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Catching Up to FI

Catching Up to FI

Bill Yount & Jackie Cummings Koski

214 episodesEN-US

Show overview

Catching Up to FI has been publishing since 2023, and across the 3 years since has built a catalogue of 214 episodes, alongside 2 trailers or bonus episodes. That works out to roughly 230 hours of audio in total. Releases follow a weekly cadence.

Episodes typically run an hour to ninety minutes — most land between 55 min and 1h 14m — and the run-time is fairly consistent across the catalogue. It is catalogued as a EN-US-language Business show.

The show is actively publishing — the most recent episode landed 5 days ago, with 26 episodes already out so far this year. Published by Bill Yount & Jackie Cummings Koski.

Episodes
214
Running
2023–2026 · 3y
Median length
1h 5m
Cadence
Weekly

From the publisher

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

Latest Episodes

View all 214 episodes

Your FIRE Plan is Screwed Without An Estate Plan! | Allison Harrison | 213

May 10, 20261h 9m

Borderless FI: Starting Over At 37 After Divorce | Bronwyn Candish | 212

May 3, 202657 min

The Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211

Apr 29, 20261h 4m

Hot Takes & Money Debates: Social Security at 62, New Trump Accounts, & more! | Bill & Jackie | 210

Apr 26, 20261h 4m

Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209

Apr 19, 20261h 0m

Ep 20820 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.

Apr 12, 20261h 10m

Ep 207Financial 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.

Apr 8, 202645 min

Ep 206I 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.

Apr 5, 202636 min

Ep 205Is 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.

Mar 29, 20261h 2m

Ep 204Here'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.

Mar 25, 202649 min

Ep 203I 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.

Mar 22, 20261h 15m

Ep 202Don'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.

Mar 15, 20261h 2m

Ep 201The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201

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.

Mar 8, 202658 min

Ep 200A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200

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.

Mar 1, 20261h 14m

Ep 199Why This DIY Investor Finally Hired A Financial Advisor | "BiggerPockets" Crossover | 199

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 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.) 🌐 BiggerPockets Money BiggerPockets Money Youtube ⏰ 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.

Feb 25, 202651 min

Ep 198The Biggest Retirement Mistake: Over Saving and Under Living | Rachael Camp & Jesse Cramer | 198

Don't be that person who becomes a hoarder in retirement! You know who you are and it's a big concern for those that are champs at saving but reluctant to spend. It almost seems like a good problem to have... but not really! Retirement planners Rachel Camp, CFP® and Jesse Cramer join the show for a tackle the topic and what's known as the "consumption gap"-- the mismatch between what retirees could safely spend and what they actually spend. They discuss how decades of frugality, and dopamine hits from watching net worth climb and similar types of thinking make it brutally hard to flip from saver to spender. In this episode we cover: ✅ The 4% rule's real origin story (it was built to avoid failure, not to optimize joy) ✅ The very human tendency to over solve for the worst-case market and under solve for lost health, time, and relationships ✅ Strategies Rachael and Jesse use with their clients to help them spend and not hoard their money in retirement ✅ Why talking through childhood money stories is often more powerful than another spreadsheet. ✅ Debunking the viral "retire later, die sooner" meme and zoom out to what actually affects longevity ✅ A challenge tailor-made for late starters: once the math says you've won, stop buy back your time, and don't die with the biggest net worth of your life. ==================== 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.) 🌐 Rachael Camp Wealth Rachael Camp Wealth Youtube 🌐 The Best Interest Blog (Jesse Cramer) Personal Finance For Long-Term Investors (Jesse Cramer's podcast) 📄Debunked: The Later You Retire, The Earlier You Die?! ⏰ Related Episodes Smart Money Moves After 50 | Bill Yount | 142 Space Telescopes, Sunflowers, and Financial Gardening | Jesse Cramer | 105 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.

Feb 22, 202659 min

Ep 197Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197

This episode is a little time-travel experiment with a flashback to the first episode (A Boat Named YOLO) that started it all. We're celebrating three years of 'Catching Up to FI' and Bill officially coming out as reaching Financial Independence (FI). He started late at 50 but now FI at 60! Be sure to go back and listen to this past Sunday's episode, where Jackie interviews Bill and he openly shares all the juicy details. ➡️Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 ==================== 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.

