Money & Taxes from Bb to XYZ

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, welcome FPFoCo Financial Planning Specialist Riley Thoubboron back to the show. Riley recently earned his Tax Planning Certified Professional® (TPCP®) designation from the American College of Financial Services. Hear Riley share what inspired him to pursue the certification, how his expanded expertise will benefit clients, and why ongoing education is essential in an ever-changing financial landscape. The conversation explores tax-efficient retirement strategies, including Roth conversions, asset location, and managing retirement distributions. With year-end tax planning just around the corner, Riley...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, tackle employee benefits open enrollment and how to make sense of that intimidating benefits guide before the deadline arrives. They walk through health, dental, vision, life, and disability insurance, along with some of the tempting extras that may or may not be worth the paycheck deduction. Rather than simply renewing last year’s choices or signing up for everything available, Regina and Jason explain how to compare what’s changed with what you actually expect to need in the coming...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, continue their equity compensation series with a look at incentive stock options (ISOs) and non-qualified stock options (NSOs). They explain how these employer-granted options work, what happens when you exercise them, and why the tax consequences can look very different depending on which type you have and when you sell. From cashless exercises and capital gains to the alternative minimum tax (AMT), Regina and Jason show why stock options can offer valuable opportunities but also require careful financial and tax...

In this special mini-episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, trade financial planning for a little financial-themed music. With the FPFoCo team heading to San Diego for their annual company retreat and an industry conference, they’ve assembled the perfect soundtrack for the trip: FPFoCo Favorite$, a team-curated playlist featuring songs about money from across genres and generations. From Wu-Tang Clan to whatever other money-minded tracks made the cut, consider this your invitation to turn up the volume and follow the money.

Hear the Spotify playlist:

...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, introduce the newest member of the FPFoCo team, Kelli Mickley! As the three of them chat, Kelli shares what she’ll be doing as FPFoCo’s new Client Service Specialist, from account paperwork and client support to keeping filing systems organized and supporting the rest of the planning team behind the scenes. The conversation also covers her 15-plus years of experience in financial services, her recent client service certification, and why attention to detail and continuing education matter so much in...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, break down restricted stock and restricted stock units (RSUs). These two common forms of equity compensation can quickly turn into a complicated mix of vesting schedules, taxes, trading restrictions, and investment decisions. They explain the important differences between restricted stock and RSUs, when each becomes taxable, and why RSUs can often be viewed much like receiving a cash bonus. The conversation also explores the risks of accumulating too much employer stock and how a thoughtful strategy can turn equity com...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, explore Coast FIRE, a retirement strategy built around saving aggressively earlier in life and then allowing those investments to compound toward retirement with little or no additional retirement contributions. They discuss how reaching a “Coast” point can create more flexibility to work less, change careers, spend more intentionally, or redirect savings toward other goals while existing retirement assets continue to grow. The conversation also covers the risks of relying on long-term assumptions — including inflation, taxes, and sequence-of-returns risk — and why regular...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, examine the latest concerns surrounding the future of Social Security and what potential benefit changes could mean for retirement planning. They discuss the projected depletion of the Social Security trust fund and three potential solutions outlined by the Social Security trustees: increasing payroll taxes, reducing benefits for everyone, or reducing benefits for future claimants. The conversation also explores why fear alone should not drive an early claiming decision and how financial planning tools can stress-test different Social Security, inflation, tax...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, explore one of the foundational questions of financial planning: Why do you invest? Using investment risk as the starting point, they explain that risk isn’t simply about stock prices rising and falling; it also includes factors like liquidity, inflation, savings rates, income needs, and the possibility of not reaching your financial goals. They distinguish between risk tolerance (the amount of investment risk you’re willing to accept) and risk capacity (the amount of risk your financial circumstances can reasona...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, unpack what "investment risk" really means and why it goes beyond simply watching account values rise and fall. They explain the difference between risk tolerance, or how much risk you’re willing to take, and risk capacity, or how much risk your financial circumstances can support. The conversation explores how goals, timelines, liquidity needs, savings rates, and retirement plans all shape an appropriate investment strategy. Regina and Jason also discuss how risk translates into asset allocation and why asset locat...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, discuss what to do when a mid-year income boost — like a raise, bonus, RSU vest, or ESPP benefit — creates new tax planning opportunities. They explain why more income can mean more taxes, but also more ways to strategically reduce taxable income and redirect cash flow. The conversation covers bonus withholding, pre-tax employer retirement plan contributions, HSAs, deferred compensation, RSUs, ESPPs, charitable giving, and donor-advised funds. Regina and Jason emphasize that the key is building a tax projection early enough in the...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, explain why mid-year tax planning can be just as or even more valuable than year-end planning. With many 2025 tax returns now filed and many months left in the 2026 tax year, they discuss how listeners can use last year’s return to identify planning opportunities while there’s still time to act. The conversation covers key tax law changes from the One Big Beautiful Bill Act, including higher standard deductions, SALT deduction changes, expanded charitable giving opportunities, and above-the-line deductions. Jason a...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, focus on three key types of personal insurance protection: life, disability, and long-term care insurance. They explain how each type of coverage fits into a broader financial plan, when different policies may make sense, and why insurance should be used intentionally. The conversation covers term versus permanent life insurance, income protection through disability insurance, and the growing costs and evolving strategies surrounding long-term care coverage, including hybrid life-and-long-term-care policies. Jason and Regina also emphasize tailoring insurance coverage to your sta...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, go back to basics on property and casualty insurance: what it covers, why it matters, and how it fits into a broader financial plan. They explain the difference between property and liability protection, common policies like homeowners or renters, auto, and umbrella insurance. The conversation highlights how deductibles, premiums, emergency savings, and coverage limits all work together, and why your Emergency and Future Opportunities Fund (EFOF) should be strong enough to cover deductibles when claims arise. Regina and Jason als...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, walk through the key questions to ask when choosing or re-evaluating a financial planning professional. They explain why titles, designations, and services can vary widely across the industry. They also review why it’s important to understand a planner’s qualifications, fiduciary status, planning scope, typical clients, fee structure, and investment philosophy. The conversation highlights potential conflicts of interest, the difference between advice and product sales, and how to check for disciplinary history using public regulatory tools. Whether you’re hiring...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, explore the idea of a digital safe deposit box: a secure, organized system for storing important personal, financial, and estate-related information in digital form. They explain the difference between physical originals that still need to be protected offline and the digital copies that can make life much easier for you and your loved ones. The conversation covers what to include, where to store it, and how tools like password managers, cloud storage, and legacy contact features can help create a p...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, walk through estate planning from a financial planning standpoint. It's important to note that neither Jason nor Regina is an attorney, and the information provided in this episode is not legal advice. They explain why it's crucial to work with a licensed attorney to create and update estate planning documents and touch on why so many people delay this important task. Jason and Regina also discuss the emotional and financial barriers that can make estate planning feel intimidating, while emp...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, break down the IRS’s annual "Dirty Dozen" list of tax scams and schemes to watch out for during tax season. They cover common threats like IRS impersonation by text, email, and even AI-generated phone calls, along with fake charities, misleading tax advice on social media, ghost preparers, and fraudulent tax credit schemes. The conversation also highlights newer issues on the IRS radar, including abusive capital gain claims and misleading offer-in-compromise marketing. Throughout the episode, Regina and Jason emphasize the i...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, step inside Jason's "tax bunker" to break down the sometimes seemingly overwhelming world of tax documents. From W-2s and 1099s to K-1s and 1098s, they explain what forms to expect, why some arrive later than others, and why filing too early can sometimes create more problems than it solves. The conversation highlights the importance of patience during tax season, especially when waiting on brokerage statements or partnership K-1s that may trigger the need for an extension. The...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, dive into the subtle but powerful impact of lifestyle creep and inflation on your financial plan. They explore how rising income, combined finances, or even small “reward” spending habits can gradually increase your cost of living, often without you noticing. Jason and Regina highlight the importance of tracking expenses, recognizing spending patterns, and making intentional adjustments before lifestyle creep begins to derail long-term goals. They also discuss the difference between lifestyle inflation (which you can control) and economic inflation (which y...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, explain why February — not January — is the ideal time to reset your budget and cash-flow plan. With holiday spending behind you and a clearer picture of your real monthly expenses available from January, February offers the opportunity to make meaningful, realistic adjustments early enough to influence the rest of the year. The conversation covers practical steps like reviewing subscriptions, right-sizing recurring expenses, planning for large upcoming purchases, as well as aligning savings with short- and long-term goals. Regina and Jason a...

