Wealthyist

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 & AccountabilityTraction/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 AndyStart 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).

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.

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.

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.” 

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 sleepMike 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.

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 rulesConcentration 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 opportunitiesThe 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 lineESOPs 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.

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.

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.

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.

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.

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.

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.

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.

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)sChecking 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 MuchEven 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 MistakesFailure 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 BeneficiaryEspecially 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 protectionProfessional management for beneficiaries who can’t handle money wellThis decision is highly personal and should be coordinated with an attorney.Disclaiming (Refusing) an InheritanceYou 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 PracticesEnsure 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 LineBrian 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.

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.

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 & AdviceWhy 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.

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 failureWhy the right people always matter more than perfect processesThe challenge high-achievers face when transitioning out of high-intensity careers — and how the drive never really turns offCurrent 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.

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.

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.

In this episode of Wealthyist, host Anthony Mlachnik interviews Jim Villa, CEO of NAIOP Wisconsin (the Commercial Real Estate Development Association). With 35 years in public policy, politics, and economic development—including roles under Governor Tommy Thompson and Scott Walker—Villa offers a grounded, insider perspective on commercial real estate as a vehicle for wealth creation and community impact.Key Highlights:Jim’s Background & NAIOP’s Mission: Villa leads efforts focused on public policy advocacy and developing the next generation of leaders (under 35). He stresses that "policy matters"—tracking local and state policies gives better market insight than national headlines.Core Challenges in Commercial Real Estate: Talent/people shortages remain the #1 issue, ahead of financing and permitting. Long-term strategies are essential to weather economic cycles.Office Sector Trends: Post-COVID hybrid work (accelerated but not created by the pandemic) continues. Demand persists for Class A spaces with premium amenities, technology, huddle areas, and “Starbucks-like” environments in vibrant locations. Downtown Milwaukee (e.g., BMO Tower) is strong; suburban markets are rebounding. Conversions and rehabs are more common than new builds.Multifamily & Housing: High-end luxury apartments in Milwaukee are filling slowly due to conservative absorption rates. Major shortage of workforce housing (for teachers, firefighters, service workers) amid high construction costs. Wisconsin saw some of the nation’s steepest rent/housing price spikes but remains more affordable overall than coastal markets.Investment Appeal of Wisconsin/Midwest: Viewed as a stable, “durable,” and good-value tertiary market. Less volatile than Sunbelt hotspots like Texas. Strong local investor participation, cautious development practices, and tangible community impact make it attractive for long-term holds. Post-COVID, some coastal capital has shown interest due to affordability and consistency.Strategies for Wealthy Investors:Diversification alongside other assets.Tax tools like 1031 exchanges, Opportunity Zones, and bonus depreciation (strengthened in recent legislation).ESG/impact focus: Local developers often deliver community benefits (childcare, retail, neighborhood revitalization) beyond pure financial returns.Partner with trusted local professionals and align with overall tax/estate plans.Future Outlook: AI-driven demand for data centers and energy generation will be critical. Wisconsin’s reliable power is a competitive advantage. Emphasis on creating “places” not just “spaces,” legacy-building, and balancing innovation (e.g., tech in buildings) with practical needs.Villa portrays commercial real estate as more than an asset class—it’s economic development that creates jobs, shapes communities, and builds lasting generational wealth when approached thoughtfully with the right team and long-term mindset. The episode is especially relevant for Midwest investors who prefer tangible, drive-by assets and balanced portfolios.

In this episode of Wealthyist, host Anthony Mlachnik(senior wealth advisor at Annex Private Client) interviews Dr. Tim Murray, an anesthesiologist and founder/CEO of Solstice Health. Murray launched the company in 2012 after witnessing pricing practices in traditional hospital systems, noting that medical bills remain the #1 cause of bankruptcy.Core Business Model:Solstice Health combines Direct Primary Care (DPC) with direct surgical care under one umbrella — a rare (and possibly unique) setup in the U.S. Patients pay a flat $59/month for unlimited primary care access (24/7, no copays, longer visits), plus labs, imaging, and medications at true wholesale cost. They also operate an ambulatory surgery center, delivering procedures like hip replacements for ~$19,500 all-in — compared to $60,000–$100,000 at traditional hospitals.Key Themes & Insights:Education is everything. Most people (and many business owners) don’t understand the difference between insurance (financial risk protection) and healthcare itself. Murray emphasizes transparency and fiduciary responsibility for self-funded employers.Why people resist change: Comfort with the status quo ("just hand over the insurance card") and lack of price visibility.Incentives matter. In DPC, providers have smaller patient panels (600–800 vs. 2,000–4,000), giving them time for real care, prevention, and even "deprescribing" medications (e.g., removing statins or metformin after lifestyle changes, especially through their medically supervised weight loss program targeting the obesity epidemic).Physician challenges: Many doctors fear leaving hospital systems due to non-competes, loss of benefits, or business unfamiliarity. Hospital lobbies exert heavy control (e.g., ACA restrictions on physician-owned hospitals).Wellness & holistic approach: Strong focus on lifestyle, nutrition (critiquing the modern food system’s sugar overload), functional medicine, IV therapy, and keeping people healthy rather than just treating sickness. Incentives in DPC align with prevention, not volume.Time savings: Huge reductions in employee absenteeism, no more wasted time on unnecessary urgent care/pharmacy runs, and more remote care options — freeing up time for family, work, and life.Wealthy trends: Concierge medicine pioneered premium direct access for the rich; DPC democratizes that model at a fraction of the cost while delivering "executive physical" level attention to everyday patients and employees.Closing Takeaways:The conversation highlights a holistic view of wealth — financial health alone isn’t enough without physical and mental well-being. Dr. Murray and Anthony both stress integrated wellness, time efficiency, and proactive decision-making for business owners, leaders, and families. Solstice positions itself as a transparent, competition-driven alternative that can dramatically lower costs while improving care quality and doctor/patient satisfaction.Overall, the episode serves as both an inspiring entrepreneurial story and a practical call-to-action for business owners and individuals frustrated with rising healthcare costs: question the system, seek transparency, and explore direct care models that realign incentives toward better health and lower spending.

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.

Host Anthony Mlachnik, Senior Wealth Advisor at Annex Private Client, interviews Rich Gray, founder of Rebrand NY—a sports and business development firm that connects brands with athletes for authentic marketing partnerships, while helping athletes (current, NIL-eligible, and retired) maximize their personal brands, off-field ventures, and long-term opportunities.Key Discussion Points:Rich's Background: Born on Chicago's South Side, basketball opened doors (first flight for a game, college at Chicago State). Post-playing, early internships with Chicago Sky exposed him to NBA stars/recruits. A pivotal chat with Hank Thomas (Octagon/Kesmai) inspired his shift to sports business. He earned a law degree (Washburn University, with time at KU), interned at Priority Sports, then joined Brooklyn Nets front office via connections. This led to his current role bridging sports, law, and brand strategy.When Athletes Become Brands: Historically, marquee college players; now, elite high school freshmen/sophomores must think this way due to NIL. Protection (legal/IP) and marketing start early.What Brands Seek in Athletes:Authenticity above all—no forced narratives. Brands want athletes whose values/lifestyle already align (e.g., health-focused athlete for nutrition brand). High performance + genuine fit creates believable stories and consumer trust. Data (social following, virality) helps, but behavior/nuance matters long-term.Cash vs. Equity in Deals: Assess brand stage—startups/white-space opportunities favor equity for massive upside (e.g., Kobe Bryant's BodyArmor investment turned a challenger into a competitor vs. Gatorade). Balance immediate cash needs with potential growth; value your time/input.Athlete Brand Value: Mix of tangible metrics (social followers, content performance) and behavioral alignment. Follow "the wealthy" (high-achievers) for strategies.Sustainable vs. Transactional Partnerships: Long-term storytelling (full lifecycle: college → pro → retirement) builds retention/value (e.g., trading card companies investing in NIL for ongoing narratives). Transactional = short-term flashes.Wellness/Mental Health Trends: Shift from taboo to open; brands now support holistic athlete health (mental, physical). Unions/retired players associations partner on lifecycle support. Some brands think long-term (today/tomorrow/future); others chase trends without red-flag awareness.Parallels to Wealth Management/Business Owners: Intentionality, values alignment, long-term planning mirror athlete branding. Athletes learn from business owners (strategic info use); vice versa. NIL democratizes opportunities—even mid-major/reserve players can build wealth thoughtfully.AI/Social Media & Rebrand's Focus: Keep IP relevant post-peak via targeted community engagement. Package legacy for businesses, nonprofits, etc. Maintain satisfaction beyond playing days.Emerging Sports: Women's volleyball exploding (e.g., daughters of NBA stars like Jermaine O'Neal, Kevin Garnett, Rajon Rondo). Dads apply pro experience to daughters' new landscape—unique mentorship, purpose, faster growth than early WNBA.Media Evolution (e.g., NBA): Shift toward centralized platforms (NBA app as hub, others as plug-ins). Testing phase; post-next TV deal, expect consolidated access.Player Empowerment: NBPA's evolution (e.g., Think450 marketing arm, player-led like Andre Iguodala) influences deals, including broadcasting rights—positive for athletes.The episode draws strong parallels between athlete career transitions/retirement and business sales/retirement planning—emphasizing intentionality, education, and long-term vision.

