How to Retire at 40: Her Debt-Crushing Path to Financial Independence | Bernadette Joy | 228
Catching Up to FI: Financial Independence for Late Starters
Release Date: 07/26/2026
3 Non-Employer Health Insurance Case Studies: More Choices Than You Thought | Lyndia Cunningham (Part 2) | 240
Catching Up to FI: Financial Independence for Late Starters
Need to figure out health insurance on your own? It's a little scary if you don't get it through an employer and too young for Medicare, but there are lots of options. In Part 2 with health insurance broker, Lyndia Cunningham, Bill and Jackie put early-retirement healthcare planning to the test with three very different case studies. Jackie rewinds to age 49 and walks through the decisions she faced before leaving work, including ACA subsidies and income planning. Bill brings a high-income household with no employer benefits and explains how stumbling into Tennessee Farm Bureau coverage...
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How to Get Health Insurance When You Retire Early | Lyndia Cunningham(Part 1) | 239
Catching Up to FI: Financial Independence for Late Starters
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 health sharing and the Affordable Care Act, Lyndia walks through the options that could change your retirement timeline. Throw in retroactive COBRA, Medicaid, college health plans and direct primary care, and suddenly the path to healthcare freedom looks a lot less mysterious. This...
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The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238
Catching Up to FI: Financial Independence for Late Starters
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 tech (like AI agents) and viral moments when he exposes dealers misbehaving. Together, they reveal how dealerships really make money, including things like dealer fees, financing, and often unnecessary ad-ons. Don’t miss this breakdown of smart ways for you to research, shop,...
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61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237
Catching Up to FI: Financial Independence for Late Starters
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 reset after losing her father, getting divorced, and getting fired within a single year. She then explains why retirees often happily spend Social Security and pensions while fiercely protecting their investment balances. Together they explore Jean’s tools that can create both...
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The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236
Catching Up to FI: Financial Independence for Late Starters
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 him up financially at 50 and how he and his wife flipped from single-digit saving to intentional wealth building. Bill also explains why reaching FI at 60 created a whole new problem: actually giving himself permission to leave work. This episode covers Bill’s financial...
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How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie’s Real #s | Bill Stecker (Part 2) | 235
Catching Up to FI: Financial Independence for Late Starters
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 their deep dive into 72(t) plans as they move from theory to execution. Jackie puts her own plan on screen to let Bill do what he does best... audit it! He scrutinizes her $240k starting balance, $15k annual withdrawals, plan timeline, and the surprising fact that her account...
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Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty | Bill Stecker (Part1) | 234
Catching Up to FI: Financial Independence for Late Starters
You won’t find a more comprehensive resource on the topic of 72(t) plans and substantially equal periodic payments (SEPP). This little-known IRS provision gives you a perfectly legal way to access your retirement money before 59½ without the 10% penalty… and almost nobody in finance wants to touch it! So, Jackie brings back the one expert that lives and breathes 72(t)s, William (Bill) Stecker, CPA and founder of 72tcalc.com. Bill picks up where he left off when he last appeared on the show in 2025. He further explains the nuances of 72(t) plans and how to avoid common mistakes. Hear how...
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Vanguard Acquires Altruist: Why Fidelity & Schwab Better Look Out! | Barry Ritholtz | Bonus
Catching Up to FI: Financial Independence for Late Starters
What happens when one of investing's original disruptors buys one of the industry's newest disruptors? Barry Ritholtz thinks investors may be the biggest winners and Bill and Jackie dig into why. This special breaking-news is an excerpt from an upcoming Catching Up to FI episode, recorded on 8/26/26. Barry reacts to Vanguard's newly announced agreement to acquire Altruist, the fast-growing technology and custody platform built for independent financial advisors. Barry also gives an important disclosure: he's an Altruist investor, so yes, he has a dog in this fight. From there, he explains...
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Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233
Catching Up to FI: Financial Independence for Late Starters
What if that old pension you barely think about is secretly one of the most valuable assets in your retirement plan? Bill and Jackie welcome back financial planner and educator, Andy Panko for a deep dive into the increasingly rare (but far from extinct) world of pensions. They explore plans from private and government employers and why a seemingly small monthly check can dramatically change the work the rest of your portfolio has to do. This episode covers Why pensions are less common but still relevant to millions of workers What it actually means when an employer "freezes" a pension How to...
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The Truth Behind Raising A Teenage Money Whiz (From The Parents Of Rishi Vamdatt) | Renu & Raag Vamdatt | 232
Catching Up to FI: Financial Independence for Late Starters
After Rishi Vamdatt’s conversation with Bill and Jackie, his parents Renu and Raag step out from behind the scenes to share how their son became the 16-year-old financial educator behind Easy Peasy Finance. They believe raising a financially savvy kid has less to do with giving money lectures and more to do with letting them swipe the credit card at the grocery store and ask "what happens next"? Their approach was surprisingly simple: money was never taboo, questions were always welcome, and Rishi was allowed to follow his curiosity rather than being scheduled into oblivion. For...
info_outlineWhat if crushing your money goals has less to do with finding the perfect formula—and more to do with getting lovingly bullied into taking action today? Bill and Jackie sit down with Bernadette Joy, a first-generation Filipino American who paid off $300,000 of debt in three years, reached her first million, and eventually built a multimillion-dollar portfolio. Bernadette also explains why she believes traditional financial literacy is dead, walks through her C-R-U-S-H framework, and reveals why the final "H" evolved from hustle to healing your money wounds.
This episode covers
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How Bernadette paid off $300,000 of debt and reached her first million
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The $100-a-day strategy that made an intimidating goal feel actionable
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Why generating more income only works when you keep and invest the difference
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How she resisted lifestyle creep while building a seven-figure business
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Why her paid-off home mattered more emotionally than optimizing every return
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Her argument that financial literacy should become financial fluency and freedom
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The five-part C-R-U-SH framework for organizing money and designing an independent life
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The $1-per-use rule for spending intentionally without guilt
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How unsubscribing, reducing drama, and creating a peace plan support financial freedom
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F.I.R.E. For Dummies
Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of “F.I.R.E. For Dummies”? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.
- Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start
- Covers everything from basics to advanced strategies in one guide
- Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties
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RESOURCES MENTIONED ON THE SHOW
Crush Your Money Goals Website
Bernadette Joy's free retirement checklist and newsletter
⏰ Related Episodes
Live Talk from the Plutus Awards: Bill’s Inspiring Message to Late Starters
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📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.