The Stacking Benjamins Show

Estate planning might not sound like the most thrilling topic—but skipping it can create a real mess for the people you care about most. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug sit down with attorney Tim Semro to cut through the noise on wills, trusts, and life insurance. Whether you’ve been putting off writing a will or you’re wondering if a trust is worth it, this conversation will give you a clearer path forward. Tim walks us through the essentials, from the differences between wills and trusts to the sneaky pitfalls that can trip up your beneficiary designations. We also tackle tricky scenarios—like probate headaches, planning across state (or even international) lines, and how to think about life insurance with living benefits. Plus, we swap stories about scams that hit a little too close to home and the simple moves you can take to protect your finances and family. This episode isn’t about scaring you into action; it’s about showing how estate planning and the right insurance can actually bring peace of mind. By the time you’re done listening, you’ll have a roadmap for protecting your family, making smarter decisions with your money, and avoiding the landmines that could derail your plan. And yes, there’s still a trivia break and plenty of the usual basement flavor to keep things moving. What You’ll Learn in This Episode: * The key differences between wills and trusts—and when you might need each * Why beneficiary designations matter more than you think * How estate taxes and probate rules can complicate things (and how to prepare) * What life insurance with living benefits is—and when it could make sense * Red flags for spotting scams and fraud before they hit your wallet * How to align your estate plan with your financial and family goals Questions to Ponder While You Listen (and maybe discuss with us in the Basement Facebook Group): 1. Do you already have a will or trust in place? If not, what’s been holding you back? 2. Have you ever discovered an outdated beneficiary designation (or seen the chaos it caused)? 3. What role do you think life insurance should play in your estate planning? FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-charitable-giving-week-1723 [https://www.stackingbenjamins.com/estate-planning-charitable-giving-week-1723] Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 [https://www.stackingbenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Some people chase “work-life balance” like it’s the Holy Grail—spending time, money, and mental energy trying to keep work and personal life perfectly split down the middle. But what if that balance doesn’t actually exist? Live from Joe’s mom’s basement (and not nearly as glamorous as it sounds), Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer pull back the curtain on whether we should be aiming for balance… or something else entirely. In this roundtable, the crew wrestles with the difference between work-life balance, alignment, and integration—and why chasing balance might actually keep you from a truly fulfilling life. You’ll hear personal stories, some hard-won lessons about productivity, and a few well-placed digs at Nautica (including the questionable financial moves Joe made in his youth). And because no basement chat is complete without it, we bring you a trivia challenge you didn’t know you needed. From managing notifications so they stop managing you, to building a life where work and personal priorities don’t compete, this episode digs into the practical steps that help you get more out of both your career and your free time. Whether you’re climbing the corporate ladder, running your own show, or plotting an early retirement, you’ll walk away with tools to rethink how you spend your hours—and why. What You’ll Learn in This Episode: * Why “work-life balance” might be the wrong target—and what to aim for instead * The difference between balance, alignment, and integration (and why it matters) * Practical ways to keep work from swallowing your personal life whole * How to reclaim your attention from constant notifications and distractions * Mindset shifts that boost productivity and satisfaction in everyday life * Lessons from real-life wins and missteps (including Joe’s Nautica saga) FULL SHOW NOTES: https://stackingbenjamins.com/all-about-work-life-balance-1722 [https://www.StackingBenjamins.com/all-about-work-life-balance-1722] Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 [https://www.StackingBenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Ever wonder how to build a career, business, or financial plan that actually lasts — no matter what life throws at you? This week, we’re bringing you lessons from someone who’s done it for more than five generations. Cheryl McKissick Daniel, president and CEO of McKissick & McKissick, joins Joe and OG to share the strategies her family has used to overcome obstacles, land major deals (like the arena in Brooklyn and countless buildings on the historic register of places), and turn