In this week's episode of Wealthyist, hosted by Anthony Mlachnik, Senior Wealth Advisor for Annex Private Client, Anthony and Rose Gray from Fox World Travel explore how the definition of luxury travel has evolved dramatically. No longer about the most extravagant, showy accommodations or vehicles to "make a statement," today's affluent travelers prioritize exceptional service, bespoke and unique itineraries, quality over quantity, and low-key, private experiences. They often keep trips understated—rooted in Midwest values of humility, family, and privacy—focusing on emotional impact (e.g., meaningful volunteer work or profound memories) rather than bragging rights.Rose shares her favorite continent is Africa (for its profound experiences), and she gently challenges the "visit all seven continents" goal by highlighting realities like Antarctica's challenges (e.g., penguin smells, zodiac landings without easy access).They address modern trends:AI in travel: Fox World Travel embraces it (with their own bot "Kobe the Cheese" for initial ideas/emails), but Rose stresses human expertise is essential—citing AI's hilarious errors (e.g., recommending a food bank as a top restaurant).Social media's double-edged sword: It amplifies misinformation (e.g., recent Puerto Vallarta shelter-in-place coverage portrayed as being "trapped," scaring people away from Mexico broadly), but Fox uses it to evoke emotion. Phones enable stunning photos (replacing bulky cameras), yet pose risks like location tagging aiding poachers in Africa or security vulnerabilities—advising delayed posting or turning off location services.Group vs. personalized travel: Rose explains how structured group trips (corporate incentives, family/multi-gen, or high-end adventures) provide "freedom within structure"—pre-planned logistics allow flexibility (e.g., skipping for ancestral visits). They balance large events with personalization by vetting partners deeply, understanding group dynamics, and incorporating individual needs.Core theme: The new pinnacle of luxury is ultimate, anticipatory service—beating clients to their needs, creating memorable "life moments" (parallels drawn to wealth management, where investment performance is table stakes, but holistic life support shines).Rose recounts a recent Puerto Vallarta trip disrupted by events, turning into a positive bonding experience with kindness and sharing among guests (mostly Canadians post-hockey game). They touch on private aviation (prices dropping, viable alternative to premium commercial), membership-style annual travel services (high-touch, family-like knowledge of clients), and preparations for remote/extreme trips (vetted partners, on-ground security intel, group compatibility).Destination highlights include:Corporate retreats: Costa Rica for adventure/team-building or Little Palm Island (Florida) for luxury.Family/multi-gen: Africa safaris for unforgettable impact.Romantic getaway: Ladera in St. Lucia (cave-like rooms with plunge pools, Michelin-level dining, ultimate relaxation).Advice for starting luxury travel: Allocate your budget intentionally (e.g., one blow-out trip vs. several solid ones, multi-gen vs. couple-focused, incorporating philanthropy/volunteerism for deeper fulfillment). Travel insurance (via partners like Travel Guard) is non-negotiable—offered every time, with clear explanations of coverage.The episode ties travel trends to broader wealthy lifestyles: emphasizing service, anticipation, emotional depth, risk management, and balancing opulence with purpose and giving back.

In this episode of Wealthyist, host Deanne Phillips, CFP® and Managing Director of Client and Community Engagement at Annex Wealth Management, interviews Dr. Suzanne Gehl (a board-certified family physician, former WAFP president, and owner of a solo Direct Primary Care practice in Hartford, Wisconsin.Dr. Gehl explains Direct Primary Care (DPC) as a membership-based model that provides unlimited access to a personal physician without insurance billing for primary care. Key features include:Ultra-accessible care: Same/next-day appointments (30–120+ minutes long), 24/7 direct phone/text/email response (often within hours), telemedicine, home visits, and no waiting rooms or phone trees.Cost savings: Covers unlimited visits, point-of-care testing (e.g., rapid strep, urine tests), drastically discounted labs (90–95% off), and low-cost generic meds (e.g., 3-month supplies under $3). No copays, deductibles, or markups.Patient experience: Direct doctor interaction from the start, comprehensive histories/exams, in-office procedures (e.g., joint injections, EKGs), and proactive management—catching issues like undiagnosed hypertension, thyroid problems, or even cancer early.Business/employer angle: Companies can cover memberships to slash group health costs (examples: 16–42% savings in first year, preventing job offshoring by reducing expenses). Employees gain easy access, leading to better preventive care and fewer ER/urgent care visits.Differences from alternatives: More affordable than concierge medicine ($2,700–$40,000+/year, often bills insurance); no middlemen, fancy lobbies, or large staffs—keeps overhead low.Medicare integration: Practices opt out of Medicare (no billing/reimbursement), but patients can use it for hospitalizations/specialists. DPC complements (doesn't replace) high-deductible or catastrophic insurance for major needs.Advanced tools: Dr. Gehl highlights innovations like multi-cancer early detection blood tests (e.g., Galleri), genetic longevity profiling (e.g., via GB Insights or New Amsterdam Genomics for personalized prevention, supplement/medication guidance), and virtual specialist consults—enabled by small patient panels (500–700 max) for deeper research and faster implementation.The discussion emphasizes DPC's growth since ~2010 (now ~9% of U.S. primary care docs), its efficiency for busy/high-net-worth individuals , and its wellness focus—promoting healthier lives, reduced overall healthcare spend, and better quality/quantity of life.Deanne ties it to strategic choices for the wealthy: using DPC as a smart, proactive complement to insurance for time savings, cost control, and superior outcomes. Listeners can find DPC providers via Mapper — Direct Primary Care | DPC Frontier.This episode positions DPC as an empowering lifestyle upgrade—restoring the doctor-patient relationship while aligning health with financial savvy. 

This week's episode of Wealthyist (the podcast exploring the lifestyles, choices, and strategies of the wealthy, produced by Annex Private Client/Annex Wealth Management) is hosted by Anthony Mlachnik, a senior wealth advisor. The guest is Brian Weis, a serial entrepreneur deeply passionate about golf. He runs multiple golf-related businesses, including GolfTrips.com (focused on golf travel), Golf Guide (product reviews), and Golf Community Living (highlighting golf-centric real estate and retirement living). He's also a board member of the Golf Course Owners of Wisconsin, and a dedicated golfer with a handicap that fluctuates between 3 and 12 (depending on whether he's betting or bragging).The conversation centers on the evolution of golf as a lifestyle and experience, particularly among affluent individuals, and how it ties into wealth, business, health, and social connections.Key Topics and Trends Discussed:Golf's Post-COVID Boom: Pre-COVID, golf was declining, but the pandemic highlighted it as a safe outdoor activity. Younger generations (30s–40s) with rising discretionary income have driven massive growth in golf travel and experiences, shifting from basic tee times to premium, immersive outings.Shift to High-End Experiences: Traditional "buddy trips" (cheap hotels, beer, cram in rounds) have evolved into luxury setups—resorts with on-site real estate, spacious homes/villas with grills, fire pits, and stocked bars. Golf now pairs with wellness (spas, unplugged time), culture (e.g., castle tours in Europe), food/wine, bourbon/cigar tastings, or events like the Super Bowl or Masters.Types of Golf Travelers:Bucket-listers chasing iconic courses (e.g., Pebble Beach, St. Andrews).Experiential groups seeking added activities.Couples blending golf with non-golf elements (spas, local sights); some spouses golf, others relax poolside/spa while the golfer sneaks in early rounds.Business and Networking Angle: Golf reveals character (handling adversity, positivity). It's a powerful tool for building relationships—better than short meetings. Many executives/entrepreneurs use it for prospecting or client entertainment. Professional athletes (e.g., Michael Jordan, Steph Curry, Aaron Rodgers) often excel at golf and cross-pollinate mindsets with business leaders.Trends in Memberships and Access:"Country club membership hoarders" collecting multiple private/national memberships for prestige, business, or vacation access.Corporate/national memberships at elite spots (e.g., Sand Valley's Lido).Shift from heavy discounting (pre-COVID) to willingness to pay for premium experiences.Luxury Travel Logistics: Helicopters/private jets for remote courses (especially in Scotland/Ireland to save time on narrow roads and fit more rounds). Transportation services (limos/buses) for groups to enjoy drinks safely.Wisconsin as a Golf Destination: Underrated no more—hosts top courses like Sand Valley (multiple), Kohler (Whistling Straits), Erin Hills (former U.S. Open site). It ranks high nationally (e.g., most in top 100 lists recently). Benefits local economy via packages, transport, beer/spirits (e.g., Spotted Cow), cheese curds/brats.Family and Inclusivity: Resorts add short/par-3 courses (e.g., Sand Valley's Sandbox) for beginners, kids, spouses. More family-friendly amenities beyond golf.Lodging Evolution: From cramped hotel rooms to spacious, configurable setups (private bedrooms/baths, common areas) to keep guests on-property and enhance revenue.Recommended Trips:International: Scotland (St. Andrews for history; Highlands/Edinburgh areas for variety) or Ireland.Domestic: Pinehurst (NC) or Pebble Beach (CA) for bucket-list appeal; strong praise for Wisconsin's concentration of elite courses.Modern Tech and Home Golf: Explosion in high-end home simulators (converting wine cellars/basements) using Trackman/software to virtually play bucket-list courses. Resorts/clubs add them for off-season or bad-weather play.Health and Longevity Benefits: Golf checks physical (walking, flexibility, strength for clubhead speed), mental (unplugging, focus), and social boxes. Ties into longevity—staying active into 80s/90s, modern training (stretching, dynamic warm-ups) mirroring pro athletes' approaches. Important for retirees/executives to maintain engagement post-career.Planning Modern Trips: Affluent golfers increasingly use golf tour operators for seamless experiences (beyond DIY tee times) to ensure smooth weekends.Brian directs listeners to GolfTrips.com for research, packages, and experiences (DIY-focused but featuring pro operators/resorts).The episode weaves golf passion with wealth themes—how high-net-worth individuals invest in experiences, relationships, health, and legacy through the game—while highlighting Brian's entrepreneurial journey in the space. 

