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by Annex Wealth Management
Wealthyist, the podcast that discusses the lifestyles, choices, and strategies of the wealthy. Each week, the Annex Private Client team talks to experts in a variety of areas to discuss trends and paths visited by people who have built or are in the process of building significant wealth.
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- 3 days ago26 min
Wealthyist E82| The Luxury of Aging Well with Ageless Elite
Host Deanne Phillips (Annex Wealth Management) interviews Gabriella “Gaby” Chomiak (founder, board-certified nurse practitioner) and Julie Boschert(board-certified nurse practitioner) of Ageless Elite, a luxury concierge mobile medical spa based in Naples, Florida.The central premise is simple: building and protecting wealth matters, but it loses value if you don’t feel well enough to enjoy the life it enables. Affluent clients increasingly treat health, energy, and appearance as part of the same lifestyle investment.What clients actually wantThey want to look good, feel good, and keep living the life they already have — energy for family, activities, and routines without physical or appearance-related limits. Looking younger, feeling younger, and functioning better are intertwined, not separate goals.The Ageless Elite modelThey bring a high-end experience to clients’ homes or gated-community wellness days in a custom luxury van (think leather treatment chair and crystal chandelier). Services combine aesthetics (Botox, fillers, microneedling, skincare) with medical wellness: comprehensive labs (including beyond standard bloodwork), hormone optimization, peptides, NAD+, IV therapies, weight management, and functional-medicine approaches that start with gut health and nutrition.Key advantages for wealthy clients:Time is the ultimate luxury — no driving, waiting rooms, or fragmented 15-minute appointments.Privacy or social option — some prefer discreet home visits; others enjoy community wellness days with friends or family.One-stop integration — aesthetics, hormones, labs, and preventative care under coordinated nurse practitioners instead of juggling multiple providers.Memberships scale from basic aesthetic plans to full wellness packages.Deeper approach to aging and longevityThey emphasize root-cause care over surface fixes. Hair loss, fatigue, or skin issues often trace to thyroid, vitamins, nutrition, or medication side effects rather than just “aging” or GLP-1s. Care is individualized: labs first, proper sourcing of compounds, education on risks/side effects, and realistic expectations (they turn people away when expectations are unrealistic). They stress ongoing access to the provider, not one-and-done treatments.What affluent people sometimes get wrongMoney makes it easy to chase the latest internet/AI/friend-recommended peptide, injection, or “longevity” protocol. That can lead to polypharmacy, conflicting advice, and wasted spending. The real edge is thoughtful, provider-guided, personalized care rather than buying every promising treatment.Host takeawayShow me your calendar and your spending, and it reveals priorities. For many wealthy people, control over time and the ability to feel well enough to use their resources have become the highest-value purchases. The ultimate luxury isn’t looking younger — it’s having more good years to actually live the life the money was meant to support.Overall, the episode frames premium concierge wellness as both a business model responding to high-net-worth priorities and a practical response to the limits of conventional care.
- 2 weeks ago26 min
Wealthyist E82 | Beyond the Scoreboard: Building Character, Navigating Club Sports, and the NIL Era with 24UP
In this episode of Wealthyist, host Kent Halleen (wealth manager with Annex Private Client) sits down with fellow Annex team member Anthony Mlachnik (senior wealth advisor) to explore youth club sports, parenting challenges, and the work of 24UP—a Milwaukee-area 501(c)(3) nonprofit Anthony co-founded.Anthony shares how 24UP (originally the Rapid Acceleration Program) began roughly 17 years ago. After college basketball and forgoing a chance to play professionally in Europe, he partnered with his brother-in-law and used connections through Marquette Law’s pro-bono nonprofit support to launch a basketball-focused program. The mission: use the sport kids actually care about as a vehicle to teach transferable life skills—perseverance, discipline, emotional intelligence, handling failure and success, and character—rather than relying on less engaging formats like PowerPoints. The program emphasizes development-first skill work (drawing on a European-style approach), camps, clinics, team coaching, and scholarships for needs-based athletes. It now reaches about 10,000 kids per year in some form and has produced alumni success stories (including NBA player Brandin Podziemski) plus community impact through