Catching Up to FI

Bill Yount & Jackie Cummings Koski

A mindset, money, and life podcast for late starters catching up to Financial Independence.

  1. 20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208

    HACE 16 H

    20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208

    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 The real money questions college students are asking before graduation Why Roth IRAs are such a powerful early-start tool How to think about saving for retirement versus nearer-term goals What happens to your 401(k) when you switch jobs Why savings rate matters more than most young adults realize The balance between being responsible and being too frugal How parents, professors, and mentors shape money mindset Why financial literacy needs to be practical, not just theoretical What late starters can teach young adults before they make the same mistakes . === SUPPORT  THE  SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website  🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 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   🌐 Dr. Karen DeLong  Farm Credit Mid-America 📘 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.

    1 h 10 min
  2. You Might Also Like: On Purpose with Jay Shetty

    HACE 16 H ·  CONTENIDO EXTRA

    You Might Also Like: On Purpose with Jay Shetty

    Introducing How to Communicate So People Actually Listen from On Purpose with Jay Shetty. Follow the show: On Purpose with Jay Shetty How many times have you said something, and it didn’t come across the way you meant it to? Today, Jay unpacks why so many of us feel unheard at work, at home, and even in our closest relationships. He shares a powerful insight: communication isn’t defined by what you say, but by how it’s received. Most of us overestimate how clearly we express ourselves, creating a hidden gap between intention and impact. Jay reframes communication as a shared responsibility, reminding us that real connection isn’t about winning arguments, but about being clear, compassionate, and protecting the relationship while speaking your truth. Jay then explores the core principles that help people actually listen, beginning with the ability to regulate your nervous system before you speak. When emotions take over, we react rather than respond, often escalating conflict instead of easing it. He highlights why clarity is more powerful than intensity, and how simple, intentional language fosters trust and cooperation, while emotional overload creates distance. In this episode, you'll learn: How to Communicate So People Actually Listen How to Regulate Your Emotions Before Speaking How to Speak Without Triggering Defensiveness How to Ask Questions That Build Understanding How to De-escalate Difficult Conversations When you focus on being understood instead of being right, conversations become safer, relationships grow stronger, and conflict loses its power. With intention, patience, and compassion, your words can become a bridge, not a barrier, to the life and relationships you truly want. With Love and Gratitude, Jay Shetty JAY’S DAILY WISDOM DELIVERED STRAIGHT TO YOUR INBOX Join 900,000+ readers discovering how small daily shifts create big life change with my free newsletter. Subscribe here.  Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast SpringFest is happening now, and our best lineup is here at http://www.lowes.com What We Discuss: 00:47 Are You a Good Communicator? 02:31 How Effective Communicators Make an Impact 03:24 #1: Regulate Before You Communicate 06:24 #2: Clarity Over Intensity 08:40 #3: People Argue with Threat NOT Facts 11:11 #4: Ask More Questions, Make Fewer Statements 12:51 #5: Tone Carries More Than Words 15:27 #6: End Conversations with Alignment 21:13 The Goal of Proper Communication See omnystudio.com/listener for privacy information. DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.

  3. Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207

    HACE 4 DÍAS

    Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207

    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 === 📩 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=== 📈 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:    🌐 Dr. Karen DeLong  Farm Credit Mid-America BetterInvesting.org  📘 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.

    45 min
  4. I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206

    5 ABR

    I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206

    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 === 📩 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=== 📈 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   🌐 Dr. Karen DeLong  Farm Credit Mid-America . ⏰ 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.

    36 min
  5. Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205

    29 MAR

    Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205

    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: Access From Home  Contributions  Beneficiaries  Investments  Rate of Return  What's Next    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   MONARCH MONEY 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 📩 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     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.

    1 h 3 min
  6. Here's What 6 Years of Early Retirement Life is Really Like | "REAL Retirees: Uncut" Crossover | 204

    25 MAR

    Here's What 6 Years of Early Retirement Life is Really Like | "REAL Retirees: Uncut" Crossover | 204

    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   MONARCH MONEY 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 📩 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     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 📕F.I.R.E. For Dummies   📘Money Letters 2 My Daughter  📈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.

    49 min
  7. I Thought the Stock Market was Gambling, Then I Retired at 44 | Jaylynn | 203

    22 MAR

    I Thought the Stock Market was Gambling, Then I Retired at 44 | Jaylynn | 203

    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: How Jaylynn's parents taught him value, bills, and stretching money without calling it "financial literacy" Why he thought investing was gambling after watching Trading Places The coworker moment that made him realize he was already an investor through his 401(k) A rare private-company benefits setup: automatic 401(k) contributions, pension, and relocation packages How he discovered the FIRE movement by researching pension payout options "Surprise FI" at age 40 using the 4% rule and liquid assets only Why he kept working after hitting FI—and what changed in 2020 Retiring at 44 with a mortgage, a tax strategy, and 15 years of runway Using ACA subsidies, Roth conversions, and a future 72(t) to bridge the early-retirement years Why the real wealth turned out to be time with his kids, not just a portfolio balance   ====================   DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS   MONARCH MONEY 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 📩 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     RESOURCES MENTIONED ON THE SHOW:    ChooseFI   BiggerPockets Money  Jill On Money  The Retirement Answer Man      ⏰ 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.

    1 h 16 min
  8. Don't Trust AI with Your Money Until You Listen To This | Jeffrey Trull | 202

    15 MAR

    Don't Trust AI with Your Money Until You Listen To This | Jeffrey Trull | 202

    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: Where AI is genuinely useful for DIY personal finance Why prompts matter, but perfection is overrated Using AI to review insurance, contracts, and 401(k) plan docs Google vs. ChatGPT vs. Claude for money questions Paid vs. free AI tools and when subscriptions are worth it AI "hallucinations" and how to fact-check outputs Privacy concerns when uploading financial documents Why AI should be a thought partner, not your financial planner Agentic AI, AI shopping assistants, and what may be coming next   ====================   DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS   MONARCH MONEY 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 📩 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     RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 🌐 Money Meets AI 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.

    1 h 3 min

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A mindset, money, and life podcast for late starters catching up to Financial Independence.

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