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Catching Up to FI

Bill Yount & Jackie Cummings Koski

A mindset, money, and life podcast for late starters catching up to Financial Independence.

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  • Thursday · 8 min

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

    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 why combining Vanguard's enormous scale with Altruist's technology could quickly reshape the custody business, put fresh pressure on Fidelity and Schwab, and potentially extend the famous "Vanguard Effect" into another corner of financial services. Bill calls it "disruptor squared." Barry sees an industry that never stands still. And if competition drives prices lower again, investors may ultimately be the ones cashing the biggest check. This episode covers Barry's immediate reaction to Vanguard's agreement to acquire Altruist His disclosure that he is an Altruist investor and financially benefits from the deal Why Altruist's clean-sheet technology made it an attractive challenger to legacy custodians How Vanguard's scale could immediately change Altruist's competitive position Why Fidelity and Schwab may suddenly have a much larger third competitor The "Vanguard Effect" and how competition can push fees lower across an industry Why Barry believes investors could be the biggest winners from the acquisition How Schwab and Robinhood previously disrupted investing through lower-cost and free trading Why Vanguard was a logical potential acquirer given its earlier relationship with Altruist Barry's larger lesson that financial technology never stands still The Full Episode with Barry Ritholtz will be coming out soon! Be sure to follow the show or subscribe to the channel on YouTube, so you don't miss it!" === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Official Vanguard announcement – Vanguard to Acquire Altruist, Expanding the Reach and Impact of Financial Advice View the August 26, 2026 Vanguard announcement Vanguard FAQ – Vanguard to Acquire Altruist Read Vanguard's acquisition FAQ Altruist's official acquisition announcement Read the Altruist announcement Ritholtz Wealth https://ritholtzwealth.com/ How Not to Invest https://a.co/d/07ZHXM8h . 📌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.

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  • Sunday · 1 hr 41 min

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

    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 think about a pension as part of your overall retirement portfolio The risks behind private, federal, state, and municipal pension promises Lump sum versus lifetime monthly payments and the trade-offs of each Single-life, joint-and-survivor, period-certain, and inflation-adjusted pension options Why guaranteed income can give retirees psychological permission to spend When comparing an employer pension with a commercial income annuity may make sense Andy's four-question framework for deciding whether lifetime payments fit your plan Jackie's pension options and her final decision to turn on lifetime monthly payments Where to find old or forgotten pensions from previous employers . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Tenon Financial website Retirement Planning Education website Andy's podcast Andy's Youtube Andy's LinkedIn Retirement Savings Lost and Found Database Pension Benefit Guaranty Corporation (PBGC) Dinkytown.net- Pension vs. Lump Sum Payout Calculator Estimate Immediate Annuities . ⏰ Related Episodes How K-12 Teachers Can Beat the Broken 403(b) System | Dan Otter & Scott Dauenhauer | 226 Retired Before 50: A Look at Her Real Finances, Numbers & Strategy | Andy Panko Crossover | 186 Retirement Planning Tips | Andy Panko | 063 . 📌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.

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  • August 19 · 30 min

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

    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 late-starting parents, the reassuring message here is that you don't need to raise another Rishi. Just talk openly, model your values, and follow the child. This episode covers How Renu and Raag recognized Rishi's unusual interest in money from a very young age Why money, income, mortgages, and family finances were never treated as taboo How everyday activities like grocery shopping became natural financial lessons The family effort behind the early years of Easy Peasy Finance Why Rishi has turned down sponsorships, including significant offers, to protect audience trust How Rishi's parents balance his mathematical approach with the emotional side of money Why letting children lead their interests can be more powerful than filling every hour with activities How Rishi balanced finance with theater, travel, fishing, scuba diving, video games, and being a regular kid What parents can do differently to build financial fluency in the next generation How financial values and openness traveled from grandparents to parents to Rishi . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Easy Peasy Finance Easy Peasy Finance YouTube 📕Easy Peasy Money Coverage on CBS News Kiplinger Article I Will Teach You To Be Rich (Ramit Sethi) . ⏰ Related Episodes This 16-Year-Old CFP Exam Passer Is Making Personal Finance "Easy Peasy" | Rishi Vamdatt | 231 Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 Money Scripts: Don't Get Scrooged! | Brad Klontz | 175 . 📌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.