In this episode of Wealthyist, host Anthony Mlachnik, a senior wealth advisor at Annex Wealth Management, sits down with Amanda Payne, President and CEO of the Waukesha County Business Alliance (the local Chamber of Commerce). The conversation explores why Waukesha County ranks among Wisconsin's wealthiest and the top 200 in the U.S., highlighting its appeal as a hub for business success, family life, and community vibrancy.Key highlights include:Attractions for the Wealthy: Amanda attributes the county's draw to a thriving business ecosystem, excellent schools, high quality of life, and family-friendly environment. As a fifth-generation Waukesha resident, she shares personal anecdotes, like her family's deep roots (e.g., her grandfather leading Waukesha Engine) and historical ties to local institutions like Carroll University.Economic Growth and Investments: The county saw a 35% surge in single-family housing permits in 2025, outpacing most areas except Dane County. Major corporate expansions were spotlighted, including GE Healthcare's $100M Waukesha campus upgrade, ABB's $100M New Berlin facility, Milwaukee Tool's $40M+ investments in Menomonee Falls and Brookfield, and Generac's new sites adding jobs. These reflect a booming economy, with biohealth emerging as a key cluster (boosted by Wisconsin's federal Biohealth Tech Hub designation and outpacing national job growth).Challenges and Trends: Discussions cover housing supply constraints (rising prices outstripping incomes), talent shortages for growing firms, and the appeal of short commutes compared to big cities like Chicago. Amanda notes the influx of high-net-worth individuals to areas like Lake Country, driven by proximity to Milwaukee's amenities (e.g., sports, arts). Future priorities include expanding I-94 to ease bottlenecks, reduce crashes, and support regional development, while maintaining small-town charm in places like Delafield.Small Businesses and Community Ecosystem: Over 90% of Waukesha businesses are small, forming the "heart and soul" of the county. Growth in larger firms fuels suppliers, restaurants, and shops, creating an interconnected ecosystem. Amanda emphasizes preserving this amid expansions from giants like Costco and Amazon.Workforce and Youth Engagement: Post-COVID shifts have aided talent attraction via remote work, low cost of living, and lifestyle perks (e.g., easy access to "up north" getaways). The Alliance runs programs exposing over 3,000 middle and high school students annually to local careers through tours, expos, and CEO interactions to foster retention and entrepreneurship.Community Leadership and Giving: Wealthy leaders excel by blending business success with philanthropy, board service, and employee support (e.g., helping with loans or cars). Programs like Leadership Waukesha County (30+ years running) build the next generation of civic-minded executives. Younger workers prioritize companies invested in community causes, as seen in initiatives like United Way campaigns.Wealth Transfer and Business Transitions: With a massive $70–120T U.S. wealth shift underway, Amanda stresses early planning for family-owned businesses (e.g., generational handoffs, ESOPs, private equity sales). Key is maintaining local involvement and community ties, especially as private equity from coasts enters for roll-ups. She sees rising interest among younger generations in buying/owning businesses, fueled by gig economy flexibility and entrepreneurial spirit.Differentiation and Collaboration: Waukesha stands out by prioritizing business growth, professional development, and regional partnerships (e.g., with Milwaukee 7). Anthony ties in Annex's fiduciary approach, emphasizing comprehensive client service aligned with community values.

In this engaging episode of Wealthyist, hosted by Anthony Mlachnik (Senior Wealth Advisor at Annex Private Client), he interviews Karissa Gretebeck, Manager of Volunteer Engagement at United Way in Greater Milwaukee and Waukesha County. With nearly 15 years at United Way, Karisa shares her journey from a small nonprofit to embracing the organization's global reach, brand strength, and collaborative impact in creating positive community change.The conversation centers on evolving philanthropy among wealthy individuals, families, and corporations. Key highlights include:A growing desire for hands-on involvement beyond financial donations—volunteering, personal engagement, and exposing children to giving back to build a family culture of philanthropy.United Way's shift toward targeted "key initiatives" (e.g., eliminating family homelessness, stable employment, technology access, and health/well-being), allowing donors to see direct, systemic impact rather than contributing to a general fund.Corporate partnerships remain a cornerstone, with tailored workplace campaigns, volunteer events, and creative activations (e.g., packing meals or backpacks during company conferences or celebrations). Examples include manufacturers donating overstock products and a shoe company leadership team personally fitting donated shoes at a homeless resource fair.The intangible benefits of giving: mood boosts, mental health gains, social connection, and modeling values for employees and children.Creative giving ideas, such as donating appreciated stock or using donor-advised funds for tax advantages, and rolling commissions into community foundations (as Anthony notes with Annex's approach).Opportunities for deeper involvement via leadership donor networks (e.g., Women United, Technology United, Leadership Society) for high-level givers ($1,200+ annually), offering social events, advocacy, and focused issue dives.Practical starting points: Reflect on personal passions, browse United Way's website for volunteer/advocacy options, and connect with resources or consultants for guidance.Karisa emphasizes that small commitments (even an hour a month) create ripple effects, and United Way excels at listening to align opportunities with personal/company values. Anthony ties it to broader wealth strategies, like tax-smart giving and leading by example.The episode closes with touching stories of impact—like a young girl joyfully choosing her own daisy-patterned backpack—illustrating how collective small actions transform lives and inspire ongoing generosity. It's an inspiring look at modern, multifaceted philanthropy that goes far beyond writing a check.

This episode focuses on the realities of selling a business, especially in the lower middle market (businesses under ~$200M in revenue). Here's a breakdown of the main points Steve covers:Role of an Investment Banker (Sell-Side): They guide owners through preparation and the structured sale process to maximize outcomes. The biggest "competitor" is often the owner trying to sell DIY—possible, but owners usually miss value-creating opportunities due to lack of specialized expertise.Preparation (Ideally 3–5 Years in Advance): Start early to boost value. Common issues include over-reliance on the owner (e.g., as top salesperson), weak teams/systems, or messy financials focused on tax minimization rather than showing true earnings power (EBITDA).EBITDA (Earnings Before Interest, Taxes, Depreciation, and Amortization) is the key metric buyers use as a proxy for cash flow.Adjust for owner perks/non-recurring items to reveal "true" earnings.Build transferable sales teams, pipelines, regional presence, clean books, accurate product costing, etc.Example: A client left money on the table by not expanding regionally; the buyer did it post-sale and doubled the company.Valuation Basics: Often an EBITDA multiple (e.g., 5–10x depending on industry, size, growth; lower end ~5x for smaller deals, higher for stronger ones).Enterprise value = EBITDA × multiple.Equity value (what owner gets pre-tax) = Enterprise value − debt + excess cash.If the business depends heavily on the owner, multiples drop because it's less attractive/transferable.Sale Process and Timeline:Preparation phase: Deep dive, recommendations (often referring to specialists like exit planners, financial consultants).Active sale: 6–12 months typical (12 more realistic); faster (e.g., 60+ days) possible with a ready buyer and clean financials, but broad auctions take longer.Outreach to many buyers (strategic/competitors vs. financial like private equity) via databases/relationships—often 100–700 prospects screened down.Private equity has massive "dry powder" (~$3T mentioned), but some owners hesitate; strategics can be easier/faster due to industry familiarity.Team and Advisors: Quarterback the deal; recommend specialized M&A attorneys (not generalists), tax experts, etc., as day-to-day pros often lack deal experience and can slow/kill transactions.Post-Sale Realities:Buyers often require "rollover" equity (e.g., 20–30% with PE buyers) for alignment/"second bite at the apple."Transition periods: Sometimes walk away clean, but often 3+ years expected if the business isn't fully independent.Plan early—build to sell (e.g., reference to books like Built to Sell).Other Notes: Emphasizes starting planning "yesterday," collaborating with advisors (financial, legal, tax) early, and avoiding last-minute tax-only focus after a sale.This is practical, grounded advice for business owners thinking about exits. It stresses that while owners know their business best, specialized advisors like Steve's firm bring buyer perspectives and process expertise to capture more value.

In this episode of Wealthyist, host Tom Berkholtz interviews Khaleel Ali, Senior Education Savings Consultant at TIAA-CREF (the plan manager for Edvest, Wisconsin's 529 college savings plan). Khaleel shares his 16+ years in financial services and his six-year tenure with the Edvest program, which has been managed by TIAA-CREF since 2012 and boasts over $6 billion in assets (with recent figures showing $5.63 billion across 238,000+ accounts as of late 2024).The discussion covers the basics of 529 plans: tax-advantaged accounts similar to retirement vehicles but dedicated to education expenses, with low entry (starting at $25) and triple tax benefits—tax-deferred growth, tax-free qualified withdrawals, and Wisconsin's generous state income tax deduction (up to $5,280 per beneficiary for 2026, with carryforward for excess contributions).Key highlights include the plan's evolution through federal legislation (e.g., SECURE Acts), expanding uses beyond traditional college to K-12 tuition (up to $20,000/year in Wisconsin), apprenticeships, trade schools, student loan repayment (up to $10,000 lifetime), post-secondary credentials, and a major game-changer: rolling over up to $35,000 lifetime to the beneficiary's Roth IRA (after the account is 15 years old).For affluent families, Khaleel emphasizes strategies like maximizing contributions beyond the state deduction (up to the annual gift tax exclusion of $19,000 per person or $38,000 for couples), front-loading five years' worth ($95,000) for time-value-of-money advantages, and dynasty-style planning by changing beneficiaries across generations. The maximum account balance for 2026 is $613,240 per beneficiary across Wisconsin plans.Other topics include avoiding overfunding fears (thanks to rollover options), non-qualified withdrawal consequences (10% federal penalty + taxes on earnings), why even wealthy families benefit from the tax deferral over regular savings accounts, Edvest's strong reputation (consistent Morningstar awards, low fees, 25+ years of operation), flexible investment options (age-based, static, or custom), and easy access via the website (edvest.com) or customer service.Tom shares a personal story of how his grandfather's Edvest account sparked his interest in finance, underscoring the plan's long-term impact. Khaleel encourages advisors and families to reach out for free consultations, highlighting Edvest's flexibility for anyone nationwide (though state tax perks are Wisconsin-specific).The episode positions Edvest as a powerful, evolving tool in wealthy families' financial strategies—beyond just college savings, it's a versatile, tax-smart vehicle for generational education funding.