Feb 18, 202650 min

Ep 196Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196

Don't miss this special 3-year anniversary of 'Catching Up to FI' as Bill marks the moment by doing something he's been helping everyone else do for years: officially 'coming out' as financially independent (FI)! It is hard to believe that the show has been around for 3 years, 196 episodes, 20k Facebook Community members, 1.4M audio downloads and 300k views on YouTube. Is this real? Today we celebrate Bill's journey from Episode #1: 'A Boat Named Yolo', to officially reaching FI, but feels more like the 'The Fog of FI'. During this interview, Jackie gets Bill to open up and vulnerably share details of his wake-up call at 50: burned out, sued, house-poor after a disastrous renovation and de-risking at the bottom of the Great Recession, and still living paycheck to paycheck despite a 'rich doctor' income. He walks through discovering FI via blogs and books, taking a full year to reclaim his money from private bankers and whole life policies (he's naming names!). Bill's real superpower was boosting his savings rate up to ~40% in his early 50s using Mr. Money Mustache's 'shockingly simple math' to accept a 10 to 15-year timeline. Fast-forward to 60 and a retirement-readiness check with a flat-fee, advice-only planner: after three years of expense tracking in Monarch Money, a comprehensive plan, and stress-testing with risk-parity portfolios, Bill gets the verdict every late starter dreams of, 'you could retire tomorrow'— and feels weirdly flat. We also dig into the emotional side: the identity crisis of possibly leaving medicine, using newfound leverage to negotiate work on his own terms, the choice to glide out over several years instead of cliff-retiring, and the shift from building wealth to giving with warm hands, mentoring younger docs, and helping his adult sons lay foundations he never had. We close with Bill's hard-earned advice: ➡️ Reverse-engineer your life from your tombstone ➡️ Focus on health span as fiercely as net worth ➡️ Stop over-identifying with your job or your number ➡️ Remember that for late starters, the real win is feeling less alone while you build a life you won't regret. ==================== 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: 📄 Bill's 'Letter of Gratitude' and 'Financial Life Policy Statement' Saving Our Retirement on Humble Dollar Bill's Financial Planner: Bryan Minogue CFP®, CFA (Kardinal Financial) ⏰ Related Episodes A Boat Named YOLO | Bill Yount | 001 The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016 The Father of Financial Life Planning (Part 1) | George Kinder | 140 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.

Feb 15, 20261h 12m

Ep 195Work Less, Live More: The New Paradigm of Financial Freedom | Andy Hill | 195

Do you want to own your time, work less, and live more? What if the point isn't maxing out every account forever, but designing a week you don't want to escape from? This is the Coast FI life built by our guest today, Andy Hill. He shares the steps you can take to put your family first and escape the 9-5 grind: for good! He takes us through the full arc: starting married life at –$50K net worth, killing the debt in a year with budget parties, saving 40–50% to hit around $500K in investments by forty, then realizing that number was enough for Coast FI. With all that, he realized that what he really wanted was time. Andy is an award-winning blogger, podcaster, and family finance coach behind Marriage, Kids, and Money. He's also author of the new book 'Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind', which walks readers through simple, yet highly effective steps families can take to achieve family financial independence. It also features real-life examples of couples who've conquered these family financial independence milestones and found better lives for themselves because of it. ==================== 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.) 🌐 Marriage Kids and Money 📕 Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind ⏰ Related Episodes Generosity and Smart Spending: A Family Affair | Andy Hill | 103 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.

Feb 8, 20261h 10m

Ep 194Back to FI Basics: How to Start Your Journey to Early Retirement | ChooseFI Crossover | 194

Strap in, because Jackie joins Brad Barrett for a crossover episode on the ChooseFI podcast, home of the world's largest FI community! Together, they rewind all the way back to 2017, when Jackie first stumbled onto ChooseFI… and everything changed. She recounts her journey to reaching early retirement by December 2019, and using that freedom to go back to school, get her CFP, and write 'F.I.R.E. for Dummies'. Then the two of them dive deep into the fundamentals and break down what financial independence really means. They explain why even ten dollars a month can spark a lifelong investing habit, and how Jackie's first investment club taught her the power of community and compounding. They decode 401(k)s, demystify fund selection, and spotlight the quiet villain of investing: expense ratios. The episode widens from there: debt payoff strategies, designing a modest but deeply rich life on $40–45K a year in Ohio, negotiating everything from internet bills to insurance premiums, and the emotional transformation from paycheck-to-paycheck lifestyle to feeling 'directionally correct.' They conclude with the realization that FI isn't just about money, it's about options. Whether you're a late starter, brand new or ten years into the journey; returning to the basics is how you stay grounded, stay motivated, and stay on course. ==================== 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.) 🌐ChooseFI 🌐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 The Godfather of FI Talks Fatherhood | JL Collins | 149 Stories, Hacks, & Tribes | Brad Barrett | 021 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.

Feb 4, 20261h 15m