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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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- 2 weeks ago1h 24m
4 Phases of Retirement Explained: The Realities of Each May Surprise You! | Dana Anspach | 244
Dana Anspach, CFP® and founder of Sensible Money, returns to explain why retirement isn't one long, predictable chapter, it's a series of distinct phases with different financial and emotional needs. Using the framework from her new book, Living Off Your Acorns, Dana walks Bill and Jackie through the pre-go, go-go, slow-go, and no-go years. This episode covers Dana's four phases of retirement: pre-go, go-go, slow-go, and no-go Why retirement planning should begin at least five years before leaving work The emotional transition from receiving a paycheck to living off your accumulated "acorns" A three-part pre-retirement checklist: cash flow, stress testing, and planning your time Why social connections and identity need as much planning as the financial side Fundedness ratios, the Critical Path, and alternatives to relying only on a safe withdrawal rate Special considerations for people retiring early, including healthcare and longer time horizons Mortgages, HELOCs, pledged asset lines, and when debt can still be useful in retirement How spending naturally changes during the slow-go years Fraud, cognitive decline, powers of attorney, and preparing for someone else to eventually help manage your finances . === 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=== NEW! Mama Are We Poor? "Mama Are We Poor?" is a new childrens book by co-host, Dr. Bill Yount and past guest, Monica Scudieri. They teamed up after the interview on episode #120 (https://youtu.be/oerxEJYrTdM?si=vt2aZSE2wgKVGeIn) in 2025. Monica shared a sweet moment she had with her son and he asked here the question "Mama are we poor". Almost two years later, they collaborated to create a heartfelt, beautifully illustrated picture book that helps parents and caregivers open up conversations about money, financial stress, and family resilience with young readers. Through a child's eyes, kids learn that worth isn't measured in dollars-and that love, stability, and gratitude can carry a family through hard times. 📕 Get Your Copy .
- 3 weeks ago1h 4m
How to Make Financial Mistakes and Still FIRE! | Doug Cunnington of Mile High FI Podcast | 243
What if getting to FI has less to do with avoiding mistakes and more to do with surviving them without setting too much money on fire? Bill joins Doug Cunnington of Mile High FI for a refreshingly imperfect look at the financial decisions they wish they could redo. Between them: credit card debt, lifestyle inflation, whole life insurance, expensive advisors, an underwater dream house, a foreclosure, selling stocks at exactly the wrong time, and the very FI-specific problem of eventually becoming too good at saving. But this isn't just a financial confession booth. Bill and Doug compare what actually helped them recover, why "good enough" beats perfect, and how both still reached FI despite getting plenty wrong along the way. This episode covers Why financial mistakes are often part of the learning process rather than proof you've failed Bill's late-start wake-up at 50 and Doug's accidental path into the FI community How missing financial education can turn needs, wants, and lifestyle inflation upside down Whole life insurance, expensive advisors, and the opportunity cost of bad financial products When DIY investing works—and when professional
- Oct 11, 20261h 4m
Debunking the Biggest Retirement Fear Tactics With Erin Talks Money | Erin Moriarity | 242
Erin Moriarity, the plain-English force behind Erin Talks Money, joins Bill and Jackie to unpack why retirement planning gets easier when we stop worshipping giant portfolio numbers and start thinking in income, spending, and real life. Erin traces her path from buying Campbell Soup stock at eight with her investing grandmother to earning the best 34 cents of her life on YouTube. She eventually grew the massive financial education platform we know today. Then the conversation moves into the stuff retirees actually worry about: whether late starters can still catch up, how Social Security may change, why the 4% rule gets mangled in headlines, and why lifelong savers often struggle more with spending than saving. This episode covers How Erin Talks Money grew from a struggling YouTube experiment into a major financial education platform The radically different money personalities in Erin's family and how they shaped her approach to finance Why painful childhood experiences with money made financial independence and control so important to Erin Why late starters can still make enormous progress with a 10–15 year runway Why retirement income can feel more meaningful than staring at a large portfolio balance The evolution of Erin's content from budgeting and FIRE to retirement income and decumulation Social Security reform, the wage base, the "donut hole," and why no single fix solves everything Why phased retirement can strengthen both your finances and your quality of life The psychological challenge of switching from lifelong saver to confident spender Why scary headlines about Social Security, long-term care, inflation, and retirement spending often need more context . === 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 Erin Moriarity website Erin Talks Money Youtube <span style= "color: #0f0f0f; font-family: Roboto, Arial, sans-serif; font-size: 16px; font-style: normal; font-variant-ligatures: normal; font-variant-caps: normal; font-weight: 400; letter-spacin
