Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196
Catching Up to FI: Financial Independence for Late Starters
Release Date: 02/15/2026
The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201
Catching Up to FI: Financial Independence for Late Starters
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”...
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A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200
Catching Up to FI: Financial Independence for Late Starters
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...
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Why This DIY Investor Finally Hired A Financial Advisor | "BiggerPockets" Crossover | 199
Catching Up to FI: Financial Independence for Late Starters
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...
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The Biggest Retirement Mistake: Over Saving and Under Living | Rachael Camp & Jesse Cramer | 198
Catching Up to FI: Financial Independence for Late Starters
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...
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Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197
Catching Up to FI: Financial Independence for Late Starters
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. ➡️ ==================== DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS: The modern way to manage money! Monarch will change the...
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Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196
Catching Up to FI: Financial Independence for Late Starters
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...
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Work Less, Live More: The New Paradigm of Financial Freedom | Andy Hill | 195
Catching Up to FI: Financial Independence for Late Starters
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...
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Back to FI Basics: How to Start Your Journey to Early Retirement | ChooseFI Crossover | 194
Catching Up to FI: Financial Independence for Late Starters
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...
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These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193
Catching Up to FI: Financial Independence for Late Starters
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, non-degree credentials, K–12 tuition, tutoring, test prep and even student loan repayment ...
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Why Your Financial Plan Will Fail (It's Not the Math) | Dan Haylett | 192
Catching Up to FI: Financial Independence for Late Starters
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 money but too few memories Unpacks why spreadsheets never quite make us feel safe Lays out...
info_outlineDon'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.
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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
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The Father of Financial Life Planning (Part 1) | George Kinder | 140
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