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  • #231
    August 16 · 1 hr 2 min

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

    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. This episode covers How Rishi passed the CFP exam at just 16 years old The childhood experiences that sparked his fascination with money Why he gave up birthday parties and started investing at age seven How Easy Peasy Finance grew from kid-friendly three-minute videos into more than 1,300 pieces of financial content What parents can do to teach kids about money without turning it into another lecture Why allowances, real-life practice, and even small money mistakes can be powerful teachers Rishi's simple approach to index funds, automation, and long-term investing Why financial education should begin before high school His take on Roth IRAs, 529 plans, Trump accounts, taxes, and estate planning What a 16-year-old financial educator wants late starters to remember about beginning today . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Easy Peasy Finance Easy Peasy Finance YouTube 📕Easy Peasy Money Coverage on CBS News Kiplinger Article I Will Teach You To Be Rich (Ramit Sethi) . ⏰ Related Episodes 20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072 . 📌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.

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  • #230
    August 9 · 50 min

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

    This is Part 2 of a 2-part Episode. Be sure to catch Part 1 that aired last week (August 2nd). 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 probably only need one or two bond funds chosen with an actual purpose. This episode covers How bond choices should change from wealth accumulation to retirement spending Why the purpose of a bond matters more than simply deciding to "own bonds" The weaknesses of total bond market funds such as BND Why retirement portfolios should prepare for a difficult first decade What Bill Bengen's research suggests about stocks, bonds, cash, and sustainable withdrawals Why TIPS disappointed Frank during both the 2008 recession and the 2022 inflation shock The limited situations where a bond or TIPS ladder may genuinely be useful Why elaborate bucket strategies often behave like ordinary 60/40 portfolios The risks of pairing a mostly stock portfolio with only two or three years of cash Frank's four principles for designing a diversified retirement portfolio === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners RESOURCES MENTIONED ON THE SHOW Risk Parity Radio ⏰ Related Episodes Are Bonds Dead?: Fixed Income Fundamentals (Part 1) | Frank Vasquez | Episode 229 The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 Mr 4% is now Mr 5% | Bill Bengen | 111 📌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.

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  • #229
    August 2 · 1 hr 2 min

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

    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 way, they visit the Witch of Wall Street, Frank's crystal balls, and the illusion that individual bonds never lose value just because nobody checks the price every day. This is Part 1 of a 2-part Episode. Be sure to catch Part 2 next week (August 9th). This episode covers What bonds are and how they differ fundamentally from stocks The three main roles bonds can play: income, stability, and diversification The differences between Treasuries, corporate bonds, municipal bonds, and TIPS Why higher yields usually come with higher credit or default risk Maturity, par value, duration, yield to maturity, and the yield curve Why individual bonds fluctuate in value even when investors do not see the daily price How interest-rate changes affect short-, intermediate-, and long-duration bonds The major risks of bond investing, including inflation, liquidity, credit, and call risk Why diversification depends on correlation, not simply owning investments with different names What 2022 taught investors about stocks, bonds, inflation, and unusual market environments === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners RESOURCES MENTIONED ON THE SHOW Risk Parity Radio ⏰ Related Episodes Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225 I Love Goooooold?! :) | Frank Vasquez | 184 📌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.

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  • #228
    July 26 · 1 hr 10 min

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

    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 Bernadette paid off $300,000 of debt and reached her first million The $100-a-day strategy that made an intimidating goal feel actionable Why generating more income only works when you keep and invest the difference How she resisted lifestyle creep while building a seven-figure business Why her paid-off home mattered more emotionally than optimizing every return Her argument that financial literacy should become financial fluency and freedom The five-part C-R-U-SH framework for organizing money and designing an independent life The $1-per-use rule for spending intentionally without guilt How unsubscribing, reducing drama, and creating a peace plan support financial freedom . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Crush Your Money Goals Website 📕 CRUSH Your Money Goals Bernadette Joy's free retirement checklist and newsletter 2026 Plutus Impact Summit 2026 Plutus Awarsds ⏰ Related Episodes Live Talk from the Plutus Awards: Bill's Inspiring Message to Late Starters . 📌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.

