Case Studies: How We Think Through Real Situations
Every financial life is a different puzzle. The three hypothetical scenarios below — drawn from the kinds of situations we see most often across Dallas–Fort Worth — show how we approach the work: a business owner preparing to sell, an executive managing equity compensation, and a retiree deciding what to do with decades of company stock. Names and details are illustrative composites, not actual clients, but the thinking is exactly how we operate. Our first priority is helping you take care of yourself and your family. We want to learn more about your personal situation, identify your dreams and goals, and understand your tolerance for risk. Long-term relationships that encourage open and honest communication have been the cornerstone of my foundation of success.
Case Study 1: The Fort Worth Business Owner Two Years from Selling1
The situation
A married couple in their late 50s owns a specialty logistics company in Fort Worth built over 25 years. A competitor has made informal overtures, and the owners believe a sale could come within two to three years. Nearly everything they own is tied up in the business, their estate documents are a decade old, and they have no clear picture of whether a sale would actually fund the retirement they want.
The complexity
Three questions had to be answered in the right order. First, what is the business realistically worth, and what would the owners actually keep after taxes under different deal structures — asset sale versus stock sale, cash at close versus earnout? Second, could any of the proceeds be repositioned before a sale — through gifting, charitable structures, or entity planning — while those strategies were still available? Third, what does life after the sale cost, and does the after-tax number cover it?
The approach
Working as the financial quarterback alongside the couple's CPA and attorney, we built a personal financial plan first — the target retirement budget, travel, a lake house, and support for aging parents — so the sale had a number to clear rather than a number to hope for. Drawing on LPL's Business Owner Solutions resources, we modeled after-tax proceeds under multiple deal structures, coordinated a pre-sale gifting strategy for their two adult children, and introduced a donor-advised fund to be funded with appreciated company stock in the sale year, aligning a long-planned charitable goal with the highest-income year of their lives. Their attorney refreshed the estate documents before any letter of intent existed, while options were still open.
The outcome
When a formal offer arrived eighteen months later, the couple negotiated from a position of clarity: they knew their walk-away number, understood the tax difference between the structures on the table, and had already moved assets that needed to move early. The transition funded the plan — and the plan, not the buyer's timeline, drove the decisions.
Just as important was what came next. For 25 years, the couple's net worth had lived in a single illiquid asset: the business. After the sale, we repositioned the proceeds into a diversified portfolio built for their new chapter — equities for long-term growth; fixed income, including municipal bonds and fixed-rate annuities, for tax-aware, dependable income; and alternative investments such as private equity, private credit, private real estate, and structured products, selected to reduce correlation with traditional markets and pursue additional income potential. The owners went from one concentrated risk they controlled to a diversified portfolio designed around the life they'd built the business to afford.
Case Study 2: The Southlake Retiree with Decades of Company Stock in a 401(k)2
The situation
A 62-year-old retiring after 30 years with a major DFW-area employer came to us with what he assumed was a straightforward plan: roll his 401(k) into a diversified portfolio with us and start retirement. It was only in reviewing his 401(k) holdings before the rollover that we noticed a large, concentrated position in his company stock — roughly a third of the balance, in shares acquired over decades at a fraction of today's price. That review changed the entire sequence of his retirement paperwork.
The complexity
The opportunity was nearly lost before it was found. Net Unrealized Appreciation (NUA) rules may allow company stock to be distributed from a 401(k) into a taxable account, with ordinary income tax due only on the original cost basis, while the appreciation can qualify for long-term capital-gains treatment when the shares are sold. But the opportunity generally disappears the moment the full balance rolls into an IRA, and the rules require a lump-sum distribution done precisely, in the right tax year, after a triggering event. One instruction to the 401(k) provider given in the wrong order can eliminate the option permanently.
The approach
Before any money moved, we ran the analysis: cost basis of the company shares versus market value, his expected tax brackets in early retirement, and a side-by-side comparison of the NUA route against a full IRA rollover — including what each meant for future required minimum distributions and for the concentrated stock position itself. The mechanics were then sequenced deliberately: company stock distributed in-kind to a taxable account under the NUA rules, the remainder of the plan rolled to an IRA, and a diversification schedule set for the company shares so a tax strategy didn't quietly become a concentration problem.
