Catching Up to FI

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 Erin Talks Money LinkedIn Root Financial Erin's forthcoming retirement-spending book (estimated release: December, 2027) Social Security Online Account   . ⏰ Related Episodes 61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237 Social Security Made Simple | Mike Piper | 054   . 📌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.

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.

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 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.

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 . This is the first part of a 2-part episode. Be sure to subscribe to the channel and catch part 2 next week (10/4/26). . === 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  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.    

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.