Wealthyist

Annex Wealth Management

Wealthyist, the podcast that discusses the lifestyles, choices, and strategies of the wealthy. Each week, the Annex Private Client team talks to experts in a variety of areas to discuss trends and paths visited by people who have built or are in the process of building significant wealth.

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#79
Friday · 20 min
Wealthyist E76| Opportunity Zones 2026: Defer the Tax, Don’t Ignore the Lockup
Qualified Opportunity Zones (QOZs), created by the 2017 Tax Cuts and Jobs Act, let investors roll capital gains (from stocks, a business sale, real estate, or other assets) into a Qualified Opportunity Fund within 180 days and defer the tax. The original 10-year window ends in 2026, so deferred gains become taxable this year even if the investment is not sold—creating a liquidity pinch for some holders. Early investors also received basis step-ups (10% after five years, another 5% after seven) and the chance for tax-free appreciation after a full decade.A subsequent tax law change revived and made the program more permanent, with rolling new zones and a shorter five-year holding period for key benefits. Funds typically target real estate or businesses in state-designated distressed areas and are structured like private-equity or private-real-estate vehicles. The hosts emphasize that the tax deferral is real but incomplete: it does not eliminate tax, and the underlying investments have often delivered modest or poor returns after fees. Liquidity is limited; few funds have built-in exit mechanisms or a developed secondary market, so investors can face multi-year lockups. Risks include concentrated exposure to higher-risk real estate, sponsor quality and fees, and opportunity cost versus simply paying the tax and investing in more liquid, diversified assets. Direct indexing and other tax-aware strategies can achieve similar goals with more flexibility. Annex’s approach is cautious: treat QOZs as a specialized tool, not a default tax strategy. Evaluate sponsor track record, expected net-of-fee returns, portfolio fit, and liquidity needs before committing. The program is being marketed heavily; the investment merits must still stand on their own.
#78
September 11 · 25 min
ICYMI: Wealthyist E44 | From 9/11 to 2 Successful Exits: Building Transferable Businesses & Planning Life After the Sale with Andy Oliver
In this replay of Wealthyist Episode 44, host Anthony Mlachnik sits down with Andy Oliver, a 30-year finance veteran, two-time business founder/exiter, and partner at Oak Hill Business Partners, a boutique consulting firm that helps lower-middle and middle-market owners dramatically increase enterprise value and prepare for a successful exit. Key highlights and takeaways: Andy’s Unusual Journey Survived 9/11 (was half a block from the South Tower), which prompted him and his wife to leave NYC and return to Milwaukee. First exit: Co-created the first municipal-bond primary-market pricing system in the 1990s (sold to a UK firm). Second exit: Founded Gear Wash, a firefighter-gear cleaning/disinfection company born from post-9/11 safety research (sold in 2020 right as COVID began). The Biggest Blind Spot for Business Owners Most owners are great at building the business but terrible at building a personal post-exit plan (financial, lifestyle, purpose). More than 50% have never calculated how much capital they actually need to replace their salary with passive income or what they’ll do with their time after the sale. What Actually Drives Enterprise Value & Exit Price The business must be transferable: owner must decentralize themselves (strong COO/GM, documented SOPs, job descriptions, integrated data systems). Lack of these = heavy valuation discounts during due diligence. Clean, real-time data and KPIs are non-negotiable in today’s market. Execution & Accountability Traction/EOS praised as a simple, proven system to create cadence and accountability. Without disciplined execution, enterprise value stalls regardless of a great product. Exit Planning Framework Andy Uses Certified Exit Planning Advisor (CEPA) via the Exit Planning Institute. “Value Acceleration Methodology”: Start with a rough valuation → align personal + financial + business plans → de-risk and grow → decide whether to exit or keep growing. Personal Advice from Andy Start entrepreneurial ventures earlier if possible. Understand compounding: save and invest early, take calculated risks. Prioritize health (he works out 6 days a week) and social connections (he jokes about starting a “ROMEO Club” – Retired Old Men Eating Out – when he retires).
