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 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.

  2. Sep 18

    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.

  3. 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).

  4. Sep 4

    Wealthyist E75: 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.

  5. 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.

  6. Aug 21

    Wealthyist E74: Not All Money Is Good Money: Building Athlete Brands, Protecting NIL Deals & Planning Beyond the Game with Griselda Aldrete

    In this episode of Wealthyist, host Deanne Phillips talks with Griselda Aldrete, founder and CEO of Star Sports Consulting Group and Andretti Law and Consulting. Aldrete’s work sits at the intersection of law, business, athletics, and family advising, helping high-school, collegiate, and professional athletes (and their parents) navigate the modern sports landscape.The conversation centers on how athletes have become entrepreneurs and brands far earlier than in the past—especially after the landmark House case opened the door to Name, Image, and Likeness (NIL) compensation. ldrete describes the “Wild West” reality of NIL: inconsistent state reporting rules, multi-state tax obligations, the student-vs-employee debate, and the flood of opportunistic or poorly advised deals. She stresses that “not all money is good money,” urging families to scrutinize contracts (including perpetual clauses), protect intellectual property and online presence (with AI now a new risk), and treat the athlete’s name and image as long-term assets.Key themes include: Starting conversations as early as age 8–12 while carefully balancing genuine athlete passion against parental dreams and avoiding burnout.Building a full support “house” (lawyer, financial advisor, marketing/PR, CPA) rather than relying on a single agent or handshake deals.Cultural and practical barriers to financial literacy—especially in minority communities—where sudden income can trigger family obligations, overspending, or risky behaviors.The critical backup plan of finishing education and developing life-after-sports skills, given that fewer than 1% of athletes go pro.Practical red flags and best practices for contracts, brand curation, and long-term wealth building versus short-term income.Aldrete’s closing advice to parents of a talented 16- or 17-year-old: ask where the athlete wants to be in five years and prepare the safest physical, mental, and financial path there; avoid chasing only the glitz without first getting the “house in order.”

  7. Aug 14

    Wealthyist E73: From Shop Floor Grind to Functional Edge: How Health Supercharges Entrepreneurial Success with Mike Chirchirillo

    On this episode of Wealthyist, host Anthony Mlachnik (senior wealth advisor) sits down with Mike Chirchirillo—certified trainer, functional medicine health coach, co-owner of Collective Flow Milwaukee, and manufacturing consultant—for a conversation that bridges business performance and personal vitality.Mike traces his path from joining a family metal-stamping and sheet-metal fabrication business in Illinois in 2008, just as the recession hit. With ~80% of revenue tied to automotive and heavy customer concentration, he worked his way up from the shop floor: implementing an ERP system for better cost accounting and decision-making, overseeing a full facility move, and eventually becoming president and director of sales. Over 3.5 years he successfully diversified the customer base, but the relentless grind left his energy and health depleted.That personal toll, combined with his wife’s long battle with ulcerative colitis (she was on a cascade of medications), led them to functional medicine. Through holistic changes in sleep, nutrition, stress management, and movement—inspired in part by approaches like those of Dr. Mark Hyman—she became symptom- and medication-free in about 2.5 years. Mike trained in the field himself, extracting practical “biohacks” he could apply as an entrepreneur for better energy, clarity, focus, and recovery. He now helps small-to-midsize manufacturing owners and high performers reduce “inflammation” in both body/brain and business, arguing that the two are deeply linked: when leaders and teams lack motivation, consistency, or resilience, health issues are often a root cause.He outlines five key lifestyle pillars that drive inflammation (and thus performance): Fitness Movement/flexibility (joint range of motion) Sleep quality (not just quantity) Stress management (breathwork, flow states) Nutrition (whole, “Mother Earth” foods)For time-poor, high-means individuals, he prioritizes nutrition as the highest-leverage starting point—aim for the colors of the rainbow plus 9–13 servings of fruits and vegetables daily, plus hydration at roughly half your body weight in ounces of water. Sleep ranks close behind. Practical hacks include: Consistent bedtime and a wind-down routine (dim lights, warm tea, bed only for sleep/sex) Morning glass of water with lemon and a pinch of Himalayan sea salt Brief balance work (standing on one foot during calls or in line) 4-minute Tabata bodyweight sessions when time is tight Breath techniques (longer exhales to calm; longer inhales to energize) Timing sleep in ~90-minute cycles so you wake at the top of a cycle rather than deep sleepMike runs two complementary businesses: consulting that primarily helps manufacturing companies (with health tools brought in as needed when focus or execution lags) and Collective Flow, a yoga studio with a functional-medicine twist that has grown to 17 instructors. He emphasizes that health is highly individual, that lasting change follows an “aware → explore → apply” loop, and that external accountability is especially powerful for CEOs who are used to holding others accountable but rarely themselves. He also advises treating social-media comparison or guilt as a “bat signal” for constructive action rather than a spiral into negativity.The discussion closes with how high achievers differ from the merely wealthy: true high performers build financial success on their own terms—with balance, relationships, energy, and a life they actually enjoy—rather than grinding at the expense of everything else. Listeners can find Mike at mikechirch.com and Collective Flow at collectiveflowmk.com.