The outcome
The retiree entered retirement with the appreciation positioned for capital-gains rather than ordinary-income treatment, a written schedule for reducing the single-stock exposure, and an income plan coordinating his accounts, Social Security timing, and Roth conversion opportunities in his lower-income early-retirement years. A holdings review done before the paperwork was filed — not after — changed the shape of his retirement taxes.
Case Study 3: The DFW Executive with Concentrated Equity Compensation3
The situation
A 52-year-old senior executive at a large public company headquartered in the DFW area has accumulated a mix of restricted stock units, non-qualified stock options, and shares purchased through an employee stock purchase plan. Company stock now represents more than 60% of her investable net worth. She believes in the company — but she also remembers colleagues at other firms who watched concentrated positions fall sharply with nowhere to hide.
The complexity
Equity compensation is really three problems wearing one badge: a tax problem (RSU vesting creates ordinary income whether or not shares are sold; option exercises have their own timing consequences), a concentration problem (single-stock risk layered on top of career risk at the same employer), and a planning problem (vesting schedules, trading windows, and 10b5-1 considerations restrict when anything can happen). Solving one carelessly can worsen the others.
The approach
We mapped every grant — vesting dates, exercise windows, cost basis, and tax character — into a single calendar, then built a multi-year diversification schedule that worked within her trading windows and spread the tax impact across several years rather than concentrating it in one. For the stock options specifically, we used StockOpter analytics to model the timing of exercises and sales: Black-Scholes-based metrics measured how much theoretical time value remained in each grant, and we set objective thresholds in advance — when a grant's remaining time value fell below its target level, it became a candidate for exercise and diversification. Decisions followed the framework, not the day's emotions. That discipline cuts both ways: it removes the fear that sells too early, and it removes the temptation to hold out for ever-higher prices — a bet that can unravel quickly if company-specific risk surfaces or the economy turns. Newly vesting RSUs were directed to diversification on arrival, and a portion of the appreciated ESPP shares funded her family's charitable giving, moving the most tax-awkward shares out of the portfolio first.
The outcome
Over the following three years, the concentrated position was reduced to a level the overall plan could absorb, taxes were spread deliberately instead of arriving by accident, and the executive stopped making stock decisions based on conversations at lunch with colleagues. When a grant hit its pre-set threshold, the trade was an execution, not a debate — the modeling had already answered the question a volatile week would otherwise re-open.
Facing Something Similar?
If one of these situations rhymes with yours — a business you may someday sell, equity compensation stacking up, or a 401(k) full of company stock — the first conversation is complimentary, and it's the right time to have it before decisions become irreversible.
1 Case Study 1 is a hypothetical composite presented for illustrative purposes only. It does not depict an actual client or actual results, and it is not a guarantee of future results. Individual circumstances vary; consult your tax and legal professionals regarding your specific situation. Alternative investments involve additional risks, including illiquidity and loss of principal, and are generally available only to investors who meet specific qualification requirements. Fixed annuities are long-term investment vehicles designed for retirement purposes; guarantees are based on the claims-paying ability of the issuing insurance company. Municipal bond income may be subject to the alternative minimum tax, and diversification does not protect against market risk.Our first priority is helping you take care of yourself and your family. We want to learn more about your personal situation, identify your dreams and goals, and understand your tolerance for risk. Long-term relationships that encourage open and honest communication have been the cornerstone of my foundation of success.
2 Case Study 2 is a hypothetical composite presented for illustrative purposes only. It does not depict an actual client or actual results, and it is not a guarantee of future results. NUA treatment depends on meeting specific IRS requirements; consult your tax professional before making distribution decisions.
3 Case Study 3 is a hypothetical composite presented for illustrative purposes only. It does not depict an actual client or actual results, and it is not a guarantee of future results. Individual circumstances vary; consult your tax and legal professionals regarding your specific situation. Analytical tools such as StockOpter and models such as Black-Scholes rely on assumptions and estimates; they are used to inform decisions, not to predict outcomes, and no modeling tool can eliminate the risk of loss.