Explore every episode of the podcast Catching Up to FI
| Title | Pub. Date | Duration | |
|---|---|---|---|
| The Ultimate Playbook On What "Not" To Do When The Stock Market Drops | Barry Ritholtz | 247 | 08 nov. 2026 | 01:43:12 | |
Legendary investor Barry Ritholtz joins the show for a wide-ranging tour through the experiences, mistakes, and behavioral quirks that shaped his investing philosophy and his book, "How Not to Invest". He tells us why becoming a better investor has less to do with being brilliant and more to do with simply being less stupid. The lesson? You don't have to predict markets, outsmart Wall Street, or find the next 100-bagger. Build a plan, let compounding work, and stop stealing returns from your future self. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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 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. . F.I.R.E. For Dummies Co-host Jackie Cummings Koski, CFP®, AFC® is 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. 📕 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 . ⏰ Related Episodes Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225 The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 Forget the Corporate Ladder, Here's How to Climb 'The Wealth Ladder' | Nick Maggiulli | 159 . CHAPTERS: 0:00 Intro- Who Barry Ritholtz was before Wall Street 3:00 Money as a tool, childhood jobs, cars, and buying experiences 8:00 Horses, bartering for opportunity, and an unconventional education 12:00 Discovering trading and behavioral finance 18:00 Bernie Madoff, statistics, fraud, and the compounding he stole 24:00 Charlie Munger, Charlie Ellis, and avoiding unforced errors 31:00 Why passive investing wins the math 34:00 Sharks, crashes and bad numbers 41:00 Process over outcome 49:00 The unbelievable power of compounding 59:00 Custodians, Altruist, and why your advisor shouldn't hold your money 1:16:00 Vanguard and Altruist 1:22:00 Barry's mentors, favorite books, and advice to his younger self . 📌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. | |||
| A Closer Look At Target-Date Funds: You Won't Believe What We Found! | David Brown & Shaun Davies | 246 | 01 nov. 2026 | 01:27:16 | |
Finance professors Shaun Davies, PhD, CFA and David Brown, PhD join the show to give us a look under the hood of target-date funds (TDFs). What they found may surprise you! Their research reveals enormous differences in fees, risk, glide paths, active management, and performance; even among funds carrying the exact same retirement year. But this isn't a target-date-fund takedown. TDFs have helped millions of people get invested, stay invested, and avoid some bad behavioral decisions. The real question is whether yours is actually doing what you think it is. Bill also brings on Jesse Cramer of Personal Finance for Long-Term Investors to join this important conversation. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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 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. . F.I.R.E. For Dummies Co-host Jackie Cummings Koski, CFP®, AFC® is 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. 📕 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
Off Target: On the Underperformance of Target-Date Funds Glidepath Financial (compare target-date funds) . ⏰ Related Episodes The Biggest Retirement Mistake: Over Saving and Under Living | Rachael Camp & Jesse Cramer | 198 Space Telescopes, Sunflowers, and Financial Gardening | Jesse Cramer | 105 How to Bake a Cake: An Asset Allocation Mashup | Rick Ferri & Paul Merriman | 134
. CHAPTERS: 0:00 Intro 4:00 How target-date funds became America's default 7:00 What's really under the hood 10:00 The 1% problem 14:00 Risk differences 18:00 How to choose a TDF 27:00 Human capital as a bond 35:00 The ten building blocks 38:00 Do we even need bonds? 44:00 The behavioral case for TDFs 56:00 Glidepath ratings
. 📌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. | |||
| Financial Freedom Beyond Spreadsheets: Writing Books and Songs on FIRE | The Donegans & Monica Scudieri | 245 | 28 oct. 2026 | 01:16:00 | |
Alan and Katie Donegan and Monica Scudieri join Bill and Jackie to explore what happens when financial survival mode finally loosens its grip and creative bandwidth comes roaring back. They talk imposter syndrome, discomfort, perfectionism, public speaking, writing books, making music, and why FI can turn passive consumers into active creators. They also announce the world debut of the new Catching Up to FI theme song and the new book "Mama Are We Poor?" authored by Bill and Monica. This episode covers
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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. . F.I.R.E. For Dummies Co-host Jackie Cummings Koski, CFP®, AFC® is 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. 📕 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 Grab Your Slice (Monica Scudieri)
. ⏰ Related Episodes "Mama, Are We Poor?": A Single Mom's Millionaire Mindset | Monica Scudieri | 120 Not Just Another Album, It's A Money Revolution! | Alan & Katie Donegan | 129 Indiana Jones and an Extraordinary Life with the Donegans | Alan and Katie Donegan | 079
. 📌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. | |||
| 4 Phases of Retirement Explained: The Realities of Each May Surprise You! | Dana Anspach | 244 | 25 oct. 2026 | 01:24:44 | |
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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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. . F.I.R.E. For Dummies Co-host Jackie Cummings Koski, CFP®, AFC® is 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. 📕 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
. ⏰ Related Episodes 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 professional before making important decisions. | |||
| How to Make Financial Mistakes and Still FIRE! | Doug Cunnington of Mile High FI Podcast | 243 | 18 oct. 2026 | 01:04:02 | |
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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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
. ⏰ Related Episodes The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236 The Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211
. 📌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. | |||
| Debunking the Biggest Retirement Fear Tactics With Erin Talks Money | Erin Moriarity | 242 | 11 oct. 2026 | 01:04:02 | |
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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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'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. | |||
| Small Money Ideas That Lead To Bigger Conversations | AICPA Crossover | 241 | 07 oct. 2026 | 00:45:55 | |
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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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. | |||
| 3 Non-Employer Health Insurance Case Studies: More Choices Than You Thought | Lyndia Cunningham (Part 2) | 240 | 04 oct. 2026 | 01:16:06 | |
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
. 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 === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 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. | |||
| How to Get Health Insurance When You Retire Early | Lyndia Cunningham(Part 1) | 239 | 27 sept. 2026 | 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
. 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 === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 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.
