Catching Up to FI

Legendary investor Barry Ritholtz joins the show for a wide-ranging tour through the experiences, mistakes, and behavioral quirks that shaped his investing philosophy and his book, "How Not to Invest". He tells us why becoming a better investor has less to do with being brilliant and more to do with simply being less stupid. The lesson? You don't have to predict markets, outsmart Wall Street, or find the next 100-bagger. Build a plan, let compounding work, and stop stealing returns from your future self. This episode covers: How Barry's childhood experiences shaped his view of money as a tool rather than a scorecard  His unconventional path from law school to a trading desk and behavioral finance  What Bernie Madoff really stole from investors: decades of lost compounding  Charlie Munger, Charlie Ellis, and the power of avoiding unforced investing errors  Why passive investing has such a powerful mathematical advantage  How scary headlines, denominator blindness, and bad statistics distort our perception of risk  Why process matters more than outcomes when evaluating investment decisions  Dunning-Kruger, metacognition, and knowing when you're outside your circle of competence  Barry's Apple and Robinhood mistakes—and what they taught him about humility  Advisor fees, AI, Altruist, Vanguard, and where Barry thinks financial advice is headed . === SUPPORT  THE  SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website  🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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) . For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners   . RESOURCES MENTIONED ON THE SHOW Ritholtz Wealth 📘 How Not to Invest Masters in Business podcast  . ⏰ Related Episodes Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225  The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 Forget the Corporate Ladder, Here's How to Climb 'The Wealth Ladder' | Nick Maggiulli | 159  . CHAPTERS: 0:00 Intro- Who Barry Ritholtz was before Wall Street  3:00 Money as a tool, childhood jobs, cars, and buying experiences 8:00 Horses, bartering for opportunity, and an unconventional education  12:00 Discovering trading and behavioral finance 18:00 Bernie Madoff, statistics, fraud, and the compounding he stole 24:00 Charlie Munger, Charlie Ellis, and avoiding unforced errors 31:00 Why passive investing wins the math 34:00 Sharks, crashes and bad numbers 41:00 Process over outcome 49:00 The unbelievable power of compounding 59:00 Custodians, Altruist, and why your advisor shouldn't hold your money 1:16:00 Vanguard and Altruist 1:22:00 Barry's mentors, favorite books, and advice to his younger self . 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Finance professors Shaun Davies, PhD, CFA and David Brown, PhD join the show to give us a look under the hood of target-date funds (TDFs). What they found may surprise you! Their research reveals enormous differences in fees, risk, glide paths, active management, and performance; even among funds carrying the exact same retirement year. But this isn't a target-date-fund takedown. TDFs have helped millions of people get invested, stay invested, and avoid some bad behavioral decisions. The real question is whether yours is actually doing what you think it is. Bill also brings on Jesse Cramer of Personal Finance for Long-Term Investors to join this important conversation. This episode covers:  What a target-date fund actually owns and how its glide path changes over time  Why two funds with the same target year can produce dramatically different results  How fees and poor active management contributed to historical TDF underperformance  Why a fund's risk level may matter more than matching its date to your expected retirement year  What late starters and FIRE investors should consider when choosing a TDF vintage Why the target-date-fund industry still lacks a useful universal benchmark  How Glidepath Financial's replicating-fund approach compares TDFs against low-cost passive alternatives The life-cycle investing idea that your future earnings effectively behave like a bond  Why TDFs can still be powerful behavioral tools despite their imperfections  Collective investment trusts, retirement decumulation, annuities, private assets, and where TDFs may go next   . === SUPPORT  THE  SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website  🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question   . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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) . For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners   . RESOURCES MENTIONED ON THE SHOW   Off Target: On the Underperformance of Target-Date Funds Glidepath Financial (compare target-date funds)  David C. Brown Shaun Davies Jesse Cramer  . ⏰ Related Episodes The Biggest Retirement Mistake: Over Saving and Under Living | Rachael Camp & Jesse Cramer | 198 Space Telescopes, Sunflowers, and Financial Gardening | Jesse Cramer | 105 How to Bake a Cake: An Asset Allocation Mashup | Rick Ferri & Paul Merriman | 134   . CHAPTERS: 0:00 Intro  4:00 How target-date funds became America's default 7:00 What's really under the hood 10:00 The 1% problem  14:00 Risk differences 18:00 How to choose a TDF  27:00 Human capital as a bond 35:00 The ten building blocks 38:00 Do we even need bonds? 