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  • July 22 · 31 min

    Bonus: Is Your School's 403(b) On The Naughty List? Here's What To Do About It | Dan Otter | 227

    What if the smartest way to fix teacher retirement is not patching the broken 403(b) machine, but quietly building an exit ramp to something better? In this bonus conversation, Bill, Jackie, and Dan Otter keep pulling the thread on the teacher-retirement mess and land on a surprisingly practical answer: the 457(b) may be the cleaner, simpler, more flexible plan that schools should be leaning into. Dan also highlights the new audio series Learned by Being Burned, Carl Fisch's 50-state teacher-retirement books, and several states that are getting it right. They end with a reminder that fixing a broken system starts with people who care enough to push back. This episode covers: Why auto-enrollment and employer matches are still rare in most teacher 403(b) plans How multi-vendor 403(b)s make even simple plan improvements harder than they should be The difference between individual and group 403(b) contracts, and why that matters How state-run 457 plans can simplify choices and lower costs for educators The role of unions, districts, and state policy in either helping or hurting teachers Real examples of school districts and states that are getting retirement plans right How teachers can organize coworkers, use advocacy tools, and pressure districts or states to improve plans . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary 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.) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW 403bwise 457bwiser https://457bwiser.org/ Learned by Being Burned (Special) Podcast Series) Man with the (Better Retirement) Plan (#262) 403bwise and 457bwiser Facebook Group Banned by the NTSA Request a Dan and Scott Presentation Teach And Retire Rich Meridian Wealth Management Fisch Financial (Karl Fisch) . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 The Wealthy Custodian Part 2: From Janitor to Millionaire | Jeff York | 076 The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072 . 📌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.

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  • #226
    July 19 · 1 hr 12 min

    How K-12 Teachers Can Beat the Broken 403(b) System | Dan Otter & Scott Dauenhauer | 226

    What if the most dangerous thing in a teacher's retirement plan isn't market volatility, it's the nice guy with free sandwiches and a terrible annuity contract? Jackie and Bill are joined by Dan Otter and Scott Dauenhauer of 403bwise, the duo who have spent decades exposing how badly K-12 educators get treated in the 403(b) world. What starts as a conversation about confusing vendor lists and a messy system, quickly turns into something bigger. This episode covers Why the K-12 403(b) system is fundamentally broken for many educators How Dan and Scott came together through the early 403bwise movement Why sales reps were able to roam campuses and sell high-cost products to teachers How 403(b)s became a multi-vendor mess while 401(k)s evolved under stronger fiduciary oversight Why newer teacher pension tiers are weaker and make supplemental retirement saving more important How bad 403(b) vendors can cost teachers hundreds of thousands of dollars over a career Why the 457(b) is increasingly the better option for many educators How state-run 457(b) plans can offer lower fees, simpler choices, and more retirement flexibility How teachers and school employees can advocate for better plans in their own districts . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary 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.) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary 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.) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW 403bwise 457bwiser https://457bwiser.org/ Learned by Being Burned (Special) Podcast Series) Man with the (Better Retirement) Plan (#262) 403bwise and 457bwiser Facebook Group Banned by the NTSA Request a Dan and Scott Presentation Teach And Retire Rich Meridian Wealth Management . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 The Wealthy Custodian Part 2: From Janitor to Millionaire | Jeff York | 076 The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072 . 📌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.

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  • #225
    July 12 · 1 hr 11 min

    Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225

    What if the biggest risk in your portfolio isn't a crash, a recession, or even inflation, but the very human urge to believe that whatever just worked will work forever? Bill and Jackie sit down with Ben Carlson of A Wealth of Common Sense and Animal Spirits for a market-history masterclass that somehow manages to be equal parts calming, nerdy, and deeply practical. This one is for anyone who's ever stared at their portfolio, read one scary headline too many, and wondered whether simplicity still works. Ben's answer is basically yes—but only if you understand the risks, respect your own behavior, and build a portfolio you can actually stick with. This episode covers: Ben Carlson's "Bob" thought experiment and why even terrible market timing can still work out over the long run Why dollar cost averaging often beats waiting for the perfect entry point The psychology of lump-sum investing versus spreading money out over time What inflation looked like before World War II versus in the modern era How to think about inflation through a personal-finance lens, not just an investing lens Why housing, transportation, income growth, and stocks are major inflation defenses What Japan's lost decades teach us about home-country bias and international diversification Why diversification matters even more in retirement because of sequence-of-returns risk How to think about bonds, cash, duration, and risk tolerance in a more nuanced way . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW A Wealth of Common Sense Animal Spirits Podcast Risk and Reward: How to handle market volatility and build long-term wealth The Compound Youtube . ⏰ Related Episodes The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 Hanging On In a Yo-Yo Economy | Sam Stovall | 147 How to Bake a Cake: An Asset Allocation Mashup | Rick Ferri & Paul Merriman | 134 "The Risk Parity Paradox" an Exercise in Simple Complexity? | Frank Vasquez | 124 . 📌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.

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  • #224
    July 8 · 44 min

    You Hit The Number, Now What? | Childfree Life By Design Crossover | 224

    What if "legacy" looks completely different when there are no kids in the picture and that difference actually unlocks a freer, more intentional version of FI? In this thoughtful crossover between Childfree Life by Design and Catching Up to FI, Dr. Jay and Bill sit down for the kind of conversation most money media skips: what happens after you hit the number and realize the bigger question is no longer "Can I retire?" but "What am I retiring to?" It's philosophical, personal, a little messy in the best way, and exactly the kind of episode that reminds listeners that FI is not the finish line. It's the moment when the real design work begins. This episode covers: The "fog of FI" and the identity shift that can come after reaching financial independence The childfree midlife crisis and why "now what?" hits harder than many expect Legacy beyond lineage and how childfree people often redefine impact Why it is more important to know what you are retiring to than what you are retiring from The tension between purpose, freedom, and drifting after hitting major goals Health span, lifespan, and why time becomes more valuable once money pressure drops How giving, service, and creativity can become the next chapter after FI Why books, podcasts, and numbers alone cannot answer life-design questions The difference between being rich on paper and living a truly wealthy life Why underspending and over-optimizing can become their own retirement risks . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Childfree Wealth https://childfreewealth.com/ . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 . 📌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.

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  • #223
    July 5 · 1 hr 30 min

    FIlanthropy: Radical Impact Giving Without Risking Your Retirement | Rebecca Herbst | 223

    Bill jumps into a last-minute solo conversation with Rebecca Herbst of Yield and Spread for a surprisingly energizing deep dive into generosity, guilt, and what happens after the finish line of financial independence. Rebecca shares how hitting FI at 32 did not lead to endless victory-lap bliss so much as an identity jolt: if money is a tool, then what is it actually for? This episode covers: Why Rebecca felt guilt, not just freedom, after reaching FI at 32 How giving can be framed as money, time, or skills—not just writing checks Why generosity is a habit and a muscle, especially for lifelong savers The surprisingly small impact that a 1% giving rate can have on your FI timeline How "effective giving" applies investing-style thinking to charitable impact The difference between reactive emotional giving and proactive intentional giving Tax-smart giving tools like appreciated securities, donor-advised funds, and QCDs Why the FI community may be uniquely positioned to normalize bold generosity How giving can become part of a "life portfolio," not just a side project References & Resources Mentioned . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Yield and Spread FI Service Corps ⏰ Related Episodes Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200 Contrarian Tax Planning Tips | Cody Garrett & Sean Mullaney | 179 . 📌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.

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  • #222
    June 28 · 26 min

    Unbanked, Buried In Payday Loans & A 500 Credit Score: This Late-starter Overcame It All! | Afra Smith | 222

