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Scott finds it difficult to manage asset allocation and buckets across multiple accounts and asks for an efficient way to coordinate everything. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this episode, Devin and John break down the key tax and retirement planning changes coming in 2026 and what they mean for your income, benefits, and long term strategy. We cover the latest Social Security COLA update, the expected increase to Medicare Part B premiums, and the new Social Security earnings test thresholds. We also walk through the shifting rules around capital gains, the standard deduction, and the return of the SALT cap. For charitable giving, we outline the new above the line deduction, the AGI floor for itemizing, the cap tied to the highest tax rate, and the updated QCD limit of one hundred eleven thousand dollars. If you want to understand how the 2026 landscape could affect your plan, this episode gives you the practical guidance you need. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this episode, John talks about the 5 things that he hates to hear from his clients. You will learn why certain statements (and thinking) slow everything down, what your attorney wishes you understood before walking into the meeting, and how to approach your plan with clarity, calm thinking, and realistic expectations. If you want to make better decisions and create an estate plan your family can actually rely on, this episode will point you in the right direction. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Meera and her husband have $4.5 million in retirement accounts and a $430K income. They want guidance on when to start Roth conversions, how much to convert each year, and whether to continue 401(k) contributions. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Everyone's wondering if this is the worst time to retire. With high valuations, stubborn inflation, and constant uncertainty, it's easy to feel uneasy about your timing. In this episode, we look at what history teaches from past "lost decades," why the order of returns matters, and how to protect your plan without panic. You'll learn three ways to prepare just in case: build a spending bucket, stress-test your plan, and rethink your risk exposure. Retirement success isn't about timing the market. It's about preparation and peace of mind. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

David asks for a general idea of what estate planning services typically cost, following up on the six-part podcast series. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

You've heard it a thousand times: "Wait until 70 to file for Social Security." But if that's such obvious advice, why do most retirees file earlier? In this episode, we uncover the hidden cost of waiting and the trade-offs most experts ignore. You'll learn how early withdrawals, taxes, and real-life emotions all change the math—and why the "right" answer isn't the same for everyone. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.

John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter's Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Many retirees think they have a plan when what they really have is an investment pitch dressed up as planning. This episode uncovers why that illusion is dangerous, the costly mistakes it hides, and how to spot the difference between true planning and portfolio sales. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and a non-raptured emergency (00:00-17:36) Is the rapture actually in the Bible? Why do people get so focused on it? (17:53-35:14) James says a person who doubts is “double minded and unstable” and shouldn't expect to get anything from God (James 1:7-8). But we all doubt, right? What does this mean? (35:19-49:15) Is there a trick to moving on from a situation (relationship, conversation, event) and not keep thinking about it all the time? (49:20-59:48) Closing Song: Macabre Feast (Tyranny of the Beast)

Winning the lottery may be rare, but estate tax mistakes aren't. In this episode, we use the recent $1.8 billion Powerball jackpot to highlight how generational wealth can be eroded by estate taxes and how tools like a BDIT can help protect growth assets. We'll also show why this strategy isn't just for lottery winners, but for anyone holding assets with explosive growth potential. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they're doing so because they're worried about cuts. But will filing early really help? In this episode, we talk about what the data shows, what most people get wrong about Social Security cuts, and how to think about your filing strategy with clarity, not fear.  Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and a Toys 'R Emergency (00:00-18:28) I hear some Christians say they “aren't political” or stuff like “Jesus is King, that's my politics.” It is often said like that is the truly evolved and Christian point of view. But I am starting to more and more see it as a cop-out. Am I being unfair? (18:33-32:50)   What do I do when my faith is starting to feel formulaic and stuck? (32:54-45:44)   In John 6:35, Jesus says “I am the bread of life. Whoever comes to me will never go hungry, and whoever believes in me will never be thirsty.” Obviously this isn't literal, but what does it mean? That I will never spiritually hunger? If so, what does that mean? (45:48-58:46) Closing Song: This Is My Father's World (Southern Harmonic)