#77
September 4 · 23 min
Wealthyist E75: Comfort With a Bit of Chaos: Why the Wealthy Are Trading Beach Resorts for Culture, Adventure, and One Night as a Local with Matt Reimer
On this week's Wealthyist, Tom Parks of Annex Wealth Management talks with Matt Reimer, U.S. director of Nerpa Travel, about how high earners can use travel as more than a reward or a padded escape. Nerpa is named after the freshwater seal of Russia’s Lake Baikal — a nod from Welsh founders Kevin and Tom (one of whom is married to a Russian). The company sells small-group trips that keep luxury lodging and logistics but add cultural immersion and “a bit of chaos.” Their tagline is comfort with adventure: nice beds, airport pickups, and planned days, plus at least one “one night local” experience so guests stop being visitors and start participating — Muay Thai and match betting in Thailand, for example.Reimer’s own path is the episode’s origin story. After years in retirement plans, he joined a seven-day, 230-mile mountain-bike trip in Wales run by Nerpa’s founders, then cashed out of his firm. He’d already done the five-star island circuit. What he wanted next was disconnection, physical effort, and a different way of seeing the world.The pitch to wealthy travelers is specific. Insulation and convenience make it too easy to open a laptop on the beach. Nerpa’s clients have often “been everywhere” and still feel like tourists. The company scouts every route itself (a “recce”), cuts the AI-famous time-wasters, and builds guardrails: a core itinerary with some daily options, groups of about 10–15, evenings together, Wi-Fi at the hotel if work can’t wait. Typical trips run about ten days, planned 18 months out so busy people can block the calendar.Status fades fast. Poor connectivity and long days outside produce an adjustment, then calm. Reimer argues that kind of “good suffering” — plus seeing how other cultures work and play — helps people think differently about stuck business and life problems. Small groups also become unexpectedly useful networks.Nerpa has three tiers: Bespoke: custom family or friend trips after a full scout, with honest pushback on weak ideas. One Night Local (the mid-tier sweet spot for executives): luxury plus one deep local night. Adventure-first (e.g., Lost in Vietnam on electric motorcycles): more freedom, slightly less polish, often a younger or more affordable crowd. Geography is expanding from a UK and Asia base toward Africa (a planned slow electric-motorcycle ride) and eventually South America. The advice isn’t “never do the beach or the cruise.” It’s: do those if you love them — and also design the second half of life around trips that take decisions off your plate, put you in the culture, and leave room to come back changed.Find Nerpa at nerpatravel.com, on X and Instagram, or Reimer on LinkedIn.
#76
August 31 · 34 min
Wealthyist E75: From One Truck To Gen Two: Building a Life—and a Business—Outdoors with Bret Achtenhagen
Kent Halleen, wealth manager for Annex Private Client, sits down with Bret Achtenhagen, president and CEO of Seasonal Services, the Wisconsin landscaping firm he launched in 1994 with a truck, a tractor, and a newly announced first child on the way. Brett walks through that first $70,000 year, the farm-kid love of dirt and seasons that pulled him out of an office, and 32 years of steady growth built on natural stone, time in clients’ kitchens, and outdoor spaces people actually use. The conversation turns to the harder work now underway: shifting from founder to second generation as his 31-year-old son begins to take over—what the next generation wants the company to become, and how to pass a family business without breaking the family. Halleen draws the parallel to wealth planning: tax, gifting versus buyouts, estate design, and the cost of leaving concentrated “plants” unpruned. Along the way they cover the firm’s process (motivation first, then design and budget), decades-long client relationships that now include the kids’ homes, and current high-end demand—wellness courtyards, year-round pavilions, and synthetic turf that still serves a deeper brief: get families off screens and back outside.