| |||
| The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238 | 20 sept. 2026 | 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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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) Shady Car Dealers are Done! Fair Pricing Summit DC 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. | |||
| 61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237 | 13 sept. 2026 | 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
. === SUPPORT THE SHOW === 📺 Watch & Subscribe to our YouTube Channel 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 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 professional before making important decisions. | |||
| The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236 | 09 sept. 2026 | 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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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
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. | |||
| How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie's Real #s | Bill Stecker (Part 2) | 235 | 06 sept. 2026 | 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
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 === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Free consultation with Bill Stecker's Firm (The Marble Group)
IRS Notice 2022-6 (sets a new floor interest rate of 5% for calculating 72(t) distributions) 72(t) Calculators
. ⏰ Related Episodes 72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131 Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133
. 📌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. | |||
| Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty | Bill Stecker (Part1) | 234 | 30 août 2026 | 00:56:05 | |
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
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 === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Free consultation with Bill Stecker's Firm (The Marble Group)
72(t) Calculators
. ⏰ Related Episodes 72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131 Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133
. 📌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. | |||
| Vanguard Acquires Altruist: Why Fidelity & Schwab Better Look Out! | Barry Ritholtz | Bonus | 27 août 2026 | 00:08:10 | |
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
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 === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Vanguard FAQ – Vanguard to Acquire Altruist Altruist's official acquisition announcement Ritholtz Wealth How Not to Invest . 📌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.
| |||
| Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233 | 23 août 2026 | 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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Retirement Planning Education website Retirement Savings Lost and Found Database Pension Benefit Guaranty Corporation (PBGC) Dinkytown.net- Pension vs. Lump Sum Payout Calculator
. ⏰ Related Episodes How K-12 Teachers Can Beat the Broken 403(b) System | Dan Otter & Scott Dauenhauer | 226 Retired Before 50: A Look at Her Real Finances, Numbers & Strategy | Andy Panko Crossover | 186 Retirement Planning Tips | Andy Panko | 063
. 📌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 Truth Behind Raising A Teenage Money Whiz (From The Parents Of Rishi Vamdatt) | Renu & Raag Vamdatt | 232 | 19 août 2026 | 00:30:11 | |
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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 I Will Teach You To Be Rich (Ramit Sethi)
. ⏰ Related Episodes This 16-Year-Old CFP Exam Passer Is Making Personal Finance "Easy Peasy" | Rishi Vamdatt | 231 Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 Money Scripts: Don't Get Scrooged! | Brad Klontz | 175
. 📌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.
| |||
| This 16-Year-Old CFP Exam Passer Is Making Personal Finance "Easy Peasy" | Rishi Vamdatt | 231 | 16 août 2026 | 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
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 I Will Teach You To Be Rich (Ramit Sethi)
. ⏰ Related Episodes 20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072
. 📌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.
| |||
| More Bonds, James, Bonds: Rethinking Your BND Strategy (Part 2) | Frank Vasquez | Episode 230 | 09 août 2026 | 00:50:45 | |
This is Part 2 of a 2-part Episode. Be sure to catch Part 1 that aired last week (August 2nd). What if the safest-looking retirement portfolio is actually protecting you from the wrong disaster? In part two of Bill's bond marathon with Frank Vasquez, the conversation moves from Bond 101 into the question that really matters: what role should fixed income play once you stop accumulating and start living from your portfolio? Frank explains why bonds should be chosen for a specific job, why a total bond fund may be trying to do too many things at once, and why retirement planning should prepare for a bad decade. The ultimate takeaway is reassuring: bonds are complicated, but most people probably only need one or two bond funds chosen with an actual purpose.
This episode covers
=== SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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
⏰ Related Episodes Are Bonds Dead?: Fixed Income Fundamentals (Part 1) | Frank Vasquez | Episode 229 The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 Mr 4% is now Mr 5% | Bill Bengen | 111
📌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.
| |||
| Are Bonds Dead?: Fixed Income Fundamentals (Part 1) | Frank Vasquez | Episode 229 | 02 août 2026 | 01:02:23 | |
What if bonds aren't dead at all—and we've just spent the last decade misunderstanding what job they were hired to do? Bill welcomes back Frank Vasquez, the hotdog-named engineer-lawyer-DIY investor behind Risk Parity Radio, for part one of a lively fixed-income deep dive. Starting with the basics, Frank explains what a bond actually is, why owning one makes you the lender rather than the shareholder, and how bonds can provide income, stability, or diversification depending on the type and duration. They work through the very real risks hiding behind the phrase "safe investment." Along the way, they visit the Witch of Wall Street, Frank's crystal balls, and the illusion that individual bonds never lose value just because nobody checks the price every day. This is Part 1 of a 2-part Episode. Be sure to catch Part 2 next week (August 9th). This episode covers
=== SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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
⏰ Related Episodes Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225 I Love Goooooold?! :) | Frank Vasquez | 184
📌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.
| |||
| How to Retire at 40: Her Debt-Crushing Path to Financial Independence | Bernadette Joy | 228 | 26 juil. 2026 | 01:10:36 | |
What if crushing your money goals has less to do with finding the perfect formula—and more to do with getting lovingly bullied into taking action today? Bill and Jackie sit down with Bernadette Joy, a first-generation Filipino American who paid off $300,000 of debt in three years, reached her first million, and eventually built a multimillion-dollar portfolio. Bernadette also explains why she believes traditional financial literacy is dead, walks through her C-R-U-S-H framework, and reveals why the final "H" evolved from hustle to healing your money wounds. This episode covers
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Crush Your Money Goals Website Bernadette Joy's free retirement checklist and newsletter
⏰ Related Episodes Live Talk from the Plutus Awards: Bill's Inspiring Message to Late Starters
. 📌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.