When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a well-built retirement plan. Devin begins by challenging the common belief that wealthy retirees do not need to think about Social Security. In reality, those with more assets often have more choices, and those choices make the timing decision even more important. You will learn about the three core priorities that should guide how and when you file: protecting a surviving spouse, maximizing guaranteed income, and coordinating Social Security with the rest of your retirement plan. Devin explains how each of these goals can shape your filing strategy and why getting the timing right can support better outcomes for both income and taxes. This episode also covers how delaying benefits can increase lifetime income for a surviving spouse, reduce tax burdens through coordinated withdrawals, and help create a stronger income floor that is not tied to the markets. If you have flexibility in when you file, use it wisely. Social Security decisions should support your long-term goals, reflect your income needs, and fit within your overall tax and investment strategy. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and a Satan-suing emergency (00:00-20:20) Is it wrong to feel/express relief or even happiness when a public figure who caused people a lot of pain passes away? (20:28-36:14) What does it mean that we are not supposed to “test God”? Is that different than asking questions or having doubts? (36:17-50:39) Galatians 6:4 says everyone should “test their own actions”. How do I actually do that? Test them for what? (50:52-01:03:47) Closing Song: This Time is Different (Front Toward Enemy)    

 For many affluent retirees, the biggest financial fear isn't market volatility or rising taxes. It's this simple question: What happens if I'm not the one here to manage the plan? In this episode, we talk about a deeply personal concern shared by countless couples. When one spouse manages the investment strategy, the tax planning, and the long-term vision, the other is often left trusting that everything will work out. That trust may work fine today, but what if something changes tomorrow? What if the surviving spouse is left with a complex financial plan they don't fully understand? Devin shares his own story, including the moment he realized his wife might struggle to carry on the plan they had built together. From that fear came action; a series of steps to make sure she would not only inherit assets, but also confidence and clarity. You'll hear about the simple, practical moves you can make to protect the person you love, including how to start the conversation, what to document, and how to choose someone you both trust. This episode is a must-listen if you've ever thought, I just want to make sure my spouse will be okay if something happens to me. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Should everyday investors be allowed to hold private equity, venture capital, or even crypto in their 401(k)s? A new executive order suggests it might soon be possible. In this episode, we walk through the real implications of this move, especially for retirement savers who may not be equipped to handle the risks. We start with a quick quiz that highlights a troubling truth: most 401(k)-only investors don't understand basic financial principles like compound interest, inflation, or diversification. If many people struggle with the fundamentals, what happens when we layer in high-fee, illiquid, and opaque investments? You'll hear what's already allowed in retirement plans, why private equity firms are pushing for broader access, and what dangers exist when complexity is added to accounts that are supposed to be simple and secure. We share a personal example from our own experience with illiquid private investments and explain why adding these as standalone options could backfire for plan participants. This episode also explores why this change might be happening now, what fiduciaries need to consider, and why protecting investors requires more than just offering new choices. It requires clear guidance, thoughtful planning, and honest conversations about financial literacy. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and a rare Inverted Emergency (00:00-18:36) People say that you should put your hope in God, not it other people, the government, etc. But I do want to be able to rely on other people. What is the difference? (18:49-34:29) How do I lovingly deal with someone who is always casting themselves as the victim in every situation? (34:33-49:37) What is the deal with the book of Proverbs? It always seemed weird to me that there is the little collection of sayings in the middle of the Bible. I feel like I don't get much out of reading them. (49:41-01:05:19) Closing Song : I Need Thee Every Hour (Lee Younger)

Ask A Question: saythatpodcast@gmail.com Intro and a pair of publicly embarrassing emergencies. (00:00-22:21) What does it mean to be a “strong believer”? Is it about being sure of what you believe? (22:42-34:13) Is there a christian way to talk people out of conspiracy theories? Does it matter that buying into that stuff will hurt someone's credibility and witness, or is that just guilting someone? (34:18-53:17) In Mark 2:27, Jesus says to the pharisees that “The Sabbath was made for man, not man for the Sabbath.” Is that an idea we can apply to wider religious stuff, even stuff that is in the Bible? Do we get to the point where we are serving religious things? If so, how do I not do that? (53:21-01:05:23 Closing Song: I Come to You (Jed Brewer)

