Wealthyist E66 | Tax Prep vs. Tax Planning: Why High-Net-Worth Families Might Need Both Under One Roof

Wealthyist E66 | Tax Prep vs. Tax Planning: Why High-Net-Worth Families Might Need Both Under One Roof

In this episode of Wealthyist, hosts Tom Berkholtz (CFP®, EA, ECA) and Eric Strom (CFP®, EA) break down the critical difference between tax preparation and tax planning — and why the distinction matters more than ever for high-net-worth individuals in 2026. Tax preparation is the annual filing process: gathering documents, accurately completing your return, and avoiding penalties. Tax planning, by contrast, is proactive, year-round, and lifetime-focused — zooming out to minimize taxes over decades, especially since taxes are often the largest single expense in retirement for affluent clients. Key Trends Discussed: * Integration is the new standard: Top firms are combining tax preparation, year-round tax planning, investment management, and comprehensive financial planning under one roof for seamless, better outcomes. * Team of specialists matters: Complex needs (equity compensation, real estate, international tax, AMT, K-1s, IRS representation) require experts like Enrolled Agents (who have unlimited representation rights before the IRS) and niche credentials. * Technology revolution: Client portals, advanced modeling, and AI are transforming tax prep (making basic returns more commoditized), but sophisticated planning still demands human expertise. * Major pain points for the wealthy: Fragmented accounts, multiple custodians, missed opportunities from new legislation (like the One Big Beautiful Bill Act), SALT deduction phaseouts, Alternative Minimum Tax (AMT) creeping back, and the risk of future tax increases due to national debt. * Actionable advice: Consolidate assets for visibility and better planning, get projected “mock” tax returns (especially after law changes), use extensions strategically, and ensure your advisor actively reviews your actual tax returns and handles IRS notices. The episode emphasizes that in today’s complex environment, settling for a once-a-year preparer separate from your advisor often leaves significant money on the table. The hosts encourage listeners to seek firms offering true 360-degree tax and wealth integration.

Wealthyist E65 | Are Beneficiary Designations Undermining Your Estate Plan?

Are Beneficiary Designations Undermining Your Estate Plan? Beneficiary designations are contractual instructions you give to financial institutions about who receives assets in accounts like: * IRAs, Roth IRAs, 401(k)s * Checking and savings accounts (often called Payable on Death - POD or Transfer on Death - TOD) These are legally binding contracts between you and the financial institution. They generally override whatever is written in your will or trust. Why They Matter So Much Even a perfectly drafted estate plan can fail if beneficiary designations don’t match it. The episode highlights numerous real-world “horror stories” where: * Assets went to ex-spouses, disowned children, or unintended relatives because designations were never updated. * A child predeceased the parent, causing their share to go through the deceased child’s estate instead of directly to grandchildren or the surviving child. * Someone opened a new account after creating their estate plan and never added beneficiaries, triggering unnecessary probate. What Happens If You Don’t Name Beneficiaries? It depends on the financial institution’s default rules (some default to spouse → children; others send everything to probate). This can force assets through court-supervised probate even if the rest of the estate plan avoids it, creating extra costs, delays, and complexity. Key Risks & Common Mistakes * Failure to update — Life changes (divorce, remarriage, death of a beneficiary, reconciled relationships, disowning someone) require updates. * New accounts / account rollovers — Beneficiary designations often don’t automatically transfer. * Inconsistent planning — Will says “everything to kids,” but beneficiary form still says “nieces and nephews.” * Not funding the trust — Signing a trust document is not enough; assets must actually be titled to it or properly designated. When to Name a Trust as Beneficiary Especially relevant for pre-tax retirement accounts (traditional IRAs, 401(k)s): * Direct to individuals is usually simpler (better tax treatment and easier administration) if the beneficiary is responsible and has no major risks. * Name the trust when you need: * Asset protection (divorce, lawsuits, creditors) * Spendthrift protection * Professional management for beneficiaries who can’t handle money well This decision is highly personal and should be coordinated with an attorney. Disclaiming (Refusing) an Inheritance You can disclaim a beneficiary designation, but you lose control. It treats you as if you predeceased the account owner, so the asset follows the next default beneficiary (often not where you want it to go). In the episode’s example, this created major complications in a step-family situation. Best Practices * Ensure beneficiary designations are consistent with your overall estate plan. * Review designations annually or every other year (more frequently than the full estate plan). * Check every new account and every rollover. * Work with your advisor — many wealth firms (like Annex) will help review and align everything. * Ultra-high-net-worth individuals may use family offices to handle this administratively. Bottom Line Brian and Alec emphasize that there is no shortcut. You must go account-by-account to set and maintain proper designations. Signing estate documents is only the first step — proper execution and ongoing maintenance are what actually make the plan work. The episode stresses that this issue affects everyone regardless of wealth level, but the consequences (and potential costs of mistakes) grow with larger account balances.

