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 f...

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...

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 Catchin...

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...

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 foreclosur...

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 gr...

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 o...

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 fac...

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 c...

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. Togethe...

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...

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...

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 p...

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...

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 techno...

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 w...

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"? T...

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 unu...

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 l...

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 sharehol...

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 beli...

What if the smartest way to fix teacher retirement is not patching the broken 403(b) machine, but quietly building an exit ramp to something better? In this bonus conversation, Bill, Jackie, and Dan Otter keep pulling the thread on the teacher-retirement mess and land on a surprisingly practical answer: the 457(b) may be the cleaner, simpler, more flexible plan that schools should be leaning into....

What if the most dangerous thing in a teacher's retirement plan isn't market volatility, it's the nice guy with free sandwiches and a terrible annuity contract? Jackie and Bill are joined by Dan Otter and Scott Dauenhauer of 403bwise, the duo who have spent decades exposing how badly K-12 educators get treated in the 403(b) world. What starts as a conversation about confusing vendor lists and a me...

What if the biggest risk in your portfolio isn't a crash, a recession, or even inflation, but the very human urge to believe that whatever just worked will work forever? Bill and Jackie sit down with Ben Carlson of A Wealth of Common Sense and Animal Spirits for a market-history masterclass that somehow manages to be equal parts calming, nerdy, and deeply practical. This one is for anyone who's ev...

What if "legacy" looks completely different when there are no kids in the picture and that difference actually unlocks a freer, more intentional version of FI? In this thoughtful crossover between Childfree Life by Design and Catching Up to FI, Dr. Jay and Bill sit down for the kind of conversation most money media skips: what happens after you hit the number and realize the bigger question is no...