What this can look like.
A few stories that show how the work actually goes, from the moment the money gets real to the day it finally feels handled. The people are illustrative. The situations are the kind this work is built for.
Illustrative. Not a specific client.
Acquisition · accelerated vestingThe acquisition that came faster than expected
Daniel, 41 · software engineer
Daniel spent twelve years writing code, the last four at a startup that just got bought. His vesting accelerated, and money he’d only ever seen on a screen suddenly became real. He’d bounced between three startups before this one, with a 401(k) left behind at each, none of which he’d touched. He’d always done his own taxes and managed his own money, and it had always worked. Now it didn’t feel like enough.
The challenge
A big payout he’d never planned for, and a tax bill he didn’t see coming. Three old 401(k)s scattered across former employers. No CPA, and a return that had quietly gotten too complicated to keep doing himself. Most of his net worth still tied up in the acquiring company’s stock. No plan, and a nagging sense he was about to make an expensive mistake without even knowing it.
What the work would cover
We would start by getting his whole picture onto a few pages, which he has never seen. We would plan for the tax from the deal before April, and show him when a CPA is worth bringing in. We would compare leaving his three old 401(k)s where they are with combining them. And we would build a schedule to bring down the concentration in the acquirer’s stock over time.
What changes
Daniel would know what he owns, what he is likely to owe and what comes next. The tax bill would be planned for. If he chose to combine his old accounts, they would sit in one place. He would be selling down on a schedule and not on a hunch. A plan cannot promise a result, and one stock stays a risk until it is sold.
If this looks like your situation, the Checkup is free →Illustrative. Not a specific client.
Pre-IPO · options & lockupThe window before the IPO
Priya, 38 · product lead at a company heading public
Priya’s company filed to go public. She was holding a pile of options and RSUs and a lot of questions she didn’t know who to ask. She’d managed her own money since her twenties and was good at it, but options, lockups, and something called AMT were a different language entirely.
The challenge
A coming IPO full of decisions she couldn’t take back. Options she wasn’t sure when to exercise, and a tax bill that could hit even if she didn’t sell a single share. A trading blackout that could stop her selling when the lockup lifted, unless a plan was already in place. And nearly everything she owned about to ride on one stock.
What the work would cover
We would run the tax math before she exercises, so the number is not a shock. We would work out whether she needs a trading plan and, if she does, help her set it up well ahead of the lockup’s end. We would check whether her shares qualify for a break that can shield a large piece of the gain. And we would map out how to turn paper into a diversified financial life once she can sell.
What changes
Priya would go into the IPO with a plan and not a guess. She would know what she means to exercise and when, what the tax is likely to be, and how she plans to sell. A plan cannot say what the stock will do, and the lockup and her company’s trading policy still decide when she can sell.
If this looks like your situation, the Checkup is free →Illustrative. Not a specific client.
Acquisition · two careers, one householdTwo careers, one windfall
Marcus and Tom, 44 and 47
Marcus’s biotech company got bought. Tom teaches high school. Between them they suddenly had a chunk of new money, a stack of accounts neither had ever organized, and very different feelings about risk. They wanted to make one good decision together, instead of a dozen anxious ones apart.
The challenge
New wealth from the acquisition and no shared plan for it. Old retirement accounts on both sides, never coordinated. Taxes they’d always filed themselves, now well past simple. And the bigger questions, what’s enough and what’s it really for, that they’d never sat down and answered together.
What the work would cover
We would bring both of them into the room and build one plan for the household, not two. We would plan for the tax from the deal and show them when a CPA is worth bringing in. We would compare leaving the old accounts on both sides where they are with combining them. And we would put real numbers to what they can afford and what they want the money to be for. No judgment about what either of them did or didn’t know walking in.
What changes
Marcus and Tom would make the big decision together, with a plan they both understand. The tax from the deal would be planned for, and the money would have a purpose they chose. If they chose to combine accounts, there would be fewer to keep track of. A plan cannot promise a result, and the big decisions in it would stay theirs.
These scenarios are illustrative, based on the kinds of situations we handle. They are not actual clients, and they are not a promise of results. What happens for you depends on your own circumstances, your goals, and the decisions you make.
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