Catching Up to FI

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
 
==========
 
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
 
==============================
 
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.
====================
 
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.