    What if the person inspiring the room didn't come from a polished finance background at all, but from payday loans, being unbanked, a credit score in the 500s, and the kind of rock bottom most FI stories rarely admit out loud? In this on-location episode from Madison, WI, Jackie sits down with Afra Smith, founder of The Melanin Project and creator of the Wealth Empowerment Conference, for a conversation that is as honest as it gets. She's a late-starter and shares how depression, financial chaos, and a painful career setback forced her to finally confront what wasn't working. She shares how one financial coach, one budget, and one decision to stop waiting for someone else to rescue her changed the direction of her life. From there, she built something much bigger than a comeback story. It's now a growing movement centered on financial wellness, lived experience, and giving people the tools to rebuild from where they actually are. Her raw truth is proof that your hardest chapter does not have to be your final one. This episode covers: Afra's journey from payday loans, ChexSystems, and depression to financial stability The career disappointment that became her wake-up call How one financial coach and a basic budget started her turnaround Why financial struggles in underserved communities are often deeper than "just spend less" The origin of The Melanin Project and the Wealth Empowerment Conference Why lived experience and emotional honesty matter in financial education The link between mental health, physical health, and wealth-building How Afra built a meaningful community event while still working a full-time job Why consumption habits and appearances can distort how we judge wealth and value What it looks like to turn pain into service and purpose . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW The Melanin Project TrueStage CLIMB USA (Bob Wynn) Madison Gas and Electric Company Summit Credit Union ⏰ Related Episodes From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007 We Found Them! Past Guests At The Women of FI Weekend | Kim H. and Lisa B. | 218 . 📌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.

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  • #221
    June 21 · 1 hr 3 min

    Intergenerational Wealth: Strategies to Help Your Family NOW (Not Later) | Allen Mueller | 221

    What if the smartest legacy move isn't leaving your kids a pile of money someday, but using your wealth right now to help them buy time, build habits, and change their future while you're still here to watch it happen? We sit down with Allen Mueller of 7 Saturdays Financial for a practical, deeply useful conversation about gifting to family with intention. The thread running through all of it is simple: money is not just for accumulating. It's for strengthening the people and values you care about most. This episode covers: Why gifting during your lifetime can be more impactful than leaving a larger inheritance later The difference between a tax threshold and a paperwork threshold for gifts How the annual gift exclusion really works Why many retirees underspend and unintentionally miss chances to help family now Smart ways to fund kids' and grandkids' futures through 529s, custodial Roths, and brokerage accounts How to think about gifting for college, healthcare, and home down payments Why "skin in the game" still matters when helping younger family members How appreciated shares can be gifted downstream or upstream for tax advantages Why wisdom and stewardship matter more than simply transferring money How FI can turn parents and grandparents into real-time wealth builders for the next generation . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW 7 Saturdays Financial Allen's LinkedIn . ⏰ Related Episodes Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193 . 📌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.

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  • S1 · E220
    June 14 · 1 hr 3 min

    Not So Big Life Design: The Architecture of Wealth | Sarah Susanka | 220

    What if the smartest move on your road to FI isn't buying a bigger house, but shrinking the footprint, clearing the clutter, and finally designing a life that actually fits? In this episode, we sit down with Sarah Susanka, the architect behind the bestselling "Not So Big House" movement. We talk about what happens when you stop building for appearances and start building for how you really live. Sarah shares how growing up in England, then landing in car-centric suburban Los Angeles made her question why Americans kept buying "hamburger bun but no hamburger" houses full of unused rooms. This episode covers: Sarah Susanka's origin story and how suburbia pushed her toward architecture The difference between building bigger and building better Why unused rooms are the housing version of lifestyle bloat - How right-sizing a home parallels right-sizing a life The design power of light, ceiling height, flow, and multi-use space How small architectural moves can create huge changes in mood and function Why old thought patterns can clutter a life just like unused rooms clutter a house The connection between beauty, sustainability, and building things that last How Bill used Sarah's ideas in his own home design and life redesign Why intentional design matters even more for late starters making a reset spaces. . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 👉🏽 https://a.co/d/01umGgeh (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Sarah's Website Not So Big Design Principles for House & Life with Sarah Susanka Sarah TedX talk 📗The Not So Big House: A Blueprint for the Way We Really Live The New Urbanism The Not So Big Bungalow . ⏰ Related Episodes How Clutter Steals Your Time (And How to Get It Back) | Rose Lounsbury | 188 . 📌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.

