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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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#241
Today · 45 min
Small Money Ideas That Lead To Bigger Conversations | AICPA Crossover | 241
What if the smartest financial planning move isn't a 100-page plan, but one question that makes you stop and say, "Wait... I can do that?" In this crossover with the AICPA Personal Financial Planning Podcast, Jackie puts on her professional hat for two conversations about the small ideas that can create much bigger financial wins. First, she and host Cary Sinnett unpack five high-impact planning opportunities involving 529s, 72(t)s, HSAs, charitable giving, and forgotten retirement accounts. Then they zoom out to the bigger question: why financial literacy, not products or strategies, is the foundation for better decisions and greater financial independence. Jackie also tackles FIRE stereotypes, the shame late starters often carry, and the "superpowers" that can emerge once people stop beating themselves up and start asking better questions. This episode covers Five small financial-planning conversations that can uncover much bigger opportunities New and expanded ways families may be able to use 529 plans How 72(t) distributions can help some people access retirement money before age 59½ Why HSAs can be much more than simple medical spending accounts Charitable-giving strategies ranging from smaller deductions to donor-advised funds How to search for forgotten 401(k)s and other unclaimed assets Why financial literacy should come before complicated products and strategies How money beliefs and behavior can overpower mathematically "correct" decisions Why FIRE doesn't require copying someone else's lifestyle The late-starter journey from shame and guilt to action, confidence, and financial "superpowers" . === 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 AICPA Personal Financial Planning Podcast Retirement Savings Lost and Found Database National Association of State Treasurers (Missing Money) . 📌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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#240
Sunday · 1 hr 16 min
3 Non-Employer Health Insurance Case Studies: More Choices Than You Thought | Lyndia Cunningham (Part 2) | 240
Need to figure out health insurance on your own? It's a little scary if you don't get it through an employer and too young for Medicare, but there are lots of options. In Part 2 with health insurance broker, Lyndia Cunningham, Bill and Jackie put early-retirement healthcare planning to the test with three very different case studies. Jackie rewinds to age 49 and walks through the decisions she faced before leaving work, including ACA subsidies and income planning. Bill brings a high-income household with no employer benefits and explains how stumbling into Tennessee Farm Bureau coverage slashed his monthly premiums by thousands. Then listener Brooke explores whether health insurance really needs to be the golden handcuffs keeping her in a W-2 job. This episode covers How Jackie could have evaluated healthcare before retiring at 49 Why retirement timing and modified adjusted gross income can dramatically affect ACA costs Bronze versus Silver plans, cost-sharing reductions, and HSA eligibility How to make sure an ACA plan actually includes the doctors you want to keep What Jackie ultimately paid for healthcare after retiring Why Bill chose Farm Bureau coverage instead of the ACA marketplace How medical underwriting and non-ACA major medical plans work Health insurance options for adult children aging off a family plan How association plans, college health plans, and HSAs can expand your choices Whether healthcare really needs to keep Brooke (or anyone else) tied to a job . This is the second part of a 2-part episode. Be sure to subscribe the show and catch part 1 (episode 239) from 9/27/26. . === 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 Move Health Move Health YouTube Health Insurance for Early Retirees ACA Health Insurance Marketplace . ⏰ Related Episodes How to Get Health Insurance When You Retire Early | Lyndia Cunningham (Part 1) | 239 Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98 Maximizing HSAs Part 2: Devising Drawdowns, Badass Scenarios, Listener Questions | Jeff York | 99 . 📌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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#239
September 27 · 1 hr 26 min
How to Get Health Insurance When You Retire Early | Lyndia Cunningham(Part 1) | 239