#75
August 21 · 33 min
Wealthyist E74: Not All Money Is Good Money: Building Athlete Brands, Protecting NIL Deals & Planning Beyond the Game with Griselda Aldrete
In this episode of Wealthyist, host Deanne Phillips talks with Griselda Aldrete, founder and CEO of Star Sports Consulting Group and Andretti Law and Consulting. Aldrete’s work sits at the intersection of law, business, athletics, and family advising, helping high-school, collegiate, and professional athletes (and their parents) navigate the modern sports landscape.The conversation centers on how athletes have become entrepreneurs and brands far earlier than in the past—especially after the landmark House case opened the door to Name, Image, and Likeness (NIL) compensation. ldrete describes the “Wild West” reality of NIL: inconsistent state reporting rules, multi-state tax obligations, the student-vs-employee debate, and the flood of opportunistic or poorly advised deals. She stresses that “not all money is good money,” urging families to scrutinize contracts (including perpetual clauses), protect intellectual property and online presence (with AI now a new risk), and treat the athlete’s name and image as long-term assets. Key themes include: Starting conversations as early as age 8–12 while carefully balancing genuine athlete passion against parental dreams and avoiding burnout. Building a full support “house” (lawyer, financial advisor, marketing/PR, CPA) rather than relying on a single agent or handshake deals. Cultural and practical barriers to financial literacy—especially in minority communities—where sudden income can trigger family obligations, overspending, or risky behaviors. The critical backup plan of finishing education and developing life-after-sports skills, given that fewer than 1% of athletes go pro. Practical red flags and best practices for contracts, brand curation, and long-term wealth building versus short-term income. Aldrete’s closing advice to parents of a talented 16- or 17-year-old: ask where the athlete wants to be in five years and prepare the safest physical, mental, and financial path there; avoid chasing only the glitz without first getting the “house in order.”
#74
August 14 · 35 min
Wealthyist E73: From Shop Floor Grind to Functional Edge: How Health Supercharges Entrepreneurial Success with Mike Chirchirillo
On this episode of Wealthyist, host Anthony Mlachnik (senior wealth advisor) sits down with Mike Chirchirillo—certified trainer, functional medicine health coach, co-owner of Collective Flow Milwaukee, and manufacturing consultant—for a conversation that bridges business performance and personal vitality.Mike traces his path from joining a family metal-stamping and sheet-metal fabrication business in Illinois in 2008, just as the recession hit. With ~80% of revenue tied to automotive and heavy customer concentration, he worked his way up from the shop floor: implementing an ERP system for better cost accounting and decision-making, overseeing a full facility move, and eventually becoming president and director of sales. Over 3.5 years he successfully diversified the customer base, but the relentless grind left his energy and health depleted.That personal toll, combined with his wife’s long battle with ulcerative colitis (she was on a cascade of medications), led them to functional medicine. Through holistic changes in sleep, nutrition, stress management, and movement—inspired in part by approaches like those of Dr. Mark Hyman—she became symptom- and medication-free in about 2.5 years. Mike trained in the field himself, extracting practical “biohacks” he could apply as an entrepreneur for better energy, clarity, focus, and recovery. He now helps small-to-midsize manufacturing owners and high performers reduce “inflammation” in both body/brain and business, arguing that the two are deeply linked: when leaders and teams lack motivation, consistency, or resilience, health issues are often a root cause.He outlines five key lifestyle pillars that drive inflammation (and thus performance): Fitness Movement/flexibility (joint range of motion) Sleep quality (not just quantity) Stress management (breathwork, flow states) Nutrition (whole, “Mother Earth” foods) For time-poor, high-means individuals, he prioritizes nutrition as the highest-leverage starting point—aim for the colors of the rainbow plus 9–13 servings of fruits and vegetables daily, plus hydration at roughly half your body weight in ounces of water. Sleep ranks close behind. Practical hacks include: Consistent bedtime and a wind-down routine (dim lights, warm tea, bed only for sleep/sex) Morning glass of water with lemon and a pinch of Himalayan sea salt Brief balance work (standing on one foot during calls or in line) 4-minute Tabata bodyweight sessions when time is tight Breath techniques (longer exhales to calm; longer inhales to energize) Timing sleep in ~90-minute cycles so you wake at the top of a cycle rather than deep sleep Mike runs two complementary businesses: consulting that primarily helps manufacturing companies (with health tools brought in as needed when focus or execution lags) and Collective Flow, a yoga studio with a functional-medicine twist that has grown to 17 instructors. He emphasizes that health is highly individual, that lasting change follows an “aware → explore → apply” loop, and that external accountability is especially powerful for CEOs who are used to holding others accountable but rarely themselves. He also advises treating social-media comparison or guilt as a “bat signal” for constructive action rather than a spiral into negativity.The discussion closes with how high achievers differ from the merely wealthy: true high performers build financial success on their own terms—with balance, relationships, energy, and a life they actually enjoy—rather than grinding at the expense of everything else. Listeners can find Mike at mikechirch.com and Collective Flow at collectiveflowmk.com.
