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Catching Up to FI: Daily Summaries Delivered
by Bill Yount & Jackie Cummings Koski
A mindset, money, and life podcast for late starters catching up to Financial Independence.
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- Today1h 35m
The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238
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 . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW CarEdge (Research, Dealer Ratings, Car-buying Service) CarEdge Podcast CarEdge YouTube CarEdge Live YouTube Shady Car Dealers are Done! Fair Pricing Summit DC Zach's AI Summit Talk Ray's letters to his late wife Suzanne . 📌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.
- 1 weeks ago1h 7m
61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237
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 . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 📺 Watch & Subscribe to our YouTube Channel 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW 📙The Forever Paycheck Her Money Her Money Podcast Guaranteed Income: A License to Spend (A research paper by David Blanchett and Michael Finke) . ⏰ Related Episodes Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233 How To Build Your Own Paycheck: From Saver to Spender | Fritz Gilbert & Dana Anspach | 171 . 📌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 profes
- 1 weeks ago1h 3m
The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236
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 . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW ChooseFI https://choosefi.com ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 . ⚠️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.
- 2 weeks ago1h 25m
How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie's Real Numbers | Bill Stecker (Part 2) | 235
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. . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW 🌐72tcalc.com Website Free consultation with Bill Stecker's Firm (The Marble Group) email: themarblegroup@wispertel.net Phone: (312) 361-0221 Official IRS Tax Code 72(t) IRS Notice 2022-6 (sets a new floor interest rate of 5% for calculating 72(t) distributions) 72(t) Calculators 72tCalc FI Tax Guy 72(t) using Google Sheet Dinkytown <a href="https:/
- 3 weeks ago56 min
Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty (Part1) | Bill Stecker | 233
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). . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW 🌐72tcalc.com Website Free consultation with Bill Stecker's Firm (The Marble Group) email: themarblegroup@wispertel.net Phone: (312) 361-0221 72(t) Calculators 72tCalc FI Tax Guy 72(t) using Google Sheet Dinkytown CalcXML UngrindFi <a href= "https://www.irs.gov
- 3 weeks ago8 min
Vanguard Acquires Altruist: Why Fidelity & Schwab Better Look Out! | Barry Ritholtz | Bonus
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! Be sure to follow the show or subscribe to the channel on YouTube, so you don't miss it!" === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Official Vanguard announcement – Vanguard to Acquire Altruist, Expanding the Reach and Impact of Financial Advice View the August 26, 2026 Vanguard announcement Vanguard FAQ – Vanguard to Acquire Altruist <a href= "https://corporate.vanguard.com/cont
- 4 weeks ago1h 41m
Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233
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 . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Tenon Financial website Retirement Planning Education website Andy's podcast Andy's Youtube Andy's LinkedIn Retirement Savings Lost and Found Database Pension Benefit Guaranty Corporation (PBGC) Dinkytown.net- Pension vs. Lump Sum Payout Calculator Estimate Immediate Annuities . ⏰ Related Episodes How K-12 Teachers Can Beat the B
- Aug 19, 202630 min
The Truth Behind Raising A Teenage Money Whiz (From The Parents Of Rishi Vamdatt) | Renu & Raag Vamdatt | 232
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 . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Easy Peasy Finance Easy Peasy Finance YouTube 📕Easy Peasy Money Coverage on CBS News Kiplinger Article I Will Teach You To Be Rich (Ramit Sethi) . ⏰ Related Episodes This 16-Year-Old CFP Exam Passer Is Making Personal Finance "
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