Catching Up to FI
- Episodes
- 249
- Released
- weekly
- Latest episode
- Nov 8, 2026
About the podcast
A mindset, money, and life podcast for late starters catching up to Financial Independence.
Episodes 249
The Ultimate Playbook On What "Not" To Do When The Stock Market Drops | Barry Ritholtz | 247
Legendary investor Barry Ritholtz joins the show for a wide-ranging tour through the experiences, mistakes, and behavioral quirks that shaped his investing philosophy and his book, "How Not to Invest". He tells …
Show notes
Legendary investor Barry Ritholtz joins the show for a wide-ranging tour through the experiences, mistakes, and behavioral quirks that shaped his investing philosophy and his book, "How Not to Invest". He tells us why becoming a better investor has less to do with being brilliant and more to do with simply being less stupid. The lesson? You don't have to predict markets, outsmart Wall Street, or find the next 100-bagger. Build a plan, let compounding work, and stop stealing returns from your future self.
This episode covers:
- How Barry's childhood experiences shaped his view of money as a tool rather than a scorecard
- His unconventional path from law school to a trading desk and behavioral finance
- What Bernie Madoff really stole from investors: decades of lost compounding
- Charlie Munger, Charlie Ellis, and the power of avoiding unforced investing errors
- Why passive investing has such a powerful mathematical advantage
- How scary headlines, denominator blindness, and bad statistics distort our perception of risk
- Why process matters more than outcomes when evaluating investment decisions
- Dunning-Kruger, metacognition, and knowing when you're outside your circle of competence
- Barry's Apple and Robinhood mistakes—and what they taught him about humility
- Advisor fees, AI, Altruist, Vanguard, and where Barry thinks financial advice is headed
.
=== SUPPORT THE SHOW ===
🌐 Visit Catching Up to FI website
☕ 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===
NEW! Mama Are We Poor?"Mama Are We Poor?" is a new childrens' book by co-host, Dr. Bill Yount and past guest, Monica Scudieri. They teamed up after the interview on episode #120 in 2025. Monica shared a sweet moment she had with her son and he asked here the question "Mama are we poor". Almost two years later, they collaborated to create a heartfelt, beautifully illustrated picture book that helps parents and caregivers open up conversations about money, financial stress, and family resilience with young readers. Through a child's eyes, kids learn that worth isn't measured in dollars-and that love, stability, and gratitude can carry a family through hard times.
.
F.I.R.E. For Dummies
Co-host Jackie Cummings Koski, CFP®, AFC® is 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.
📕 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
.
⏰ Related Episodes
Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225
The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201
Forget the Corporate Ladder, Here's How to Climb 'The Wealth Ladder' | Nick Maggiulli | 159
.
CHAPTERS:
0:00 Intro- Who Barry Ritholtz was before Wall Street
3:00 Money as a tool, childhood jobs, cars, and buying experiences
8:00 Horses, bartering for opportunity, and an unconventional education
12:00 Discovering trading and behavioral finance
18:00 Bernie Madoff, statistics, fraud, and the compounding he stole
24:00 Charlie Munger, Charlie Ellis, and avoiding unforced errors
31:00 Why passive investing wins the math 34:00 Sharks, crashes and bad numbers
41:00 Process over outcome 49:00 The unbelievable power of compounding
59:00 Custodians, Altruist, and why your advisor shouldn't hold your money
1:16:00 Vanguard and Altruist
1:22:00 Barry's mentors, favorite books, and advice to his younger self
.
📌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.
A Closer Look At Target-Date Funds: You Won't Believe What We Found! | David Brown & Shaun Davies | 246
Finance professors Shaun Davies, PhD, CFA and David Brown, PhD join the show to give us a look under the hood of target-date funds (TDFs). What they found may surprise you! Their research reveals enormous …
Show notes
Finance professors Shaun Davies, PhD, CFA and David Brown, PhD join the show to give us a look under the hood of target-date funds (TDFs). What they found may surprise you! Their research reveals enormous differences in fees, risk, glide paths, active management, and performance; even among funds carrying the exact same retirement year. But this isn't a target-date-fund takedown. TDFs have helped millions of people get invested, stay invested, and avoid some bad behavioral decisions. The real question is whether yours is actually doing what you think it is. Bill also brings on Jesse Cramer of Personal Finance for Long-Term Investors to join this important conversation.
