The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074
Catching Up to FI: Financial Independence for Late Starters
Release Date: 05/12/2024
Broke at 50 ā”ļø Retired at 60! | BiggerPockets Crossover | 182
Catching Up to FI: Financial Independence for Late Starters
We love collaborations and this time we teamed up with Mindy and Scott from BiggerPockets Money to tackle a case study you don't want to miss: "How to go from Broke at 50 to Retired at 60!" This originally aired on BiggerPockets Money in August, and since then it received over 300,000 views and quickly moved up to the second most popular video on their YouTube Channel. Needless to say, this topic, got people talking! We spell out exactly what we would do to go from a zero-dollar net worth to a million dollars in retirement! This is a step-by-step plan that anyone who wants to retire on time...
info_outline
Drowning in Debt at 48, Retired at 58: Hereās How She Did It! | Kim Hunter-Borst | 181
Catching Up to FI: Financial Independence for Late Starters
At 48, Kim Hunter-Borst was drowning in debt even though she had a solid New York income. Where was the money going? How did she fix it and reach early retirement by 58? We find out in this no-shame late-starter conversation that was recorded live in Bali at the FI Freedom Retreat (please excuse the background noise!) Kim was firmly in the messy middle and retraces the moment she decided to stop winging it. She shares some simple systems that finally stuck, and the handful of brave choicesāasking for more at work, saying no to status buys, and saying yes to purposeāthat changed her...
info_outline
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 ā 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 purposeānot status Using behavior science to close the gap between 'knowing' and 'doing' Downshifting lifestyle...
info_outline
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...
info_outline
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 allānot '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,...
info_outline
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, CFPĀ®-- 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 callsāit'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...
info_outline
Live from Bali! Donāt 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...
info_outline
Money Scripts: Donāt 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 ā 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 whatās 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...
info_outline
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. šš½ 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...
info_outline
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 arcādivorce 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...
info_outlineJeff York is a remarkable individual whose journey from custodian to millionaire offers a wealth of inspiration and practical advice. Jeff's story breaks down conventional barriers, showcasing the power of education, financial literacy, and personal responsibility. From his unique investment strategies and the importance of health to his experiences with divorce and the insights gained therefrom, the conversation delves into the essence of achieving financial independence and living a fulfilled life. Stay tuned for part 2!
š Connect with us
Thank you to our sponsors:
Personal Finance Club (Use code CUTOFI to get $30 OFF any course or PFC investing course only!)
Measure Twice Money ($100 OFF "Create Your Own Financial Plan" Comprehensive Video Course)
Nectarine: Advice-Only Financial Advisors
Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.
Resources mentioned on the show: As an Amazon Associate I earn from qualifying purchases.
CalPERS (California Public Employeesā Retirement System)
CalSTRS (California State Teachersā Retirement System)
Disclaimer: We are not lawyers, financial advisors, accountants or tax experts. Please consult your own professional advisors before making any important decisions. Our content is for entertainment and education purposes only.