Why This DIY Investor Finally Hired A Financial Advisor | "BiggerPockets" Crossover | 199
Catching Up to FI: Financial Independence for Late Starters
Release Date: 02/25/2026
The Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211
Catching Up to FI: Financial Independence for Late Starters
What if the biggest shift in your FI journey isn't hitting the number—but finally realizing you need a life plan, a tax plan, and maybe even a fiduciary teammate to help you spend it? Bill steps into the guest chair with Morningstar's Christine Benz for a thoughtful, surprisingly candid conversation about going from financially illiterate "rich doctor syndrome" to fully conscious wealth stewardship. He walks through the entire arc. But this episode goes deeper than a standard "how I retired" story. This episode covers: ➡️ Bill's path from paycheck-to-paycheck physician to...
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Hot Takes & Money Debates: Social Security at 62, New Trump Accounts, & more! | Bill & Jackie | 210
Catching Up to FI: Financial Independence for Late Starters
What happens when the two co-hosts stop being polite, start being honest, and publicly debate the money moves they still don't agree on? We throw open the doors on four of our favorite friction points: Simple index-fund investing versus "modest complexity" Whether high school personal finance classes are actually helping What to make of the new 530A Trump accounts Taking Social Security at 62 versus waiting The fun here is that neither of us is playing a character. Jackie comes in swinging for simplicity, practical execution, and "please stop overcomplicating this...
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Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209
Catching Up to FI: Financial Independence for Late Starters
What if the real reason family wealth disappears by the third generation has almost nothing to do with investing, and everything to do with what parents fail to teach at home? We sit down with Dr. Julia Myers, founder of Generational Wisdom, for a conversation that goes way past trusts, spreadsheets, and "someday" estate plans. Julia shares the medical crisis that abruptly ended her pharmacy career, the mindset shift that followed, and why she now believes legacy is not what you leave to your kids, but what you leave IN them. Together we unpack the three silent killers of generational wealth:...
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20 Questions from 20-Somethings About Money | Dr. DeLong, Emilie Stewart. Britton Carver | 208
Catching Up to FI: Financial Independence for Late Starters
APRIL IS FINANCIAL LITERACY MONTH! What do you get when two late starters hand the mic to two twenty-somethings and let the money questions fly? In this unusually fun follow-up to the University of Tennessee classroom visit, we bring Dr. Karen DeLong and two of her students, Emilie and Britton, onto the podcast to tackle the real questions young adults ask when money stops being theoretical and starts getting personal. Emilie – Majoring in Finance and International Business with a minor in Agricultural Business and will be pursuing a career in Wealth Management. Britton – Interning with...
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Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207
Catching Up to FI: Financial Independence for Late Starters
APRIL IS FINANCIAL LITERACY MONTH! What happens when you hand a room full of almost-graduates a microphone, a few $2 bills, and permission to ask the money questions most adults still avoid? In this special on-the-road episode, we take you inside the financial literacy presentation at the University of Tennessee to share a few highlights of our recent talk. It's energetic, imperfect, and deeply encouraging. Financial literacy doesn't have to be stiff or scary. Sometimes it just looks like showing up, telling the truth about your mistakes, and helping the next person get a much earlier start...
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I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206
Catching Up to FI: Financial Independence for Late Starters
APRIL IS FINANCIAL LITERACY MONTH! What if one passionate professor, one classroom, and a few brave money questions could change hundreds of financial lives before graduation? We head to Knoxville for a special Financial Literacy Month episode with Dr. Karen DeLong, the University of Tennessee professor quietly doing the work most schools still don't: making sure students leave campus with more than a degree. Karen shares how three advanced degrees somehow included zero personal-finance education and how that gap pushed her to build an annual money session for her students. Bill and Jackie...
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Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205
Catching Up to FI: Financial Independence for Late Starters
April is Financial Literacy Month and we're starting a little early! That's because we are so excited to launch a new project called "The Great 401(k) Cleanup." What if the easiest way to boost your retirement odds this year isn't reducing your spending or a side hustle, but cleaning up that messy, confusing 401(k) you've been ignoring? We are using Financial Literacy Month to launch a full-on 401(k) intervention with a step-by-step guide including: Access From Home Contributions Beneficiaries Investments Rate of Return What’s Next 401(k)s and...
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Here's What 6 Years of Early Retirement Life is Really Like | "REAL Retirees: Uncut" Crossover | 204
Catching Up to FI: Financial Independence for Late Starters
What if the best retirement advice didn't come from a spreadsheet—but from a real retiree saying, "I wish I'd done it sooner"? Jackie crosses over to "REAL Retirees: Uncut" for a refreshingly candid, walk through of what six years of early retirement have actually looked like. She also shares her top five reasons to retire early, from time freedom and better mental health to the surprising new opportunities that open up when your job no longer runs your calendar. And because this is still Catching Up to FI, she closes with a message straight to late starters: most people wake up later than...
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I Thought the Stock Market was Gambling, Then I Retired at 44 | Jaylynn | 203
Catching Up to FI: Financial Independence for Late Starters
What if you were already financially independent at 40… and didn’t realize it until a random pension search and a couple of podcasts blew the whole thing open? This was Jaylynn's "Surprise FI" and he joins the show to take us blow by blow. He gives us look back to his childhood of money orders, loving parents, and “value over flash” shaped him. He shares how he went from thinking the stock market was gambling to maxing out a 401(k), building a brokerage account, and accidentally discovering he had already hit FI in his forties. But this isn’t just a “run the numbers and quit”...
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Don't Trust AI with Your Money Until You Listen To This | Jeffrey Trull | 202
Catching Up to FI: Financial Independence for Late Starters
Today we’re putting AI (Artificial Intelligence) to the test with AI money expert Jeffrey Trull. He's founder of the blog and newsletter, Money Meets AI where he shares tested prompts for your money. He joins us to sort the genuinely useful from the wildly overhyped when it comes to AI. We expand our conversation into prompts, privacy, hallucinations, portfolio questions, Google vs. ChatGPT, paid vs. free tools, and where AI can actually save real time for DIYers. Along the way, Bill wrestles with the tradeoff between efficiency and original thought, Jackie pushes the "AI as thought partner"...
info_outlineWhat happens when a "late-starter" ER doc finally hits FI at 60, then must figure out how to actually spend the money without blowing it—or hoarding it forever? Bill joins Mindy and Scott on the BiggerPockets Money podcast to walk through his full "caught up to FI" debrief. Here his decade-long sprint from single-digit savings to 40%, taking his money back from a private bank, and the 60th-birthday retirement-readiness check that came back with a 100% success rate. From there, they dig into his move from a simple three-fund portfolio to a risk-parity setup, why he hired a flat-fee planner after years as a DIY investor, and how he's using FI to buy back time and jump-start his kids' wealth with Roth IRAs, HSAs, and tax-savvy living gifts.
This episode covers:
➡️ Going from "rich but broke doctor" to FI in about 10 years
➡️ Boosting a savings rate from single digits to ~40% without feeling deprived
➡️ Shifting from a three-fund portfolio to a risk-parity decumulation strategy
➡️ Using flat-fee, advice-only planner instead of 1% AUM
➡️ Order of withdrawals: taxable, pre-tax, Roth, plus asset location
➡️ Modeling taxes, RMDs, and Social Security timing in real life
➡️ Building a "3-1-1" spending plan for needs, comfort, and luxury/giving
➡️ Helping adult kids fill Roth IRAs and HSAs as part of generational wealth
➡️ Weighing when to actually leave medicine once money is no longer the boss
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