This episode covers:
- What a target-date fund actually owns and how its glide path changes over time
- Why two funds with the same target year can produce dramatically different results
- How fees and poor active management contributed to historical TDF underperformance
- Why a fund's risk level may matter more than matching its date to your expected retirement year
- What late starters and FIRE investors should consider when choosing a TDF vintage
- Why the target-date-fund industry still lacks a useful universal benchmark
- How Glidepath Financial's replicating-fund approach compares TDFs against low-cost passive alternatives
- The life-cycle investing idea that your future earnings effectively behave like a bond
- Why TDFs can still be powerful behavioral tools despite their imperfections
- Collective investment trusts, retirement decumulation, annuities, private assets, and where TDFs may go next
.
=== SUPPORT THE SHOW ===
🌐 Visit Catching Up to FI website
☕ 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===
NEW! Mama Are We Poor?"Mama Are We Poor?" is a new childrens' book by co-host, Dr. Bill Yount and past guest, Monica Scudieri. They teamed up after the interview on episode #120 in 2025. Monica shared a sweet moment she had with her son and he asked here the question "Mama are we poor". Almost two years later, they collaborated to create a heartfelt, beautifully illustrated picture book that helps parents and caregivers open up conversations about money, financial stress, and family resilience with young readers. Through a child's eyes, kids learn that worth isn't measured in dollars-and that love, stability, and gratitude can carry a family through hard times.
.
F.I.R.E. For Dummies
Co-host Jackie Cummings Koski, CFP®, AFC® is 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.
📕 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
Off Target: On the Underperformance of Target-Date Funds
Glidepath Financial (compare target-date funds)
.
⏰ Related Episodes
The Biggest Retirement Mistake: Over Saving and Under Living | Rachael Camp & Jesse Cramer | 198
Space Telescopes, Sunflowers, and Financial Gardening | Jesse Cramer | 105
How to Bake a Cake: An Asset Allocation Mashup | Rick Ferri & Paul Merriman | 134
.
CHAPTERS:
0:00 Intro
4:00 How target-date funds became America's default
7:00 What's really under the hood
10:00 The 1% problem
14:00 Risk differences
18:00 How to choose a TDF
27:00 Human capital as a bond
35:00 The ten building blocks
38:00 Do we even need bonds?
44:00 The behavioral case for TDFs
56:00 Glidepath ratings
.
📌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.
Financial Freedom Beyond Spreadsheets: Writing Books and Songs on FIRE | The Donegans & Monica Scudieri | 245
Alan and Katie Donegan and Monica Scudieri join Bill and Jackie to explore what happens when financial survival mode finally loosens its grip and creative bandwidth comes roaring back. They talk imposter …
Show notes
Alan and Katie Donegan and Monica Scudieri join Bill and Jackie to explore what happens when financial survival mode finally loosens its grip and creative bandwidth comes roaring back. They talk imposter syndrome, discomfort, perfectionism, public speaking, writing books, making music, and why FI can turn passive consumers into active creators. They also announce the world debut of the new Catching Up to FI theme song and the new book "Mama Are We Poor?" authored by Bill and Monica.
This episode covers
- How financial independence can free up mental bandwidth for creativity
- Moving from passive consumption to actively creating and sharing what you know
- Imposter syndrome and why people convince themselves investing, or creativity, is "not for people like me"
- Why discomfort, fear, and mistakes often signal that you're actually growing
- Public speaking, preparation, perfectionism, and getting started before you feel ready
- The story behind Bill and Monica's children's book, Mama, Are We Poor?
- How Alan, Katie, and Finn turned financial independence concepts into music
- Why work optionality doesn't necessarily mean quitting work completely
- Rediscovering the creative interests you may have left behind in childhood
- A seven-day challenge to stop overthinking, get sloppy, and create something
.
=== SUPPORT THE SHOW ===
🌐 Visit Catching Up to FI website
☕ 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===
NEW! Mama Are We Poor?"Mama Are We Poor?" is a new childrens book by co-host, Dr. Bill Yount and past guest, Monica Scudieri. They teamed up after the interview on episode #120 (https://youtu.be/oerxEJYrTdM?si=vt2aZSE2wgKVGeIn) in 2025. Monica shared a sweet moment she had with her son and he asked here the question "Mama are we poor". Almost two years later, they collaborated to create a heartfelt, beautifully illustrated picture book that helps parents and caregivers open up conversations about money, financial stress, and family resilience with young readers. Through a child's eyes, kids learn that worth isn't measured in dollars-and that love, stability, and gratitude can carry a family through hard times.