44:00 The behavioral case for TDFs 56:00 Glidepath ratings   . 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Alan and Katie Donegan and Monica Scudieri join Bill and Jackie to explore what happens when financial survival mode finally loosens its grip and creative bandwidth comes roaring back. They talk imposter syndrome, discomfort, perfectionism, public speaking, writing books, making music, and why FI can turn passive consumers into active creators. They also announce the world debut of the new Catching Up to FI theme song and the new book "Mama Are We Poor?" authored by Bill and Monica. This episode covers  How financial independence can free up mental bandwidth for creativity  Moving from passive consumption to actively creating and sharing what you know  Imposter syndrome and why people convince themselves investing, or creativity, is "not for people like me"  Why discomfort, fear, and mistakes often signal that you're actually growing  Public speaking, preparation, perfectionism, and getting started before you feel ready  The story behind Bill and Monica's children's book, Mama, Are We Poor?  How Alan, Katie, and Finn turned financial independence concepts into music  Why work optionality doesn't necessarily mean quitting work completely Rediscovering the creative interests you may have left behind in childhood  A seven-day challenge to stop overthinking, get sloppy, and create something . === SUPPORT  THE  SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website  🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question   . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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: catchinguptofi.com/our-partners   . RESOURCES MENTIONED ON THE SHOW Grab Your Slice (Monica Scudieri) The Donegans Rebelutionaries on Spotify   . ⏰ Related Episodes "Mama, Are We Poor?": A Single Mom's Millionaire Mindset | Monica Scudieri | 120 Not Just Another Album, It's A Money Revolution! | Alan & Katie Donegan | 129 Indiana Jones and an Extraordinary Life with the Donegans | Alan and Katie Donegan | 079   . 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Dana Anspach, CFP® and founder of Sensible Money, returns to explain why retirement isn't one long, predictable chapter, it's a series of distinct phases with different financial and emotional needs. Using the framework from her new book, Living Off Your Acorns, Dana walks Bill and Jackie through the pre-go, go-go, slow-go, and no-go years. This episode covers Dana's four phases of retirement: pre-go, go-go, slow-go, and no-go Why retirement planning should begin at least five years before leaving work The emotional transition from receiving a paycheck to living off your accumulated "acorns" A three-part pre-retirement checklist: cash flow, stress testing, and planning your time Why social connections and identity need as much planning as the financial side Fundedness ratios, the Critical Path, and alternatives to relying only on a safe withdrawal rate Special considerations for people retiring early, including healthcare and longer time horizons Mortgages, HELOCs, pledged asset lines, and when debt can still be useful in retirement How spending naturally changes during the slow-go years Fraud, cognitive decline, powers of attorney, and preparing for someone else to eventually help manage your finances . === SUPPORT  THE  SHOW === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website  🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question   . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 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: catchinguptofi.com/our-partners   . RESOURCES MENTIONED ON THE SHOW Sensible Money    📙Living Off Your Acorns   The Retirement Manifesto   . ⏰ 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.

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 === 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website  🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question   . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  📕 Get Your Copy  (currently 40% off on Amazon) For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners   . RESOURCES MENTIONED ON THE SHOW Mile High FI Podcast  Mile High FI YouTube    . ⏰ Related Episodes The Income Trap: How Not to Become A Millionaire | ChooseFI Crossover | 236  The Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211    . 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.