| |||
| Bonus: Is Your School's 403(b) On The Naughty List? Here's What To Do About It | Dan Otter | 227 | 22 juil. 2026 | 00:31:37 | |
What if the smartest way to fix teacher retirement is not patching the broken 403(b) machine, but quietly building an exit ramp to something better? In this bonus conversation, Bill, Jackie, and Dan Otter keep pulling the thread on the teacher-retirement mess and land on a surprisingly practical answer: the 457(b) may be the cleaner, simpler, more flexible plan that schools should be leaning into. Dan also highlights the new audio series Learned by Being Burned, Carl Fisch's 50-state teacher-retirement books, and several states that are getting it right. They end with a reminder that fixing a broken system starts with people who care enough to push back. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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===
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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 457bwiser https://457bwiser.org/ Learned by Being Burned (Special) Podcast Series) Man with the (Better Retirement) Plan (#262) 403bwise and 457bwiser Facebook Group Request a Dan and Scott Presentation . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 The Wealthy Custodian Part 2: From Janitor to Millionaire | Jeff York | 076 The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072
. 📌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.
| |||
| How K-12 Teachers Can Beat the Broken 403(b) System | Dan Otter & Scott Dauenhauer | 226 | 19 juil. 2026 | 01:12:43 | |
What if the most dangerous thing in a teacher's retirement plan isn't market volatility, it's the nice guy with free sandwiches and a terrible annuity contract? Jackie and Bill are joined by Dan Otter and Scott Dauenhauer of 403bwise, the duo who have spent decades exposing how badly K-12 educators get treated in the 403(b) world. What starts as a conversation about confusing vendor lists and a messy system, quickly turns into something bigger. This episode covers
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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===
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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===
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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 457bwiser https://457bwiser.org/ Learned by Being Burned (Special) Podcast Series) Man with the (Better Retirement) Plan (#262) 403bwise and 457bwiser Facebook Group Request a Dan and Scott Presentation . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 The Wealthy Custodian Part 2: From Janitor to Millionaire | Jeff York | 076 The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072 . 📌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. | |||
| Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225 | 12 juil. 2026 | 01:11:07 | |
What if the biggest risk in your portfolio isn't a crash, a recession, or even inflation, but the very human urge to believe that whatever just worked will work forever? Bill and Jackie sit down with Ben Carlson of A Wealth of Common Sense and Animal Spirits for a market-history masterclass that somehow manages to be equal parts calming, nerdy, and deeply practical. This one is for anyone who's ever stared at their portfolio, read one scary headline too many, and wondered whether simplicity still works. Ben's answer is basically yes—but only if you understand the risks, respect your own behavior, and build a portfolio you can actually stick with. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Risk and Reward: How to handle market volatility and build long-term wealth . ⏰ Related Episodes The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 Hanging On In a Yo-Yo Economy | Sam Stovall | 147 How to Bake a Cake: An Asset Allocation Mashup | Rick Ferri & Paul Merriman | 134 "The Risk Parity Paradox" an Exercise in Simple Complexity? | Frank Vasquez | 124
. 📌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. | |||
| You Hit The Number, Now What? | Childfree Life By Design Crossover | 224 | 08 juil. 2026 | 00:44:24 | |
What if "legacy" looks completely different when there are no kids in the picture and that difference actually unlocks a freer, more intentional version of FI? In this thoughtful crossover between Childfree Life by Design and Catching Up to FI, Dr. Jay and Bill sit down for the kind of conversation most money media skips: what happens after you hit the number and realize the bigger question is no longer "Can I retire?" but "What am I retiring to?" It's philosophical, personal, a little messy in the best way, and exactly the kind of episode that reminds listeners that FI is not the finish line. It's the moment when the real design work begins. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Childfree Wealth https://childfreewealth.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. | |||
| FIlanthropy: Radical Impact Giving Without Risking Your Retirement | Rebecca Herbst | 223 | 05 juil. 2026 | 01:30:35 | |
Bill jumps into a last-minute solo conversation with Rebecca Herbst of Yield and Spread for a surprisingly energizing deep dive into generosity, guilt, and what happens after the finish line of financial independence. Rebecca shares how hitting FI at 32 did not lead to endless victory-lap bliss so much as an identity jolt: if money is a tool, then what is it actually for? This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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
⏰ Related Episodes Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200 Contrarian Tax Planning Tips | Cody Garrett & Sean Mullaney | 179 . 📌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. | |||
| Unbanked, Buried In Payday Loans & A 500 Credit Score: This Late-starter Overcame It All! | Afra Smith | 222 | 28 juin 2026 | 00:26:31 | |
What if the person inspiring the room didn't come from a polished finance background at all, but from payday loans, being unbanked, a credit score in the 500s, and the kind of rock bottom most FI stories rarely admit out loud? In this on-location episode from Madison, WI, Jackie sits down with Afra Smith, founder of The Melanin Project and creator of the Wealth Empowerment Conference, for a conversation that is as honest as it gets. She's a late-starter and shares how depression, financial chaos, and a painful career setback forced her to finally confront what wasn't working. She shares how one financial coach, one budget, and one decision to stop waiting for someone else to rescue her changed the direction of her life. From there, she built something much bigger than a comeback story. It's now a growing movement centered on financial wellness, lived experience, and giving people the tools to rebuild from where they actually are. Her raw truth is proof that your hardest chapter does not have to be your final one. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 Madison Gas and Electric Company
⏰ Related Episodes From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007 We Found Them! Past Guests At The Women of FI Weekend | Kim H. and Lisa B. | 218
. 📌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. | |||
| Intergenerational Wealth: Strategies to Help Your Family NOW (Not Later) | Allen Mueller | 221 | 21 juin 2026 | 01:03:53 | |
What if the smartest legacy move isn't leaving your kids a pile of money someday, but using your wealth right now to help them buy time, build habits, and change their future while you're still here to watch it happen? We sit down with Allen Mueller of 7 Saturdays Financial for a practical, deeply useful conversation about gifting to family with intention. The thread running through all of it is simple: money is not just for accumulating. It's for strengthening the people and values you care about most. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
📕 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 .
Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193
. 📌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. | |||
| Not So Big Life Design: The Architecture of Wealth | Sarah Susanka | 220 | 14 juin 2026 | 01:03:20 | |
What if the smartest move on your road to FI isn't buying a bigger house, but shrinking the footprint, clearing the clutter, and finally designing a life that actually fits? In this episode, we sit down with Sarah Susanka, the architect behind the bestselling "Not So Big House" movement. We talk about what happens when you stop building for appearances and start building for how you really live. Sarah shares how growing up in England, then landing in car-centric suburban Los Angeles made her question why Americans kept buying "hamburger bun but no hamburger" houses full of unused rooms.
This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
👉🏽 https://a.co/d/01umGgeh (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 Not So Big Design Principles for House & Life with Sarah Susanka 📗The Not So Big House: A Blueprint for the Way We Really Live
.
How Clutter Steals Your Time (And How to Get It Back) | Rose Lounsbury | 188
. 📌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. | |||
| Shocking Truths About Women's Financial History You Need to Know | Our Sheconomy Gameshow | 219 | 10 juin 2026 | 01:36:29 | |
What if the fastest way to understand women's financial power isn't another lecture, but a trivia game that quietly reveals how recent, fragile, and still unfinished so much of women's economic progress really is? In this special "Sheconomy" quiz-show episode, Jackie and Bill join Janine Firpo and financial planner Sarah-Catherine Gutierrez for a lively game show. They move from Equal Pay Day and credit-card rights to why women often outperform men as investors, why female-led companies and firms still get shut out, and what could happen if women intentionally shifted even a slice of their wealth toward their values. The tone is playful, but the message is serious: money is power, and women stepping into that power changes families, businesses, markets, and maybe the whole economy. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
👉🏽 https://a.co/d/01umGgeh (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 . Vote Your Money: Values Aligned Investing | Janine Firpo | 139 The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016
. 📌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. | |||
| We Found Them! Past Guests At The Women of FI Weekend | Kim H. and Lisa B. | 218 | 07 juin 2026 | 00:30:47 | |
What happens when women in the financial independence community finally get a room of their own and use it not just to talk numbers, but to unpack the invisible stuff they've been carrying for years? In this on-location episode, Jackie takes us inside the Women of FI annual weekend in Maryland. This was a rare women-centered FI retreat that blends case studies, life design, laughter, and vulnerability. She catches up with two familiar voices from past episodes, Kim Hunter-Borst and Lisa B. to hear what retirement, sabbaticals, and post-FI life actually look like in motion, not just on paper. Other attendees also share why a women-only space hits differently: less posturing, more honesty, more room to talk about emotional labor, caregiving, identity, and the inner work that often gets skipped in mixed-money spaces. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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.
👉🏽 https://a.co/d/01umGgeh (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
WE Wealth Collective Facebook Group EconoMe Conference https://economeconference.com . Drowning in Debt at 48, Retired at 58: Here's How She Did It! | Kim Hunter-Borst | 181 Case Study: The Real Numbers That Told Her She Could Quit her Job, Now! | Lisa B | 161 The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016
. 📌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. | |||
| Why "One More Year" Isn't Always a Mistake | Bill, Jackie, Patrick | 217 | 31 mai 2026 | 01:01:02 | |
What if "one more year" isn't a failure of courage. What if it's a messy, human, sometimes wise transition between the life you built and the life you're finally ready to choose? In this spontaneous, unusually raw episode, Bill, Jackie, and Patrick crack open the emotional side of financial independence. They go beyond the surface of the hesitation, identity shift, grief, relief, and weird freedom that can show up when the math says you're done but your nervous system is still catching up. Bill shares what it feels like to downshift after unexpectedly reaching FI, why he's enjoying work more now that he doesn't need it, and how a heartbreaking night in the ER sharpened his thinking about what really counts. Jackie reflects on her own two-year "one more year" phase and why she no longer sees it as a mistake so much as a cushion she needed. Patrick adds the planner's lens: if a choice still serves your life, it may not be "one more year" syndrome at all. This episode is a heartfelt reminder that the real work isn't just reaching the number but learning how to let go when the time comes. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup
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 Catching Up to FI Facebook Community . Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007 Our Team is Growing: Welcome Patrick! | Patrick McDonnal | 136 The Three Kinder Questions (Part 2) | George Kinder | 141 The pURPOSE Code | Jordan Grumet | 115 Hard & Soft Sides of Retirement | Fritz Gilbert | 019 .
| |||
| How to Retire Sooner and Spend More: Risk-Based Guardrails Explained | Aubrey Williams | 216 | 24 mai 2026 | 00:51:38 | |
What if the real danger in retirement isn't running out of money, but spending so cautiously that you accidentally work too long, live too small, and die with a portfolio that never got a chance to do its job? In part two with Aubrey Williams, we go deeper into the "fog of FI" (that weird, anxious place where the spreadsheet says you're free, but your nervous system absolutely does not believe it). This episode covers:
. S U P P O R T T H E S H O W 📩 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=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup
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 Aubrey's EconoMe Talk (2026): Coming soon! Open Source Guardrails Simulation (Roger Cost) . ⏰ Related Episodes Part 1: Why Your Brain is Hardwired to Keep You Working (and How to Fix It) | Aubrey Williams | 214 A Richer Retirement: The 4.7% Rule | Bill Bengen | 169 Sequence of Returns Risk: What Every Retiree Needs to Know | Karsten Jeske | 106
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! .