#73
August 4 · 16 min
Wealthyist E72 | ESOPs: The Quiet Path from Company Stock to Wealth (and How to Keep the IRS from Taking Too Much)
In this episode of Wealthyist, financial planning manager Tom Berkholtz sits down with senior wealth strategist Brian Lamborne of Annex Private Client to demystify Employee Stock Ownership Plans (ESOPs) What an ESOP really isAn ESOP lets a business owner sell the company to its employees. Employees rarely have cash to buy it outright, so a trust/fund is created that purchases the owner’s stock. Over time, shares are allocated to workers. For the seller, this can mean a large liquidity event (e.g., tens of millions of dollars) that requires careful planning. For employees, it functions much like a 401(k): it is ERISA-governed, tax-deferred, and funded primarily by employer contributions of company stock—no employee contributions required. Shares vest over time, and the stock of private companies is independently valued each year. Real-world impactFamiliar employee-owned companies such as Wisconsin’s Woodman’s, Hy-Vee, and Publix illustrate the upside. Long-tenured cashiers and other rank-and-file workers have walked into Annex with ESOP balances exceeding $1 million—and sometimes several million—after decades of steady contributions and company growth. These “secret millionaires next door” often never attended college yet built substantial wealth simply by staying and performing well. Key features and rules Concentration risk: Most of the account sits in employer stock while you work there. Diversification window: Once you reach age 55 and have 10 years of service, you can diversify up to 25% of the company stock over five years, then up to 50% in the sixth year—tax-free, just like selling inside a 401(k). Retirement liquidity: When you leave or retire (and are vested), the company typically buys back your shares, giving you cash that can be rolled into an IRA. Tax time bomb: The balance is pre-tax. Large accounts can produce very high Required Minimum Distributions (RMDs) starting at age 75 and push retirees into top tax brackets—especially if both spouses have sizable ESOPs. Planning opportunities The roughly 15–20-year window between the diversification age (55) and RMD age (75) is critical. Strategies discussed include: Gradually diversifying out of concentrated company stock Incremental Roth conversions in lower tax brackets over many years Qualified Charitable Distributions (QCDs) starting at age 70½—direct transfers from the IRA to 501(c)(3) charities (including churches) that never hit taxable income and can be split among multiple organizations Bottom line ESOPs are simultaneously simple in concept and highly complex in the details—every plan has its own documents and quirks. Employees should not wait until the “retirement red zone” (within five years of leaving) to understand vesting, diversification rights, buy-back rules, and tax consequences. Working with advisors who grasp both the plan mechanics and broader retirement-tax planning can turn a multi-million-dollar ESOP into lasting, tax-efficient wealth rather than a deferred tax surprise.
#72
July 27 · 20 min
Wealthyist E71 | RSUs Unlocked: How Restricted Stock Units Can Create Wealth
In this episode of Wealthyist, host Brian Lamborne (Senior Wealth Wtrategist) sits down with Tom Berkholtz (Manager of Financial Planning at Annex Wealth Management) for a clear, practical breakdown of restricted stock units (RSUs)—one of the most common forms of equity compensation. They start by defining RSUs as a company grant (a promise of stock value) that vests over time, aligning employee and employer incentives while helping attract and retain talent at competitive firms (especially tech giants). Vesting is typically graded (e.g., 25% per year) or cliff-style (all at once after a set period). Unlike cash pay, RSUs offer upside if the stock appreciates Key discussion points include: Equity compensation as part of a broader total-rewards package (beyond base salary). Real-world impact: Early-stage or high-growth company grants can create significant wealth (with SpaceX and Meta examples cited). Taxation: RSUs are taxed as ordinary income (plus FICA) at vesting based on fair market value and appear on the W-2. Later sales trigger capital gains/losses. Companies often withhold only a flat 22% federal rate, which can leave high earners under-withheld and facing big tax bills or penalties—making estimated payments or withholding adjustments important. Planning strategies: Projecting tax impact in advance, using charitable tools like donor-advised funds for appreciated shares (avoid capital gains, get a deduction, and reduce concentration risk), and overall diversification. Contrast with stock options (NSOs/ISOs): Options require the employee to exercise (buy at a set price), adding decision complexity and different tax rules, whereas RSUs simply deliver the shares upon vesting. Berkholtz and Lamborne emphasize that the terminology, tax rules, and decisions around equity compensation are complex and frequently overwhelm employees. They strongly recommend working with advisors experienced in this niche to organize grants, model scenarios, avoid “tax torpedoes,” and make informed choices rather than relying on gut feel.
