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
Release Date: 03/29/2026
Are Bonds Dead?: Fixed Income Fundamentals (Part 1) | Frank Vasquez | Episode 229
Catching Up to FI: Financial Independence for Late Starters
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...
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How to Retire at 40: Her Debt-Crushing Path to Financial Independence | Bernadette Joy | 228
Catching Up to FI: Financial Independence for Late Starters
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...
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Bonus: Is Your School’s 403(b) On The Naughty List? Here’s What To Do About It | Dan Otter | 227
Catching Up to FI: Financial Independence for Late Starters
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. Dan also highlights the new audio series Learned by Being Burned, Carl Fisch’s 50-state teacher-retirement books, and several states that are getting it right. They end with a reminder that fixing...
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How K-12 Teachers Can Beat the Broken 403(b) System | Dan Otter & Scott Dauenhauer | 226
Catching Up to FI: Financial Independence for Late Starters
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 messy system, quickly turns into something bigger. This episode covers Why the K-12 403(b) system is fundamentally broken for many educators How Dan and Scott came together through the early...
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Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225
Catching Up to FI: Financial Independence for Late Starters
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 ever stared at their portfolio, read one scary headline too many, and wondered whether simplicity still works. Ben's answer is basically yes—but only if you understand the risks, respect your own...
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You Hit The Number, Now What? | Childfree Life By Design Crossover | 224
Catching Up to FI: Financial Independence for Late Starters
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 longer “Can I retire?” but “What am I retiring to?” It’s philosophical, personal, a little messy in the best way, and exactly the kind of episode that reminds listeners that FI is not...
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FIlanthropy: Radical Impact Giving Without Risking Your Retirement | Rebecca Herbst | 223
Catching Up to FI: Financial Independence for Late Starters
Bill jumps into a last-minute solo conversation with Rebecca Herbst of Yield and Spread for a surprisingly energizing deep dive into generosity, guilt, and what happens after the finish line of financial independence. Rebecca shares how hitting FI at 32 did not lead to endless victory-lap bliss so much as an identity jolt: if money is a tool, then what is it actually for? This episode covers: Why Rebecca felt guilt, not just freedom, after reaching FI at 32 How giving can be framed as money, time, or skills—not just writing checks Why generosity is a habit and a muscle, especially for...
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Unbanked, Buried In Payday Loans & A 500 Credit Score: This Late-starter Overcame It All! | Afra Smith | 222
Catching Up to FI: Financial Independence for Late Starters
What if the person inspiring the room didn’t come from a polished finance background at all, but from payday loans, being unbanked, a credit score in the 500s, and the kind of rock bottom most FI stories rarely admit out loud? In this on-location episode from Madison, WI, Jackie sits down with Afra Smith, founder of The Melanin Project and creator of the Wealth Empowerment Conference, for a conversation that is as honest as it gets. She’s a late-starter and shares how depression, financial chaos, and a painful career setback forced her to finally confront what wasn’t working. She shares...
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Intergenerational Wealth: Strategies to Help Your Family NOW (Not Later) | Allen Mueller | 221
Catching Up to FI: Financial Independence for Late Starters
What if the smartest legacy move isn't leaving your kids a pile of money someday, but using your wealth right now to help them buy time, build habits, and change their future while you're still here to watch it happen? We sit down with Allen Mueller of 7 Saturdays Financial for a practical, deeply useful conversation about gifting to family with intention. The thread running through all of it is simple: money is not just for accumulating. It's for strengthening the people and values you care about most. This episode covers: Why gifting during your lifetime can be more impactful than leaving a...
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Not So Big Life Design: The Architecture of Wealth | Sarah Susanka | 220
Catching Up to FI: Financial Independence for Late Starters
What if the smartest move on your road to FI isn't buying a bigger house, but shrinking the footprint, clearing the clutter, and finally designing a life that actually fits? In this episode, we sit down with Sarah Susanka, the architect behind the bestselling "Not So Big House" movement. We talk about what happens when you stop building for appearances and start building for how you really live. Sarah shares how growing up in England, then landing in car-centric suburban Los Angeles made her question why Americans kept buying "hamburger bun but no hamburger" houses full of unused rooms. ...
info_outlineApril 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 similar workplace plans like the TSP, 403(b), and 457 have become the backbone of retirement for most Americans. Yet they are often confusing and complicated to the average employee. No wonder so many accounts get neglected and become messy over time. The good news is that 2026 can be the year you clean it all up. This friendly and straightforward guide was created independent of any employer or plan provider, and will help you get going. By the time you’re done you’ll better understand your 401(k) and feel more empowered to use it as a real tool to build wealth and support your money goals. This episode covers:
➡️ How to clean up a messy 401(k) in less than an hour
➡️ Why year-to-date returns can mislead and longer time frames matter more
➡️ How contribution rate and savings rate shape your retirement timeline
➡️ Employer match, vesting schedules, and why "free money" still confuses people
➡️ Target date funds and simple one- to three-fund strategies
➡️ How to spot low-cost index funds inside an ugly 401(k) menu
➡️ What to do with old 401(k)s when you change jobs
➡️ How AI can help decode plan documents and confusing fund lists
➡️ Why forgotten 401(k)s now total a jaw-dropping $2.1 trillion
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DOWNLOAD GUIDE & EDITABLE CHECKLIST
📄 Cleaning up your 401(k) in less than an hour (complete guide with references)
📄 Cleaning up your 401(k) in less than an hour- Editable Checklist (download first)
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