partnerships with groups like the Pat Connaughton Foundation, Marquette NIL collectives, Make-A-Wish, Children’s Wisconsin, and Thanksgiving food drives.Key advice for parents (especially those with the resources of wealthier families):Start with passion at home. The best results come from parents leading by example—playing catch, shooting hoops, or just making it fun—rather than early pressure or expensive individual training. Kids need to discover genuine love for the activity so they don’t burn out or participate only to meet expectations. Timing varies (sometimes earlier for boys, later for girls); patience matters.When to step up. Club sports or extra training often make sense once a child is among the top one or two on their school/feeder team and shows competitive drive (typically mid-elementary to middle school). “Iron sharpens iron”—playing up or with stronger competition can accelerate growth while protecting confidence.Choosing coaches and programs. Prioritize trusted recommendations and real-world experience over certifications alone. Look for character, a development-focused culture, and coaches who avoid extreme intensity. Interview the people and the organization.Equipment and brands. Shoes and gear provide some confidence and association benefits, but they matter far less than coaching quality, work ethic, passion, and development. Anthony notes that top programs (including 24UP’s New Balance partnership) focus on the player first; elite kids eventually attract brand attention rather than needing to chase it.The NIL shift. Name, Image, and Likeness opportunities are already reaching high-school sophomores (and younger) among top national talent, with shoe companies heavily involved and significant money on the table. This brings European-soccer-style academy dynamics, early contracts, and the need for business/financial guidance so young athletes (and families) don’t mishandle opportunities. The landscape is evolving quickly, creating both upside and confusion for players, parents, and college coaches.Throughout, Anthony stresses that the real goal is raising good people who happen to play sports—not just athletes—and that community and family involvement have been central to 24UP’s growth and sustainability through alumni giving and partnerships.The conversation offers practical perspective for parents entering or already in the club-sports world, while highlighting how a development-oriented nonprofit can deliver both athletic and life-long value.
- 4 weeks ago25 min
Wealthyist E81 |What Do I Want This Money to Do? From Accumulation to Intention with Deanna Tillisch
In this episode of Wealthyist (from Annex Wealth Management), host DeAnne Phillips sits down with Deanna Tillisch, a longtime philanthropy and community leader who previously ran the Northwestern Mutual Foundation and led the United Performing Arts Fund for nearly a decade. The conversation explores the pivotal shift many wealthy individuals and families eventually face: moving beyond “How do I build and protect wealth?” to the more intentional question, “What do I want this money to do?”Tillisch distinguishes between simply leaving money (often by defaulting to familiar organizations) and leaving a true intention or legacy. The latter requires strategic, multi-generational planning, due diligence, family conversations, and collaboration with advisors and attorneys. She notes that effective philanthropists typically start with a clear “why”—whether rooted in personal experience (such as her own daughter Casey’s disability and the creation of Cassie’s Fund, which supports arts accessibility and has raised far more than expected by telling a genuine story) or by identifying a systemic need (such as education gaps). Sophisticated donors go beyond writing checks: they volunteer, join boards, involve family, meet beneficiaries, and build relationships so they can see impact during their lifetimes.The discussion addresses psychological barriers common in wealth (including “bag lady syndrome” and fear of getting it wrong or losing control), the value of giving while alive rather than only through an estate, focusing deeply on a few organizations instead of spreading gifts widely, the balance of donor guidelines versus micromanagement, and the choice between perpetual endowments and spending down for urgent needs. Tillisch also covers passing values (not just causes) to the next generation through role-modeling and involvement, and how visible recognition can serve as a useful endorsement that inspires others. In a rapid-fire segment, she advocates giving while alive, focusing on fewer organizations deeply, public giving, a mix of permanent and spend-down approaches, and teaching children responsibility by example.The episode closes on the idea that a meaningful legacy is one whose impact you can witness and help sustain while you’re still here—turning accumulated assets into values, stories, and lasting change.
