The Ultimate Playbook On What "Not" To Do When The Stock Market Drops | Barry Ritholtz | 247
Épisode 247
dimanche 8 novembre 2026 • Durée 01:43:12
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
"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.
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.
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
Épisode 246
dimanche 1 novembre 2026 • Durée 01:27:16
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
Financial Freedom Beyond Spreadsheets: Writing Books and Songs on FIRE | The Donegans & Monica Scudieri | 245
Épisode 245
mercredi 28 octobre 2026 • Durée 01:16:00
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
☕ Like what you hear on Catching Up to FI? Support the show at
NEW! Mama Are We Poor?
4 Phases of Retirement Explained: The Realities of Each May Surprise You! | Dana Anspach | 244
Épisode 244
dimanche 25 octobre 2026 • Durée 01:24:44
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
☕ Like what you hear on Catching Up to FI? Support the show at
NEW! Mama Are We Poor?
How to Make Financial Mistakes and Still FIRE! | Doug Cunnington of Mile High FI Podcast | 243
Épisode 243
dimanche 18 octobre 2026 • Durée 01:04:02
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
Debunking the Biggest Retirement Fear Tactics With Erin Talks Money | Erin Moriarity | 242
Épisode 242
dimanche 11 octobre 2026 • Durée 01:04:02
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
Small Money Ideas That Lead To Bigger Conversations | AICPA Crossover | 241
Épisode 241
mercredi 7 octobre 2026 • Durée 45:55
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"
3 Non-Employer Health Insurance Case Studies: More Choices Than You Thought | Lyndia Cunningham (Part 2) | 240
Épisode 240
dimanche 4 octobre 2026 • Durée 01:16:06
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 ===
📩
How to Get Health Insurance When You Retire Early | Lyndia Cunningham(Part 1) | 239
Épisode 239
dimanche 27 septembre 2026 • Durée 01:26:46
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).
The Hidden Truth Behind Car Buying: Fighting For Transparency Over Deception | Ray & Zach Shefska | 238
Épisode 238
dimanche 20 septembre 2026 • Durée 01:35:06
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
"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.
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.
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.
"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.
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.
📌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.
"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.
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.
📌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.
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
📌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.
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
📌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.
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
📌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.
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
📌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.
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
📌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.
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
📌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.
Détails sur Catching Up to FI, podcast de Bill Yount & Jackie Cummings Koski
Découvrez des podcasts liées à Catching Up to FI. Explorez des podcasts avec des thèmes, sujets, et formats similaires. Ces similarités sont calculées grâce à des données tangibles, pas d'extrapolations !