#71
July 21 · 33 min
Wealthyist E70 | Heart, Wealth & Legacy: Tax-Smart Giving Strategies That Outlive You with Gunnar Crowell
In this episode of Wealthiest, host Anthony Mlachnik sits down with Gunnar Crowell, Senior Advisor of Charitable Estate Planning for the American Heart Association. Gunnar shares his journey from college football defensive lineman and practicing attorney to helping high-net-worth families create meaningful, tax-efficient legacies. The conversation dives deep into practical philanthropy: why health is the ultimate foundation of wealth, how personal experiences with heart disease fuel genuine giving, and the most powerful ways to give during life and at death. Gunnar breaks down proven strategies including Qualified Charitable Distributions from IRAs, gifting highly appreciated stock, Donor-Advised Funds (DAFs) for multi-generational giving, Charitable Remainder Trusts (using farmland and other illiquid assets), and when a private foundation makes sense.He also covers the latest changes from the “One Big Beautiful Bill,” including the new above-the-line charitable deduction for non-itemizers and updated limits for high earners. Listeners will walk away with actionable ideas for turning assets like real estate, business interests, and retirement accounts into lasting impact while reducing taxes and involving children and grandchildren in a culture of giving.Whether you’re planning your estate or simply want to align your wealth with purpose, this episode delivers clear, advisor-friendly insights on building a legacy that matters — especially for those passionate about fighting heart disease and stroke.
#70
July 10 · 24 min
Wealthyist E69 | Luxury Homes That Live Well: Kitchens, Wellness Suites & Future-Proof Design for the Wealthy with Amber Kolacki-Hake
In this episode of Wealthyist, host Austin Grandinetti sits down with Amber Kolacki-Hake, designer at Wise Design Builders, to explore how affluent homeowners in the Lake Country area (and beyond) are thoughtfully redesigning their homes to match evolving lifestyles. Key highlights include: The rise of multi-zone kitchens — entertainment/show kitchens with clean, streamlined islands for gathering, paired with hidden “dirty” working kitchens for serious cooking and prep, plus dedicated walk-in pantries. Wellness-focused spaces — spa-like primary bathrooms and dedicated wellness suites featuring steam showers, multi-sensory experiences, hot/cold therapy, and calming retreats. Future-proofing & aging in place — wider doorways, barrier-free showers, lever handles, drawers instead of cabinets, and holistic planning that considers resale value versus “forever home” needs. Four-season living — enclosed four-season rooms and lower-level remodels to maximize Wisconsin’s seasons. Smart, timeless technology — layered lighting controls (Lutron Caseta/RadioRA), scene settings, and flexible systems that avoid fast-outdated tech. Design philosophy — a holistic, “begin with the end in mind” approach that mirrors financial planning: long-term vision, master planning, education, and avoiding unnecessary spending or trendy mistakes. The conversation draws clear parallels between strategic home design and wealth management — both emphasize clarity on goals, future needs, and building something that truly supports your desired lifestyle for decades to come.