Wealthyist E64 | Luxury Isn't a Price Tag: Redefining the 'Biggest Day' with Wedding Pros Ashley Kuehnel & Koryn Bennett

In this episode, host Austin Grandinetti sits down with Ashley Kuehnel of Midwestern Bride and Koryn Bennett  of Ivy Lane Photo Company . The conversation dives into the evolving world of luxury and premium weddings, particularly in the Midwest. Key highlights include: * What "luxury" really means: It varies wildly by couple—some prioritize an intimate experience with 10 guests and heavy investment in florals or photography, while others focus on hosting a large crowd. True luxury often boils down to how the day feels: seamless, stress-free, personal, and emotionally supportive. It's less about a fixed dollar amount and more about priorities, vendor treatment, attention to detail (like fetching Birkenstocks for a bride's sore feet), and peace of mind. * The role of key vendors: Ashley explains her consultative, relationship-driven approach at Midwestern Bride. With nearly 15 years in the industry (drawing from hospitality, floral, dress shops, and catering), she acts as a "quarterback," curating vendors, aligning budgets and timelines, and handling the behind-the-scenes logistics so couples can actually enjoy their day. Koryn shares how her photography emphasizes collaboration, extended shoots, backup security for images (including long-term hard drive storage), and treating couples as individuals rather than assembly-line clients. Both stress the value of experienced vendors who understand the full ecosystem—preventing disasters like no-shows or lost photos that cheaper or less reliable options can cause. * Budgets and realities: Full-planning clients with Ashley often land at six figures or more (one standout reached over $500K for a multi-day, highly intentional event on private property with custom tents, flooring, multiple floral teams, and army-truck loads of flowers). "Average" weddings (without full planning) trend toward $60K–$70K in their markets, far above outdated Google averages due to rising venue costs, inflation, and demand for experiential elements. Backyard or DIY options can ironically cost more than venues because of hidden logistics (electricity, staffing, etc.). * Generational shifts and trends: Gen Z couples lean toward smaller, more intentional weddings, questioning traditions (e.g., skipping long ceremony-to-reception gaps), and valuing vendor friendliness and honesty about family dynamics. They're prioritizing presence over pomp. Parents' involvement varies—some provide gifts with full autonomy, others buffer budgets thoughtfully. Experiential details shine: sentimental surprises (like restoring a late father's car for photos), personalized guestbooks (e.g., a surfboard with embedded flowers), interactive elements (Polaroid walls with real-time seating integration), and guest-focused flow (quick bar service, props to energize the dance floor). * Why hire pros? Peace of mind is the ultimate luxury. Planners and photographers prevent chaos, anticipate needs, foster smooth vendor teamwork, and create space for couples (and families) to be fully present. The guests' experience—hospitality from the first moment, no downtime, entertainment that keeps energy high—often separates memorable events from standard ones. The discussion ties back to wealth strategies: Spending on a wedding reflects values around experiences, relationships, and intentionality, much like financial planning. It's not about mindless extravagance but curating what matters most while trusting experts to handle the rest. Ashley and Koryn emphasize building trust, open communication (especially across generations), and delivering feelings of care and joy that last far beyond the photos. Overall, the episode offers practical insights for anyone planning (or paying for) a high-end wedding: Focus on alignment with vendors who "get" you, invest in expertise for security and smoothness, and remember that luxury is ultimately about emotion and execution, not just the bottom line. Great listen for couples, parents, or anyone curious about how the wealthy approach life's milestone celebrations.

