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.

  1. 6h ago

    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 organizationsBottom 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.

  2. Jul 27

    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 appreciatesKey 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.

  3. Jul 21

    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.

  4. Jul 10

    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.

  5. Jun 26

    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.

  6. Jun 19

    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.

  7. Jun 12

    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.

  8. Jun 5

    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.

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About

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.

Information

  • Creator
    Annex Wealth Management
  • Years Active
    2026
  • Episodes
    73
  • Rating
    Clean
  • Copyright
    © 2026 Annex Wealth Management