Guest: Jake Biernbaum, renowned horse trainer and founder of Pear Tree Ranch in Ocala, Florida. Known for his large YouTube following and expertise in natural horsemanship.Key Points from the Episode:Origin and Growth of Pear Tree RanchFounded in 2011 when Jake went independent after working with Parelli Natural Horsemanship. Started with almost nothing — living on ramen and PB&J, no truck or trailer. Grown into an international operation: clients fly in from Europe, South Africa, and across the US; offers in-person training, lessons, clinics, camps, and online video content (YouTube & Patreon). Now a family business run primarily by Jake and his wife Stephanie (also a skilled trainer); their 8-year-old son Johnny helps occasionally but isn’t pushed into the horse world.Training PhilosophyFocuses on developing both horses and humans, emphasizing that horses are “honest” while humans often complicate things. Starts with the horse first to establish clear, reliable behavior, then teaches the owner to match that level. Goal: Make clients independent (“I want you to not need me anymore”) while offering ongoing education for those who want it. Motto: “Less crying and less dying” — safer, happier horses and riders.Jake’s BackgroundNot a lifelong horse person — got into horses in his 20s after wilderness survival training (Tom Brown Jr.’s school), various odd jobs (bouncer, carpenter, daycare, etc.), and discovering Parelli Natural Horsemanship. Spent years working for Parelli (from ranch hand to touring arena manager and instructor) before going fully independent in 2017.Business Strategy & GrowthLocated in Ocala, “Horse Capital of the World,” for the density of horses, warm climate, and lifestyle (palm trees, beaches). Deliberately keeps the business small and family-run to avoid over-expansion risks; learned from past experiences with employees/interns leaving suddenly. Diversifies income through scalable online content (YouTube, Patreon) — “making money while sleeping” — rather than just trading hours for dollars. Offers various formats: private lessons, workshops, multi-day clinics/camps, and horse training programs.Clients & Wealth ObservationsWide range: backyard hobbyists to Olympic-level competitors; some barely afford lessons, others spend hundreds of thousands on imported horses. Notes that true success with horses requires consistent work and discipline — money helps (better horses, more lessons), but doesn’t replace effort. Many wealthy clients are driven and hands-on because they built their own success the same way.Work-Life Balance & Future PlansHorses were once 24/7; now prioritizes family time, beach trips, and off-roading/camping in his customized Jeep to avoid burnout. Future: Expand reach through online education and brand exposure (e.g., coaching competitors for “Road to the Horse” colt-starting championship). Long-term legacy: Build the physical ranch into an asset that can be leased or handed to a dedicated successor; no pressure on son to take over.Closing Wisdom: Five Stages Toward MasteryAwareness → Understanding → Doing → Reproducing (consistent results) → Teaching Follow Jake & Pear Tree at https://www.patreon.com/peartreeranch  & https://www.youtube.com/@peartreeranch

In this episode of the Wealthiest podcast (hosted by Anthony Mlachnik, Senior Wealth Advisor at Annex Private Client), guest Chellee Siewert (President and Founder of Capture Sports & Entertainment) discusses how her firm helps professional athletes, entertainers, and organizations develop authentic philanthropic strategies.Key highlights include:End-of-Year Giving Trends — About 30% of annual charitable donations occur in December, with examples like athletes hosting shopping events for kids, fulfilling both wants and needs (e.g., debate team ties for a high schooler).Building an Authentic "Why" — Capture guides clients to identify personal stories and passions, define 2-3 impact pillars, align philanthropy with their brand, and create realistic plans that fit busy lifestyles (from weekly involvement to a few annual events).Legacy Beyond the Game — Emphasis on defining identity outside of sports, building post-career legacies, and ensuring giving feels genuine and enjoyable.Heartwarming Stories — Touching anecdotes, such as Aaron Jones' "Yards for Shoes" campaign (donating shoes based on rushing yards, revealing a child's need for properly fitted new shoes), J.J. Watt events honoring veterans, and meaningful make-a-wish connections.Human Side of Athletes — Discussion of Vin Baker's recovery from addiction, losing over $100 million, and rebuilding his life, underscoring that athletes face public highs and lows like anyone else.Practical Structures and Benefits — Overview of giving vehicles: Donor-Advised Funds (DAFs) for tax-deductible donations, fiscal sponsorships (preferred for most clients due to compliance support), and private 501(c)(3)s. Insights on offsetting "jock taxes" (state taxes on games played away), donating appreciated stock to avoid capital gains, and leveraging league/team matching programs or awards.Team Support — Importance of a trusted core team (advisors, agents, accountants) to maximize impact, endorsements, and opportunities.Chellee shares her own journey founding Capture 14 years ago to balance motherhood and entrepreneurship, starting with clients like J.J. Watt, and finding her "why" in amplifying athletes' ability to change lives. The conversation draws parallels between athletes/entertainers and busy executives in purposeful, tax-smart giving.

Host: Anthony Mlachnik (Senior Wealth Advisor, Annex Private Client)Guest: Anna Franklin – Founder & Creative Director of Stonehouse Collective (Milwaukee/Wisconsin-based luxury interior design firm)Anna’s JourneyGrew up in small-town Wisconsin → studied Public Relations → moved to Chicago for event planning & major-gift fundraising (10 years).Met husband in Chicago, moved back to Wisconsin (Whitefish Bay, Milwaukee area) ~10 years ago to raise family (now 3 kids).After first child, rediscovered creative passion → accidentally fell into home staging → became “the stager of Milwaukee” → pivoted to full interior design during 2020/COVID.Not a formally trained designer; acts as creative director/entrepreneur.Grew Stonehouse Collective to 15 employees (5 full-time designers), opened first retail store in Shorewood in March 2023, and hit record revenue in 2025.Key Themes & Insights on Wealthy ClientsTwo Types of Clients TodayHigh-customization, unique, heirloom-quality (willing to pay $30k for a sofa).Want the “look” but at the lowest possible price (tariffs & cost pressures pushing this segment).Psychology of SpendingWealth does not equal willingness to spend on furniture/design.Some ultra-wealthy clients buy the $3k sofa because “they don’t care about furniture.”Some middle/upper-middle clients will stretch or max out credit for fully U.S.-made, 40-hands-touched heirloom pieces because that is what they value.It’s never about the dollar amount; it’s about personal values, legacy, memories, and emotional connection.Trends by DemographicYounger / Millennial / Liquidity-Event WealthFull smart-home integration (Lutron, Sonos, automated showers, security, lighting scenes controlled by phone).Wellness spas at home: cold plunges, saunas, steam, red-light therapy — all ideally in one integrated wellness room.Hitting all five senses the moment they walk in (scent, sound, light temperature, etc.).Boomers / 60s–70sSurprisingly also adding wellness/spa elements (many now want saunas & cold plunges too).Grandkid-focused spaces (arcade rooms, integrated TV/gaming areas with sleek motion furniture instead of old dedicated theaters).Aging-in-place planning: wider doors, future elevator shafts, curbless showers.Strong aversion to bold 90s-style patterns/color that millennials are embracing (“grand-millennial” trend).Tech & Smart HomesAlmost everything is now phone-controlled; wall panels and whole-house distributed audio are largely out.TVs hidden or pop-up, projectors still used, but giant TVs are cheap and ubiquitous.Some boomers initially resist phone control but warm up once they see it in action.Outdoor & Extended LivingBig focus on indoor-outdoor flow, pool houses with saunas, outbuildings (elevated “she-sheds,” homeschool barns, wellness barns).Layered exterior lighting (down-lights, up-lights, feature lighting on stone/wood) is huge.Emerging & Fun RequestsFlower rooms / cutting rooms (glass conservatory-style for arranging bouquets).Dog washes still popular but no longer novel.Lighting as “jewelry” of the house — heavy layering (picture lights, sconces, pin spots, etc.).Social Media & Pinterest Effect97% of clients arrive with a Pinterest board or saved Instagram images.Pros: helps clients communicate when they lack design vocabulary.Cons: creates unrealistic expectations about cost, lead times, and customization (Amazon-effect).Anna actively discourages excessive scrolling and digs deep (“You say you love this photo — is it the lamp or the feeling?”).Closing Message from AnnaEmphasizes timeless, classic design with layers of trend so homes don’t need gutting every 5–10 years.Stonehouse Collective retail store in Shorewood, Milwaukee is open to the public.Instagram: @stonehousecollectivecoOverall, the episode highlights how deeply personal luxury design is — wealth buys options, but values and life stage dictate what people actually spend money on and how they want their home to feel.

In this week’s Wealthyist episode, 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 JourneySurvived 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 OwnersMost 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 PriceThe 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 & AccountabilityTraction/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 UsesCertified 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 AndyStart 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).

In this episode of Wealthyist, host Dr. Brian Jacobsen speaks with Tom Berkholtz, Financial Planning Manager about Equity Compensation – what it is, why companies use it, the main types, tax pitfalls, and planning tips.Tom and Brian discuss why companies offer equity compensation, including its primary goal: to attract, retain, and motivate top talent (especially in tech/AI race – Google, Apple, Nvidia, etc.).Equity compensation can act as “golden handcuffs” via vesting schedules (e.g., 25% per year over 4 years or a 3-year cliff). The strategy can work for both public and private companies, but private-company equity is riskier (needs a liquidity event like IPO or buyout to have real value.Tom details the main types of Equity Compensation: Restricted Stock Units (RSUs) – where an employer gives you actual shares (not an option to buy).  IN that strategy, the RSU vests over 3–4 years → treated as ordinary income on vest date (shows up on W-2).  Tax trap: Employers often withhold only 22% federal tax; high earners (37% bracket) can owe big at tax time + possible underpayment penalty.  The conventional advice is to “Sell immediately after vesting” (because you already paid tax at the vest price). Tom says not always best — if you believe in the company and it’s not too concentrated, holding some can make sense.They then discuss Non-Qualified Stock Options (NSOs/NQSOs), which are the right (not obligation) to buy shares at a fixed “strike price” (usually within 10 years).  When you exercise and sell, a NSO, the bargain element (market price − strike price) is taxed as ordinary income.  Employer gets a tax deduction, which is sometimes why employers prefer NSOs over ISOs.Incentive Stock Options (ISOs) are less common now.  There's a potential for long-term capital gains treatment if holding-period rules are met.  Big catch: The bargain element is an AMT (Alternative Minimum Tax) preference item → can trigger AMT and create a huge surprise tax bill.  2025 may be a sweet spot to exercise ISOs because current AMT exemptions are still high (TCJA rules); exemptions drop in 2026, so more people could get hit.Performance Share Units (PSUs) are another option. The payout (number of shares) depends on company performance over ~3 years (e.g., stock price, EBITDA targets).  Aligns employee and shareholder incentives perfectly (Elon Musk–style packages are an extreme example).Key Tax & Planning Takeaways RSUs and exercised NSOs = ordinary income (up to 37% federal + state).  Under-withholding on RSUs is extremely common → fix by increasing paycheck withholding or making quarterly estimated payments.  High earners: Consider donating appreciated vested shares (RSUs or exercised options) to charity or a Donor-Advised Fund instead of selling → avoid capital gains tax and get a deduction.  End-of-year must-do’s for equity-comp recipients:  Project upcoming vest/exercise events.  Strategically exercise NSOs or ISOs to fill lower tax brackets or stay under AMT.  Harvest gains/losses, diversify concentrated positions (especially when market is at all-time highs).Bottom line from Tom: Equity compensation is powerful but requires proactive, annual planning — it’s not a “set it and forget it” asset like a 401(k). Work with a financial planner and tax pro who can model the scenarios (especially AMT for ISOs) to avoid nasty surprises.

