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From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007

Catching Up to FI: Financial Independence for Late Starters

Release Date: 03/26/2023

The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236 show art The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236

Catching Up to FI: Financial Independence for Late Starters

What happens when you finally reach financial independence and your brain responds with, ā€œGreat, now what?ā€ In this special crossover from ChooseFI, Ginger turns the microphone on Bill and digs into the part of financial independence that spreadsheets rarely prepare us for. He shares how a lawsuit and burnout woke him up financially at 50 and how he and his wife flipped from single-digit saving to intentional wealth building. Bill also explains why reaching FI at 60 created a whole new problem: actually giving himself permission to leave work. This episode covers Bill’s financial...

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How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie’s Real #s | Bill Stecker (Part 2) | 235 show art How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie’s Real #s | Bill Stecker (Part 2) | 235

Catching Up to FI: Financial Independence for Late Starters

A 72(t) plan is little-known IRS provision which gives you a perfectly legal way to access your retirement money before 59½ without the 10% penalty. In this second half of the 2-part episode, Jackie brings back Mr. 72t, William (Bill) Stecker, CPA and founder of 72tcalc.com. This episode takes on the practical half of their deep dive into 72(t) plans as they move from theory to execution. Jackie puts her own plan on screen to let Bill do what he does best... audit it! He scrutinizes her $240k starting balance, $15k annual withdrawals, plan timeline, and the surprising fact that her account...

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Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty | Bill Stecker (Part1) | 234 show art Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty | Bill Stecker (Part1) | 234

Catching Up to FI: Financial Independence for Late Starters

You won’t find a more comprehensive resource on the topic of 72(t) plans and substantially equal periodic payments (SEPP). This little-known IRS provision gives you a perfectly legal way to access your retirement money before 59½ without the 10% penalty… and almost nobody in finance wants to touch it! So, Jackie brings back the one expert that lives and breathes 72(t)s, William (Bill) Stecker, CPA and founder of 72tcalc.com. Bill picks up where he left off when he last appeared on the show in 2025. He further explains the nuances of 72(t) plans and how to avoid common mistakes. Hear how...

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Vanguard Acquires Altruist: Why Fidelity & Schwab Better Look Out! | Barry Ritholtz | Bonus show art Vanguard Acquires Altruist: Why Fidelity & Schwab Better Look Out! | Barry Ritholtz | Bonus

Catching Up to FI: Financial Independence for Late Starters

What happens when one of investing's original disruptors buys one of the industry's newest disruptors? Barry Ritholtz thinks investors may be the biggest winners and Bill and Jackie dig into why. This special breaking-news is an excerpt from an upcoming Catching Up to FI episode, recorded on 8/26/26. Barry reacts to Vanguard's newly announced agreement to acquire Altruist, the fast-growing technology and custody platform built for independent financial advisors. Barry also gives an important disclosure: he's an Altruist investor, so yes, he has a dog in this fight. From there, he explains...

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Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233 show art Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233

Catching Up to FI: Financial Independence for Late Starters

What if that old pension you barely think about is secretly one of the most valuable assets in your retirement plan? Bill and Jackie welcome back financial planner and educator, Andy Panko for a deep dive into the increasingly rare (but far from extinct) world of pensions. They explore plans from private and government employers and why a seemingly small monthly check can dramatically change the work the rest of your portfolio has to do. This episode covers Why pensions are less common but still relevant to millions of workers What it actually means when an employer "freezes" a pension How to...

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The Truth Behind Raising A Teenage Money Whiz (From The Parents Of Rishi Vamdatt) | Renu & Raag Vamdatt | 232 show art The Truth Behind Raising A Teenage Money Whiz (From The Parents Of Rishi Vamdatt) | Renu & Raag Vamdatt | 232

Catching Up to FI: Financial Independence for Late Starters

After Rishi Vamdatt’s conversation with Bill and Jackie, his parents Renu and Raag step out from behind the scenes to share how their son became the 16-year-old financial educator behind Easy Peasy Finance. They believe raising a financially savvy kid has less to do with giving money lectures and more to do with letting them swipe the credit card at the grocery store and ask "what happens next"? Their approach was surprisingly simple: money was never taboo, questions were always welcome, and Rishi was allowed to follow his curiosity rather than being scheduled into oblivion. For...

