Wealthyist

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.

Perfect episode for any entrepreneur who knows they’ll eventually sell but hasn’t yet faced the question: “What then?”In this week’s Wealthiest 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).

Equity Compensation – what it is, why companies use it, the main types, tax pitfalls, and planning tips.Why Companies Offer Equity CompensationPrimary goal: Attract, retain, and motivate top talent (especially in tech/AI race – Google, Apple, Nvidia, etc.).Acts as “golden handcuffs” via vesting schedules (e.g., 25% per year over 4 years or a 3-year cliff).Works for both public and private companies, but private-company equity is riskier (needs a liquidity event like IPO or buyout to have real value).Main Types of Equity CompensationRestricted Stock Units (RSUs) – Most common & simplest Company gives you actual shares (not an option to buy). Vest 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. Conventional advice: “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.Non-Qualified Stock Options (NSOs/NQSOs) Right (not obligation) to buy shares at a fixed “strike price” (usually within 10 years). When you exercise and sell, the bargain element (market price − strike price) is taxed as ordinary income. Company gets a tax deduction → why employers prefer NSOs over ISOs.Incentive Stock Options (ISOs) – Less common now 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) 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.