Core Theme: How a middle-class Wisconsin upbringing, strong family values, and an athlete’s mindset of consistent small improvements shaped Steve Novak’s approach to money, lifestyle, and giving back — and kept him far away from the “broke ex-athlete” stereotype.Key Takeaways from the Conversation:Grounded Upbringing as the AnchorGrew up in Brown Deer, WI (middle/lower-middle class); dad was a teacher/coach, mom a nurse. Saw bigger houses and nicer cars as a kid → early motivation that real wealth required success without debt. Even after making NBA money, never felt the need for a mansion. Bought a normal house in Whitefish Bay (“looks like all the other houses”) and still lives a relatively modest lifestyle.Financial Philosophy = Athletic MindsetTranslated his shooting training mantra (“get 0.1% better every day”) into investing. Very conservative investor: prioritizes steady compounding over home-run bets or crypto. Learned the hard way with a few bad private deals/restaurants → “losing money felt worse than winning felt good.” Focus: never move backward; small, consistent forward progress compounds over a 50+ year post-basketball timeline.Lifestyle ChoicesPlayed on 9 teams, lived in Houston, LA, NY, Toronto, etc. → realized Milwaukee/SE Wisconsin is one of the most underrated places to live and raise a family. Chose walkable, community-oriented neighborhoods (Whitefish Bay) over sprawling estates. Family now owns two homes in Wisconsin (North Shore + Lake Country) instead of the typical athlete Florida/Arizona second home — “Wisconsin summers are the best in the world.”Giving Back & Full-Circle MomentDad coached generations of kids → Steve now runs shooting clinics all over SE Wisconsin, passing on the “aha” moments he had after thousands of hours in the gym. Wants the next generation to say, “Steve taught me footwork and motivated me.”NBA Financial Realities & LessonsRookie paycheck shock, royalty checks with no withholding, surprise tax bills when income jumps, jock taxes, escrow, etc. NBA’s unusually generous 401(k) match (up to 150%) and bridge annuities show the league/NBPA actively try to protect players. Mandatory financial-literacy meetings ($10k fine if you skip) — education is there, but players still have to act on it.Current LifeJust hired as Walt “Clyde” Frazier’s backup Knicks broadcaster (full-circle: New York was where he played his best ball). Still lives in Milwaukee; kids cheer for both the Bucks and Knicks.Bottom Line (in Steve’s words):“Don’t try to hit home runs. Just keep the money you worked hard for moving 0.1% in the right direction every day, make it last a long time, and don’t end up on a ‘broke’ documentary.”A refreshingly grounded, Midwestern take on wealth from someone who’s seen both the NBA flash and the long-term reality — and consciously chose the latter.

In this episode of Wealthyist, host Brian Lamborne (Senior Wealth Strategist at Wealth Management) welcomes Nick Kozik, Director and Shareholder at TKO Miller, a Milwaukee-based boutique investment banking firm specializing in sell-side transactions for family-owned businesses (typically $15M–$250M enterprise value). The discussion dives into the current M&A landscape, strategies for business owners eyeing an exit, and pitfalls to avoid when selling.Key HighlightsTKO Miller's Focus and Nick's RoleTKO Miller helps family-founder businesses navigate sales, emphasizing education and "bedside manner" for first-time sellers. Nick leads transaction teams (4–5 people per deal) in sectors like industrial/infrastructure services, plastics/packaging, consumer goods, food & beverage, and tech-enabled services. The firm marks its 10th anniversary in 2026.Current M&A Market DynamicsBifurcated Landscape: High demand for recession-resistant service businesses (e.g., HVAC, healthcare, recurring maintenance), trading at peak valuations (10–12x EBITDA) due to abundant private equity capital chasing limited deals. Challenges: Tariff-exposed manufacturing/distribution or consumer-discretionary sectors face lower interest and multiples, though deals still close. Advice: Sell now if in a hot sector; wait if trade-impacted. Personal timelines (e.g., health, retirement) often trump market conditions—consult experts for tailored assessments.Buyer Types ExplainedPrivate Equity (PE): Pools of capital for majority buyouts (leveraged, using debt); focused on growth, not just cost-cutting. They prioritize services over risky sectors, paying premiums for "safe" deals. Strategic Buyers: Operating companies seeking synergies (e.g., one chemical firm buying another); more cautious in uncertain times. Quasi-Strategics: PE-backed portfolio companies doing add-ons for operational alignment. ESOPs (Employee Stock Ownership Plans): Ideal for owners prioritizing employee ownership and business continuity; involves seller financing and tax perks, but yields lower upfront proceeds than PE/strategic sales.Planning for a Successful SaleTimeline: Start 1–5 years out for max value—focus on management succession (e.g., 18–24 month transition team) and data readiness (accurate reporting to handle buyer requests). Define Goals: Clarify priorities like max proceeds, growth partnership, or legacy preservation to shape the process. Build Your Team: RoleWhy EssentialTimingInternal Management | Runs the business post-sale; needs ops leader, finance expert, and sales rep. | OngoingTransaction Attorney | Handles deal terms to avoid clawbacks. | 6–12 months pre-saleAccountant/Quality of Earnings | Tax planning, financial audits tailored for transactions. | 1–2 years pre-saleWealth Manager | Post-sale lifestyle/investment strategy. | 1–2 years pre-saleInvestment Banker | Runs competitive process for $10M+ deals to maximize value/options. | 1+ year pre-saleValuation InsightsPrivate businesses are hard to value without market testing—multiples vary wildly by sector (e.g., HVAC at 10–12x vs. metal fabrication at 5x). Free initial assessments from firms like TKO Miller reveal true worth via broad auctions, avoiding guesses that skew net worth planning.Common Mistakes to AvoidSelling to the first buyer without alternatives (erodes leverage, invites "chipping away" on terms). Fire sales due to unpreparedness (no team/data = higher risk, lower price). Dropping performance during the 7–9 month process (e.g., growth stalls = deal death).Closing ThoughtsLambourne and Kozik emphasize proactive planning over reactive exits, noting that even in a volatile market, the right process unlocks life-changing value. Kozik offers free consultations for owners curious about their business's worth. 

In this empowering episode of Wealthyist—the podcast exploring the lifestyles, choices, and strategies of the affluent—host Deanne Phillips (a CFP and bodybuilding enthusiast) interviews Dr. Tes Jordens. Dr. Jordens, founder of 1988 Wellness (named for the year U.S. women gained independent access to small business loans), shares insights on midlife women's health, debunking myths around menopause, hormone replacement therapy (HRT), and obesity. The conversation ties into "wealthyist" trends, emphasizing proactive, private-pay investments in vitality as foundational to financial success and confidence.Key Discussion ThemesMenopause Realities and Patient Journeys  Menopause symptoms (fatigue, weight gain, sleep disruption, hot flashes) often start in the 30s-40s but peak in the 40s-50s, exacerbated by estrogen decline, which spikes cardiovascular risk ~10 years later than in men.  Typical patients: Frustrated women dismissed by primary care as "anxious" or "normal," seeking holistic answers. Host shares her thyroid struggles and early menopause at 46, leading to 45-pound gain and life crisis.  Shift from "disease care" to prevention: Women increasingly seek to "capture that 30s-40s feeling" before decline, rejecting it as a "rite of passage."HRT Myths, Benefits, and Options  Debunks 2002 Women's Health Initiative (WHI) fallout: Media sensationalism linked HRT to cancer/strokes, but flaws (e.g., average participant age 63, not perimenopausal) caused mass hysteria. Science now shows HRT (estradiol, progesterone, testosterone) is safe and protective when started within 10 years of menopause or before 60.  Benefits: Reduces dementia/osteoporosis risk (only proven preventive for bones), supports heart health, boosts energy for workouts/career. Can continue indefinitely unless major contraindications (e.g., active breast/endometrial cancer, recent stroke).  Delivery methods: Tailored to needs—pills (liver-processed for brain protection), patches/gels/sprays, pellets (host switched due to glute workouts displacing them), vaginal creams for UTIs/frequency in 70s-80s.  Advice: Persist beyond dismissive docs; seek certified specialists. No "magic pill," but HRT sparks virtuous cycles (e.g., energy for strength training).Obesity and "Menopause Belly" Strategies  Visceral fat (around organs) drives inflammation, insulin resistance, diabetes/heart risks—not just aesthetic.  Tools: GLP-1 meds (e.g., Ozempic) as aids, not cures; combine with protein/fiber-rich nutrition, movement. Focus on building strength for 70s-80s independence, not restriction/diet culture.  Trifecta approach: HRT + meds + habits (e.g., trainers, dietitians) for sustainable results. Host credits HRT for reigniting her bodybuilding passion at 60.Wealthyist Trends in Self-Pay Health  Affluent women prioritize out-of-pocket empowerment: Comprehensive blood panels (e.g., ferritin, CRP for inflammation/hemochromatosis), DEXA scans (~$100-300, gold standard for bone/muscle/fat composition—insurance covers only post-65, too late).  Lifestyle shifts: Strength training (future-proofing against frailty), creatine (debunking "gym bro" stigma; aids muscle, cognition), peptides/collagen for skin/energy.  Mindset: Health as wealth foundation—invest like education/wardrobes. Bucket finances for "personal care" (HRT ~$50-200/month) to sustain vitality post-retirement. Women unafraid to hire experts, rejecting "suffer silently."Closing TakeawaysDr. Jordens urges midlife women: Don't quit seeking help; it's not "just aging." For parents in their 70s-80s, consider vaginal estrogen for UTI prevention. Host, prepping for a 60-year-old bodybuilding comp, embodies the episode's vibe: Midlife is for thriving, not surviving. Reach Dr. Jordens at 1988wellness.com or @drtesjordens on socials.  This ~45-minute chat blends vulnerability, science, and aspiration—perfect for wealthy women redefining aging as an asset. Tune in for motivation to audit your health plan today!