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  • June 10 · 1 hr 36 min

    Shocking Truths About Women's Financial History You Need to Know | Our Sheconomy Gameshow | 219

    What if the fastest way to understand women's financial power isn't another lecture, but a trivia game that quietly reveals how recent, fragile, and still unfinished so much of women's economic progress really is? In this special "Sheconomy" quiz-show episode, Jackie and Bill join Janine Firpo and financial planner Sarah-Catherine Gutierrez for a lively game show. They move from Equal Pay Day and credit-card rights to why women often outperform men as investors, why female-led companies and firms still get shut out, and what could happen if women intentionally shifted even a slice of their wealth toward their values. The tone is playful, but the message is serious: money is power, and women stepping into that power changes families, businesses, markets, and maybe the whole economy. This episode covers: The surprising timeline of women's financial rights in the US What Equal Pay Day reveals about how far women still have to go Why women often outperform men as investors How overconfidence and overtrading hurt returns Why women-led businesses still receive a tiny share of venture capital The rise of advice-only and flat-fee financial planning models What values-aligned and ESG investing actually mean Why women's money choices can reshape markets and communities How much wealth women are expected to control in the coming years The collective impact women could have by shifting capital intentionally . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 👉🏽 https://a.co/d/01umGgeh (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Our Sheconomy . ⏰ Related Episodes Vote Your Money: Values Aligned Investing | Janine Firpo | 139 The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016 . 📌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.

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  • #218
    June 7 · 30 min

    We Found Them! Past Guests At The Women of FI Weekend | Kim H. and Lisa B. | 218

    What happens when women in the financial independence community finally get a room of their own and use it not just to talk numbers, but to unpack the invisible stuff they've been carrying for years? In this on-location episode, Jackie takes us inside the Women of FI annual weekend in Maryland. This was a rare women-centered FI retreat that blends case studies, life design, laughter, and vulnerability. She catches up with two familiar voices from past episodes, Kim Hunter-Borst and Lisa B. to hear what retirement, sabbaticals, and post-FI life actually look like in motion, not just on paper. Other attendees also share why a women-only space hits differently: less posturing, more honesty, more room to talk about emotional labor, caregiving, identity, and the inner work that often gets skipped in mixed-money spaces. This episode covers: What happened at the Women of FI annual women's weekend in Maryland Why women-centered FI spaces create a different kind of openness and trust Kim Hunter-Borst's vision for building a smaller, more vulnerable, more intentional retreat The 2026 theme of "release" and what women said they were ready to put down A retirement update from Kim after leaving full-time work A follow-up from Lisa B. on quitting her job, taking a summer break, and what happened next Why women said they needed space for both the "outer" and "inner" work of FI How attendees are thinking about Coast FI, sabbaticals, community, and post-FI life . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined. Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start Covers everything from basics to advanced strategies in one guide Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 👉🏽 https://a.co/d/01umGgeh (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Women Of FI WE Wealth Collective Facebook Group EconoMe Conference https://economeconference.com CampFI FinTalks Events . ⏰ Related Episodes Drowning in Debt at 48, Retired at 58: Here's How She Did It! | Kim Hunter-Borst | 181 Case Study: The Real Numbers That Told Her She Could Quit her Job, Now! | Lisa B | 161 The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016 . 📌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.

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  • #217
    May 31 · 1 hr 1 min

    Why "One More Year" Isn't Always a Mistake | Bill, Jackie, Patrick | 217

    What if "one more year" isn't a failure of courage. What if it's a messy, human, sometimes wise transition between the life you built and the life you're finally ready to choose? In this spontaneous, unusually raw episode, Bill, Jackie, and Patrick crack open the emotional side of financial independence. They go beyond the surface of the hesitation, identity shift, grief, relief, and weird freedom that can show up when the math says you're done but your nervous system is still catching up. Bill shares what it feels like to downshift after unexpectedly reaching FI, why he's enjoying work more now that he doesn't need it, and how a heartbreaking night in the ER sharpened his thinking about what really counts. Jackie reflects on her own two-year "one more year" phase and why she no longer sees it as a mistake so much as a cushion she needed. Patrick adds the planner's lens: if a choice still serves your life, it may not be "one more year" syndrome at all. This episode is a heartfelt reminder that the real work isn't just reaching the number but learning how to let go when the time comes. This episode covers: Why "one more year syndrome" may not actually be a bad thing The emotional transition from being FI on paper to actually changing your life Bill's intentional downshift and how FI gave him leverage at work Jackie's two-year hesitation and why she now sees it with more grace How fear, identity, purpose, and burnout all shape retirement timing Why working after FI can still make sense if it serves your life The difference between choosing one more year and drifting into it unconsciously How tragedy and loss can change the way you think about time Why the second chapter of life requires more than just good math How late starters can prepare emotionally, not just financially, for freedom . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Catching Up to FI Facebook Community Jackie's FIRE Letter . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007 Our Team is Growing: Welcome Patrick! | Patrick McDonnal | 136 The Three Kinder Questions (Part 2) | George Kinder | 141 The pURPOSE Code | Jordan Grumet | 115 Hard & Soft Sides of Retirement | Fritz Gilbert | 019 . 📌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.