You've done the hard work. You saved consistently, built a seven-figure portfolio, and are ready to enjoy retirement. But even millionaire retirees can make mistakes that put their plans at risk. In this episode, Devin shares the five most common retirement mistakes he sees among high-net-worth clients. These include missing long-term tax planning opportunities, underestimating healthcare and long-term care costs, failing to plan for success as well as failure, approaching income withdrawals without structure, and overpaying for financial advice. If you want to get the most out of what you've saved, this episode will help you avoid costly missteps and retire with more clarity and control. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social Security taxation, and a brand-new "Senior Deduction"—there's a lot packed into this legislation. We'll walk you through the major provisions, highlight how they may affect your retirement income strategy, and share practical planning moves to consider. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and a mystery sign emergency (00:00-20:11) Jesus talks about not praying in public like the hypocrites. What does that mean for praying in front of a church? Or famous people having pictures taken of them praying? Or non-famous people, like wedding pictures of people praying over the couple? Is that a sin? Just weird? (20:20-39:12) I know it is not my place to judge anyone else's salvation. But, At some point, people who believe things like God loves rich people more than poor people or God wants us to treat immigrants badly are just not Christian by any definition that I recognize. How do I acknowledge that without judging? (39:18-01:00:06) A lot of talk about being honest with God is about being angry at Him? What about being disappointed, or sad about things he has done, are those okay feelings to have? (01:00:09-01:15:12) Closing Song: Psalm 147:3 (The Poolhouse Guru)

Today we answer a question from Ken, a recent retiree at 63, about how his Social Security claiming decision impacts his wife's future spousal benefit. We break down how spousal benefits are calculated, whether the FRA (Full Retirement Age) amount is frozen when you claim early, and how COLA (Cost of Living Adjustments) factor into the equation. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Most retirees think tax planning ends with knowing their tax bracket, but that's just the beginning. In this episode, we unpack how different income sources interact in retirement, and how seemingly smart decisions can trigger hidden taxes, Medicare surcharges, and other costly surprises. Learn how to avoid the traps and make your retirement income work smarter. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Today we answer a question from Chris about The Good Life Abroad and whether we plan to take a trip with the company. We share our thoughts on the concept, what interests us about their offerings, and whether a future review might be on the horizon. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and a guitar-drowing, pastor-dangling emergency (00:00-19:30) I found something on youtube [The pilot of the TV Show The Promised Land] I loved it and i'm curious to hear your thoughts on this christian media. i could be overthinking but want to make sure this is okay to watch before i get too attached. (19:34-37:52) How to deal with people who lack empathy? Who are so blinded by the comforts they now have that they are indifferent to the hardships of others? (37:56-55:01) What does Paul mean in 1 Corinthians 11:27 when he warns about taking communion in “an unworthy manner”. That seems like a very different vibe than Jesus' description of communion. (55:04-01:08:07) Closing Song: All Hail The Power of Jesus' Name (Glenn Kaiser)

Comprehensive coverage of the day's news with a focus on war and peace; social, environmental and economic justice. Sen. Alex Padilla (official photo) CA senator Padilla dragged from news conference when he tried to ask Homeland Security Secretary Noem a question Heavy rains, floods in South Africa kills dozens as climate crisis impacts African countries Activists planning “No Kings” rallies across country during Saturday military parade on Trump's birthday TX governor Abbot ordering 5,000 national guard and 2,000 state police to manage protests UN says complete collapse of internet and data services in Gaza paralyzing aid operations UN marks World Day against Child Labor, as millions of children denied fair chance The post CA senator Padilla dragged from immigration news conference when he tried to ask a question; South Africa floods kill dozens as climate crisis impacts African countries – June 12, 2025 appeared first on KPFA.