- Oct 12, 202618 min
Wealthyist E80 | Turning The Page: Roth, State & Local Taxes, and the Moves That Matter Before 2026 Ends
This episode of Wealthyist features Kent Halleen, wealth manager at Annex Private Client, with Jenny Jesse, manager of the financial planning team and principal author of Annex’s year-end guide, Turning the Page on 2026. Jessee has been at Annex Wealth Management about five years, starting as a college intern and moving through specialist and senior planner roles. Her focus is creative strategy for clients now that the Tax Cuts and Jobs Act provisions are no longer facing a sunset, thanks to the One Big Beautiful Bill.With rates locked in for the planning horizon, Roth conversions are a frequent recommendation, especially in the 12%, 22%, and 24% brackets. The higher State And Local Tax (SALT) cap is another lever: state and local taxes can include state income tax, property tax on a primary or vacation home, and, in no-income-tax states, sales tax.The changes are federal, though some states (Arizona is cited) have adopted pieces such as relief on tips, overtime, or an enhanced senior deduction. Itemizing remains less common than in prior decades unless SALT, medical costs, or large charitable gifts push a return over the standard deduction.New 2026 rules get close attention. Catch-up 401(k) contributions for those 50 and older must go to Roth if prior-year W-2 wages exceeded $150,000—a revenue offset for other tax cuts. Trump accounts (set up only through the official app or IRS Form 4547, not unsolicited emails) function as a child retirement vehicle; children born 2025–2028 can receive a $1,000 government seed, and balances can later be converted to Roth once the child has earned income. Leftover 529 funds can also move to Roth, subject to a roughly $35,000 lifetime cap and annual earned-income limits, not as a single bulk rollover.On estates, the federal exemption is $15 million per person ($30 million joint), which removes many families from estate-tax concern, though lifetime gifts and “living legacy” transfers still matter for larger estates or when heirs can use money sooner. Gifts above the $19,000 annual exclusion are not immediately taxed; they use lifetime exemption and are reported on a gift-tax return. Some states, notably Illinois, keep much lower exemptions.Charitable tactics include donor-advised funds funded with appreciated stock (unchanged in structure, but now subject to a 0.5% of Adjusted Gross Income (AGI) deduction floor) and qualified charitable distributions from Individual Retirement Accounts up to $111,000 once the owner is 70½.Qualified Charitable Distributions (QCDs) can satisfy Required Minimum Distributions (RMDs)—age 73 for those born 1959 or earlier, 75 for those born 1960 or later—while keeping AGI lower for Income-Related Monthly Adjustment Amount (IRMAA), Social Security taxation, and the new senior deduction. Non-itemizers can also claim a new cash charity deduction of $1,000 single / $2,000 joint.The guide is at annexwealth.com. Jesse’s closing point is that the goal is lifetime (and family-unit) tax minimization, not just this year’s return—something Annex approaches with pro forma tax projections tied to investments and estate plans.
- Oct 2, 202614 min
Wealthyist E77 | Selling Your Business: Is Your Company Worth What You Think? Don't Be Surprised
Most owners know they should have an exit plan. Fewer than half do, usually because they do not know where to start. Brian Lambourne talks with Amy Kiiskila, Director of Wealth Strategies for Annex Private Client, about the do’s and don’ts of selling a business.The starting point is a decision tree, not a signed deal. Internal sale to key employees or family, third-party buyer, or private equity. You do not need the answer today. You do need the universe of options, and a team in place early: attorney, CPA, and financial advisor. The advisor is the role owners most often skip. That is a mistake. The sale price is not the lifestyle. After taxes, debt, and what the family actually spends, the check may not be enough, and money parked in a money market because no one planned the next chapter is a common result.Family businesses add another layer. Do not assume what active and inactive children want. Selling to one child so siblings are not disadvantaged can work, but only if you have already worked through how that child pays for it and how the family functions afterward.The biggest advantage is time. A four- or five-year runway means more control over structure, asset sale versus stock sale, charitable planning, and gifts to children or trusts. For higher-net-worth owners, gifts made far enough before a sale can move future appreciation out of the estate. The 2026 estate-tax exemption is $15 million per person, but a valuable business can still make estate tax the issue, and that planning is timing-sensitive. Show up two months before closing asking to “save taxes now,” and the buyer has the leverage.What not to do: rely on a verbal agreement, download a form and call it a sale, or treat TikTok, YouTube, or ChatGPT as the plan. AI can surface useful questions. It is a starting point, not a valuation or a legal opinion. Owners routinely misjudge what the company is worth. A valuation expert, investment banker, or accountant running real multiples takes the emotion out of the number.Start earlier. Document the plan. Put the team in the room before you pick a buyer.
