A painting business owner who didn't know what he didn't know

A decade running his own crew, steady local demand, young family at home. Also: no LLC, no retirement account, no disability insurance, no estate plan, and a personal checking account doubling as the business account. None of this was a bad decision. He had just never been walked through the options.

What we worked on

• Formed an LLC and separated personal and business finances
• Set up a Safe Harbor 401(k) for the business, which lets him max his own contributions while also building retirement benefits for his crew without running into nondiscrimination testing problems
• Own-occupation disability insurance, the single most important policy a tradesman doesn't have when he walks in the door
• Term life sized to replace his income through his youngest child's college years
• Estate documents: will, powers of attorney, and a minor's trust naming a guardian and trustee

Ryan didn't pick us on a fee comparison. He wanted someone he knew, and someone who understood running a small business. We run one. We know what cash flow looks like when a truck breaks down or a job goes sideways. That context shapes the advice.

"If you got a $10,000 cash bonus, would you buy company stock with it?"

Alex was doing what most tech sales people do with their RSUs: nothing. Shares vested every quarter, the company sold a portion to cover the 22% federal withholding, and the rest sat in his brokerage account. After three years, his single-stock concentration in his employer was larger than his 401(k). He hadn't decided to hold the stock. He had defaulted into it.

The answer was obvious. But that's effectively what he had been doing every quarter, simply by not selling what vested.

The other issue was tax. His employer withheld 22% at vest. He was in the 35% bracket. Every vest was under-withholding, and the gap was coming due in April.

What we built

We treated RSU vests as funding capacity, not as an asset class. As each tranche vested, we sold the shares and routed the proceeds through tax-advantaged accounts in sequence:

• Mega backdoor Roth via after-tax 401(k) contributions, converted in-plan
• Backdoor Roth IRA for both spouses
• HSA maxed and invested rather than spent on current healthcare
• 529 plans for the kids

Same income. Different destination. Assets that would have stayed concentrated in a single stock in a fully taxable account were systematically shifted into tax-advantaged accounts and diversified.

"How do I actually know if I can retire?"

David had been working with another advisor for two years. Managed portfolio, quarterly statements, annual meetings. He had what looked like a financial advisor relationship. What he didn't have was an answer to the question he actually cared about.

That was the first sentence of our first conversation. Sixty-four, decades of consistent saving, a pension on the way, and a portfolio that grew nicely. Nobody had ever sat down with him and modeled what his actual life looked like after his paycheck stopped.

So we did that first. Pension, projected Social Security at different claiming ages, portfolio drawdown — layered into one picture and stress-tested against a longer-than-average lifespan, an early market downturn, and a long-term care event. The answer was yes. He could retire. He had been able to retire for a while. That was the light-bulb moment.

The technical work

Once the income picture was settled, we mapped Roth conversions across the window between his retirement date and his Required Minimum Distribution age. His income would drop substantially the year he stopped working, and he planned to delay Social Security to take advantage of the increased benefit. That created several years of unusually low taxable income.

We sized conversions each year to fill his current bracket without pushing into the next one. The result: he pays tax on a portion of his pre-tax savings now, at a known low rate, instead of paying tax on much larger RMDs later. It also reduces what his widow would face as a single filer in higher brackets later in life.

Investment management is one input into a retirement plan. It is not the plan. David hired an advisor to manage his money. He needed one to answer his question.