Today we answer a question from Sandi about how much umbrella insurance coverage you really need — especially as you approach retirement. We discuss why someone might choose a $2 million policy, how assets like home value, retirement accounts, and savings factor in, and share real-world examples to help you gauge whether you're over- or underinsured. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Today we answer a question from Peter about what happens when a parent dies with a fully planned estate that avoids probate — and how the Small Estate Affidavit process works in practice. We discuss handling unexpected estate assets like refund checks, whether you can open an estate bank account without letters testamentary, and who's responsible for final taxes and bills Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this special episode, we catch up on a backlog of insightful listener questions—covering everything from estate planning and Social Security taxation to Roth conversions and Medicare rules. If you've been wrestling with real-world retirement planning decisions, you're not alone. Today's episode delivers practical answers to the kinds of issues many people face but few have clearly explained. We tackle: IRMAA and Social Security Taxation – Does IRMAA include Social Security income if it's not taxable? Capital Gains on a Vacation Home – Should you delay estate planning until after the sale of a property? What about the "2 out of 5 years" exemption? Paying Inheritance Taxes – If all your accounts list beneficiaries, how will state inheritance taxes (like Pennsylvania's) get paid on time? Step-Up in Basis with TOD Deeds – In Oklahoma, does property with a Transfer on Death deed still receive a step-up in basis? Impact of Home Sale on IRMAA and Roth Conversions – How does selling a vacation home affect your income-based Medicare premiums and Roth conversion strategies? Medicare Enrollment Rules at Age 65 – Are you legally required to enroll in Medicare at 65 if not on a qualifying employer plan? Trusts and Anonymity – How can you use estate planning tools while keeping your affairs private and self-directed? Probate Friendliness by State – Which states make probate easy, and which ones almost demand a trust-based plan? Inherited IRAs and Roth Conversions – Can a beneficiary convert inherited IRA funds into a Roth IRA for future tax-free growth? If you've ever had a nuanced question about retirement or estate planning, chances are someone else has too—and we're tackling them head-on in this packed Q&A episode. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and we discuss what makes a true Chicago pope (00:00-19:14) People talk about feeling something profound during worship, but I people also feel stuff while singing secular songs or being at concerts. Is worship something different, or just that same emotional high that music gives? (19:26-41:19) How do I know if someone can't change what they are doing or if they just won't? Those things feel very different. (41:23-56:39) What does it mean that we died in Christ, but we also live in Him? (56:45-01:09:27) Closing Song: As I Am (Lee Younger)    

In the final installment of our 3-part estate planning series, we dive into one of the most overlooked—but critically important—aspects of planning: protecting your heirs' inheritance. It's not enough to simply leave assets to your loved ones. Without proper planning, those assets could be exposed to divorce, lawsuits, creditors, or mismanagement. We'll explore how using trusts can provide long-term protection and flexibility, and why leaving assets outright may be a costly mistake. You'll learn how to: Safeguard inheritances from a beneficiary's divorce or personal liabilities Provide for special needs or disabled heirs without jeopardizing government benefits Handle contingency planning, including what happens if a beneficiary predeceases you Protect minor children using trusts instead of relying on court-supervised guardianships We also highlight common mistakes—like failing to update your estate plan after major life events—and share practical steps to avoid them. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Today we answer Jeff's question about using home equity to pay for end-of-life care — from tapping into equity for in-home support to selling the home to cover nursing home costs. In high-cost states like California, many seniors are house rich and cash poor, and this episode explores strategies to help families navigate that challenge. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this episode, we shine the light on common estate planning mistakes that can derail even the best intentions. We discuss the risks of failing to update beneficiary designations and why relying solely on joint ownership can create unexpected complications. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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Today we answer a question from Cathy about helping aging parents in California navigate care costs, preserve limited resources, and explore options like pro bono legal support. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this episode, we cover key tax considerations around wealth transfer. We cover the differences between federal estate tax and state inheritance tax, and explain why the stepped-up basis is such a powerful tool for minimizing capital gains taxes for heirs. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this episode, Brian asks some great questions about using Net Unrealized Appreciation (NUA) for company stock inside a 401(k). We dive into the rules, timing, and strategies that could lead to major tax savings—if you do it right. We cover: What exactly is NUA and why it matters Can you use NUA before retirement? Do you need to be age 59½? Can you move the stock out in segments, or does it have to be all at once? Common mistakes that could cost you Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and a Jeepin' emergency (00:00-19:30) How do you distinguish between hypocrisy and when people just being people and falling short of something they talk about? (19:42-36:59) I have been praying about a situation in my life. What am I looking for now to tell if God is answering me? (37:03-48:36) In John 21, what is the significance of Jesus asking Peter if he loves Him 3 times? I get that it mirrors Peter's denial, but what does that mean for us? (48:45-01:02:20) Closing Song: Women, God, and Rock and Roll (Jed Brewer)