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  • #216
    May 24 · 51 min

    How to Retire Sooner and Spend More: Risk-Based Guardrails Explained | Aubrey Williams | 216

    What if the real danger in retirement isn't running out of money, but spending so cautiously that you accidentally work too long, live too small, and die with a portfolio that never got a chance to do its job? In part two with Aubrey Williams, we go deeper into the "fog of FI" (that weird, anxious place where the spreadsheet says you're free, but your nervous system absolutely does not believe it). This episode covers: Why the 4% rule can make FI people overwork and underspend How future income streams like Social Security can move your FI date forward Why flexible spending is more realistic than flat, inflation-adjusted withdrawals How risk-based guardrails help you know when to cut or increase spending Why many FI people need more help increasing spending than reducing it How personal inflation can differ from CPI and affect retirement planning Why historical analysis may be more useful than Monte Carlo for some FI decisions How small amounts of income in retirement can meaningfully reduce portfolio pressure Why engineers and analytical types often need better data to trust they're "done" How Bill is using these ideas to finally get clearer about leaving work sooner . S U P P O R T T H E S H O W 📩 Sign up for our newsletter https://catchinguptofi.com/contact-us/#newsletter 🌐 Visit Catching Up to FI website https://catchinguptofi.com 👥 Connect with us https://linktr.ee/cutfi ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" https://www.buymeacoffee.com/catchinguptofi 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question https://catchinguptofi.com/contact-us/#voicemails ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Open Path Financial Aubrey's EconoMe Talk (2026): Coming soon! Income Lab FIREproof (Lauren Boland) Projection Lab Open Source Guardrails Simulation (Roger Cost) . ⏰ Related Episodes Part 1: Why Your Brain is Hardwired to Keep You Working (and How to Fix It) | Aubrey Williams | 214 A Richer Retirement: The 4.7% Rule | Bill Bengen | 169 Sequence of Returns Risk: What Every Retiree Needs to Know | Karsten Jeske | 106 If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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.

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  • #215
    May 20 · 1 hr 3 min

    Why You Should Stop Beating Yourself Up for Starting Late | "How To Money" Crossover | 215

    What if the biggest difference between someone who starts at 22 and someone who starts at 50 isn't intelligence or income, but simply the moment they finally decide, nobody's coming to save me? In this crossover episode, Bill joins Joel on "How to Money" to tell the brutally honest and surprisingly hopeful truth. He shares his story of becoming financially independent after a 20-year sleepwalk through lifestyle inflation, doctor money mistakes, and zero real financial plan. It's candid, practical, and exactly the kind of episode that makes you stop saying "I'm behind" and start asking "What's my next move?" This episode covers: Bill's late-starter journey from paycheck-to-paycheck doctor to financially independent at 60 How "rich doctor syndrome" and lifestyle inflation can keep high earners broke Why debt, overspending, and delayed gratification derailed his early money life The wake-up call that came from burnout, a malpractice lawsuit, and turning 50 How downsizing, geo-arbitrage, and a higher savings rate changed everything Why savings rate matters more than most people realize for late starters How to think about debt payoff versus investing when you feel behind Why college funding, generational wealth, and retirement planning are all connected How Bill thinks about using a financial advisor after a long DIY phase Why financial independence is really about buying back time, autonomy, and health . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 🆕Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW How To Money The White Coat Investor George Kinder William Bernstein . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197 . If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! . 📌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.

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