connections into opportunities. Whether you’re growing a business, climbing the career ladder, or managing your money, you’ll walk away with practical ideas to strengthen your network, protect your reputation, and keep moving forward. From the art of negotiation to turning big challenges into bigger wins, Cheryl offers insights you can use right now to build momentum. We’ll explore how revisiting your financial plan regularly can help you avoid surprises, why reputation is an asset you can’t afford to neglect, and how a strong team can take you further, faster. Plus, we’ll take a break for our TikTok Minute to look at what happens when your vacation budget disappears in the name of “fun” spending. And in our headline segment, we’ll cover important Medicare and insurance updates that could save you money and headaches later. Here’s what you’ll learn in this episode: * How to use your reputation as a currency that opens doors and attracts opportunities * Strategies for building a network that works for you (even when you’re not in the room) * Lessons from landing multi-million-dollar deals — and how to apply them to your own negotiations * Why regularly reviewing your financial plan can save you from costly surprises * Smart adjustments to Medicare and insurance that protect your money and peace of mind * How to turn adversity into momentum, whether in your career or personal finances * A lighthearted look at how “just a little fun” can destroy your budget faster than you think FULL SHOW NOTES: https://stackingbenjamins.com/story-about-building-america-1721 [https://www.stackingbenjamins.com/story-about-building-america-1721] Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 [https://www.stackingbenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Is your 401(k) quietly working for you… or quietly working against you? In the first half of this episode, Joe Saul-Sehy, OG, and Neighbor Doug tackle the most common 401(k) slip-ups that even seasoned savers make—and how to turn yours into a retirement-building machine. Then, in the second half, we turn to a problem many Stackers don’t see coming: going from saving to spending in retirement. Stacker Joel in Cleveland asks how to make the leap without feeling like you’re sabotaging your future. Drawing on OG’s real-world experience guiding clients through this tricky transition and Joe’s research into the psychology of money, we share practical steps to help you spend without guilt, align your withdrawals with your values, and actually enjoy the freedom you’ve worked so hard for. Here’s what you’ll learn in this episode: * The most expensive 401(k) mistakes—and how to fix them today * Why employer matches are truly “free money” (and how to grab them) * Smart moves for rolling over old 401(k)s and navigating vesting schedules * The pros and cons of holding company stock in your retirement account * Why the saving-to-spending switch can feel so uncomfortable—and how to get past it * A simple mindset shift that helps retirees live more fully without blowing their plan * How to turn your nest egg into a joy-producing income stream Whether you’re in the middle of your career or staring down your first year of retirement, this episode will help you protect what you’ve built, optimize your plan, and make the most of your money—without second-guessing yourself. FULL SHOW NOTES: https://stackingbenjamins.com/common-401-k-mistakes-1720 [https://www.stackingbenjamins.com/common-401-k-mistakes-1720] Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 [https://www.stackingbenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Get ready for a rapid-fire roundtable packed with personal finance opinions that might challenge your own money playbook. In this episode, Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Don McDonald (Talking Real Money) join Joe and OG to declare whether they're in or out on some of the most polarizing financial strategies. Whether you're just getting started or leveling up your financial life, this episode is full of practical wisdom, contrarian views, and a few laughs along the way. Oh—and somewhere in there, we may or may not sneak in a birthday surprise for one of our favorite Stackers. 🎂😉 * Why some pros still say "cash only" is best for beginners—and why others strongly disagree * The real trade-offs of delaying homeownership in today’s market * What types of insurance you actually need (and which may just be money drains) * When hiring a CPA is a gamechanger vs. when it's overkill * How to evaluate target date funds: genius or lazy? * Whether it’s finally time to drop collision insurance on that 15-year-old car * How to choose between Roth and Traditional 401(k) strategies * The one estate planning move nearly everyone overlooks FULL SHOW NOTES: https://stackingbenjamins.com/jeff-lund-birthday-special-1719 [https://www.StackingBenjamins.com/jeff-lund-birthday-special-1719] Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 [https://www.StackingBenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]