Client stories

Four founders, four different years.

What working with us looks like in practice, told plainly: what the situation was, what we did, and where it landed.

These stories are fictional. Each is a composite written to show how we work. Names, numbers and details are invented. They aren’t testimonials, and they don’t describe any real client’s experience or results.

Calm, dark ocean at dusk under low clouds.

Story one

The biotech founder and the lockup

Company
Clinical-stage biotech, recently public
Situation
Most of her net worth in one stock
Timeline
Two years
Worked with
A partner, an associate, company counsel

The situation

A scientist-founder whose company had gone public eighteen months earlier. Her 180-day lockup had long since ended, but she hadn’t sold a share. Every time the stock dropped she didn’t want to sell low, and every time it rose she didn’t want to miss more upside. Meanwhile, a single trial readout could halve her net worth.

What we did

We started with a number: how much she needed, invested plainly, to never have to work again. Then we worked backward to how much stock that meant selling. With company counsel, we set up a 10b5-1 trading plan that sold on a fixed schedule over eighteen months, so the decision was made once, in advance, instead of every morning.

“I didn’t need a prediction. I needed to stop checking the price at 5 a.m.”

Where it landed

The plan ran as written. She kept a meaningful stake in the company she believes in, and the rest now pays for the life she’d already planned. She still checks the stock, just not first thing.

Story two

The brewery owners and the earnout

Company
San Diego craft brewery, 40 employees
Situation
Sale to a national brewer, three-year earnout
Timeline
Fourteen months before close, ongoing since
Worked with
A partner, their deal attorney and CPA

The situation

Two cofounders who had built the brewery from a garage. The offer was generous, but a third of it depended on hitting volume targets for three years after the sale, under an owner they didn’t control. They also didn’t want to walk away rich while the people who’d brewed the beer got nothing.

What we did

We modeled the offer in after-tax dollars, with the earnout valued at what it would likely pay, not what it could pay. That changed the negotiation: working with their attorney, they traded some earnout for more cash at closing. We helped them set aside a share of the proceeds as a retention bonus for staff, and planned their own spending as if the earnout would pay nothing.

“Every banker we met wanted to manage the money. They were the only ones who asked what we wanted our lives to look like first.”

Where it landed

The earnout paid out partly, which was fine, because nothing depended on it. Both founders left after the first year. One is building a small farm in Ramona. The other opened a bottle shop because, it turns out, some people just like working.

Story three

Employee number seven and the tender offer

Company
Venture-backed software company
Situation
Vested options and a company tender offer
Timeline
Six weeks to decide, then ongoing
Worked with
A partner and an associate

The situation

An early engineer with a large block of incentive stock options, most never exercised, and a tender offer that closed in six weeks. The paper value was life-changing. So was the potential tax bill: exercising the wrong way could trigger alternative minimum tax on shares that might never be worth that price again.

What we did

We ran the numbers for five scenarios, from selling nothing to selling everything the tender allowed, each showing the cash in hand after tax and what would be left in the company. The engineer chose to sell about a quarter: enough to pay off the house and fund a real emergency reserve, without betting against the company.

“Five scenarios on one page. That’s all I wanted, and nobody had ever shown me that.”

Where it landed

No surprise tax bill in April. A paid-off mortgage. And a written plan for the next tender, so the decision next time takes an afternoon instead of six weeks.

Story four

Selling the family business after forty years

Company
Precision-parts manufacturer she founded
Situation
Sale to a private equity firm, rollover equity
Timeline
Three years, beginning well before the sale
Worked with
A partner, her attorney and CPA, her three children

The situation

A founder in her sixties who started a machine shop at twenty-five and grew it to supply parts to aerospace companies up and down the coast. None of her children wanted to run it. She wanted to sell, keep the employees safe, and be fair to three adult children without turning the money into the family’s main topic of conversation.

What we did

Three years before the sale, working with her attorney, she moved part of her ownership into trusts for the children while the company was valued lower. At the sale, she rolled some equity into the buyer’s new company, which kept her involved and deferred part of the tax. We ran two family meetings, with her permission, so the children heard the plan from her and from us at the same time.

“The best meeting was the one where my kids asked all the questions I’d been afraid they’d ask.”

Where it landed

She retired with more than she needed and a plan for giving the rest away in her lifetime, not after. The shop still runs, under a new name, with most of the same people.

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