What if the biggest thing standing between you and early retirement isn't your savings... it's your health insurance? Bill and Jackie welcome Lyndia Cunningham of Move Health to tackle the healthcare headache that keeps so many Americans working until 65. From COBRA and short-term medical plans to faith-based health sharing and the Affordable Care Act, Lyndia walks through the options that could change your retirement timeline. Throw in retroactive COBRA, Medicaid, college health plans and direct primary care, and suddenly the path to healthcare freedom looks a lot less mysterious. This episode covers The health insurance options available to early retirees before Medicare at 65 How COBRA, short-term medical insurance, Farm Bureau plans and healthcare-sharing programs compare The important differences between ACA-compliant insurance and other types of coverage How spouses, dependents and college students can access alternative coverage Retroactive COBRA and planning for the transition out of employer-sponsored insurance ACA essential health benefits, provider networks and out-of-state coverage limitations How ACA premium subsidies interact with household income, Roth conversions and HSA contributions Medicaid eligibility and the complications that can arise for early retirees and their families Dental, vision, accident and critical illness coverage beyond a basic health insurance plan How HSAs and direct primary care can fit into a broader retirement healthcare strategy . This is the first part of a 2-part episode. Be sure to subscribe to the channel and catch part 2 next week (10/4/26). . === 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 Move Health Move Health YouTube ACA Health Insurance Marketplace . ⏰ Related Episodes Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98 Maximizing HSAs Part 2: Devising Drawdowns, Badass Scenarios, Listener Questions | Jeff York | 99 . 📌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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#238
September 20 · 1 hr 35 min
The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238
Exposed! We go behind the scenes with industry experts and disrupters in the retail car-buying market, Ray and Zach Shefska. They are the powerful father-son team behind CarEdge, a car-buying platform that's fighting fiercely for transparency. Ray brings 43 years of dealership experience and Zach brings the modern tech (like AI agents) and viral moments when he exposes dealers misbehaving. Together, they reveal how dealerships really make money, including things like dealer fees, financing, and often unnecessary ad-ons. Don't miss this breakdown of smart ways for you to research, shop, avoid games some dealers play, and get the fairest price on your next car. This episode covers How dealerships use monthly payments to distract buyers from the total cost of a car Why negotiating a vehicle can be especially difficult for women and minority buyers Using AI agents to obtain and negotiate real dealer pricinng The fees, add-ons, and protection packages buyers should question Why "if it's taxable, it's negotiable" is one of Ray's favorite rules How to get and compare a true out-the-door price Why a pre-purchase inspection is critical when buying a used vehicle The pros and cons of CarMax and Carvana How pre-approved financing can protect you from dealer interest-rate markups Cash versus financing, leasing and total cost of ownership Ray's ultimate rule: buy what you need, not just what you want . === 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 CarEdge (Research, Dealer Ratings, Car-buying Service) CarEdge Podcast CarEdge YouTube CarEdge Live YouTube Shady Car Dealers are Done! Fair Pricing Summit DC Zach's AI Summit Talk Ray's letters to his late wife Suzanne . 📌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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#237
September 13 · 1 hr 7 min
61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237
What if the biggest retirement risk isn't running out of money, but being too afraid to spend the money you worked decades to build? Personal finance icon Jean Chatzky joins Bill and Jackie to tackle the psychology and math behind turning a lifetime of savings into a Forever Paycheck. Jean shares her own late-start reset after losing her father, getting divorced, and getting fired within a single year. She then explains why retirees often happily spend Social Security and pensions while fiercely protecting their investment balances. Together they explore Jean's tools that can create both security and permission to spend. Jackie even runs her own numbers and discovers her forever-income gap might be surprisingly easy to fill. This episode covers Jean Chatzky's own financial reset after a series of major life changes at 40 Why retirees can become surprisingly reluctant to spend their accumulated savings The "decumulation gap" and the psychology behind creating a retirement paycheck How to build a "moat budget" around essential expenses and important wants How risk tolerance and FOMO can shape your retirement-income strategy Why Jean changed her long-held opinion about annuities How home equity, insurance, HSAs, and other assets can become retirement resources Why late starters need forgiveness, benchmarks, and trusted guidance, not perfection . === SUPPORT THE SHOW === 📩 Sign up for our newsletter 📺 Watch & Subscribe to our YouTube Channel 🌐 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 Forever Paycheck Her Money Her Money Podcast Guaranteed Income: A License to Spend (A research paper by David Blanchett and Michael Finke) . ⏰ Related Episodes Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233 How To Build Your Own Paycheck: From Saver to Spender | Fritz Gilbert & Dana Anspach | 171 . 📌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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#236