In this episode of Money and Taxes from Bb to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, focus on retirement planning in 2026. They discuss how small, intentional decisions early in the year can have a big, long-term impact. Using real-life examples, they discuss the importance of prioritizing tax-advantaged accounts like Roth IRAs, HSAs, and 401(k)s while still maintaining a strong emergency and future opportunities fund (EFOF) to support flexibility when life happens. The conversation highlights how time, compounding, and cash-flow planning work together — and why retirement planning should never exist in isolation from the rest of yo...

In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, kick off the new year by exploring why January often feels like the perfect time for a fresh financial start — but isn't the only right time to revisit your plan. They discuss the difference between building a brand-new financial plan, doing a full plan refresh, and simply "polishing" specific areas like cash flow, investments, or taxes. The conversation highlights common life and financial changes that signal it may be time for an update, such as salary increases, shifting goals, or la...

In this special holiday episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, reflect on a year of growth — both for the podcast and for clients at FPFoCo — while helping listeners prepare for what’s ahead in 2026. They share key milestones from the past year, including client successes, expanded planning services, in-house tax preparation, team education achievements, and charitable giving in Northern Colorado. The conversation then turns toward breaking down important 2026 tax and financial planning updates, such as higher contribution limits for IRAs, 401(k)s, and HSAs, updated Roth IRA income ph...

It’s getting close to year-end, and Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, are here to explain what Roth IRA conversions are, why they can be a powerful long-term tax-planning tool, and when they make the most sense. They’ll walk through situations where converting traditional IRA funds to a Roth IRA can reduce lifetime taxes — especially when current tax rates are low or future required minimum distributions (RMDs) might push someone into higher brackets. They also outline the practical steps for completing a conversion, emphasize the importance of having cash available to pay the tax bill, and...

Listen in as Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, break down the most important year-end tax planning strategies for 2025. We'll explain gift tax limits, upcoming 401(k) catch-up contribution changes, and how the expanded SALT deduction cap could help more taxpayers benefit from itemizing instead of taking the standard deduction. We'll also cover smart opportunities for Roth conversions, tax-loss harvesting, and tax-gain harvesting before December 31, helping listeners minimize taxes now and optimize for the potential to build long-term tax-free growth. Whether you're preparing for retirement, maximizing your deductions, or looking for last-minute tax savings, this episode offers act...

'Tis the season for tax planning — and considering charitable giving! In this episode, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, dive into how charitable contributions could impact your taxes in a positive way. As year-end approaches, they explain who might benefit from giving before December 31, how deductions work with the 2025 standard deduction, and what’s changing in 2026. From donor-advised funds to donating appreciated stocks instead of cash, the duo breaks down smart ways to give — without missing out on valuable tax savings.

You’ll learn

Why would Regi need life insurance? Jason Speciner, CFP®, EA, passes the pop quiz at the beginning of this episode. Then he and Regina Neenan, CFP®, ABFP®, talk about why some people generally need life insurance — and why others don’t. Listen in to better understand whether you might want to purchase a policy — or not — and how it could benefit those you leave behind.

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future episode! We’ll release a new one every other Thur...

It’s time to get your health insurance in order! Open enrollment is right around the corner for many, whether you get your coverage through your employee benefits or a health care exchange. Are you confused about health insurance jargon and how it relates to the plan you choose? Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, are here to help. Listen in as they explain premiums, deductibles, coinsurance and copays, maximum out of pocket, and more — all in time for you to review what’s available to you.

Have a money or tax question for us? Send it...

You’ve probably heard of a will. But what makes up a full estate plan? Regina Neenan, CFP®, and Jason Speciner, CFP®, EA, review the high points of creating a real estate plan. From beneficiary designations to using technology tools to build a basic estate plan or working through everything with an estate attorney, they’ll discuss why it’s important and what goes into it from a financial perspective. 

