Catching Up to FI

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
🌐 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.

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.

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.

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
 
==========
 
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.