You did the hard part. Then the money got complicated.
The stock you were paid in is about to turn into real money, or it just did. Now there are tax questions you’ve never had, one position that is most of your net worth, and a stack of accounts nobody ever organized. I help tech and biotech professionals get these decisions right, from your side of the table, with no products to sell.
Everyone around you has an opinion, and most of them are guessing. I make these calls every day, and I answer only to you.
It usually looks like this.
Your company got acquired, or it’s heading for an IPO, and for the first time there’s real money on the table. Maybe the vesting accelerated. Maybe a chunk has already landed.
You’ve got a couple of old 401(k)s from jobs you’ve left, and you’ve never done much with them. You’ve been doing your own taxes. You’ve managed your own money this whole time, and it worked fine, right up until it got a lot bigger and a lot more complicated.
Maybe your partner has equity too, and the two of you have never said the whole number out loud. There’s a kid a few years from college, maybe a parent who’s starting to need help, and the money has to do more than sit there.
You don’t have a CPA yet. You don’t have a plan. And lately it’s started to feel like the stakes are too high to keep figuring it out as you go.
You’re not looking for someone to make you feel behind for not having this handled already. You’re looking for someone who has done this a hundred times to sit on your side of the table, bring some order to it, and help you get the big calls right.
If that’s you, you’re in the right place. No judgment, no jargon you didn’t ask for, just a straight read.
The things that cost people the most are the ones nobody warned them about.
The 20% tax that can land after your company is acquired
280GAn acquisition can trigger an extra 20% excise tax under the golden-parachute rules, on top of everything else you’ll owe. The time to handle it is before the deal closes, because the best options narrow fast after.
A tax bill on shares you never sold
AMT on ISO exercisesAn ISO exercise can trigger a tax bill even if you don’t sell a single share, with no proceeds to cover it. The cliff is invisible until it isn’t.
The day you can finally sell, and can’t
10b5-1 plansIf you hold material nonpublic information, or you’re in a blackout window, you generally can’t sell when you want. The plan to sell on a legal schedule has to be set up before you need the money, not once the need is urgent.
A tax break worth a fortune, gone if the dates are wrong
QSBSThe right shares can shield a large piece of the gain from federal tax, if the issuance date, holding period, and timing all line up. Get the timing wrong and a break worth a fortune can shrink or disappear.
One stock that quietly became most of your net worth
ConcentrationCompany stock that quietly grew into most of your net worth, in a company you want to believe in and shouldn’t bet everything on.
Money that goes where your will can’t reach
Titling and beneficiariesAccount titling and beneficiary designations can send money in directions your will doesn’t control. An old 401(k) still naming an ex-spouse does exactly what it says.
Most people walk into the biggest financial moment of their lives advised by someone who’s never run a 280G analysis or weighed the AMT on an exercise, because that isn’t their job. Catching it first is the work.
What’s keeping people like you up at night.
Your company stock just turned into real money, and there was no dress rehearsal.
Read: The biggest money calls of your life come with no practice →Most of your net worth is riding on one stock, at prices like these.
Read: You bought it again this morning →Layoffs at profitable companies, and every plan you have assumes the paycheck.
Read: Can your money plan take a bad year? →New letters every Tuesday and Friday. See them all
Protect.
Subtract.
Align.
Build.
Most advisors start at build. They add accounts, products, and positions before ever addressing what could unwind it. We work in reverse. Protection before optimization, clarity before complexity, and only then, growth.
Simplicity is the product.
Read the full method →Two free calls to find out if we’re right for you.
No pitch, no pressure, and a straight answer either way. The path from there is below.
The Checkup
Free · 15 minA quick fit-check, not an advice session. We confirm whether what we do matches what you need.
The Full Picture
Free · 60 minAn hour on your whole situation, both partners welcome. We map it and put rough numbers on what may be at stake, so you can decide whether the Plan makes sense. No recommendations on this call. That is what the Plan is for.
The Plan
$5,000 · built for delivery in 30 daysAt the end you have a written plan built for your situation, yours to keep and implement however you choose.
Put it to work
OngoingThe plan tells you what to do. This is where we do it with you: portfolio built, every move implemented, and managed from there. The plan is yours either way. That freedom is why people stay.
The decisions you make in the 12 to 18 months around an acquisition, an IPO, or a big vest will shape your net worth more than any other stretch of your career.
For most people, it isn’t close. And it was never meant to be navigated alone.
Two letters a week, on money and the life it’s actually for.
No tips, no hype. The same thinking I’d share across the table. Read a few before we ever talk.
Read the letters →