  8. Aug 4

    Wealthyist E72 | ESOPs: The Quiet Path from Company Stock to Wealth (and How to Keep the IRS from Taking Too Much)

    In this episode of Wealthyist, financial planning manager Tom Berkholtz sits down with senior wealth strategist Brian Lamborne of Annex Private Client to demystify Employee Stock Ownership Plans (ESOPs)What an ESOP really isAn ESOP lets a business owner sell the company to its employees. Employees rarely have cash to buy it outright, so a trust/fund is created that purchases the owner’s stock. Over time, shares are allocated to workers. For the seller, this can mean a large liquidity event (e.g., tens of millions of dollars) that requires careful planning. For employees, it functions much like a 401(k): it is ERISA-governed, tax-deferred, and funded primarily by employer contributions of company stock—no employee contributions required. Shares vest over time, and the stock of private companies is independently valued each year.Real-world impactFamiliar employee-owned companies such as Wisconsin’s Woodman’s, Hy-Vee, and Publix illustrate the upside. Long-tenured cashiers and other rank-and-file workers have walked into Annex with ESOP balances exceeding $1 million—and sometimes several million—after decades of steady contributions and company growth. These “secret millionaires next door” often never attended college yet built substantial wealth simply by staying and performing well.Key features and rules Concentration risk: Most of the account sits in employer stock while you work there. Diversification window: Once you reach age 55 and have 10 years of service, you can diversify up to 25% of the company stock over five years, then up to 50% in the sixth year—tax-free, just like selling inside a 401(k). Retirement liquidity: When you leave or retire (and are vested), the company typically buys back your shares, giving you cash that can be rolled into an IRA. Tax time bomb: The balance is pre-tax. Large accounts can produce very high Required Minimum Distributions (RMDs) starting at age 75 and push retirees into top tax brackets—especially if both spouses have sizable ESOPs.Planning opportunities The roughly 15–20-year window between the diversification age (55) and RMD age (75) is critical. Strategies discussed include: Gradually diversifying out of concentrated company stock Incremental Roth conversions in lower tax brackets over many years Qualified Charitable Distributions (QCDs) starting at age 70½—direct transfers from the IRA to 501(c)(3) charities (including churches) that never hit taxable income and can be split among multiple organizationsBottom line ESOPs are simultaneously simple in concept and highly complex in the details—every plan has its own documents and quirks. Employees should not wait until the “retirement red zone” (within five years of leaving) to understand vesting, diversification rights, buy-back rules, and tax consequences. Working with advisors who grasp both the plan mechanics and broader retirement-tax planning can turn a multi-million-dollar ESOP into lasting, tax-efficient wealth rather than a deferred tax surprise.

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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
    80
  • Rating
    Clean
  • Copyright
    © 2026 Annex Wealth Management