| |||
| Why You Should Stop Beating Yourself Up for Starting Late | "How To Money" Crossover | 215 | 20 mai 2026 | 01:03:26 | |
What if the biggest difference between someone who starts at 22 and someone who starts at 50 isn't intelligence or income, but simply the moment they finally decide, nobody's coming to save me? In this crossover episode, Bill joins Joel on "How to Money" to tell the brutally honest and surprisingly hopeful truth. He shares his story of becoming financially independent after a 20-year sleepwalk through lifestyle inflation, doctor money mistakes, and zero real financial plan. It's candid, practical, and exactly the kind of episode that makes you stop saying "I'm behind" and start asking "What's my next move?" This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 🆕Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup
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 . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| Why Your Brain is Hardwired to Keep You Working (and How to Fix It) | Aubrey Williams | 214 | 17 mai 2026 | 00:59:21 | |
What if the thing keeping you from Financial Independence (FI) isn't your income, your portfolio, or your math. It's probably the quiet belief that you still need "one more year" when you actually don't. Our guest on this episode is Aubrey Williams, a former particle physicist, radar-tech leader, debt-slayer, and now advice-only financial planner. In this conversation, he flips some of the FI community's favorite assumptions on their head. This is the first of a 2-part episode with Aubrey so be sure to follow the podcast to be notified of the second part of this fascinating conversation. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup
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 Aubrey's EconoMe Talk (2026): Coming soon! . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Enoughness: Your Life or Your Money | Vicki Robin | 95 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| Your FIRE Plan is Screwed Without An Estate Plan! | Allison Harrison | 213 | 10 mai 2026 | 01:09:17 | |
You've worked twice as hard to catch up on your path to financial independence, so why leave your legacy to chance? To help keep your FI plan from going up in smoke we sit down with estate planning and small business attorney, Allison Harrison. It's a fast, funny and slightly alarming deep dive into estate planning for normal people who assume they're "not rich enough" to need one. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== STUDENT LOAN PLANNER Big changes with student loans in 2026! Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup
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 Allison's EconoMe Talk (2026) -Coming soon- Free Estate Planning Guides, Infographics and More (no email required) Safe Sendoff (Legal Planning for Young Adults) . ⏰ Related Episodes Attorney Spilling all the Legal Tea on Estate Planning | Jenny Rozelle | 121 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| Borderless FI: Starting Over At 37 After Divorce | Bronwyn Candish | 212 | 03 mai 2026 | 00:57:28 | |
What do you do when your accountant brain knows the numbers, your life blows up anyway, and the answer turns out to be halfway around the world in a weird little movement called FIRE? We head to New Zealand to talk with Bronwyn Candish, a chartered accountant, community builder, and one of the clearest Kiwi voices in financial independence movement. She talks to us about starting over after divorce, rebuilding from the middle, and discovering that "doing money right" has a lot less to do with credentials than with courage, alignment, and actually taking action. This episode covers:
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 🆕Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup
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 KiwiFI and Black FI Day website PocketSmith Personal Finance Software . ⏰ Related Episodes Borderless FI: The Happy KiwiSaver | Ruth Henderson | 165 Borderless FI: Australian Paramedic Healing Her Own Trauma | Tasch Rogers | 143 Indiana Jones and an Extraordinary Life with the Donegans | Alan and Katie Donegan | 079 Borderless FI: Thunder Down Under | Late Starter Fire | 004 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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 Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211 | 29 avr. 2026 | 01:04:30 | |
What if the biggest shift in your FI journey isn't hitting the number—but finally realizing you need a life plan, a tax plan, and maybe even a fiduciary teammate to help you spend it? Bill steps into the guest chair with Morningstar's Christine Benz for a thoughtful, surprisingly candid conversation about going from financially illiterate "rich doctor syndrome" to fully conscious wealth stewardship. He walks through the entire arc. But this episode goes deeper than a standard "how I retired" story. This episode covers: ➡️ Bill's path from paycheck-to-paycheck physician to financially independent late starter ➡️ How childhood money scripts and "rich doctor syndrome" shaped his early financial mistakes ➡️ Why the Great Financial Crisis and burnout became a wake-up call ➡️ What changed when Bill moved from financial consumer to conscious wealth steward ➡️ Why accumulation can be DIY—but decumulation often gets more complex ➡️ How Bill searched for a fiduciary, flat-fee, life-planning-oriented advisor ➡️ Why risk parity appealed to him for retirement and sequence-of-returns protection ➡️ The role of a modern advisor as behavioral buffer, tax strategist, and cognitive-risk safeguard ➡️ Why FI gave Bill leverage to redesign work instead of just quit cold turkey ➡️ How Bill is thinking about legacy, living giving, and helping the next generation now, not just later . === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial. 👉🏼 Be sure to use this link to get started: Go.boldin.com/catchingup
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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 . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197 Retirement Remix: Crafting Financial Futures with Purpose | Christine Benz | 117 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| Hot Takes & Money Debates: Social Security at 62, New Trump Accounts, & more! | Bill & Jackie | 210 | 26 avr. 2026 | 01:04:51 | |
What happens when the two co-hosts stop being polite, start being honest, and publicly debate the money moves they still don't agree on? We throw open the doors on four of our favorite friction points:
The fun here is that neither of us is playing a character. Jackie comes in swinging for simplicity, practical execution, and "please stop overcomplicating this for normal people," while Bill makes the case for curiosity, customization, and not sleepwalking through important financial choices. Along the way, we swap real stories about helping kids with 401(k)s, seeing bad default investments in the wild, what personal finance education gets wrong, and why Social Security advice may be more nuanced than the "always wait until 70" crowd admits. It's a reminder that thoughtful disagreement can sharpen your own plan faster than blindly copying someone else's. . === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial. 👉🏼 Be sure to use this link to get started: Go.boldin.com/catchingup
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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 Check your social security estimates Mike Piper's Open Social Security Calculator . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072 Social Security Made Simple | Mike Piper | 054 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 | 19 avr. 2026 | 01:00:30 | |
What if the real reason family wealth disappears by the third generation has almost nothing to do with investing, and everything to do with what parents fail to teach at home? We sit down with Dr. Julia Myers, founder of Generational Wisdom, for a conversation that goes way past trusts, spreadsheets, and "someday" estate plans. Julia shares the medical crisis that abruptly ended her pharmacy career, the mindset shift that followed, and why she now believes legacy is not what you leave to your kids, but what you leave IN them. Together we unpack the three silent killers of generational wealth: no skills, no goals, no expectations, and explore what it looks like to raise kids who understand money and values, before the world teaches them. If you've ever wondered how to build wealth without accidentally raising entitlement, or how to recover from your own money story before passing it on, this episode is a gold mine. This episode covers
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial. 👉🏼 Be sure to use this link to get started: Go.boldin.com/catchingup
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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 Charity: Hope International Say This, Not That (free guide) Free Audiobook "Wealthy and Well Known" . ⏰ Related Episodes Enoughness: Your Life or Your Money | Vicki Robin | 95
Doña Quixote, Life Energy, and The Coming of Aging | Vicki Robin | 94 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| 20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208 | 12 avr. 2026 | 01:10:03 | |
APRIL IS FINANCIAL LITERACY MONTH! What do you get when two late starters hand the mic to two twenty-somethings and let the money questions fly? In this unusually fun follow-up to the University of Tennessee classroom visit, we bring Dr. Karen DeLong and two of her students, Emilie and Britton, onto the podcast to tackle the real questions young adults ask when money stops being theoretical and starts getting personal. Emilie – Majoring in Finance and International Business with a minor in Agricultural Business and will be pursuing a career in Wealth Management. Britton – Interning with Wells Fargo in their Investment Banking - Commercial Real Estate division and will be pursuing a career in that post grad. . This episode covers
. === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial. 👉🏼 Be sure to use this link to get started: Go.boldin.com/catchingup
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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
📘 If You Can: How Millennials Can Get Rich Slowly (Bill Bernstein) 📕 The Simple Path to Wealth- Updated 2025 (JL Collins) 📗 Your Money or Your Life (Vicki Robin & Joe Dominguez) 📙F.I.R.E. For Dummies (Jackie Cummings Koski) 📘Money Letters 2 My Daughter (Jackie Cummings Koski) . ⏰ Related Episodes I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206 Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207 | 08 avr. 2026 | 00:45:20 | |
APRIL IS FINANCIAL LITERACY MONTH! What happens when you hand a room full of almost-graduates a microphone, a few $2 bills, and permission to ask the money questions most adults still avoid? In this special on-the-road episode, we take you inside the financial literacy presentation at the University of Tennessee to share a few highlights of our recent talk. It's energetic, imperfect, and deeply encouraging. Financial literacy doesn't have to be stiff or scary. Sometimes it just looks like showing up, telling the truth about your mistakes, and helping the next person get a much earlier start than you did. This episode covers: ➡️ Highlights from Bill and Jackie's live financial literacy presentation at UT Knoxville ➡️ Why young adults need practical money education before entering the workforce ➡️ The difference between being rich and being wealthy ➡️ Why savings rate matters so much for financial independence ➡️ How to think about 401(k)s, employer match, vesting, and job changes ➡️ Why index funds and simple investing often beat picking individual stocks ➡️ Jackie's $2 bill story and how tiny saving habits can shape a lifetime ➡️ Bill's "rich doctor syndrome" story and the danger of lifestyle inflation ➡️ How listeners can adapt this presentation for their own school, church, or community . === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial. 👉🏼 Be sure to use this link to get started: Go.boldin.com/catchingup
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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:
📘 If You Can: How Millennials Can Get Rich Slowly (free digital download) 📄 Copy of Our Presentation Slides to UT Students
⏰ Related Episodes I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206 Questions from Students (coming in April) . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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. | |||
| I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206 | 05 avr. 2026 | 00:36:20 | |
APRIL IS FINANCIAL LITERACY MONTH! What if one passionate professor, one classroom, and a few brave money questions could change hundreds of financial lives before graduation? We head to Knoxville for a special Financial Literacy Month episode with Dr. Karen DeLong, the University of Tennessee professor quietly doing the work most schools still don't: making sure students leave campus with more than a degree. Karen shares how three advanced degrees somehow included zero personal-finance education and how that gap pushed her to build an annual money session for her students. Bill and Jackie reflect on what it was like to teach these soon-to-be graduates and how any late starter can become a powerful financial literacy advocate in their own little corner of the world.
