you a perfectly legal way to access your retirement money before 59½ without the 10% penalty. In this second half of the 2-part episode, Jackie brings back Mr. 72t, William (Bill) Stecker, CPA and founder of 72tcalc.com. This episode takes on the practical half of...