In this episode, we explore how to pass on your assets smoothly and efficiently—without dragging your loved ones through probate court. You'll learn why probate can be costly and time-consuming, and how non-probate strategies like beneficiary designations, joint ownership, and revocable living trusts can help you keep more money in your family's hands and less in legal fees. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In this inbox episode, we break down how the Social Security earnings limit works—especially for C corp owners who split income between salary and dividends. Learn what counts toward the limit, what doesn't, and how smart income structuring can help you avoid benefit reductions. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In the first part of our series on estate planning, we laid the groundwork for why incapacity planning matters and what documents you need to get started. But there's more to it than just having your paperwork in order. In this second episode on planning for incapacity, we take the conversation further by focusing on what happens when long-term care is needed. We'll walk through the different types of care—home care, assisted living, and nursing homes—and how to plan ahead financially using private pay, long-term care insurance, or Medicaid planning. We'll also highlight common pitfalls like outdated or missing Powers of Attorney, and the risks of DIY estate planning that can create real problems down the road. If you haven't reviewed your incapacity planning documents lately—or if you've never had them in place—this episode is your call to action. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Ask A Question: saythatpodcast@gmail.com Intro and the guys try to get on a blessings grift (00:00-18:25) What are we supposed to make of Judas? Jesus seems to say he is a unique kind of bad. But also things couldn't have happened the way they were supposed to without him, right? (18:38-32:36) Why are there different accounts of the resurrection in the Bible? (33:50-47:33) What does it mean to personally have peace when the world around you is so crazy? (47:39-59:05) Closing Song: Break of Day (Lee Younger)

Today kicks off a brand-new series on estate planning. Estate planning is one of those things everyone knows they should do—but far too many people put it off, sometimes until it's too late. And the truth is, whether your financial situation is complex or pretty straightforward, having a solid estate plan isn't just about what happens after you're gone. It's also about making things easier for your loved ones—and protecting yourself—while you're still here. That's why we're launching this special series to break estate planning down into simple, practical steps. We'll walk through the essential documents you need, the common mistakes that can derail a plan, and some of the more advanced strategies for protecting and passing on your wealth efficiently. Whether you're starting from scratch or just need to update an existing plan, this series will give you the roadmap you need. Now, we originally thought we could cover the first part of this in a single episode—but planning for incapacity turned out to be too important to rush. In this episode, we'll cover why incapacity planning is essential, real-life scenarios that make it critical, and the foundational documents every adult should have: Financial and Medical Powers of Attorney, and Advance Directives. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

John asks about buying the individual sectors of the S&P 500 and rebalancing based on performance instead of simply buying an index fund. Devin shares the pros and cons that he can see with this strategy and shares what he thinks is a better approach.  Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Rosemary's husband is scaling back to 32 hours a week as part of his transition plan before switching careers. With Social Security in mind, she asks: Will this reduced income impact their future benefits? In this episode, we break down how Social Security calculates benefits, whether lower earnings in the final working years can reduce your check, and what to consider before making the shift. If you're thinking about adjusting your workload before retirement, this is an episode you won't want to miss! Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.