Estate planning is uncomfortable (addresses incapacity and death) but essential; integrate it naturally into life/financial discussions for comprehensive planning.Key Checklist of Must-Have Documents & DesignationsPowers of Attorney (POA):Financial & Healthcare POAs: Needed at age 18 (even for adult children, e.g., college prep). Parents lose decision rights post-18 without them.Will:Names executor; directs asset distribution at death.Critical for parents: Only place to name guardians for minor children.Works with trusts; "pour-over" will funnels forgotten assets into trust.Revocable Trust:Manages assets during life & at death; avoids probate.Becomes irrevocable at death (can't change).Complements (not replaces) a will.Irrevocable Trusts (Lifetime):For gifting assets (to spouse/kids) to reduce estate taxes.Removes assets + future appreciation from estate.Estate Tax Context: 2026 exemption rises to ~$15M/person ($30M/couple). Plan flexibly for future law changes; project asset growth vs. inflation/spending.Other Documents (state-specific):Living will/advance directive (end-of-life wishes).Funeral arrangements.Beneficiary Designations:Override wills/trusts (e.g., IRAs, 401(k)s, life insurance).Common Mistake: Outdated designations (e.g., ex-spouse or parent instead of kids) cause assets to go wrong.Review & Update Best PracticesFrequency: Every 3–5 years; or trigger by:Life events (marriage, divorce, birth, death).Law changes (e.g., recent tax bills).Pet Peeves/Common Errors:Mismatched beneficiaries vs. will/trust.Outdated successors (e.g., naming parents/siblings when kids are now adults; shift to children as agents/trustees).Communication, Storage & ExecutionSharing with Family: Family-specific; no one-size-fits-all.Some share full details/drafts (à la Warren Buffett) for transparency.Others share structure only (flow of assets, roles, advisors) without dollar amounts.Ensure heirs know document locations, attorney, advisors.Successor Roles: Choose capable people; consider corporate trustee (fees apply, but justified for complex dynamics).Advisor Support: Professionals guide grieving families; nobody navigates alone.Probate: Not as Bad as FearedProcess: File will with court; appoint executor; notify creditors; resolve claims.Pros: Structured (good for family disputes/disharmony); time-bound creditor claims.Cons: Time/cost, but avoidable via revocable trusts.Goal: Avoid if possible, but not catastrophic.Closing: Estate planning ensures control, minimizes regrets/taxes, and eases transitions. Review regularly; coordinate with financial plans.

In this episode of the "Wealthyist" podcast, hosted by Anthony Mlachnik, senior wealth manager for Annex Private Client, the focus is on private investments and their role in a diversified portfolio. Mlachnik is joined by Brian Jacobsen, Annex’s chief economic strategist, to discuss the nuances of private markets and their relevance for high-net-worth individuals.The episode begins by defining private markets in contrast to public markets. Private markets include investments like private equity, private credit, private real estate, and private infrastructure, which are not publicly traded and thus don’t appear on stock tickers. Jacobsen addresses misconceptions about private markets being inherently riskier or opaque, emphasizing that Annex focuses on aligning investments with clients’ goals through thorough due diligence and understanding the client’s financial objectives.The discussion highlights the importance of a macro-level investment policy statement, especially for clients experiencing liquidity events, such as business sales or sudden wealth accumulation. Private markets are presented as a tool for diversification, particularly for accredited investors or qualified purchasers who meet specific net worth or sophistication requirements. Jacobsen notes that while public markets offer around 4,000–4,500 companies, private markets provide access to a much larger pool of 40,000–45,000 companies, including innovative firms that may not need public funding due to technological advancements.The conversation explores why many companies choose to remain private, citing reduced regulatory burdens (e.g., post-Sarbanes-Oxley) and the ease of raising capital through private channels, facilitated by technologies like DocuSign. Private markets offer opportunities to invest in early-stage, disruptive companies—potentially the “next Google or Facebook”—before they go public. However, Jacobsen stresses the importance of due diligence, understanding the investment’s philosophy, process, partners, pricing, and structure, especially when investing through funds managed by general partners.Mlachnik and Jacobsen also discuss the behavioral challenges of private investments, such as the temptation to overcommit to opportunities presented by friends or networks. A disciplined framework helps investors say “no” when an investment doesn’t align with their strategy. They touch on the concept of the illiquidity premium, where private investments, being less liquid than public securities, often trade at lower valuations to compensate for the inability to sell quickly. This illiquidity can act as a “pre-commitment device,” preventing impulsive decisions during market volatility, akin to Odysseus tying himself to the mast to resist the sirens’ call.The episode briefly addresses private infrastructure, particularly relevant in Wisconsin due to the rise of data centers. Jacobsen explains that private infrastructure investments (e.g., ports, airports, energy distribution) blend growth potential with income generation, distinguishing them from private real estate, which focuses on physical assets like buildings.The episode concludes with a reminder to approach private investments with a clear plan and a trusted fiduciary advisor to ensure decisions align with long-term financial goals, rather than chasing trendy opportunities. The discussion underscores the importance of strategic planning, due diligence, and a disciplined process in navigating the complexities of private markets.

The podcast "Wealthyist," hosted by Austin Grandinetti with guest Dr. Brian Jacobson from Annex Wealth Management, discusses a Forbes article highlighting shifts in the investment priorities of high net worth individuals. Key points include:Shift to Income Generation: 82% of affluent investors now prioritize generating income over growth, a change observed over the past two years. This shift follows strong market returns in 2023, prompting investors to focus on locking in gains and securing income, possibly through fixed income or realizing capital gains for tax efficiency.High Net Worth Mindset: The focus on income is more prevalent among high net worth and institutional investors, who act as trendsetters, compared to retail investors who tend to chase trends.Happiness Through Giving: High net worth individuals increasingly prioritize creating happiness for others, often through charitable giving or legacy planning. Strategies include bunching charitable donations, using donor-advised funds, private foundations, or gifting appreciated stock to optimize tax benefits, especially under the "One Big Beautiful Bill" tax provisions.Expert Guidance and Emerging Tech: 71% of affluent investors work with financial advisors, valuing expert guidance. Annex Wealth Management emphasizes a client-centric approach, defining problems, designing solutions, and delivering comprehensive plans that integrate tax, estate, charitable, and investment strategies.Status Symbols and Travel: Affluent individuals prioritize status symbols like travel (up 20% from 2024), luxury vehicles, watches, and designer clothes. Travel is particularly valued for the experiences, stories, and personal connections it fosters, seen as a status symbol post-Covid.The podcast underscores the importance of tailored financial planning for high net worth individuals, balancing income generation, tax efficiency, charitable goals, and lifestyle aspirations like travel.

Recently Dr. Brian Jacobsen and Brian Lamborne discussed implications of the OBBBA on Business Owners. In this episode of Wealthyist, hosted by Brian Jacobsen, Chief Economist at Annex Wealth Management, and featuring Brian Lamborne, Senior Wealth Strategist, the discussion focuses on the implications of the "one big beautiful bill" (likely referring to the Tax Cuts and Jobs Act or a similar tax legislation) for business owners across the lifecycle of a business: starting, running, and selling or winding up. Here's a summary of the key points:1. Starting a BusinessChoosing the Business Structure: The decision between forming a pass-through entity (e.g., S corporation, LLC) or a C corporation depends on long-term goals. S corporations offer pass-through taxation, avoiding double taxation, and allow deductions like the Qualified Business Income (QBI) deduction, which isn't available for C corporations. C corporations, however, offer benefits like Qualified Small Business Stock (QSBS) exclusions for capital gains upon sale, but face double taxation (corporate tax at 21% plus dividend tax).Course Correction: Business owners can change their entity structure (e.g., from LLC to S or C corporation) based on evolving goals, though some changes, like qualifying for QSBS, have strict requirements (e.g., the business must be a C corporation for at least 80% of its life).QSBS Considerations: QSBS allows exclusion of capital gains (up to $15 million) if the business is a C corporation from inception, held for at least five years, and meets specific criteria (e.g., under $75 million in assets, not in excluded industries like hospitality or professional services). The bill introduced tiered exclusions: 50% for three years, 75% for four years, and 100% for five years.Planning Ahead: Many business owners start without proper tax planning, often defaulting to a C corporation or sole proprietorship. Engaging tax professionals early can optimize tax outcomes.2. Running a BusinessDeductions and Incentives: The bill expanded key deductions, including:Bonus Depreciation: Allows 100% expensing of certain assets (e.g., equipment, cars) in the year of purchase, incentivizing business investment. However, it applies to entire asset categories, and some businesses may prefer standard depreciation to manage taxable income over time, especially for banking covenants.Research and Experimentation (R&D) Credits/Deductions: These apply broadly to problem-solving activities, not just traditional lab work. Examples include designing custom machinery or solving technical manufacturing challenges. Many businesses are unaware they qualify.QBI Deduction: Offers up to a 20% deduction on business income for pass-through entities. The bill expanded the income threshold from $100,000 to $150,000, benefiting more professional service businesses (e.g., doctors, lawyers), though high earners in these fields may still be excluded unless they lower their adjusted gross income (AGI) via strategies like retirement plan contributions.Tax Planning vs. Preparation: Most accountants focus on tax preparation, not proactive planning. Business owners often miss opportunities to optimize deductions due to reluctance to pay for planning services, which are themselves tax-deductible.3. Selling or Winding Up a BusinessStock vs. Asset Sales:Sellers Prefer Stock Sales: Selling stock (especially in a C corporation) can qualify for QSBS exclusions, offering capital gains tax relief, and transfers liabilities to the buyer.Buyers Prefer Asset Sales: Buyers favor purchasing assets to pick and choose what they want, gain depreciation benefits, and avoid inheriting liabilities. However, asset sales in C corporations lead to double taxation (21% corporate tax plus dividend tax), potentially approaching a 50% effective tax rate.Negotiation Tension: This creates a "tug of war" between buyers and sellers, requiring careful negotiation and legal structuring to balance tax implications and price.QSBS Stacking: QSBS exclusions apply per individual (up to $15 million each). Owners can gift stock to family members or trusts (e.g., spouse, children) to maximize exclusions, especially in non-community property states. In community property states like Wisconsin, a married couple can exclude up to $30 million. Planning must occur well before the sale to maximize benefits.Course Correction Post-Sale: Some owners discover QSBS eligibility after a sale and can amend returns, but late planning limits optimization (e.g., missing the chance to gift stock for stacking).Key TakeawaysThe "one big beautiful bill" introduced or expanded tax provisions like bonus depreciation, R&D credits, QBI deductions, and QSBS rules, significantly impacting business planning.Strategic tax planning is critical at all stages of a business. Many owners fail to plan early, missing deductions or optimal structures.Engaging professionals like those at Annex Wealth Management can help navigate complex decisions, from entity selection to sale structuring, to minimize tax liabilities and maximize benefits.The episode emphasizes the importance of long-term planning, understanding buyer-seller dynamics, and leveraging tax code provisions like QSBS and R&D credits to enhance business outcomes.The discussion highlights the complexity of tax decisions and the need for proactive, professional guidance to avoid costly oversights.

