Catching Up to FI

Off Target: On the Underperformance of Target-Date Funds

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===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.

📕 Get Your Copy

.

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)

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For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: https://catchinguptofi.com/our-partners/

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RESOURCES MENTIONED ON THE SHOW

Glidepath Financial (compare target-date funds)

David C. Brown

Shaun Davies

Jesse Cramer

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⏰ 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

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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

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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.

Nov 1, 2026 1 hr 27 min

Financial Freedom Beyond Spreadsheets: Writing Books and Songs on FIRE | The Donegans & Monica Scudieri | 245

Episode 245

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

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=== SUPPORT THE SHOW ===

Grab Your Slice (Monica Scudieri)

☕ 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.

📕 Get Your Copy

.

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: https://catchinguptofi.com/our-partners/

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RESOURCES MENTIONED ON THE SHOW

The Donegans

Rebelutionaries on Spotify

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⏰ 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

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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.

Oct 28, 2026 1 hr 16 min

4 Phases of Retirement Explained: The Realities of Each May Surprise You! | Dana Anspach | 244

Episode 244

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

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=== SUPPORT THE SHOW ===

How To Build Your Own Paycheck: From Saver to Spender | Fritz Gilbert & Dana Anspach | 171

☕ 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.

📕 Get Your Copy

.

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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Sensible Money

📙Living Off Your Acorns

The Retirement Manifesto

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⏰ Related Episodes

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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.

Oct 25, 2026 1 hr 25 min

How to Make Financial Mistakes and Still FIRE! | Doug Cunnington of Mile High FI Podcast | 243

Episode 243

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 ===

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

☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"

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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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Mile High FI Podcast

Mile High FI YouTube

.

⏰ Related Episodes

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.

Oct 18, 2026 1 hr 4 min

Debunking the Biggest Retirement Fear Tactics With Erin Talks Money | Erin Moriarity | 242

Episode 242

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

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=== SUPPORT THE SHOW ===

Erin Talks Money LinkedIn

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Erin Moriarity website

Erin Talks Money Youtube

Root Financial

Erin's forthcoming retirement-spending book (estimated release: December, 2027)

Social Security Online Account

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⏰ 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.

Oct 11, 2026 1 hr 4 min

Small Money Ideas That Lead To Bigger Conversations | AICPA Crossover | 241

Episode 241

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"

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=== SUPPORT THE SHOW ===

AICPA Personal Financial Planning Podcast

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

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.

Oct 7, 2026 46 min

3 Non-Employer Health Insurance Case Studies: More Choices Than You Thought | Lyndia Cunningham (Part 2) | 240

Episode 240

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

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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.

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=== SUPPORT THE SHOW ===

Health Insurance for Early Retirees

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Move Health

Move Health YouTube

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

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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.

Oct 4, 2026 1 hr 16 min

How to Get Health Insurance When You Retire Early | Lyndia Cunningham(Part 1) | 239

Episode 239

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).

.

=== SUPPORT THE SHOW ===

ACA Health Insurance Marketplace

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Move Health

Move Health YouTube

.

⏰ Related Episodes

Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98

Maximizing HSAs Part 2: Devising Drawdowns, Badass Scenarios, Listener Questions | Jeff York | 99

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Sep 27, 2026 1 hr 27 min

The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238

Episode 238

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 ===

Shady Car Dealers are Done! Fair Pricing Summit DC

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

CarEdge (Research, Dealer Ratings, Car-buying Service)

CarEdge Podcast

CarEdge YouTube

CarEdge Live YouTube

Zach's AI Summit Talk

Ray's letters to his late wife Suzanne

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Sep 20, 2026 1 hr 35 min

61% of Americans Fear Outliving Their Money: Here's the Fix | Jean Chatzky | 237

Episode 237

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

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

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

📙The Forever Paycheck

Her Money

Her Money Podcast

Guaranteed Income: A License to Spend (A research paper by David Blanchett and Michael Finke)

.

⏰ Related Episodes

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.

Sep 13, 2026 1 hr 8 min

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

Episode 236

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 ===

ChooseFI https://choosefi.com

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

⏰ 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.

Sep 9, 2026 1 hr 4 min

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

Episode 235

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 ===

Official IRS Tax Code 72(t)

☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"

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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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

🌐72tcalc.com Website

Free consultation with Bill Stecker's Firm (The Marble Group)

• email: themarblegroup@wispertel.net
• Phone: (312) 361-0221

IRS Notice 2022-6 (sets a new floor interest rate of 5% for calculating 72(t) distributions)

72(t) Calculators

• 72tCalc
• FI Tax Guy 72(t) using Google Sheet
• Dinkytown
• CalcXML
• UngrindFi

.

⏰ Related Episodes

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

72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131

Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Sep 6, 2026 1 hr 25 min

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

Episode 234

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 ===

Official IRS Tax Code 72(t)

☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"

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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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

🌐72tcalc.com Website

Free consultation with Bill Stecker's Firm (The Marble Group)

• email: themarblegroup@wispertel.net
• Phone: (312) 361-0221

72(t) Calculators

• 72tCalc
• FI Tax Guy 72(t) using Google Sheet
• Dinkytown
• CalcXML
• UngrindFi

.

⏰ 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.

Aug 30, 2026 56 min

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

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 ===

https://ritholtzwealth.com/

☕ 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: https://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

https://a.co/d/07ZHXM8h

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Aug 27, 2026 8 min

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

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 ===

Retirement Planning Education 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Tenon Financial website

Andy's podcast

Andy's Youtube

Andy's LinkedIn

Retirement Savings Lost and Found Database

Pension Benefit Guaranty Corporation (PBGC)

Dinkytown.net- Pension vs. Lump Sum Payout Calculator

Estimate Immediate Annuities

.

⏰ Related Episodes

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

Retired Before 50: A Look at Her Real Finances, Numbers & Strategy | Andy Panko Crossover | 186

Retirement Planning Tips | Andy Panko | 063

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Aug 23, 2026 1 hr 41 min

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

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 ===

Easy Peasy Finance YouTube

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Easy Peasy Finance

📕Easy Peasy Money

Coverage on CBS News

Kiplinger Article

I Will Teach You To Be Rich (Ramit Sethi)

.

⏰ Related Episodes

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

Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209

Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205

Money Scripts: Don't Get Scrooged! | Brad Klontz | 175

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Aug 19, 2026 30 min

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

Episode 231

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

.

=== SUPPORT THE SHOW ===

Easy Peasy Finance YouTube

☕ 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: https://catchinguptofi.com/our-partners/

.

RESOURCES MENTIONED ON THE SHOW

Easy Peasy Finance

📕Easy Peasy Money

Coverage on CBS News

Kiplinger Article

I Will Teach You To Be Rich (Ramit Sethi)

.

⏰ Related Episodes

20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208

Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Aug 16, 2026 1 hr 2 min

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

Episode 230

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 ===

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

☕ 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: https://catchinguptofi.com/our-partners/

RESOURCES MENTIONED ON THE SHOW

Risk Parity Radio

⏰ Related Episodes

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.

Aug 9, 2026 51 min

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

Episode 229

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

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

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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

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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

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How unsubscribing, reducing drama, and creating a peace plan support financial freedom

.

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