Real Personal Finance

Scott Frank
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Your REAL personal finance questions answered by CERTIFIED FINANCIAL PLANNER™ professionals, Scott Frank and Nick Covyeau. With all of the misinformation and jargon in the financial industry, it's no wonder most people are confused about how to best manage their money. Scott and Nick are here to give clear answers to the important questions they hear most often. If you're ready to use your finances to create a more secure financial future, this show is for you.

  1. 5D AGO

    Navigating the High Stakes of Tech Stock Concentration

    Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. —  Most tech and biotech executives we know have too much of their net worth in one stock. They know they should do something about it, but they usually end up just closing the tab on their stock comp page. In this episode, Scott and Nick break down the framework for moving from a "home run" mindset to a "nest egg" reality. Using a real-world scenario of a client with over 30% concentration in one company, they walk through the math of de-risking without losing the upside. They discuss the "sequencing" of tax brackets, the psychological barrier of "break-even-itis," and why you should treat your RSUs exactly like a cash bonus.  It’s not just about selling shares; it’s about understanding your "enough number" and separating your vested security from your unvested potential.  If you’ve been watching your company stock climb and wondering if you're taking too much risk, this episode is for you. It’s about building a plan that protects the life you want to live, even if your company hits a 16-year plateau.  Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial Nick Covyeau on LinkedInSwell Financial Leave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial or Swell Financial.

    23 min

  2. APR 30

    The Tab You Keep Closing (And Why You Need to Open It)

    Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. —  There's a tab a lot of tech professionals have open right now. It's from Fidelity or E-Trade, it shows how much company stock they're sitting on, and most of them close it without doing a thing. Because the moment you start thinking about selling, it gets complicated. In this episode, Scott and Nick break down what to actually do when a big chunk of your net worth is tied to your employer's stock, whether that's RSUs, ISOs, ESPPs, or some combination of all three. They walk through why concentration happens quietly and compounds fast, especially when you're getting promoted, the stock is climbing, and new grants keep coming in. And they explain why "just diversify" is technically correct advice that leaves out everything that actually matters. The real conversation is about sequencing. How to unwind a concentrated position across multiple years, in a tax aware way, without triggering a bill you didn't plan for. That means looking at your income year by year, understanding which shares to sell first, knowing how to stop feeding the position, and factoring in the unvested shares that don't show up on your balance sheet yet but still count. If more than 10 to 20% of your net worth is sitting in a single stock, and especially if you're within five to ten years of retirement, this episode is for you. Scott and Nick close with a clear framework for building a plan before, during, and after, and why the clients who act earlier always walk a little lighter. Concentration isn't the problem. Concentration without a plan is. Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial Nick Covyeau on LinkedInSwell Financial Leave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial or Swell Financial.

    24 min

  3. APR 17

    How To Stress-Test Your Finances Against Single-Employer Risk

    Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. —  Your plan might be able to handle market volatility, but it might not handle your income disappearing. In this episode, Scott breaks down the uncomfortable blind spot facing many high earners—what happens if your paycheck stops sooner than expected. Using a real-world scenario of someone with nearly $3M saved and a large amount of unvested RSUs, he walks through the question most people avoid: “If the job goes away in 3–5 years instead of 7-10, are we actually okay?” It’s actually a timeline problem, not just a market risk problem. Scott explains how to pressure-test an early exit scenario, separate RSU strategy from income dependency, and ask the bigger question most plans ignore: what is your career capital actually worth if your role changes? If a large portion of your wealth and income is tied to one company, this episode is for you. It’s about understanding the assumptions your plan is making—and making sure they hold up when it matters most. Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial  Leave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

    12 min

  4. APR 2

    Your Biggest Asset Might Be Your Biggest Tax Problem

    Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. —  You did everything right. You maxed your 401(k) for decades, watched the balance grow, and felt good about where you were headed. Then someone showed you a tax projection for retirement and it was a lot bigger than you expected. In this episode, Scott walks through why a large, traditional 401(k) balance can quietly become a future tax trap. He breaks down a real world example of how required minimum distributions (RMDs), Social Security, and Medicare premiums can stack up in ways most people never saw coming and what a surviving spouse could face alone. But this isn't a story about regret. It's about having a window of time to act before the IRS starts making decisions for you. If 70 to 80% of your investable wealth sits in pre-tax accounts, this episode is for you. Scott walks through four practical levers: savings direction, Roth conversions, taxable bridge accounts, and asset location and closes with three concrete steps you can take right now to get clarity on where you actually stand. Your401(k) isn't the issue, having one that is overly concentrated without a plan is. Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial  Leave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