#69
June 26 · 23 min
Wealthyist Replay| Passion Assets: Turning Your Treasures (and Pets!) into Lasting Legacies – Don't Let Love Become a Burden
The episode of Wealthyist (the podcast exploring the lifestyles, choices, and strategies of the wealthy, produced by Annex Wealth Management) features host Tom Parks, Director of Retirement Plan Services, interviewing his colleague Deanne Phillips, Managing Director of Client and Community Engagement. The focus is on "passion assets"—personal items acquired out of genuine love and passion rather than primarily as investments, which often lack formal beneficiary designations unlike financial accounts. Key Points from the Discussion: Definition: Passion assets include art, classic cars, wine collections, musical instruments, rare books, watches, sports memorabilia, jewelry, and even pets (highlighted as America's favorite, with Americans spending over $140 billion annually on them). These can represent significant value (hundreds of thousands of dollars) in high-net-worth households but are frequently overlooked in estate planning. Why They're Overlooked: Unlike retirement or brokerage accounts with built-in beneficiary forms and professional management, passion assets are often stored informally (basements, attics, wine cellars). Heirs may not know their worth, leading to hasty disposal ("haul it all away") or emotional oversights. Real-World Examples: Deanne shares a personal story of inheriting a hoarded family home filled with hidden treasures like over 100 pieces of Cristal d'Arques and Orrefors crystal, vintage fabrics concealing a pristine 1940s Deanna Durbin doll, old slides, and more. Surprises can include vintage electronics (e.g., original Apple computers or iPods), comic books, first-edition books, mid-century furniture, early Rolex watches, or even flip phones amid modern trends. Planning Importance — Three main reasons for valuation and documentation: Insurance: Standard homeowners policies often fall short; specialized riders or coverage are needed, especially for older/antique items. Estate Planning: Prevents family disputes over unequal values (e.g., one child getting a high-value painting) and ensures fair division. Taxes: Collectibles face higher capital gains rates upon sale; appraisals help with accurate reporting. Preservation Tips: Protect items from damage (e.g., temperature-controlled wine storage, UV/humidity control for art, regular servicing for watches/cars, archival methods for paper ephemera like Civil War letters). Before donating or discarding anything 30–40+ years old, consult appraisers or experts—markets are cyclical and surprising. Pets as Passion Assets: A major focus, given generational pet ownership trends (e.g., 76% of millennials). If a pet outlives the owner (e.g., parrots or tortoises), plan for care. Pet trusts (recognized in all states, though provisions vary) allocate funds for a designated caregiver, specify care standards/vet/groomer, and name a contingent beneficiary (e.g., charity) for remaining funds after the pet's life. Famous example: Leona Helmsley's trust for her dog (reduced by courts but spotlighted the concept). Actionable Steps (Deanne's five key recommendations): Take inventory (use video for ease). Photograph/document everything. Get appraisals (update every few years as markets shift). Ensure proper insurance coverage. Communicate with heirs (e.g., confirm they're willing/able to care for a pet or want specific items). Final Takeaway: Passion assets enrich life, but without planning, they can burden the next generation. Proactive steps turn them into meaningful legacies rather than problems.
#68
June 19 · 29 min
Wealthyist E68 | Roots of Wealth: Mastering Tree Care for Luxury Estates with Third-Gen Arborist Freddie Hoppe
In this episode of Wealthyist, host Kent Halleen sits down with Freddie Hoppe, co-owner and sales manager of Hoppe Tree Service and a third-generation arborist whose family business dates back to 1972. They explore how professional tree care and landscape management serve as essential services for high-net-worth properties and estates, where owners often invest six figures annually in maintenance to preserve beauty, safety, and value. Freddie explains that successful tree care begins with clients who genuinely care about their trees—whether a single specimen in a modest yard or hundreds on sprawling estates. The conversation covers: Customized maintenance programs — Starting with detailed inventories, assessing tree species, site conditions, insect/disease risks, and client priorities. Services include targeted treatments (insecticides, fungicides), soil amendments, root invigoration, and precise pruning—often treating legacy trees (like a 200+ year-old burr oak) with “full-size bonsai” attention. The science and benefits of trees — Ecological advantages, boosted property values, reduced crime, and improved human health in greener areas. Trees become assets rather than liabilities when properly managed. Practical estate strategies — Balancing manicured lawns with tree health through mulch rings, soil injection, and mimicking natural forest floors. Freddie emphasizes prevention over reaction, noting that healthy trees better withstand storms, climate fluctuations, and pests like emerald ash borer. Trends and future outlook — Shifting toward planting “better” (larger, longer-lived) trees, adapting to climate change and moving hardiness zones, and managing invasives like buckthorn. He highlights the resilience of underappreciated species like box elders and willows. Risk management and business advice — Annual inspections are crucial. For listeners seeking similar premium service, he recommends companies with certified arborists on staff and Tree Care Industry Association (TCIA) accreditation. The episode blends practical arboriculture insights with a philosophical appreciation for trees as living legacies. Freddie stresses Hoppe Tree Service’s mission: caring for people first, then their trees—turning potential burdens into long-term assets through proactive, tailored programs.
