How to Get Health Insurance When You Retire Early (Part 1) | Lyndia Cunningham | 239
Episode 239
Sunday, September 27, 2026 • Duration 01:26:46
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 episode covers
The health insurance options available to early retirees before Medicare at 65
How COBRA, short-term medical insurance, Farm Bureau plans and healthcare-sharing programs compare
The important differences between ACA-compliant insurance and other types of coverage
How spouses, dependents and college students can access alternative coverage
Retroactive COBRA and planning for the transition out of employer-sponsored insurance
ACA essential health benefits, provider networks and out-of-state coverage limitations
How ACA premium subsidies interact with household income, Roth conversions and HSA contributions
Medicaid eligibility and the complications that can arise for early retirees and their families
Dental, vision, accident and critical illness coverage beyond a basic health insurance plan
How HSAs and direct primary care can fit into a broader retirement healthcare strategy
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
📌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.
The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238
Episode 238
Sunday, September 20, 2026 • Duration 01:35:06
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, avoid games some dealers play, and get the fairest price on your next car.
This episode covers
How dealerships use monthly payments to distract buyers from the total cost of a car
Why negotiating a vehicle can be especially difficult for women and minority buyers
Using AI agents to obtain and negotiate real dealer pricinng
The fees, add-ons, and protection packages buyers should question
Why "if it's taxable, it's negotiable" is one of Ray's favorite rules
How to get and compare a true out-the-door price
Why a pre-purchase inspection is critical when buying a used vehicle
The pros and cons of CarMax and Carvana
How pre-approved financing can protect you from dealer interest-rate markups
Cash versus financing, leasing and total cost of ownership
Ray's ultimate rule: buy what you need, not just what you want
61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237
Episode 237
Sunday, September 13, 2026 • Duration 01:07:37
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 security and permission to spend. Jackie even runs her own numbers and discovers her forever-income gap might be surprisingly easy to fill.
This episode covers
Jean Chatzky's own financial reset after a series of major life changes at 40
Why retirees can become surprisingly reluctant to spend their accumulated savings
The "decumulation gap" and the psychology behind creating a retirement paycheck
How to build a "moat budget" around essential expenses and important wants
How risk tolerance and FOMO can shape your retirement-income strategy
Why Jean changed her long-held opinion about annuities
How home equity, insurance, HSAs, and other assets can become retirement resources
Why late starters need forgiveness, benchmarks, and trusted guidance, not perfection
The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236
Episode 236
Wednesday, September 9, 2026 • Duration 01:03:36
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 wake-up call at age 50 and his "trifecta" of late-starter mistakes
How he and his wife moved from single-digit saving to a 30–40% savings rate
Working through regret, shame, anger, and scarcity after a late start
Why lifestyle downsizing felt more freeing than depriving
The "fog of FI" and why reaching your number does not automatically make retirement easy
One-more-year syndrome, professional identity, and creating a gradual glide path out of work
How FI gave Bill leverage to cut shifts, reduce night work, and reclaim his time
The advantages late starters still have despite missing decades of compounding
Why health, relationships, community, and purpose become more important after the math is solved
Bill's belief that relationships may compound even better than money
How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie's Real #s | Bill Stecker (Part 2) | 235
Episode 235
Sunday, September 6, 2026 • Duration 01:25:15
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 has actually grown even though she's been taking money out.
This episode covers
Why Bill strongly favors the amortization method for most practical 72(t) plans
How the 5% interest-rate floor changed SEPP planning
The three basic inputs needed to calculate a 72(t)
How to document the correct starting IRA balance
What records to keep in case the IRS ever asks questions
Why annual withdrawals may reduce opportunities for mistakes
How to handle a 1099-R that says "early distribution, no known exception"
Jackie's real-life 72(t) setup, asset allocation, and withdrawal schedule
How 72(t)s can work alongside Roth conversions and other income strategies
Why some people may qualify for better early-withdrawal exceptions and not need a SEPP at all
This is the second part of a 2-part episode. Be sure to subscribe the show and catch part 1 (episode 234) from 8/30/26.
Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty | Bill Stecker (Part1) | 234
Episode 234
Sunday, August 30, 2026 • Duration 56:05
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 72(t)s can be incredibly powerful tools for early retirees, laid-off workers, and anyone ready to leave the traditional "hours-for-dollars" trade.
This episode covers
What a 72(t) or SEPP plan actually is
Access to retirement accounts before age 59½ without the 10% penalty tax
Why so many financial professionals hesitate to work with 72(t) plans
The minimum plan period and why modifying a SEPP can become extremely expensive
How to determine how much early retirement income you actually need
The differences between the Rule of 55 and a 72(t) strategy
Why Bill usually prefers moving money from employer "plan land" into "IRA land"
How brokerage accounts, Roth contributions, part-time work, and SEPPs can work together
Why inflation and unexpected expenses need to be built into an early-retirement income plan
How splitting an IRA into separate accounts can create flexibility and isolate potential mistakes
This is the first part of a 2-part episode. Be sure to follow the show and catch part 2 next week (9/6/26).
