PODCAST

Catching Up to FI

Bill Yount & Jackie Cummings Koski

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

business investing

All Episodes

01:10:03

20 Questions from 20-Somethings About Money | Dr....

Catching Up to FI ·

2026/04/12

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

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45:20

Financial Literacy 101: Live Inside the Classroom at...

Catching Up to FI ·

2026/04/08

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

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36:20

I Have a PhD in Business but Never Had a Personal...

Catching Up to FI ·

2026/04/05

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

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01:02:41

Is Your 401(k) a Mess? Do This Now (Step-by-Step...

Catching Up to FI ·

2026/03/29

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

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49:05

Here's What 6 Years of Early Retirement Life is...

Catching Up to FI ·

2026/03/25

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

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01:15:31

I Thought the Stock Market was Gambling, Then I...

Catching Up to FI ·

2026/03/22

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

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01:02:44

Don't Trust AI with Your Money Until You Listen To...

Catching Up to FI ·

2026/03/15

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

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58:05

The 5 Investing Hurdles You Can't Ignore | Bill...

Catching Up to FI ·

2026/03/08

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

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01:14:37

A Donor-Advised Fund For You (Daffy): Democratizing...

Catching Up to FI ·

2026/03/01

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

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51:48

Why This DIY Investor Finally Hired A Financial...

Catching Up to FI ·

2026/02/25

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

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59:07

The Biggest Retirement Mistake: Over Saving and Under...

Catching Up to FI ·

2026/02/22

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

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50:34

Flashback to Episode 1: 'A Boat Named YOLO' | Bill...

Catching Up to FI ·

2026/02/18

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

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01:12:18

Founder of 'Catching Up to FI' Just Hit Financial...

Catching Up to FI ·

2026/02/15

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

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01:10:56

Work Less, Live More: The New Paradigm of Financial...

Catching Up to FI ·

2026/02/08

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

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01:15:13

Back to FI Basics: How to Start Your Journey to Early...

Catching Up to FI ·

2026/02/04

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

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01:17:32

These New Rules Will Change The Way You Think About ...

Catching Up to FI ·

2026/02/01

529 plan expert Patricia Roberts blows up the myth that 'it's too late' and '529s are just for rich people with toddlers and Ivy League dreams'. She is author of the book 'Route 529' and shares some big changes with 529 plans that make them an incredibly flexible savings vehicle for more than just college. In this episode we cover: How state tax deductions, credits and 'parity states' work for contributions The shockingly long list of qualified uses including trade schools, apprenticeships,

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01:13:35

Why Your Financial Plan Will Fail (It's Not the Math)...

Catching Up to FI ·

2026/01/25

Dan Haylett gives us a late-starter masterclass on why retirement is a human problem long before it's a math problem. Dan is a UK financial planner, creator of 'Humans vs Retirement' podcast, and author of 'The Retirement You Didn't See Coming'. He walks us through how that outdated 'retire from work and fade away' script clashes with modern 50- and 60-somethings who still have health, curiosity, and huge ambitions. In this episode he also: Reframes risk as the possibility of dying with plenty of

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01:21:02

The College Discount Game You Need To Know Before...

Catching Up to FI ·

2026/01/18

The cost of college is skyrocketing! To make sure you're not paying those sticker prices, we brought in New York Times 'Your Money' columnist, Ron Lieber. He is also author of 'The Price You Pay for College' and joins the show for a brutally honest walkthrough of what is actually going on behind the scenes. In this episode he breaks down: List price vs. cost of attendance Why most families don't pay rack rate How to read a school's 'Common Data Set' Merit vs. need-based aid How net price

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48:52

Can AI Plan Your Retirement? Testing ChatGPT's...

Catching Up to FI ·

2026/01/14

Bill joins Jordan 'Doc G' Grumet for a community episode on the Earn & Invest podcast. They stress-test what happens when someone asks ChatGPT: 'What should I do if I'm retiring in five years?' Bill talks about turning 60, being told he's officially reached financial independence, and shifting from accumulation to a more defensive, retirement-ready nest egg. DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS: MONARCH MONEY The modern way to manage money! Monarch will change the way you organize

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01:08:48

Stop Paying for College and Use These High-Return...

Catching Up to FI ·

2026/01/11

Chris Corinthian is the 'Fin Lit Guy' and knows his way around scholarships and other high-return ways to earn money for college. He joins the show to give us a masterclass on paying for college without wrecking your retirement. Chris opens with his own financial setbacks, including a layoff and a devastating fire, which helped him realize the importance of financial literacy. In this episode, you will learn: Chris' Debt-free degree triangle How teens as young as 13 can earn free college credits

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Catching Up to FI

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