Bonus Episode: The Market is Crashing, Now What? | Bill & Jackie | 135
Catching Up to FI: Financial Independence for Late Starters
Release Date: 04/07/2025
The Soul of Wealth | Dr. Daniel Crosby | 180
Catching Up to FI: Financial Independence for Late Starters
Dr. Daniel Crosby took a circuitous path to the world of money — starting as a psychologist and ending up as one of the most engaging voices in behavioral finance. He is Chief Behavioral Officer at Orion and author of The Soul of Wealth. Dr. Crosby goes beyond the math to the meaning: identity, autonomy, and why 'you don't really want to be rich, you want to be free.' He joins the show to talk us through: Reframing money as a tool for time freedom, relationships, and purpose—not status Using behavior science to close the gap between 'knowing' and 'doing' Downshifting lifestyle...
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Contrarian Tax Planning Tips | Cody Garrett & Sean Mullaney | 179
Catching Up to FI: Financial Independence for Late Starters
Sean 'FI Tax Guy' Mullaney and Cody 'Measure Twice' Garrett are two of the smartest financial planning pros who are best known for sharing their deep knowledge in the financial independence community and beyond. They join us today to break down tax planning in a way you may not have ever heard before. They don't agree with some of the conventional advice and make a case for the contrarian views they share in their new book, 'Tax Planning To and Through Early Retirement'. In this conversation, we dive into: Top year-end tax tips for later starters Affordable Care Act (ACA) premium tax credits...
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Live from Bali: Are They Really Retired? (Part 2) | Jackie & Doc G | 178
Catching Up to FI: Financial Independence for Late Starters
Recorded live in Bali, at the FI Freedom Retreat (the 2nd one in 2025), Jackie teams up with Doc G from the Earn & Invest Podcast. They ask the spiciest FI question of all—not 'can I retire yet?' but 'should I?' Three very different journeys take the mic: Fara's 'accidental FIRE' at 47 and her boomerang back to a cause-driven job (then boomerang away again) Gene's post-quit LinkedIn relapse and the search for purpose without a W-2 Rachel Richard's pivot from real estate and a viral brand (Money Honey Rachel) to doing the inner work, ditching external validation,...
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What To Do When It's Time To Manage Your Mom's Money | Beth Pinsker | 177
Catching Up to FI: Financial Independence for Late Starters
Our guest today is Beth Pinsker, CFP®-- seasoned financial journalist, MarketWatch columnist and author of the new book, My Mother's Money: A Guide to Financial Caregiving. She represents the sandwich generation and gives us tips, advice, and cautionary tales about her firsthand experience after finding herself caring for her mother and her finances. She explains that caregiving isn't just forms and bank calls—it's love, logistics, and a dash of stubborn grit. Beth also shares: The "death file" story that changed everything How to survive bank pushbacks on powers of attorney Why a tiny...
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Live from Bali! Don’t Miss These FI Stories From Around The Globe | Jackie & Captain FI | 176
Catching Up to FI: Financial Independence for Late Starters
50 people (now friends), 9 countries... all in one room, speaking the same language: Financial Independence! This is a special episode recorded live from in beautiful Bali, Indonesia at the FI Freedom Retreat. Australian blogger and podcaster, 'Captain FI', joins Jackie as guest co-host to share the FI stories of three of the extraordinary individuals we met at the retreat: Claire (Dubai via Ireland)- Restarting and living by the philosophy of 'trust your gut' Michael (Seattle)- Newly nomadic, choosing FI-enough over perfection Val (Hong Kong)- Taking a gap year that feels like several...
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Money Scripts: Don’t Get Scrooged! | Brad Klontz | 175
Catching Up to FI: Financial Independence for Late Starters
Dr. Brad Klontz is a leading expert in financial psychology, professor, bestselling author, and, oh yeah — an internet influencer with millions of followers who tune in for his mix of straight talk and practical money wisdom. He joins Bill for a deep dive into why most money problems aren't math problems. Instead, they are about what’s going on in our heads and in our habits. In this episode, Brad discusses: Why smart people still make dumb money mistakes The difference between poor and broke The 4 money scripts (avoidance, worship, status, vigilance) Why he argues that an internal...