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 why combining Vanguard's enormous scale with Altruist's technology could quickly reshape the custody business, put fresh pressure on Fidelity and Schwab, and potentially extend the famous "Vanguard Effect" into another corner of financial services. Bill calls it "disruptor squared." Barry sees an industry that never stands still. And if competition drives prices lower again, investors may ultimately be the ones cashing the biggest check.
This episode covers
Barry's immediate reaction to Vanguard's agreement to acquire Altruist
His disclosure that he is an Altruist investor and financially benefits from the deal
Why Altruist's clean-sheet technology made it an attractive challenger to legacy custodians
How Vanguard's scale could immediately change Altruist's competitive position
Why Fidelity and Schwab may suddenly have a much larger third competitor
The "Vanguard Effect" and how competition can push fees lower across an industry
Why Barry believes investors could be the biggest winners from the acquisition
How Schwab and Robinhood previously disrupted investing through lower-cost and free trading
Why Vanguard was a logical potential acquirer given its earlier relationship with Altruist
Barry's larger lesson that financial technology never stands still
The Full Episode with Barry Ritholtz will be coming out soon! "
Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233
Sunday, August 23, 2026 • Duration 01:41:06
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 think about a pension as part of your overall retirement portfolio
The risks behind private, federal, state, and municipal pension promises
Lump sum versus lifetime monthly payments and the trade-offs of each
Single-life, joint-and-survivor, period-certain, and inflation-adjusted pension options
Why guaranteed income can give retirees psychological permission to spend
When comparing an employer pension with a commercial income annuity may make sense
Andy's four-question framework for deciding whether lifetime payments fit your plan
Jackie's pension options and her final decision to turn on lifetime monthly payments
Where to find old or forgotten pensions from previous employers
☕ Like what you hear on Catching Up to FI? Support the show at
The Truth Behind Raising A Teenage Money Whiz (From The Parents Of Rishi Vamdatt) | Renu & Raag Vamdatt | 232
Wednesday, August 19, 2026 • Duration 30:11
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 late-starting parents, the reassuring message here is that you don't need to raise another Rishi. Just talk openly, model your values, and follow the child.
This episode covers
How Renu and Raag recognized Rishi's unusual interest in money from a very young age
Why money, income, mortgages, and family finances were never treated as taboo
How everyday activities like grocery shopping became natural financial lessons
The family effort behind the early years of Easy Peasy Finance
Why Rishi has turned down sponsorships, including significant offers, to protect audience trust
How Rishi's parents balance his mathematical approach with the emotional side of money
Why letting children lead their interests can be more powerful than filling every hour with activities
How Rishi balanced finance with theater, travel, fishing, scuba diving, video games, and being a regular kid
What parents can do differently to build financial fluency in the next generation
How financial values and openness traveled from grandparents to parents to Rishi
This 16-Year-Old CFP Exam Passer Is Making Personal Finance "Easy Peasy" | Rishi Vamdatt | 231
Episode 231
Sunday, August 16, 2026 • Duration 01:02:25
What if the person explaining money to your kids has already been doing it for more than half his life, and passed the CFP exam before he could legally vote? Bill and Jackie sit down with 16-year-old Rishi Vamdatt, founder of Easy Peasy Finance. Rishi started learning about money at six, investing at seven, and teaching personal finance on YouTube at eight. But this isn't just a story about an unusually motivated teenager. Rishi offers a surprisingly universal lesson: money gets easier when we strip away the jargon, practice with real dollars, automate the basics, and start where we are.
This episode covers
How Rishi passed the CFP exam at just 16 years old
The childhood experiences that sparked his fascination with money
Why he gave up birthday parties and started investing at age seven
How Easy Peasy Finance grew from kid-friendly three-minute videos into more than 1,300 pieces of financial content
What parents can do to teach kids about money without turning it into another lecture
Why allowances, real-life practice, and even small money mistakes can be powerful teachers
Rishi's simple approach to index funds, automation, and long-term investing
Why financial education should begin before high school
His take on Roth IRAs, 529 plans, Trump accounts, taxes, and estate planning
What a 16-year-old financial educator wants late starters to remember about beginning today
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
📌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.
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
📌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.
☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"
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
⚠️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.
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
📌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.
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
📌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.
Be sure to follow the show or subscribe to the channel on YouTube, so you don't miss it!
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
📌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.
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
📌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.
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
📌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.
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
📌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.
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