Wealthyist

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

  1. 1d ago

    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.

  2. 5d ago

    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.

  3. Oct 2

    Wealthyist E79 | 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.

  4. Sep 25

    Wealthyist E78 | 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.

  5. Sep 18

    Wealthyist E77| 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.

  6. Sep 11

    ICYMI: Wealthyist E44 | From 9/11 to 2 Successful Exits: Building Transferable Businesses & Planning Life After the Sale with Andy Oliver

    In this replay of Wealthyist Episode 44, host Anthony Mlachnik sits down with Andy Oliver, a 30-year finance veteran, two-time business founder/exiter, and partner at Oak Hill Business Partners, a boutique consulting firm that helps lower-middle and middle-market owners dramatically increase enterprise value and prepare for a successful exit. Key highlights and takeaways: Andy’s Unusual Journey  Survived 9/11 (was half a block from the South Tower), which prompted him and his wife to leave NYC and return to Milwaukee. First exit: Co-created the first municipal-bond primary-market pricing system in the 1990s (sold to a UK firm). Second exit: Founded Gear Wash, a firefighter-gear cleaning/disinfection company born from post-9/11 safety research (sold in 2020 right as COVID began).The Biggest Blind Spot for Business Owners  Most owners are great at building the business but terrible at building a personal post-exit plan (financial, lifestyle, purpose). More than 50% have never calculated how much capital they actually need to replace their salary with passive income or what they’ll do with their time after the sale. What Actually Drives Enterprise Value & Exit Price  The business must be transferable: owner must decentralize themselves (strong COO/GM, documented SOPs, job descriptions, integrated data systems). Lack of these = heavy valuation discounts during due diligence. Clean, real-time data and KPIs are non-negotiable in today’s market.Execution & Accountability Traction/EOS praised as a simple, proven system to create cadence and accountability. Without disciplined execution, enterprise value stalls regardless of a great product. Exit Planning Framework Andy Uses  Certified Exit Planning Advisor (CEPA) via the Exit Planning Institute. “Value Acceleration Methodology”: Start with a rough valuation → align personal + financial + business plans → de-risk and grow → decide whether to exit or keep growing. Personal Advice from Andy Start entrepreneurial ventures earlier if possible. Understand compounding: save and invest early, take calculated risks. Prioritize health (he works out 6 days a week) and social connections (he jokes about starting a “ROMEO Club” – Retired Old Men Eating Out – when he retires).

  7. Sep 4

    Wealthyist E76: Comfort With a Bit of Chaos: Why the Wealthy Are Trading Beach Resorts for Culture, Adventure, and One Night as a Local with Matt Reimer

    On this week's Wealthyist, Tom Parks of Annex Wealth Management talks with Matt Reimer, U.S. director of Nerpa Travel, about how high earners can use travel as more than a reward or a padded escape. Nerpa is named after the freshwater seal of Russia’s Lake Baikal — a nod from Welsh founders Kevin and Tom (one of whom is married to a Russian). The company sells small-group trips that keep luxury lodging and logistics but add cultural immersion and “a bit of chaos.” Their tagline is comfort with adventure: nice beds, airport pickups, and planned days, plus at least one “one night local” experience so guests stop being visitors and start participating — Muay Thai and match betting in Thailand, for example.Reimer’s own path is the episode’s origin story. After years in retirement plans, he joined a seven-day, 230-mile mountain-bike trip in Wales run by Nerpa’s founders, then cashed out of his firm. He’d already done the five-star island circuit. What he wanted next was disconnection, physical effort, and a different way of seeing the world.The pitch to wealthy travelers is specific. Insulation and convenience make it too easy to open a laptop on the beach. Nerpa’s clients have often “been everywhere” and still feel like tourists. The company scouts every route itself (a “recce”), cuts the AI-famous time-wasters, and builds guardrails: a core itinerary with some daily options, groups of about 10–15, evenings together, Wi-Fi at the hotel if work can’t wait. Typical trips run about ten days, planned 18 months out so busy people can block the calendar.Status fades fast. Poor connectivity and long days outside produce an adjustment, then calm. Reimer argues that kind of “good suffering” — plus seeing how other cultures work and play — helps people think differently about stuck business and life problems. Small groups also become unexpectedly useful networks.Nerpa has three tiers: Bespoke: custom family or friend trips after a full scout, with honest pushback on weak ideas.One Night Local (the mid-tier sweet spot for executives): luxury plus one deep local night.Adventure-first (e.g., Lost in Vietnam on electric motorcycles): more freedom, slightly less polish, often a younger or more affordable crowd.Geography is expanding from a UK and Asia base toward Africa (a planned slow electric-motorcycle ride) and eventually South America. The advice isn’t “never do the beach or the cruise.” It’s: do those if you love them — and also design the second half of life around trips that take decisions off your plate, put you in the culture, and leave room to come back changed.Find Nerpa at nerpatravel.com, on X and Instagram, or Reimer on LinkedIn.

  8. Aug 31

    Wealthyist E75: From One Truck To Gen Two: Building a Life—and a Business—Outdoors with Bret Achtenhagen

    Kent Halleen, wealth manager for Annex Private Client, sits down with Bret Achtenhagen, president and CEO of Seasonal Services, the Wisconsin landscaping firm he launched in 1994 with a truck, a tractor, and a newly announced first child on the way. Brett walks through that first $70,000 year, the farm-kid love of dirt and seasons that pulled him out of an office, and 32 years of steady growth built on natural stone, time in clients’ kitchens, and outdoor spaces people actually use. The conversation turns to the harder work now underway: shifting from founder to second generation as his 31-year-old son begins to take over—what the next generation wants the company to become, and how to pass a family business without breaking the family. Halleen draws the parallel to wealth planning: tax, gifting versus buyouts, estate design, and the cost of leaving concentrated “plants” unpruned. Along the way they cover the firm’s process (motivation first, then design and budget), decades-long client relationships that now include the kids’ homes, and current high-end demand—wellness courtyards, year-round pavilions, and synthetic turf that still serves a deeper brief: get families off screens and back outside.

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About

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

Information

  • Creator
    Annex Wealth Management
  • Years Active
    2025 - 2026
  • Episodes
    83
  • Rating
    Clean
  • Copyright
    © 2026 Annex Wealth Management