    15 min

  5. MAR 5

    Retire From the Wrong Job, Not From Work

    Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. —  Most people don’t actually want retirement, but they do want relief. Relief from the schedule. Relief from the pressure. Relief from feeling like they can’t step off the treadmill. But what if the question isn’t “When can I retire?” and it’s “What would I do if I knew I wasn’t trapped?” In this conversation, Scott and Nick explore the tensions so many professionals feel but almost never say out loud: the golden handcuffs, the benefits package, the identity wrapped up in a title. And underneath all of it, another question: do I actually need this job… or am I just afraid to look? Retirement doesn’t always have to mean stopping work. Sometimes it means choosing work, some others it’s testing something new, and every once in a while it means building enough cushion that you walk into Monday differently. If you’ve ever felt stuck in a role you’ve outgrown, this episode of Real Personal Finance might open a door you didn’t realize was already unlocked. Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial Nick Covyeau on LinkedInSwell Financial Leave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

    26 min

  6. FEB 19

    Rethinking Inheritance: Give It Now or Leave It Later?

    There’s a common belief people have about money: you build it, you protect it, and whatever’s left gets passed on at the end. But what if the timing matters more than the total? As lifespans stretch into the 90s and portfolios grow beyond what many families will realistically spend, the question starts to change. Would a gift mean more when your kids are buying their first home, raising young children, or launching something meaningful? Would you rather see the impact while you’re here to experience it? And how do taxes, fairness, and family dynamics shape that decision? This conversation invites you to switch your thinking into a more intentional approach. The big takeaway? Giving isn’t just about numbers, but about when the help lands, how it changes someone’s life, and whether you want to be part of that moment. If you’ve ever wondered whether to give now or later, this episode of Real Personal Finance will stretch how you think about your legacy. —  Mentioned in this episode: Die With Zero by Bill Perkins on Amazon: https://www.amazon.com/Die-Zero-Getting-Your-Money/dp/0358567092 —  Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial Nick Covyeau on LinkedInSwell Financial Leave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

    22 min

  7. FEB 5

    Deferred Compensation: Smart Planning or a Risky Bet?

    Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. —  Deferred compensation tends to enter the picture when work is going well and income has outgrown the basics. Cash flow feels stable, taxes start to sting, and suddenly there’s a new option on the table that promises flexibility later. Scott and Nick explore what sits underneath that promise. Deferred comp changes the timing of income, but it also ties future choices to today’s assumptions. Employer stability matters. Payment schedules matter. So does the simple reality that once income is deferred, access and control look very different than they do inside a traditional retirement account. This episode of Real Personal Finance is an opportunity to slow down before checking the box. To think about how much certainty you actually have about your career path, your tax brackets, and the version of retirement you’re planning toward. Deferred compensation can play a useful role in the right situation, but only when it fits the rest of the picture you’re building. Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial Nick Covyeau on LinkedInSwell FinancialLeave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

    21 min

  8. JAN 22

    How to Stay Ahead of Taxes and Avoid Penalties

    Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. —  Taxes tend to fade into the background until something feels off, like a larger bill than expected, a penalty you didn’t see coming or a moment where you wonder whether you handled the year correctly or just got lucky. In this episode of Real Personal Finance, Scott and Nick talk about how the tax system actually works and why the idea of making one payment on April 15 simply won’t cut it. For example, did you know there’s a pay-as-you-go structure? Or that different types of income can change your tax reality? Scott and Nick go through salaried employees, executives with bonuses or stock compensation, small business owners, and retirees whose income has started to shift. When you understand what the IRS is looking for and how to build a simple system around it, taxes can stop being a surprise and become something you can manage with less stress throughout the year. Ready to learn more?  Scott Frank on LinkedIn Stone Steps Financial Nick Covyeau on LinkedInSwell FinancialLeave us a question!  Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

    21 min
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About

Your REAL personal finance questions answered by CERTIFIED FINANCIAL PLANNER™ professionals, Scott Frank and Nick Covyeau. With all of the misinformation and jargon in the financial industry, it's no wonder most people are confused about how to best manage their money. Scott and Nick are here to give clear answers to the important questions they hear most often. If you're ready to use your finances to create a more secure financial future, this show is for you.

Information

  • Creator
    Scott Frank
  • Years Active
    2019 - 2026
  • Episodes
    246
  • Rating
    Clean
  • Copyright
    © 2026 Real Personal Finance
  • Show Website
    Real Personal Finance

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