This discussion about estate planning does not constitute legal advice.

Have a money or tax question for us? Send it to [email protected], and Jason or...

When is the most optimal age to begin Social Security, how much can you expect, and how much of your expenses will it cover? Regina Neenan, CFP®, and Jason Speciner, CFP®, EA, discuss how to time when to begin your benefit, ideas for individuals and couples, and more. Plus, Jason shares his opinion on whether Social Security will even be around in the future (hint: they both strongly believe that it will!).

Plus, if you listened to the end, this one’s for you! https://forms.gle/VKt1UkxnGxTojacr5

Have a money or tax question for...

If Regina Neenan, CFP®, uses Monarch and Jason Speciner, CFP®, EA, uses YNAB, why do the majority of FPFoCo’s cash-flow tracking clients use Monarch? Learn the answer — and get a step-by-step walk-through of how Regi sets Monarch up on behalf of FPFoCo clients. Plus, make an easy-to-use tool even simpler as you follow along to set up your Monarch account, too!

Looking for that Monarch Money discount code? It’s right here!

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a fut...

How well do you know your own cash flow — and how much does Jason really know about Regi’s? In this episode, Regina Neenan, CFP®, shares their biggest spending categories. Then  Jason Speciner, CFP®, EA, chats with them about how to appropriately track expenses as a cornerstone of an accurate and effective financial plan.

Looking for that Monarch Money discount code? It’s right here!

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future episode! We’ll release a new one ever...

We’re back with more One Big Beautiful Bill Act updates. With tax cuts come some potential pitfalls that could affect you, from reduced federal health care spending to limited tax deductions, eliminated credits, and more. Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, are here to highlight some so you know what to watch out for — and what you might want to be ready for come tax time. 

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future episode! We’ll release a...

Riley’s back, and he’s here to chat about the tax implications of the One Big Beautiful Bill Act! On this episode, Riley Thoubboron, CFP®, joins colleagues Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, to review the tax-specific changes that the O-tripple-B brings — and what they could mean for you.

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future episode! We’ll release a new one every other Thursday, and they’re ad-free for everyone — no subscription required.

Learn more abo...

It’s investment planning month for Jason Speciner, CFP®, EA, here at FPFoCo! In this episode, Regina Neenan, CFP®, chats with him about active and passive investment management and gets his take on choosing a more passive style for our clients. Plus, hear about target-date funds, rebalancing, the importance of your risk assessment, and more!

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future episode! We’ll release a new one every other Thursday, and they’re ad-free for everyone — no subscripti...

Financial planning doesn’t end when you stop working! If you’re preparing for retirement, recently retired, or hitting a milestone — like three, five, or 10 years in — it’s probably a good time for a check-up. Where's your money coming from? Where's it going? And what are you doing when you’re no longer working? Wherever you're at in the retirement process, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, have some ideas you can use to do it the right way. 

Plus, here’s the elder millennial meme that Jason mentioned and the Spotify link to the Die With Zero a...

Introducing the newest member of our team to earn a professional designation! On this episode, Christin Hutchcraft, FPQP®, joins Regina Neenan, CFP®, and Jason Speciner, CFP®, EA, to share her experience in completing the Financial Paraplanner Qualified Professional™ course and earning the credential. From the rigorous education program to how what she’s learned translates to her work in operations here at FPFoCo, listen in to hear all about Christin’s latest achievement!

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future ep...

What would you do with a windfall? Jason Speciner, CFP®, EA, definitely knows what he would do! Listen in as he and Regina Neenan, CFP®, chat about different types of windfalls. They’ll discuss what you can do if one lands in your lap and how a financial plan could ground you emotionally as you make big decisions and navigate opportunities.

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future episode! We’ll release a new one every other Thursday, and they’r...

Put your savings to work for you! Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, share why it’s important to have an emergency and future opportunities fund (EFOF) — and why your money should be productive. Plus, if you’re looking for a high-yield savings account where you can keep your EFOF safe and earning interest, check out a few resources below!

Have a money or tax question for us? Send it to [email protected], and Jason or Regina might answer your question in a future episode! We’ll release a new one every other...