.
F.I.R.E. For Dummies
Co-host Jackie Cummings Koski, CFP®, AFC® is 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.
📕 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
Grab Your Slice (Monica Scudieri)
.
⏰ Related Episodes
"Mama, Are We Poor?": A Single Mom's Millionaire Mindset | Monica Scudieri | 120
Not Just Another Album, It's A Money Revolution! | Alan & Katie Donegan | 129
Indiana Jones and an Extraordinary Life with the Donegans | Alan and Katie Donegan | 079
.
📌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.
4 Phases of Retirement Explained: The Realities of Each May Surprise You! | Dana Anspach | 244
Dana Anspach, CFP® and founder of Sensible Money, returns to explain why retirement isn't one long, predictable chapter, it's a series of distinct phases with different financial and emotional needs. Using the …
Show notes
Dana Anspach, CFP® and founder of Sensible Money, returns to explain why retirement isn't one long, predictable chapter, it's a series of distinct phases with different financial and emotional needs. Using the framework from her new book, Living Off Your Acorns, Dana walks Bill and Jackie through the pre-go, go-go, slow-go, and no-go years.
This episode covers
- Dana's four phases of retirement: pre-go, go-go, slow-go, and no-go
- Why retirement planning should begin at least five years before leaving work
- The emotional transition from receiving a paycheck to living off your accumulated "acorns"
- A three-part pre-retirement checklist: cash flow, stress testing, and planning your time
- Why social connections and identity need as much planning as the financial side
- Fundedness ratios, the Critical Path, and alternatives to relying only on a safe withdrawal rate
- Special considerations for people retiring early, including healthcare and longer time horizons
- Mortgages, HELOCs, pledged asset lines, and when debt can still be useful in retirement
- How spending naturally changes during the slow-go years
- Fraud, cognitive decline, powers of attorney, and preparing for someone else to eventually help manage your finances
.
=== SUPPORT THE SHOW ===
🌐 Visit Catching Up to FI website
☕ 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===
NEW! Mama Are We Poor?"Mama Are We Poor?" is a new childrens book by co-host, Dr. Bill Yount and past guest, Monica Scudieri. They teamed up after the interview on episode #120 (https://youtu.be/oerxEJYrTdM?si=vt2aZSE2wgKVGeIn) in 2025. Monica shared a sweet moment she had with her son and he asked here the question "Mama are we poor". Almost two years later, they collaborated to create a heartfelt, beautifully illustrated picture book that helps parents and caregivers open up conversations about money, financial stress, and family resilience with young readers. Through a child's eyes, kids learn that worth isn't measured in dollars-and that love, stability, and gratitude can carry a family through hard times.
.
F.I.R.E. For Dummies
Co-host Jackie Cummings Koski, CFP®, AFC® is 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.
📕 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
.
⏰ Related Episodes
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.
How to Make Financial Mistakes and Still FIRE! | Doug Cunnington of Mile High FI Podcast | 243
What if getting to FI has less to do with avoiding mistakes and more to do with surviving them without setting too much money on fire? Bill joins Doug Cunnington of Mile High FI for a refreshingly imperfect …
Show notes
What if getting to FI has less to do with avoiding mistakes and more to do with surviving them without setting too much money on fire? Bill joins Doug Cunnington of Mile High FI for a refreshingly imperfect look at the financial decisions they wish they could redo. Between them: credit card debt, lifestyle inflation, whole life insurance, expensive advisors, an underwater dream house, a foreclosure, selling stocks at exactly the wrong time, and the very FI-specific problem of eventually becoming too good at saving. But this isn't just a financial confession booth. Bill and Doug compare what actually helped them recover, why "good enough" beats perfect, and how both still reached FI despite getting plenty wrong along the way.
This episode covers
- Why financial mistakes are often part of the learning process rather than proof you've failed
- Bill's late-start wake-up at 50 and Doug's accidental path into the FI community
- How missing financial education can turn needs, wants, and lifestyle inflation upside down
- Whole life insurance, expensive advisors, and the opportunity cost of bad financial products
- When DIY investing works—and when professional advice can uncover expensive blind spots
- Doug's housing mistake, rental losses, and strategic foreclosure
- Bill's over-renovated home, car payments, debt, and the cost of "too much house"
- Investing mistakes including selling during crashes and chasing recent winners
- Why aggressive savers can eventually struggle to give themselves permission to spend
- Bill's "fog of FI," phased retirement, and learning to use financial independence instead of merely reaching it
.
