What this looks like in real life.
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 composites, but the situations are exactly the ones we see.
The 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 we did
We started by getting his whole picture onto a few pages, which he’d never actually seen. We handled the tax hit from the deal before it could surprise him in April, and got him a CPA who does real planning, not just filing. We rolled the three orphaned 401(k)s into one account he could actually manage. And we built a schedule to bring down the concentration in the acquirer’s stock over time, instead of betting his future on one name.
Where he landed
Daniel knows what he owns, what he owes, and what comes next. The tax surprise never happened. His old accounts are consolidated and working. He’s diversifying on a plan instead of a hunch. For the first time since the money landed, he isn’t lying awake wondering what he’s missing.
If this looks like your situation, the Checkup is free →The 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. No way to sell freely once the lockup lifted unless a plan was already in place. And nearly everything she owned about to ride on one stock.
What we did
We ran the tax math before she exercised, so the number wasn’t a shock. We got a plan in place well ahead of the lockup so she could actually sell on a schedule when the time came. We checked whether her shares qualified for a break that could shield a big piece of the gain. And we mapped out how to turn paper into a real, diversified financial life once she could sell.
Where she landed
Priya went into the IPO with a plan instead of a guess. She knew what to exercise and when, what the tax would be, and exactly how she’d sell. The thing that could have cost her the most, doing it all on instinct, never happened.
If this looks like your situation, the Checkup is free →Two 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 we did
We brought both of them into the room and built one plan for the household, not two. We handled the tax hit from the deal and got them a CPA. We consolidated and coordinated the accounts on both sides. And we put real numbers to what they could afford and what they wanted the money to be for. No judgment about what either of them did or didn’t know walking in.
Where they landed
Marcus and Tom made the big decision together, with a plan they both understand. The accounts are organized, the tax surprise is handled, and the money has a purpose they chose on purpose. They stopped worrying about money and started using it.
These case studies are illustrative composites 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.