This episode covers: ➡️ Why Dr. Karen DeLong started bringing personal finance into her classroom ➡️ How someone can earn multiple degrees and still never take a money class ➡️ Why college students are hungry for practical money conversations ➡️ The kinds of personal finance questions students are asking before graduation ➡️ How Bill and Jackie prepare for live financial literacy teaching sessions ➡️ Why financial literacy fits into almost any curriculum, not just finance classes ➡️ How Farm Credit Mid-America helped support this student enrichment work ➡️ Why late starters can still become mentors and financial literacy advocates ➡️ A preview of the student follow-up episode answering unanswered questions . === SUPPORT THE SHOW === 🌐 Visit Catching Up to FI website ☕ 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=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial. 👉🏼 Be sure to use this link to get started: Go.boldin.com/catchingup
Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course
Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)
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
. ⏰ Related Episodes Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207 Questions from Students (coming in April)
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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. | |||
| Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 | 29 mars 2026 | 01:02:41 | |
April is Financial Literacy Month and we're starting a little early! That's because we are so excited to launch a new project called "The Great 401(k) Cleanup." What if the easiest way to boost your retirement odds this year isn't reducing your spending or a side hustle, but cleaning up that messy, confusing 401(k) you've been ignoring? We are using Financial Literacy Month to launch a full-on 401(k) intervention with a step-by-step guide including:
401(k)s and similar workplace plans like the TSP, 403(b), and 457 have become the backbone of retirement for most Americans. Yet they are often confusing and complicated to the average employee. No wonder so many accounts get neglected and become messy over time. The good news is that 2026 can be the year you clean it all up. This friendly and straightforward guide was created independent of any employer or plan provider, and will help you get going. By the time you're done you'll better understand your 401(k) and feel more empowered to use it as a real tool to build wealth and support your money goals. This episode covers: ➡️ How to clean up a messy 401(k) in less than an hour ➡️ Why year-to-date returns can mislead and longer time frames matter more ➡️ How contribution rate and savings rate shape your retirement timeline ➡️ Employer match, vesting schedules, and why "free money" still confuses people ➡️ Target date funds and simple one- to three-fund strategies ➡️ How to spot low-cost index funds inside an ugly 401(k) menu ➡️ What to do with old 401(k)s when you change jobs ➡️ How AI can help decode plan documents and confusing fund lists ➡️ Why forgotten 401(k)s now total a jaw-dropping $2.1 trillion
====================
DOWNLOAD GUIDE & EDITABLE CHECKLIST 📄 Cleaning up your 401(k) in less than an hour (complete guide with references) 📄 Cleaning up your 401(k) in less than an hour- Editable Checklist (download first)
====================
DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS
The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners
SUPPORT THE SHOW 🌐 Visit Catching Up to FI website ☕ 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
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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. | |||
| Here's What 6 Years of Early Retirement Life is Really Like | "REAL Retirees: Uncut" Crossover | 204 | 25 mars 2026 | 00:49:05 | |
What if the best retirement advice didn't come from a spreadsheet—but from a real retiree saying, "I wish I'd done it sooner"? Jackie crosses over to "REAL Retirees: Uncut" for a refreshingly candid, walk through of what six years of early retirement have actually looked like. She also shares her top five reasons to retire early, from time freedom and better mental health to the surprising new opportunities that open up when your job no longer runs your calendar. And because this is still Catching Up to FI, she closes with a message straight to late starters: most people wake up later than they wanted, but that doesn't mean they're doomed. It means they need a new frame and a little grace. This episode covers: ➡️ Jackie's real-life retirement story, six years in ➡️ Retiring at 49 after corporate life ➡️ Building a nest egg using FIRE math and the 4% rule ➡️ Living off brokerage assets, Roth contributions, and a 72(t) strategy before 59½ ➡️ ACA health insurance subsidies and managing income in early retirement ➡️ Why Jackie kept her mortgage and doesn't regret it ➡️ Her top five reasons to retire early ➡️ The hidden superpowers late starters already have ➡️ Why retirement success is really about freedom, health, and impact
====================
DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS
The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners
SUPPORT THE SHOW 🌐 Visit Catching Up to FI website ☕ 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
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 🌐REAL Retirees: Uncut http://www.youtube.com/@REALRetireesUncut 🌐Jackie's website FInomenalWoman.com 📈Jackie's Investment Club through BetterInvesting.org
⏰ RELATED EPISODES From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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. | |||
| I Thought the Stock Market was Gambling, Then I Retired at 44 | Jaylynn | 203 | 22 mars 2026 | 01:15:31 | |
What if you were already financially independent at 40… and didn't realize it until a random pension search and a couple of podcasts blew the whole thing open? This was Jaylynn's "Surprise FI" and he joins the show to take us blow by blow. He gives us look back to his childhood of money orders, loving parents, and "value over flash" shaped him. He shares how he went from thinking the stock market was gambling to maxing out a 401(k), building a brokerage account, and accidentally discovering he had already hit FI in his forties. But this isn't just a "run the numbers and quit" story. Jaylynn talks through Surprise FI, staying in a job he loved until COVID burnout changed the equation, retiring at 44, managing ACA subsidies, planning Roth conversions and a future 72(t). He's now using time freedom to become the dad his son would later call his "best friend." He leaves us with the reminder that progress beats perfection—especially for late starters. This episode covers:
====================
DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS
The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners
SUPPORT THE SHOW 🌐 Visit Catching Up to FI website ☕ 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
RESOURCES MENTIONED ON THE SHOW:
⏰ Related Episodes 72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131 Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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. | |||
| Don't Trust AI with Your Money Until You Listen To This | Jeffrey Trull | 202 | 15 mars 2026 | 01:02:44 | |