=== SUPPORT THE SHOW ===
🌐 Visit Catching Up to FI website
☕ 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
.
⏰ Related Episodes
The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236
The Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211
.
📌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.
Debunking the Biggest Retirement Fear Tactics With Erin Talks Money | Erin Moriarity | 242
Erin Moriarity, the plain-English force behind Erin Talks Money, joins Bill and Jackie to unpack why retirement planning gets easier when we stop worshipping giant portfolio numbers and start thinking in …
Show notes
Erin Moriarity, the plain-English force behind Erin Talks Money, joins Bill and Jackie to unpack why retirement planning gets easier when we stop worshipping giant portfolio numbers and start thinking in income, spending, and real life. Erin traces her path from buying Campbell Soup stock at eight with her investing grandmother to earning the best 34 cents of her life on YouTube. She eventually grew the massive financial education platform we know today. Then the conversation moves into the stuff retirees actually worry about: whether late starters can still catch up, how Social Security may change, why the 4% rule gets mangled in headlines, and why lifelong savers often struggle more with spending than saving.
This episode covers
- How Erin Talks Money grew from a struggling YouTube experiment into a major financial education platform
- The radically different money personalities in Erin's family and how they shaped her approach to finance
- Why painful childhood experiences with money made financial independence and control so important to Erin
- Why late starters can still make enormous progress with a 10–15 year runway
- Why retirement income can feel more meaningful than staring at a large portfolio balance
- The evolution of Erin's content from budgeting and FIRE to retirement income and decumulation
- Social Security reform, the wage base, the "donut hole," and why no single fix solves everything
- Why phased retirement can strengthen both your finances and your quality of life
- The psychological challenge of switching from lifelong saver to confident spender
- Why scary headlines about Social Security, long-term care, inflation, and retirement spending often need more context
.
=== SUPPORT THE SHOW ===
🌐 Visit Catching Up to FI website
☕ 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
Erin's forthcoming retirement-spending book (estimated release: December, 2027)
Social Security Online Account
.
⏰ Related Episodes
61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237
Social Security Made Simple | Mike Piper | 054
.
📌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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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.
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 …
Show notes
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).
.
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===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
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RESOURCES MENTIONED ON THE SHOW
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
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📌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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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===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)
Shady Car Dealers are Done! Fair Pricing Summit DC
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.
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 …
Show notes
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 ===
📺 Watch & Subscribe to our YouTube Channel
🌐 Visit Catching Up to FI website
☕ 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
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===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
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
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📌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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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===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
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⚠️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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
Free consultation with Bill Stecker's Firm (The Marble Group)
- email: [email protected]
- Phone: (312) 361-0221
IRS Notice 2022-6 (sets a new floor interest rate of 5% for calculating 72(t) distributions)
72(t) Calculators
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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===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
Free consultation with Bill Stecker's Firm (The Marble Group)
- email: [email protected]
- Phone: (312) 361-0221
72(t) Calculators
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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===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
How Not to Invest
.
📌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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
Retirement Planning Education website
Retirement Savings Lost and Found Database
Pension Benefit Guaranty Corporation (PBGC)
Dinkytown.net- Pension vs. Lump Sum Payout Calculator
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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.
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 …
Show notes
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
.
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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
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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
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===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
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
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===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
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
Bernadette Joy's free retirement checklist and newsletter
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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===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
457bwiser https://457bwiser.org/
Learned by Being Burned (Special) Podcast Series)
Man with the (Better Retirement) Plan (#262)
403bwise and 457bwiser Facebook Group
Request a Dan and Scott Presentation
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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 ===
🌐 Visit Catching Up to FI website
☕ 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
457bwiser https://457bwiser.org/
Learned by Being Burned (Special) Podcast Series)
Man with the (Better Retirement) Plan (#262)
403bwise and 457bwiser Facebook Group
Request a Dan and Scott Presentation
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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 and Reward: How to handle market volatility and build long-term wealth
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
Madison Gas and Electric Company
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
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===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
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
Not So Big Design Principles for House & Life with Sarah Susanka
📗The Not So Big House: A Blueprint for the Way We Really Live
.
⏰ 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.
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 …
Show notes
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 ===
🌐 Visit Catching Up to FI website
☕ 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
. ⏰ 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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