Episodios

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

    Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207
    Apr 8 2026
    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.
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    45 m
  • I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206

    I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206
    Apr 5 2026
    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 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: 🌐 Dr. Karen DeLong Farm Credit Mid-America ⏰ Related Episodes Highlights from Bill and Jackie presenting at UT Knoxville (coming in April) 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.
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    36 m
  • Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205

    Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205
    Mar 29 2026
    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.
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    1 h y 3 m
  • Here's What 6 Years of Early Retirement Life is Really Like | "REAL Retirees: Uncut" Crossover | 204

    Here's What 6 Years of Early Retirement Life is Really Like | "REAL Retirees: Uncut" Crossover | 204
    Mar 25 2026
    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.
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    49 m
  • I Thought the Stock Market was Gambling, Then I Retired at 44 | Jaylynn | 203

    I Thought the Stock Market was Gambling, Then I Retired at 44 | Jaylynn | 203
    Mar 22 2026
    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.
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    1 h y 16 m
  • Don't Trust AI with Your Money Until You Listen To This | Jeffrey Trull | 202

    Don't Trust AI with Your Money Until You Listen To This | Jeffrey Trull | 202
    Mar 15 2026

    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

    ====================

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    SUPPORT THE SHOW

    📩 Sign up for our newsletter

    🌐 Visit Catching Up to FI website

    🔗Connect with us

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    🎙️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.
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    1 h y 3 m
  • The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201

    The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201
    Mar 8 2026
    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 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.) 🌐 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.
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    58 m
  • A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200

    A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200
    Mar 1 2026
    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 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.) ➡️ 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™) ▶️ :Daffy on YouTube 📄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.
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    1 h y 15 m