Today we're putting AI (Artificial Intelligence) to the test with AI money expert Jeffrey Trull. He's founder of the blog and newsletter, Money Meets AI where he shares tested prompts for your money. He joins us to sort the genuinely useful from the wildly overhyped when it comes to AI. We expand our conversation into prompts, privacy, hallucinations, portfolio questions, Google vs. ChatGPT, paid vs. free tools, and where AI can actually save real time for DIYers. Along the way, Bill wrestles with the tradeoff between efficiency and original thought, Jackie pushes the "AI as thought partner" framing, and Jeffrey stresses that it's great for lower-risk questions but terrible as your all-knowing financial planner. This episode covers:
====================
DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS
The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners
SUPPORT THE SHOW 🌐 Visit Catching Up to FI website ☕ 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
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) Top 5 Prompts for the Money Math You've Been Avoiding
⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 | 08 mars 2026 | 00:58:05 | |
What if the guy who literally wrote the book on asset allocation told you your biggest risk isn't the market…it's the person in your bathroom mirror? Neurologist-turned-market-historian William (Bill) Bernstein joins us for a fascinating conversation about his unlikely path from photochemistry to medicine to becoming the quiet godfather of Boglehead-style investing. He shares what shaped his "simple but not easy" philosophy, why he thinks all of investing is "half math, half Shakespeare," and how a homemade website in the 1990s turned into "The Intelligent Asset Allocator" and a second career. This episode covers: ✅ How a frustrated young scientist became a neurologist, then a financial theorist and writer ✅ Early investing mistakes (Palladium futures, hot funds, overconfidence) and what finally clicked ✅ The five hurdles from If You Can and why history and psychology matter as much as math ✅ What makes a true bubble: social buzz, career-changing speculators, hostility to skeptics, wild predictions ✅ Predictions vs forecasts, and how Bill "called" the dot-com bubble and GFC without betting the farm ✅ His current mix: modest small/value tilts, cash/T-bills for sanity, and a TIPS ladder for 30 years of expenses ✅ Why a TIPS ladder feels different from a TIPS fund and why most investors still won't use one ✅ The 30-years-working / 30-years-retired "toy model" and why it implies 20–25%+ savings rates ✅ Teaching kids about money via your own behavior, crappy college jobs, and tiny three-fund portfolios ✅ A sober view of FIRE as a way out of the cubicle and into meaningful work—not a 36-year-old beach fantasy ====================
DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS
The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners
SUPPORT THE SHOW 🌐 Visit Catching Up to FI website ☕ 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
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 🌐 Efficient Frontier (Bernstein's website) 🌐 The John C. Bogle Center for Financial Literacy 📘If You Can: How Millennials Can Get Rich Slowly (free digital download) 📗 Your Money and Your Brain (Jason Zweig) https://a.co/d/07bgnfz1
⏰ Related Episodes The $1,000 Gift From Jonathan Clements To 18-Year-Olds | Bill Bernstein & Christine Benz | 160
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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. | |||
| A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200 | 01 mars 2026 | 01:14:37 | |
What if your giving plan felt as intentional and optimized as your FI plan, and just as easy to automate? In walks Daffy, the new and modern donor-advised fund that is democratizing giving! Adam Nash, co-founder and CEO of Daffy, joins us today to explain how donor-advised funds (DAFs) went from stuffy tools for the ultra-wealthy to something you can open on your phone. Daffy is a fast-growing fintech platform and community for charitable giving, made for everyday people. Adam shares the pandemic-era "why now" behind Daffy, how traditional donor-advised funds quietly skim high AUM fees while setting eye-watering minimums, and walks through Daffy's flat-fee, app-first model.
This episode also covers: ✅ What donor-advised funds are and why they've been hidden from most everyday givers ✅ DAFs for tax optimization (bunching, appreciated stock, estate planning) ✅ How to turn giving into a family and workplace culture (campaigns, matching, gift links) ✅ Why Adam sees a DAF as a simple "charitable 401(k)" or mini family foundation without the lawyers, board meetings, or overhead, built to help you be more generous
==========
DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS
The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners
SUPPORT THE SHOW 🌐 Visit Catching Up to FI website ☕ 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
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)
➡️ Join Bill or Jackie on :Daffy and receive an extra $25 bonus for charity in your new account 🌐 :Daffy (The Donor-Advised Fund For You™) 📄The One Big Beautiful Bill Act (OBBBA) is Telling Donors One Thing: Get a Donor-Advised Fund Donor-Advised Fund fee comparison calculator Stock vs. Cash Donation Calculator
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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. | |||
| Why This DIY Investor Finally Hired A Financial Advisor | "BiggerPockets" Crossover | 199 | 25 févr. 2026 | 00:51:48 | |
What happens when a "late-starter" ER doc finally hits FI at 60, then must figure out how to actually spend the money without blowing it—or hoarding it forever? Bill joins Mindy and Scott on the BiggerPockets Money podcast to walk through his full "caught up to FI" debrief. Here his decade-long sprint from single-digit savings to 40%, taking his money back from a private bank, and the 60th-birthday retirement-readiness check that came back with a 100% success rate. From there, they dig into his move from a simple three-fund portfolio to a risk-parity setup, why he hired a flat-fee planner after years as a DIY investor, and how he's using FI to buy back time and jump-start his kids' wealth with Roth IRAs, HSAs, and tax-savvy living gifts. This episode covers: ➡️ Going from "rich but broke doctor" to FI in about 10 years ➡️ Boosting a savings rate from single digits to ~40% without feeling deprived ➡️ Shifting from a three-fund portfolio to a risk-parity decumulation strategy ➡️ Using flat-fee, advice-only planner instead of 1% AUM ➡️ Order of withdrawals: taxable, pre-tax, Roth, plus asset location ➡️ Modeling taxes, RMDs, and Social Security timing in real life ➡️ Building a "3-1-1" spending plan for needs, comfort, and luxury/giving ➡️ Helping adult kids fill Roth IRAs and HSAs as part of generational wealth ➡️ Weighing when to actually leave medicine once money is no longer the boss
==============================
DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS
The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners
SUPPORT THE SHOW 🌐 Visit Catching Up to FI website ☕ 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
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)
⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
📌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. | |||