Wealthyist E63: Dream Machines & Detroit Steel: Corvette Joy, Classic Car Investing, and Reviving Milwaukee Concours

In this engaging Wealthyist episode, host Kent Haleen and co-host David Panitzke (both proud new owners of the same-year manual-transmission Corvettes) welcome Jay Shiek, aka Jay the Car Guy — a passionate collector, appraiser, broker, and key figure reviving the Milwaukee Concours d’Elegance. Jay shares his origin story: a lifelong car enthusiast who turned his passion into a business helping clients buy, sell, and appraise vintage and collector cars. His favorite part? The priceless look on someone’s face when they finally get behind the wheel of a car tied to childhood memories or long-held dreams — whether it’s a nostalgic Sunday driver, a race-pedigree machine, or a serious investment piece. Key Highlights & Advice * Why classics hit different: Modern cars lack the emotional history; older ones reconnect people with their past (e.g., “My uncle had one”). * Jay’s personal passion: Unrestored, original “survivor” cars like his beloved Packard (bought new in Wisconsin, passed through careful owners, now a family wedding chariot). He’s a caretaker, not a modifier — no power steering/brakes, original everything. * Common mistakes for wealthy newcomers: * Impulse/heartstring buys or auction bidding wars (set a hard budget). * Skipping professional appraisals (leads to overpaying, under-insuring, or missing provenance value). * Sentimental restorations that don’t make financial sense. * Market insights: Values fluctuate dramatically (muscle cars, limited-production models like Charger Daytonas or GNX). Japanese 90s icons (Supra, RX-7) are heating up. Rarity, provenance, and condition drive big premiums — but buy what you love and will actually enjoy. * Car collections: Get them appraised, properly insured, stored (especially Wisconsin winters with battery tenders), and driven. Enjoy them, show them, share them. Don’t let them sit and degrade out of fear or sentiment. * Driving vintage cars: Requires extra care — they’re not modern in braking/handling, and other drivers don’t always respect them. Milwaukee Concours d’Elegance: J is leading the revival (post-COVID) with plans for next year at the zoo in partnership with Autism United. It aims to be “Middle America’s Pebble Beach” — competitive, invitation-only, judged classes celebrating original/unrestored excellence. They need deep-pocket sponsors and ~450 volunteers. Get involved via carguymke.com or “Jay the Car Guy” on social media. Final advice for successful retirees entering the hobby: Buy what tugs at your heartstrings, not what others think is cool. Work with experts to avoid pitfalls, and drive/enjoy your collection. The episode blends lifestyle passion, practical wealth strategies for automotive assets, and community-building around classic cars. It’s motivational for enthusiasts and informative for those treating them as investments. Perfect listen for anyone with (or eyeing) a garage full of steel dreams.

Wealthyist E61 | From Navy SEAL to Building Impact-Driven Businesses: Leadership Lessons from the Battlefield to the Boardroom with John Choate

In this episode of The Wealthyist, Kent Halleen sits down with John Choate — former Navy SEAL officer, successful entrepreneur, and founder of Apogee Travel, a transparent hotel booking platform that supports veteran causes and charities like St. Jude. John shares hard-earned leadership lessons from the SEAL teams that translate directly to building high-performing businesses and living a wealthy, purposeful life. Key topics include: * Anticipating the “adversary’s vote” and stress-testing plans (the military “murder board” approach) * The power of decentralized command and building a culture that allows smart failure * Why the right people always matter more than perfect processes * The challenge high-achievers face when transitioning out of high-intensity careers — and how the drive never really turns off * Current trends in physical security for ultra-high-net-worth individuals (the shift to low-visibility, concierge-style protection) Blending battlefield discipline with entrepreneurial wisdom, John delivers practical, no-nonsense insights on leadership, legacy, risk, and staying grounded while chasing meaningful success. A must-listen for executives, founders, and anyone building wealth with impact.