- Sep 25, 202618 min
Wealthyist E77 | 2026 Year-End Tax Planning: The Sunset That Never Came
This week on Wealthyist, Kent Haleen sits down with Jenny Jesse, manager of Annex’s financial planning team and lead author of the firm’s year-end guide, Turning the Page on 2026.Jenny traces her path from intern to planning lead and gets to the point: OBBBA locked in the TCJA rates, so high-net-worth families are no longer planning against a sunset. The work this year is using the code that is actually in place.The moves she sees most: Roth conversions while the 12%, 22%, and 24% brackets are still historically cheap, and using the higher SALT cap—income tax, property tax, and, in no-income-tax states, sales tax. Arizona has adopted pieces of the federal bill; Florida has not, so the federal picture is the same but the state overlay is not.They unpack the surprise Roth catch-up: if you are 50+ and had 2025 W-2 box 3 wages over $150,000, 2026 catch-ups to a 401(k), 403(b), or 457(b) must go Roth. Congress wanted revenue now.On kids’ money: Section 530A “Trump” accounts are real, but nobody is opening one for you—ignore the spam, use the official app or IRS Form 4547. Kids born 2025–2028 may get a $1,000 federal seed. Pair that with leftover 529 dollars, which can move to a Roth only over time, with earned income, and with a $35,000 lifetime cap—not as a lump sum.Estate planning got quieter and more personal. The federal exemption is $15 million per person / $30 million joint, so fewer families face a 40% federal estate tax. Annual $19,000 gifts still matter if the estate will clear that bar, and for “living legacy”—grandparents who would rather watch the money get used than leave a pile later. Gifts above $19,000 are generally not taxed when given; they use lifetime exemption and get reported on a gift-tax return. State rules still bite: Illinois is the nearby example with a much lower threshold.Charitable giving is the other lever. New for 2026: up to $1,000 / $2,000 of cash charity for people who take the standard deduction, and a 0.5% of AGI floor if you itemize. Donor-advised funds still work for appreciated stock and bunching. Once RMDs start (73 or 75, depending on birth year), QCDs—up to $111,000 per person from an IRA at 70½+—can satisfy the RMD, stay off the return, and help with IRMAA, Social Security taxation, and the new senior deduction.Jenny’s words to think on: do not optimize only 2026. Annex builds a pro forma return, then ties tax, investments, estate, and the financial plan across decades. Minimize tax for the family line, not just this filing season.
- Sep 18, 202620 min
Wealthyist E76| Opportunity Zones 2026: Defer the Tax, Don’t Ignore the Lockup
Qualified Opportunity Zones (QOZs), created by the 2017 Tax Cuts and Jobs Act, let investors roll capital gains (from stocks, a business sale, real estate, or other assets) into a Qualified Opportunity Fund within 180 days and defer the tax. The original 10-year window ends in 2026, so deferred gains become taxable this year even if the investment is not sold—creating a liquidity pinch for some holders. Early investors also received basis step-ups (10% after five years, another 5% after seven) and the chance for tax-free appreciation after a full decade.A subsequent tax law change revived and made the program more permanent, with rolling new zones and a shorter five-year holding period for key benefits. Funds typically target real estate or businesses in state-designated distressed areas and are structured like private-equity or private-real-estate vehicles.The hosts emphasize that the tax deferral is real but incomplete: it does not eliminate tax, and the underlying investments have often delivered modest or poor returns after fees. Liquidity is limited; few funds have built-in exit mechanisms or a developed secondary market, so investors can face multi-year lockups. Risks include concentrated exposure to higher-risk real estate, sponsor quality and fees, and opportunity cost versus simply paying the tax and investing in more liquid, diversified assets. Direct indexing and other tax-aware strategies can achieve similar goals with more flexibility.Annex’s approach is cautious: treat QOZs as a specialized tool, not a default tax strategy. Evaluate sponsor track record, expected net-of-fee returns, portfolio fit, and liquidity needs before committing. The program is being marketed heavily; the investment merits must still stand on their own.
- Sep 11, 202625 min
ICYMI: Wealthyist E44 | From 9/11 to 2 Successful Exits: Building Transferable Businesses & Planning Life After the Sale with Andy Oliver
In this replay of Wealthyist Episode 44, host Anthony Mlachnik sits down with Andy Oliver, a 30-year finance veteran, two-time business founder/exiter, and partner at Oak Hill Business Partners, a boutique consulting firm that helps lower-middle and middle-market owners dramatically increase enterprise value and prepare for a successful exit.Key highlights and takeaways:Andy’s Unusual Journey Survived 9/11 (was half a block from the South Tower), which prompted him and his wife to leave NYC and return to Milwaukee. First exit: Co-created the first municipal-bond primary-market pricing system in the 1990s (sold to a UK firm). Second exit: Founded Gear Wash, a firefighter-gear cleaning/disinfection company born from post-9/11 safety research (sold in 2020 right as COVID began).The Biggest Blind Spot for Business Owners Most owners are great at building the business but terrible at building a personal post-exit plan (financial, lifestyle, purpose). More than 50% have never calculated how much capital they actually need to replace their salary with passive income or what they’ll do with their time after the sale.What Actually Drives Enterprise Value & Exit Price The business must be transferable: owner must decentralize themselves (strong COO/GM, documented SOPs, job descriptions, integrated data systems). Lack of these = heavy valuation discounts during due diligence. Clean, real-time data and KPIs are non-negotiable in today’s market.Execution & 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).
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About Wealthyist
Wealthyist, the podcast that discusses the lifestyles, choices, and strategies of the wealthy. Each week, the Annex Private Client team talks to experts in a variety of areas to discuss trends and paths visited by people who have built or are in the process of building significant wealth.
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