September 9 · 1 hr 3 min
The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236
What happens when you finally reach financial independence and your brain responds with, "Great, now what?" 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 wake-up call at age 50 and his "trifecta" of late-starter mistakes How he and his wife moved from single-digit saving to a 30–40% savings rate Working through regret, shame, anger, and scarcity after a late start Why lifestyle downsizing felt more freeing than depriving The "fog of FI" and why reaching your number does not automatically make retirement easy One-more-year syndrome, professional identity, and creating a gradual glide path out of work How FI gave Bill leverage to cut shifts, reduce night work, and reclaim his time The advantages late starters still have despite missing decades of compounding Why health, relationships, community, and purpose become more important after the math is solved Bill's belief that relationships may compound even better than money . === 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 ChooseFI https://choosefi.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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#235
September 6 · 1 hr 25 min
How to Build a Bulletproof 72(t) Plan: CPA Audits Jackie's Real #s | Bill Stecker (Part 2) | 235
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 has actually grown even though she's been taking money out. This episode covers Why Bill strongly favors the amortization method for most practical 72(t) plans How the 5% interest-rate floor changed SEPP planning The three basic inputs needed to calculate a 72(t) How to document the correct starting IRA balance What records to keep in case the IRS ever asks questions Why annual withdrawals may reduce opportunities for mistakes How to handle a 1099-R that says "early distribution, no known exception" Jackie's real-life 72(t) setup, asset allocation, and withdrawal schedule How 72(t)s can work alongside Roth conversions and other income strategies Why some people may qualify for better early-withdrawal exceptions and not need a SEPP at all This is the second part of a 2-part episode. Be sure to subscribe the show and catch part 1 (episode 234) from 8/30/26. . === 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 🌐72tcalc.com Website Free consultation with Bill Stecker's Firm (The Marble Group) email: themarblegroup@wispertel.net Phone: (312) 361-0221 Official IRS Tax Code 72(t) IRS Notice 2022-6 (sets a new floor interest rate of 5% for calculating 72(t) distributions) 72(t) Calculators 72tCalc FI Tax Guy 72(t) using Google Sheet Dinkytown CalcXML UngrindFi . ⏰ Related Episodes Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty | Bill Stecker (Part1) | 234 72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131 Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133 . 📌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.
- Transcript
#234
August 30 · 56 min
Retiring Early? CPA Explains How To Use A 72(t) to Escape The 10% Penalty | Bill Stecker (Part1) | 234
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 72(t)s can be incredibly powerful tools for early retirees, laid-off workers, and anyone ready to leave the traditional "hours-for-dollars" trade. This episode covers What a 72(t) or SEPP plan actually is Access to retirement accounts before age 59½ without the 10% penalty tax Why so many financial professionals hesitate to work with 72(t) plans The minimum plan period and why modifying a SEPP can become extremely expensive How to determine how much early retirement income you actually need The differences between the Rule of 55 and a 72(t) strategy Why Bill usually prefers moving money from employer "plan land" into "IRA land" How brokerage accounts, Roth contributions, part-time work, and SEPPs can work together Why inflation and unexpected expenses need to be built into an early-retirement income plan How splitting an IRA into separate accounts can create flexibility and isolate potential mistakes This is the first part of a 2-part episode. Be sure to follow the show and catch part 2 next week (9/6/26). . === 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 🌐72tcalc.com Website Free consultation with Bill Stecker's Firm (The Marble Group) email: themarblegroup@wispertel.net Phone: (312) 361-0221 72(t) Calculators 72tCalc FI Tax Guy 72(t) using Google Sheet Dinkytown CalcXML UngrindFi Official IRS Tax Code 72(t) . ⏰ Related Episodes 72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131 Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133 . 📌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.
- Transcript
August 27 · 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.
- Transcript
August 23 · 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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