#67
June 12 · 24 min
Wealthyist E67 | Your Business's 401(k): A Strategic Tool To Attract & Retain Employees
In this episode of Wealthyist, host Greg Batiansila sits down with Tom Parks, Director of Retirement Plan Services at Annex Wealth Management. Tom leads Annex’s 401(k) advisory team and brings over 25 years of experience helping business owners optimize their retirement plans. The conversation challenges the common view of 401(k) plans as just another compliance checkbox or “fine for now” employee benefit. Instead, Tom reframes them as a strategic tool that can reduce employee financial stress, improve company culture, boost productivity, aid retention, and even support long-term business value. Key points discussed include: What Annex’s 401(k) team actually does: They act as advisors and consultants (not recordkeepers). They work with both business owners/plan fiduciaries and employees to make plans more effective. The shift in employee expectations: Today’s workforce looks at total compensation — including benefits and financial wellness — not just salary. An effective 401(k) is now part of what attracts and keeps talent. Common problems Tom sees when reviewing existing plans: Outdated investment lineups, high or inefficient fees, low participation rates, lack of automatic enrollment features, and employees who don’t even know who their plan advisor is. Modern solutions: Greater use of lower-cost Collective Investment Trusts (CITs), automatic enrollment, and better plan design — changes that many advisors are (or should be) recommending. The bigger picture — financial wellness: Annex goes beyond investments by providing ongoing education through videos, webinars, one-on-one meetings, and creative communications. This helps reduce the real financial stress employees feel (a major driver of burnout and lost productivity). Impact on business owners: While there isn’t always a direct line item on a balance sheet, improving a 401(k) plan can positively affect company culture, employee engagement, and even the intrinsic value of the business over time. Practical next steps: Business owners don’t always need to move their entire plan. Often, the first step is simply having Annex review the current plan to see what can be improved where it already sits. Tom emphasizes that a well-run 401(k) isn’t just good for employees — it’s good for the business owner who wants a more focused, less financially stressed, and more aligned team. Overall takeaway: If your 401(k) plan was set up years ago and hasn’t been reviewed since, you’re likely leaving both money and morale on the table. A thoughtful, well-communicated retirement plan can become a genuine competitive advantage.
#66
June 5 · 32 min
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.
#65
May 29 · 17 min
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.
#61
May 15 · 48 min
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.
#64
May 8 · 28 min
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.
#63
May 1 · 22 min
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.
#62
April 22 · 38 min
Wealthyist E60 | Philanthropy From The Heart: How Ultra-Wealthy Donors Turn Simple Giving Into Transformation with Joan Nesbitt
In this engaging episode of Wealthyist, host Anthony Mlachnik (Senior Wealth Advisor at Annex Private Client) sits down with Joan Nesbitt, Vice Chancellor for University Advancement at the University of Wisconsin-Milwaukee (UWM). With over 30 years in higher education fundraising—including more than a decade in a similar role at Missouri S&T—Nesbitt shares insights from the front lines of partnering with ultra-high-net-worth individuals, families, and philanthropists to create lasting impact through education. The conversation opens with Nesbitt's journey from Oklahoma roots (complete with a relaxed attitude toward Midwest tornado warnings and tennis during sirens) through Missouri to her current role in Wisconsin. She reflects on her accidental entry into fundraising in the 1980s and the shift from smaller nonprofits to better-resourced higher ed environments. Key topics include: Evolving donor strategies: Most annual gifts still come simply as checks or credit cards from income, but high-capacity donors leverage sophisticated vehicles like stock donations, charitable remainder trusts, donor-advised funds, and planned/legacy giving tied to life events (e.g., business sales, liquidity events, or RMDs). Shifting alumni engagement: The old assumption of natural alumni loyalty has faded, especially among younger graduates burdened by student debt. Millennials and Gen Z prioritize broad societal impact, justice, and fairness over "helping someone just like me." Nesbitt discusses