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Hidden Messages In The New Tax Law You May Have Missed | Bill & Jackie | 174
Catching Up to FI: Financial Independence for Late Starters
On July 4th, 2025 an 870-page tax bill called the 'One Big Beautiful Bill Act' (OBBBA) was signed into to law. Some parts have been heavily discussed and others not so much. So we dug around ourselves and pulled out some hidden messages you may have missed that could have major implications to your FI (Financial Independence) journey. 👉🏽 Updates to 2017 'Tax Cuts and Jobs Act' Makes permanent the lowered individual tax brackets established by the Tax Cuts and Jobs Act and keeps the larger standard deduction in place. Also makes permanent the higher lifetime estate gift tax exemption and...
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How A Single Mom Reached F.I.R.E. by 49 | Jackie Cummings Koski | 173
Catching Up to FI: Financial Independence for Late Starters
Jackie joins our friends to the north in Canada for a live taping of TD Direct Investing's 'Inside Investing', turning her late-starter playbook into a friendly masterclass for Canadians and Americans alike. Host Rob Moysey tees up her arc—divorce in her 30s with ~$20k in retirement savings, millionaire a decade later, retired at 49. Jackie fills in the human bits: purpose after FI, why 'precision is not required,' and how a BetterInvesting club cured her market fear. She also walks through: The simple engine that did the work: Maxing out an employer retirement plan, Roth...
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First Time Ever! The 2 Most Important Women in the Life of JL Collins | Jane & Jess Collins | 172
Catching Up to FI: Financial Independence for Late Starters
Today’s episode is something TRULY special— something that’s never happened before! For the first time ever… we’re joined by two remarkable women who’ve lived alongside one of the most influential voices in the FI community, JL Collins. In this one-of-a-kind episode we introduce you to his wife, Jane Collins and daughter, Jessica Collins. This is their first-ever joint podcast appearance. We’re pulling back the curtain to hear their perspectives. What was it like living with someone so passionate about financial independence? How did his philosophy shape their lives, their...
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How To Build Your Own Paycheck: From Saver to Spender | Fritz Gilbert & Dana Anspach | 171
Catching Up to FI: Financial Independence for Late Starters
If you're within ten years of retirement (early or traditional age) or just want to get a head start on going from being a saver to a spender, this episode is for you. Decumulation without drama—that’s the mission as retirement pros Dana Anspach (Sensible Money) and Fritz Gilbert (The Retirement Manifesto) join the show to turn “build-your-own paycheck” into a repeatable process. Dana lays out why drawdown is a hundred small decisions, not one big leap; and Fritz brings in the field notes. Together they demystify: Tax Pitfalls Timing Social Security Asset Allocation and Location Why...
info_outline📈 Between April 3rd and 4th, the stock market dropped 10% and the S&P 500 is down nearly 15% so far this year. That's huge in such a short period of time and downright frightening! So, what do you do? Start by listening to this episode where Bill and Jackie take a deep breath, and discuss the impact of these recent market declines. There is a natural human reaction of fear, but they share tips on tempering those emotions and remaining levelheaded during volatile times. They also talk through the importance of understanding stock market history and cover practical strategies like rebalancing and tax-loss harvesting. They highlight personal experiences from past market drops like the 2008 financial crisis and the COVID-19 market scare, stressing the significance of maintaining a long-term perspective.
Tell us how you're feeling about this market drop and any tips you have for other late starters:🎙️ Record a Voice Message here
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RESOURCES MENTIONED ON THE SHOW:
A Guided Meditation for When the Stock Market is Dropping (JL Collins)
Bogleheads Investment Policy Statement
Rob Berger: Trump, Tariffs and Turmoil | Live Q&A (recording)
AP News Article: A 10% drop for stocks is scary, but isn’t that rare
Forbes Article: How Long Do Recessions Last?
Tax Loss Harvesting (Jesse Cramer)
How to Tax-Loss Harvest – Step-by-Step Guide (White Coat Investor)
'Catching Up to FI Episodes'
Space Telescopes, Sunflowers, and Financial Gardening | Jesse Cramer | 105
Pathfinders: Stories of Success and Financial Independence | JL Collins | 069
Pathfinders: Triumphs and Trials on the Road to Financial Independence | JL Collins | 070
F-You Money Part 1 | JL Collins | 023
F-You Money Part 2 | JL Collins | 024
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⚠️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.