Wealthyist

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.

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.

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.

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.

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).