how UWM is adapting with personalized digital strategies and even piloting AI-driven platforms for scalable, avatar-based donor engagement (surprisingly appealing to those over 50). The power of storytelling and experiences: Annual galas, alumni awards, and heartfelt reflections highlight how connections—with professors, mentors, dorm friends, or campus moments—create enduring emotional ties. Donors often express genuine humility and surprise when recognized. Major gifts and ultra-wealthy mindsets: Nesbitt recounts standout stories, including a record-breaking $300 million gift (in ETFs) from a billionaire engineer who wanted transformative impact beyond "just a building." She emphasizes holistic donors who blend cash, time, volunteering, corporate resources, and networks. Even during UWM's 414 Day giving campaign, a major donor made seven targeted gifts across challenges, showing deep alignment with personal values. Sports, NIL, and the "front porch" of the university: Athletics draws attention and enrollment for many schools, but Nesbitt notes it varies by institution (less central at her prior engineering-focused school). She stresses operating with integrity amid the "Wild West" of NIL, keeping student-athlete education and experience first while collaborating across advancement and athletics. Personalization as the secret sauce: Whether for philanthropy or wealth management, success comes from understanding individual goals, values, and passions. Sophisticated donors leverage giving to amplify networks, teach family members, and create community connections—much like high-net-worth clients intentionally align time, relationships, and resources. Nesbitt closes by inviting listeners to explore UWM's role as a community-engaged institution (recognized by the Carnegie Foundation) that transforms potential into opportunity through education, workforce development, and public events. The episode offers wealthy listeners practical takeaways on intentional philanthropy, legacy planning, and building meaningful impact—while drawing thoughtful parallels to personalized wealth strategies. It's a warm, insightful look at how ultra-wealthy families turn resources into societal transformation, with a forward-looking nod to AI's role in advancement. A great listen for anyone interested in higher ed giving, donor psychology, or blending personal values with strategic generosity.
#60
April 10 · 22 min
Wealthyist E59: Private Jets Without Owning the Plane: How Jet OUT’s Co-Ownership Reclaims Time for the Wealthy
In this remote episode of Wealthyist, recorded live from Jet OUT’s new hangar in Waukesha, Wisconsin, host Anthony Mlachnik (Senior Wealth Advisor at Annex Private Client) sits down with Evan Rossiter, Sales Director at Jet OUT — a Milwaukee-based private aviation company. Evan clearly explains Jet OUT’s co-ownership model: it’s not traditional fractional ownership (like NetJets), not a jet card, and not aircraft management. Instead, it’s structured like tenant-in-common real estate — multiple co-owners share one Cessna Citation CJ4 Gen2 jet, but Jet OUT owns and operates the entire fleet. Co-owners simply call and fly. JETOUT handles all maintenance, piloting, flight planning, and heavy lifting. Key highlights include: Strategic expansion — Bases in Milwaukee, Southwest & East Florida, Scottsdale, and Dallas (with 6 more CJ4s arriving in 2026, bringing the fleet to ~16 aircraft). The efficiency niche — Matching co-owners flying the same day or opposite directions (especially Midwest-to-Florida runs), which reduces costs and boosts utilization. Time as the ultimate luxury — Dramatic contrast vs. commercial travel: 15-minute airport arrivals, no TSA, direct flights to smaller airports, and multi-stop business days that let executives be home for dinner. Real-world use cases — Business owners hitting 3–4 cities in one day; families reaching second homes in Florida or Arizona; even light-hearted stories like flying pets solo. Entry points — Ideal for 4–5+ round trips per year; a shorter “dip-your-toe” one-year program is also available. Community & lifestyle angle — Like-minded co-owners often connect (when desired), and different paint schemes on each jet preserve anonymity. Future outlook — Continued growth in private aviation driven by commercial frustrations post-COVID and TSA issues; possible larger aircraft coming. Anthony ties the conversation back to wealth management: how high-net-worth clients are “time poor,” and how strategic choices like smart private aviation can protect family time, reduce stress, and align with values — exactly the kind of lifestyle optimization Wealthyist explores.

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