In this republished episode of "Wealthyist" podcast Episode 24, host Brandon Lehman interviews Dale Kooyenga, president of the Metro Milwaukee Association of Commerce, about economic development in the Milwaukee region, specifically the Milwaukee Seven (M7), which represents seven counties in southeast Wisconsin: Milwaukee, Kenosha, Ozaukee, Racine, Walworth, Waukesha, and Washington. The M7 focuses on regional economic development to attract large companies like Microsoft, Eli Lilly, and Hasbro by leveraging the area’s strengths.Key Points:Attracting Companies: Companies choose Milwaukee over other regions like Chicago or Atlanta due to factors like access to water, a reliable energy grid, and a strong talent pool, particularly in advanced manufacturing and food and beverage industries. The region’s livability, with amenities like professional sports, golf courses, and a vibrant downtown, also appeals to companies recruiting talent.Cost of Living and Housing: Milwaukee offers relatively affordable housing compared to other metros of its size, though housing costs are rising due to high labor, material costs, and interest rates. The region’s high per capita income and affordability make it attractive, but property taxes are approaching those of Chicago’s suburbs, raising concerns about competitiveness.Lifestyle and Amenities: Milwaukee’s appeal includes its lively downtown, proximity to Lake Michigan, professional sports teams (Bucks and Brewers), and short commutes (20 minutes vs. 1-1.5 hours in larger cities), allowing for a balance of family and professional life. The Wall Street Journal recently highlighted Milwaukee as the nation’s hottest housing market.Water and Energy: Access to abundant water from Lake Michigan is a major draw for industries like data centers and manufacturing, which require significant water and energy resources. Wisconsin’s reliable energy grid and leadership in nuclear technology (e.g., micro nuclear) position it well for future growth.Economic Shifts: Milwaukee’s economy is transitioning from traditional blue-collar manufacturing to high-tech and financial services, with a strong presence of mid-tier manufacturers and private equity firms. Manufacturing output is up despite fewer jobs, reflecting productivity gains.Challenges and Opportunities: Kooyenga highlights three priorities for Milwaukee’s growth: (1) establishing a top-tier R1 research university, (2) adopting advanced nuclear technology for sustainable energy, and (3) attracting more immigrants, who are more likely to start businesses and drive economic growth. Milwaukee’s population growth is strong in the Midwest but lags due to lower immigration compared to cities like Chicago.Policy Concerns: High income taxes (e.g., 7.65% vs. Illinois’ 5% flat tax) and rising property taxes are barriers to attracting executives and talent. Kooyenga suggests a flatter, lower tax rate (3-4%) to boost competitiveness, warning that overturning reforms like Act 10 could worsen property tax burdens.Vision for M7: The ultimate goal is to enhance Milwaukee’s appeal as a top destination by integrating it more closely with Madison (a one-hour commute) to create a powerhouse region combining Milwaukee’s amenities with Madison’s capital and university assets. Reducing the psychological and logistical divide between the two cities could make the region globally competitive.The podcast emphasizes Milwaukee’s strengths, ongoing challenges, and strategies to elevate its economic and lifestyle appeal, with a focus on attracting businesses, talent, and wealth to the region.

In this week's episode of the "Wealthyist" podcast, hosted by Dr. Brian Jacobsen, Chief Economist at Annex Wealth Management, with guest Brian Lamborne, Senior Wealth Strategist at Annex Private Client, discussion focused on Qualified Small Business Stock (QSBS) and comparisons to the Qualified Business Income Deduction (QBID) from their previous episode. Here's a summary: QSBS applies to stock in a C corporation that has spent most of its life as a C corporation. Unlike QBID, which is a deduction for pass-through entities (e.g., partnerships, S corporations), QSBS offers an exclusion of capital gains when selling the stock of a qualifying C corporation.Key Differences:QBID: Provides a deduction (up to 20%) on income from pass-through entities, beneficial for businesses generating ongoing cash flow.QSBS: Offers a capital gains exclusion (up to 100% depending on holding period) when selling C corporation stock, ideal for businesses planning a sale.QSBS Rules:The business must be a C corporation at issuance and for most of its life, though it can temporarily elect S corporation status.The company’s gross assets cannot exceed $50 million (increased to $75 million under new rules) at the time of stock issuance.Certain businesses (e.g., hospitality, professional services like doctors or lawyers, or investment companies) do not qualify.Stock must be acquired directly from the company (e.g., through capital infusion or stock options), not purchased from another shareholder.Holding Period Changes: The "One Big Beautiful Bill" modified QSBS rules, reducing the holding period for exclusions:Old rule: 5 years for 100% capital gains exclusion.New rule: 4 years for 75% exclusion, 3 years for 50% exclusion, providing more flexibility.The exclusion cap increased from $10 million to $15 million in gains.Strategic Considerations:Switching between C and S corporation status to game the system is risky and could lead to losing QSBS benefits, as the IRS enforces rules to prevent abuse.Businesses can start as partnerships or sole proprietorships and later convert to C corporations, but tax implications must be carefully planned.Planning early is critical, as choices made at incorporation (e.g., C vs. S corporation) can limit future options.Takeaway: QSBS and QBID serve different purposes depending on whether a business owner prioritizes income deductions or capital gains exclusions. Due to the complexity, consulting with wealth strategists early is essential to maximize benefits.

 Exploring key tax provisions like Qualified Business Income (QBI) deduction and Qualified Small Business Stock (QSBS), and their implications for starting and selling a business, as influenced by the "One Big Beautiful Bill" (OBB).Synopsis:In this episode of Wealthyist, Dr. Brian Jacobsen and Brian Lamborne dive into the complexities of business tax strategies, likening them to an "alphabet soup" of acronyms like QBI and QSBS. They discuss how these provisions impact business formation, tax planning, and eventual business sales, particularly in light of the OBB's changes. The conversation highlights the importance of strategic entity selection (e.g., C corporation, S corporation, or LLC) and how it affects eligibility for tax benefits like the QBI deduction. They also touch on common pitfalls, such as business owners making uninformed decisions based on incomplete advice from non-experts or social media. The episode emphasizes the need for tailored professional guidance to optimize tax outcomes and asset protection.Key Takeaways: QBI Deduction Overview: QBI (Qualified Business Income) allows a deduction of up to 20% on pass-through entity income (e.g., S corporations, LLCs, sole proprietorships) reported on personal tax returns. C corporations, taxed as separate entities, are ineligible for QBI unless they elect S corporation tax status via IRS filing. LLCs default to sole proprietorship (Schedule C) for single-member LLCs, automatically qualifying for QBI, but can elect S or C corporation tax status for strategic reasons. The OBB expanded QBI phase-in thresholds from $100,000–$500,000 to $150,000–$550,000, offering more room for high earners (e.g., doctors, lawyers) to benefit, though professionals face stricter rules above the threshold. Strategic planning, like using retirement plans (e.g., cash balance plans), can lower adjusted gross income to maximize QBI eligibility.QSBS and Entity Choice: Qualified Small Business Stock (QSBS) applies only to C corporations, offering significant tax exclusions on gains from selling stock, making it attractive for businesses (e.g., tech startups) aiming for a future sale. Choosing an LLC or S corporation precludes QSBS benefits, as these entities don’t issue stock. Investors must align entity choice with their goals (e.g., income stream vs. future sale).Accidental Entrepreneurs and Poor Advice: Many business owners become "accidental entrepreneurs," starting businesses without proper planning, often choosing entities (LLC or corporation) based on casual advice from friends, accountants, or social media (e.g., TikTok, YouTube). Entity choice impacts asset protection and tax outcomes. Corporations are designed for asset protection, with tax rules layered on, while LLCs offer flexibility in tax elections.OBB’s Impact: The OBB extended QBI phase-in ranges, benefiting high-income professionals by providing more flexibility to claim the deduction. The episode hints at further discussion on QSBS in a future part, suggesting OBB may also influence QSBS-related strategies.Decision-Making Framework: Business owners and investors should clarify goals (e.g., income stream vs. exit strategy) before choosing an entity. Consulting professionals (not social media or peers) ensures informed decisions about entity structure, tax elections, and deductions like QBI or QSBS.Actionable Advice: Work with a wealth strategist or tax professional to align business entity choices with long-term financial goals. Evaluate QBI eligibility and consider tax planning strategies (e.g., retirement contributions) to stay within favorable income thresholds. For businesses eyeing a future sale, explore C corporation status for QSBS benefits, but weigh against loss of QBI.Next Episode Tease: Part two will compare QBI and QSBS in depth, offering a decision tree for business owners and investors. Note: For detailed tax planning, listeners should consult professionals, as individual circumstances vary. 

