Live from Bali: Are They Really Retired? (Part 2) | Jackie & Doc G | 178
Catching Up to FI: Financial Independence for Late Starters
Release Date: 11/12/2025
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...
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What Would 'Your Money' Look Like In a Simple Sketch? | Carl Richards | 170
Catching Up to FI: Financial Independence for Late Starters
Carl Richards is one of the leading voices when it comes to money and emotions. For over a decade, he was the creator of the Sketch Guy column in The New York Times, where his hand-drawn sketches made financial complexity surprisingly simple—and deeply emotional. He joins us to ask the question that instantly ties our brain in knots: 'What is money, really?' From there, he discusses: Why we unknowingly organize life around money and work Why 'enough' is a way of being (not a number) How we keep handing money jobs it can't do—like self-worth, love, and happiness Come for the doodles;...
info_outlineRecorded 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, and—surprise—catching the spark to write again.
Stay for the after-show hot seat where more attendees share their own takes on whether they'll ever 'work' again. Hear from Scott, Dave, Sophie, Selene, Justin, Kim, and Amy.
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Next Retreat: Sept 11 - 15, 2026
Rachel Richards- Money Honey Rachel
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