Catching Up to FI

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

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RESOURCES MENTIONED ON THE SHOW

🌐 Dr. Karen DeLong

Farm Credit Mid-America

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⏰ 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.

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:

1. Access From Home
2. Contributions
3. Beneficiaries
4. Investments
5. Rate of Return
6. 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

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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)

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For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners

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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.

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

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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

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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.

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

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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.

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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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.

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.

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

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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.

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

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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.

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.

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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.

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

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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.