- Oct 7, 202645 min
Small Money Ideas That Lead To Bigger Conversations | AICPA Crossover | 241
What if the smartest financial planning move isn't a 100-page plan, but one question that makes you stop and say, "Wait... I can do that?" In this crossover with the AICPA Personal Financial Planning Podcast, Jackie puts on her professional hat for two conversations about the small ideas that can create much bigger financial wins. First, she and host Cary Sinnett unpack five high-impact planning opportunities involving 529s, 72(t)s, HSAs, charitable giving, and forgotten retirement accounts. Then they zoom out to the bigger question: why financial literacy, not products or strategies, is the foundation for better decisions and greater financial independence. Jackie also tackles FIRE stereotypes, the shame late starters often carry, and the "superpowers" that can emerge once people stop beating themselves up and start asking better questions. This episode covers Five small financial-planning conversations that can uncover much bigger opportunities New and expanded ways families may be able to use 529 plans How 72(t) distributions can help some people access retirement money before age 59½ Why HSAs can be much more than simple medical spending accounts Charitable-giving strategies ranging from smaller deductions to donor-advised funds How to search for forgotten 401(k)s and other unclaimed assets Why financial literacy should come before complicated products and strategies How money beliefs and behavior can overpower mathematically "correct" decisions Why FIRE doesn't require copying someone else's lifestyle The late-starter journey from shame and guilt to action, confidence, and financial "superpowers" . === 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 AICPA Personal Financial Planning Podcast Retirement Savings Lost and Found Database National Association of State Treasurers (Missing Money) . 📌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.
- Oct 4, 20261h 16m
3 Non-Employer Health Insurance Case Studies: More Choices Than You Thought | Lyndia Cunningham (Part 2) | 240
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 slashed his monthly premiums by thousands. Then listener Brooke explores whether health insurance really needs to be the golden handcuffs keeping her in a W-2 job. This episode covers How Jackie could have evaluated healthcare before retiring at 49 Why retirement timing and modified adjusted gross income can dramatically affect ACA costs Bronze versus Silver plans, cost-sharing reductions, and HSA eligibility How to make sure an ACA plan actually includes the doctors you want to keep What Jackie ultimately paid for healthcare after retiring Why Bill chose Farm Bureau coverage instead of the ACA marketplace How medical underwriting and non-ACA major medical plans work Health insurance options for adult children aging off a family plan How association plans, college health plans, and HSAs can expand your choices Whether healthcare really needs to keep Brooke (or anyone else) tied to a job . This is the second part of a 2-part episode. Be sure to subscribe the show and catch part 1 (episode 239) from 9/27/26. . === 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 Move Health Move Health YouTube Health Insurance for Early Retirees ACA Health Insurance Marketplace . ⏰ Related Episodes How to Get Health Insurance When You Retire Early | Lyndia Cunningham (Part 1) | 239 Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98 <a href= "https://directory.libsyn.com/episode/index/show/965474e8-0ed6-4527-a513-26a270f7ae31/id/33213567" target="_b
- Sep 27, 20261h 26m
How to Get Health Insurance When You Retire Early (Part 1) | Lyndia Cunningham | 239
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 === 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 Move Health Move Health YouTube ACA Health Insurance Marketplace . ⏰ Related Episodes Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98 Maximizing HSAs Part 2: Devising Drawdowns, Badass Scenarios, Listener Questions | Jeff York | 99 . 📌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.
- Sep 20, 20261h 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.
- Sep 13, 20261h 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
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