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This 16-Year-Old CFP Exam Passer Is Making Personal Finance This 16-Year-Old CFP Exam Passer Is Making Personal Finance "Easy Peasy" | Rishi Vamdatt | 231

Catching Up to FI: Financial Independence for Late Starters

What if the person explaining money to your kids has already been doing it for more than half his life, and passed the CFP exam before he could legally vote? Bill and Jackie sit down with 16-year-old Rishi Vamdatt, founder of Easy Peasy Finance. Rishi started learning about money at six, investing at seven, and teaching personal finance on YouTube at eight. But this isn't just a story about an unusually motivated teenager. Rishi offers a surprisingly universal lesson: money gets easier when we strip away the jargon, practice with real dollars, automate the basics, and start where we are....

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More Bonds, James, Bonds: Rethinking Your BND Strategy (Part 2) | Frank Vasquez | Episode 230 show art More Bonds, James, Bonds: Rethinking Your BND Strategy (Part 2) | Frank Vasquez | Episode 230

Catching Up to FI: Financial Independence for Late Starters

What if the safest-looking retirement portfolio is actually protecting you from the wrong disaster? In part two of Bill’s bond marathon with Frank Vasquez, the conversation moves from Bond 101 into the question that really matters: what role should fixed income play once you stop accumulating and start living from your portfolio? Frank explains why bonds should be chosen for a specific job, why a total bond fund may be trying to do too many things at once, and why retirement planning should prepare for a bad decade. The ultimate takeaway is reassuring: bonds are complicated, but most people...

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Are Bonds Dead?:  Fixed Income Fundamentals (Part 1) | Frank Vasquez | Episode 229 show art Are Bonds Dead?: Fixed Income Fundamentals (Part 1) | Frank Vasquez | Episode 229

Catching Up to FI: Financial Independence for Late Starters

What if bonds aren't dead at all—and we've just spent the last decade misunderstanding what job they were hired to do? Bill welcomes back Frank Vasquez, the hotdog-named engineer-lawyer-DIY investor behind Risk Parity Radio, for part one of a lively fixed-income deep dive. Starting with the basics, Frank explains what a bond actually is, why owning one makes you the lender rather than the shareholder, and how bonds can provide income, stability, or diversification depending on the type and duration. They work through the very real risks hiding behind the phrase "safe investment." Along the...

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How to Retire at 40: Her Debt-Crushing Path to Financial Independence | Bernadette Joy | 228 show art How to Retire at 40: Her Debt-Crushing Path to Financial Independence | Bernadette Joy | 228

Catching Up to FI: Financial Independence for Late Starters

What if crushing your money goals has less to do with finding the perfect formula—and more to do with getting lovingly bullied into taking action today? Bill and Jackie sit down with Bernadette Joy, a first-generation Filipino American who paid off $300,000 of debt in three years, reached her first million, and eventually built a multimillion-dollar portfolio. Bernadette also explains why she believes traditional financial literacy is dead, walks through her C-R-U-S-H framework, and reveals why the final "H" evolved from hustle to healing your money wounds. This episode covers How...

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Jackie Cummings Koski, CFP, has been featured on CNBC, The Rachel Ray Show, Marketwatch, Forbes, and People Magazine. She is a single mother and a force in financial education who grew up in poverty, started late on her path to FI, and "finished early" with a net worth of $1.4M at 49 years old.  Her story is incredible.  Her wisdom is vast.  Her dream of a financially literate society is a palpable passion.  She is not done yet!

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