In this episode of Wealthyist, host Anthony Mlachnik, a senior wealth manager at Annex Wealth Management, interviews Collin Yelich, a former professional baseball player turned high-end real estate professional in southeast Wisconsin. The discussion focuses on Yelich’s transition from athletics to real estate, his integration into the Milwaukee community, and his work helping professional athletes and others settle into new environments.Key points:Career Transition: Yelich shares the challenges of moving from a structured life as a professional athlete to navigating the uncertainty of a new career during the COVID-19 pandemic. He describes the sense of being "lost" after retiring from baseball and how his family’s real estate background, particularly his mother’s experience, eased his transition into the industry.Community Integration: Yelich highlights Milwaukee’s welcoming community, which made his move from California easier. He emphasizes the importance of community support for athletes and others relocating, drawing parallels between his experiences and those of entrepreneurs or retirees facing major life transitions.Helping Athletes and Newcomers: As a real estate professional, Yelich uses his athletic background to empathize with clients, particularly athletes, helping them navigate housing needs and settle into Milwaukee. He focuses on understanding their preferences and making the process efficient, given their busy schedules.Financial Strategy: The conversation touches on the importance of financial planning for athletes, balancing immediate desires (e.g., buying a dream car) with long-term stability. Yelich notes that these discussions often start early in an athlete’s career, such as when they receive a signing bonus.Community Impact: Yelich discusses his family’s Christian Home Plate Charity, which hosts an annual charity concert supporting local Milwaukee organizations like Live Like Lou, Visit Milwaukee, and the Brewers Community Foundation. The event fosters community engagement and is open to the public.Business and Sports Intersection: Yelich observes the growing integration of sports and business, particularly through social media and brand partnerships, which amplifies opportunities for athletes and entrepreneurs. He sees this trend expanding at both professional and college levels.Mental Strategies: Yelich shares insights on mental resilience, drawing from his athletic experience. He emphasizes focusing on a few key strategies to navigate challenges, a principle applicable to both athletes and entrepreneurs facing ups and downs.Memorable Experience: Yelich recounts his first home sale in Wisconsin, a modest $212,000 transaction, as particularly meaningful due to the trust a family placed in him as a young agent. He values building lasting relationships with clients, who often become friends.The episode underscores themes of adaptability, community connection, and strategic planning, drawing parallels between the experiences of athletes, entrepreneurs, and others navigating significant life changes.

In this episode of "Wealthyist", hosted by Anthony Malachnik, Senior Wealth Manager, and Brian Jacobsen, Chief Economist at Annex Wealth Management, the discussion focuses on the implications of the "One Big Beautiful Bill" (OBBB), signed into law on July 4, for business owners planning their exit strategies. Key points include:Importance of Exit Planning: Business owners are often deeply involved in daily operations, which can delay exit planning. The hosts emphasize the need for a proactive approach, supported by a team of advisors to navigate complex decisions.Impact of the OBBB: The bill provides clarity on tax provisions, particularly by extending the Tax Cuts and Jobs Act of 2017, which was set to sunset in 2025. This allows business owners to shift from a reactive "use it or lose it" mindset to a proactive strategy.Estate Planning Opportunities: The OBBB increases the estate tax exemption to approximately $15 million per person (indexed for inflation), enabling strategic moves like transferring business interests into trusts or family limited partnerships early to benefit from valuation discounts and growth outside the estate.Business Structure and Taxation: The bill affects how businesses are taxed and sold. For C corporations, qualified small business stock (QSBS) provisions allow significant capital gains exclusions if shares meet specific criteria. However, buyers may prefer asset purchases for immediate depreciation benefits (100% bonus depreciation or Section 179 deductions), influencing whether a business should be structured as a C corporation or a pass-through entity (e.g., LLC or S corporation) to optimize for different buyers (e.g., family, management, or private equity).Proactive Strategy and Flexibility: The hosts stress that early planning with professional guidance can maximize value and align with the owner’s goals. Even if initial structures are suboptimal, course corrections are possible with the right team.Call to Action: The episode encourages business owners to consult with wealth management professionals to explore options, using a personal anecdote about a friend seeking advice to illustrate the value of collaborative planning.The discussion underscores the importance of strategic, proactive exit planning with professional support to leverage the opportunities provided by the OBBB.

In this episode of the "Wealthyist" podcast, hosted by Dr. Brian Jacobsen, Chief Economist at Annex Wealth Management, and featuring Erik Strom, Director of Financial Planning, the discussion centers on the impact of the "big beautiful bill" on charitable giving and tax-efficient strategies. Key points include:Standard Deduction Increase: The 2017 Tax Cuts and Jobs Act doubled the standard deduction starting in 2018, leading many taxpayers, including Strom and his wife, to stop itemizing deductions, which contributed to a decline in charitable giving. The recent bill permanently extends this larger standard deduction with an additional boost, and a new senior deduction is available even for those taking the standard deduction.State and Local Tax (SALT) Deduction: Previously capped at $10,000, the SALT deduction has been increased to $40,000 through 2029, potentially encouraging more taxpayers to itemize. However, for incomes exceeding $500,000, the SALT deduction phases out rapidly up to $600,000, creating a steep effective tax rate.New Charitable Deduction for Non-Itemizers: Starting in 2026, non-itemizers can deduct up to $1,000 (single filers) or $2,000 (married filers) for charitable contributions, incentivizing record-keeping for donations.Charitable Deduction Floor for Itemizers: A new rule effective in 2026 introduces a floor for charitable deductions, set at 0.5% of adjusted gross income (AGI). For example, with a $200,000 AGI, the first $1,000 of charitable contributions is non-deductible, making strategies like bunching donations or using donor-advised funds (DAFs) more critical.Donor-Advised Funds (DAFs): DAFs are highlighted as a tax-efficient way to frontload charitable contributions, especially in high-income years, to avoid the new AGI-based floor. Contributions to DAFs in 2025 can bypass this floor, allowing distributions to charities over time.Qualified Charitable Distributions (QCDs): For those over 70.5 with required minimum distributions (RMDs), QCDs allow direct IRA donations to charities, excluding the amount from taxable income, which can help manage income levels to avoid SALT deduction phase-outs.High-Income Considerations: For those in the top 37% tax bracket, a new limitation claws back itemized deductions, reminiscent of the Alternative Minimum Tax (AMT), which was largely mitigated by the 2017 Act but still affects those with incomes over $1 million. This adds complexity for high-income earners navigating tax planning.The episode emphasizes the importance of strategic tax planning, such as bunching donations, using DAFs, or leveraging QCDs, to maximize the impact of charitable giving while minimizing tax burdens. Jacobsen and Strom stress the value of professional guidance, like that offered by Annex Wealth Management, to navigate these complex changes effectively.

In this episode of Wealthyist, hosted by Brian Lamborne, senior wealth strategist at Annex Private Client, and featuring new team member Anthony Mlachnik, the discussion focuses on strategic financing as a tool for the wealthy. Continuing from a prior conversation on tax-aware investing, they explore how strategic financing leverages assets to borrow money tax-free, providing liquidity without triggering taxable gains. This approach is particularly useful for short-term needs, such as relocating from Wisconsin to Florida, funding college, or buying a car, by using options like margin accounts, pledged asset lines of credit, or home equity lines of credit.Key points include:Tax Efficiency: Borrowing against assets (e.g., stocks or home equity) avoids capital gains taxes, offering a cost-effective alternative to selling investments.Flexibility: Clients can bank with multiple institutions, and advisors help negotiate competitive rates, potentially saving on interest costs.Applications: Strategic financing supports personal transitions, business needs, charitable giving, and estate planning, such as gifting to children without selling stocks or using low-interest loans to facilitate business succession.Advisory Role: As fee-only fiduciaries, the team collaborates with clients’ professionals (e.g., lawyers, bankers) to tailor solutions, ensuring the best interest of the client over bank profits.Options and Customization: Strategies vary by situation, from using personal loans to family-held notes, emphasizing the importance of exploring all possibilities with a wealth manager.The episode highlights the value of professional guidance in navigating financing options and optimizing taxes, with plans to delve deeper into advanced topics in future episodes.

In this episode of "Wealthyist," hosted by Brian Lamborne, Senior Wealth Strategist with the Annex Private Client Team, the focus is on tax-aware investing and aligning financial strategies with clients' purposes. Brian introduces Anthony Mlachnik, a new senior wealth manager at Annex Private Client, who shares his background and his experience working with complex clients nationwide.The discussion centers on the importance of tax-aware investing, which involves aligning estate planning, investments, and tax strategies to optimize client outcomes. Anthony emphasizes the need to define a client’s purpose—such as family happiness or legacy building—to guide financial decisions. Key strategies discussed include:Tax-Aware Investing: Making investment decisions with tax implications in mind, such as minimizing taxes through asset allocation and loss harvesting.Purpose-Driven Planning: Helping clients identify their goals (e.g., spending time with family or passing wealth to future generations) to align financial strategies.Tax Loss Harvesting: Selling assets at a loss to offset capital gains, either in the current year or carried forward, to reduce tax liabilities.Managing Large Gains: Gradually reducing concentrated stock positions to avoid large tax hits, using tools like loss harvesting, donor-advised funds, or exchange funds for tax efficiency.Long-Term vs. Short-Term Gains: Prioritizing long-term capital gains for better tax rates and considering charitable giving to manage highly appreciated assets.Estate and Distribution Planning: Tailoring strategies based on whether clients want to spend wealth during their lifetime or pass it to heirs, leveraging tax benefits like step-up in basis at death.Anthony stresses making investment decisions first and tax decisions second to avoid missing opportunities. The episode highlights the power of compounding tax savings over time and the importance of working with professionals to navigate dynamic tax laws and emotional decision-making, especially during retirement distributions. The episode concludes with a promise to continue the discussion in the next installment.