Peter Thiel's $5 Billion Roth IRA, and What You Can Copy
How Peter Thiel built a $5B tax-free Roth IRA, and which parts of the strategy senior tech employees with early equity can actually use today.
For households with $3M+ in assets — navigating stock options, tax bills, and life decisions that have outgrown what a weekend and a spreadsheet can handle.
Book an Intro CallSomewhere between the first RSU grant and the second tax bill, you became the de facto CFO of your household. You’ve figured out most of it. But nobody checks your work, and you’re still not sure what you’re missing.
“I wouldn’t make a call at work with this little information. And this one’s worth more than my salary.”
AI will tell you how stock options work in five minutes, and do it well. But it doesn’t know what they’re for. The information you’re missing isn’t in the stock. It’s the house you want, what your life actually costs to run, and when you want the option to stop working. We start there, model the scenarios side by side, and work through the trade-offs until we agree on a path. Then we do it with you.
“I exercised my ISOs in March. The stock’s down, and I still don’t know what I owe in taxes.”
Your tax bill doesn’t care what the stock is worth today. It cares about what it was worth at exercise. And it’s real cash, due next April, even if you haven’t sold a share. We run the AMT math before you exercise, so the number is a choice instead of a discovery. If the year hasn’t closed, there’s still time to change it.
“My net worth swings six figures on an earnings call. I just don’t know what to do about it.”
Everyone tells you to diversify. Nobody accounts for the taxes you’ll pay or the upside you’ll lose if the stock runs. Those are real reasons, and they’re why you haven’t moved. But the company doesn’t have to fail for concentration to hurt. One ordinary quarter can rewrite the price, and everything you’ve planned goes with it. We build your diversification plan around the upside you want to keep, the downside you can’t accept, and the taxes you’re willing to trigger.
“This has been on my list for two years. I know it isn’t right, but it’s not an issue right now.”
The old 401(k) sitting in a target date fund. Disability coverage sized to a salary you’ve since doubled. An estate plan that never named a guardian for your kids. None of them jump out at you. They all have a price. We fix what your life outgrew, then stay ahead of what comes next, so it’s off your list for good.
“I’m paying for answers, and every one of them starts with ‘well, that depends.’”
Your CPA doesn’t know your company’s stock jumped 35%. Your attorney doesn’t know you moved states. They only know what you remember to tell them, so every handoff runs through you. We take that over. We already know what changed and which of them needs to hear it, so “that depends” turns into an answer.
When’s the last time you didn’t have to think about any of this?
See How We WorkThe announcement comes. A tender offer, an acquisition, or the lockup finally expiring. Whichever one it is, you have 20 business days to make a decision you were never sure would come.
The Slack channel is blowing up. Somebody’s selling everything, somebody’s selling nothing, and everybody has a number. None of those numbers work for you.
Do you sell any of it? If you do, do you sell shares you already own, or exercise options first? Which lots, the early ones with the low basis or the recent ones? How much: enough for the down payment, enough to stop checking the stock price, or as much as they’ll let you?
The questions nobody can answer: is this the last opportunity like this, or the first of several? What if I sell and the price goes up? What if I hold and it goes down?
You put in hours you don’t have, on dozens of decisions, and send in your answer. Nothing comes back to tell you whether it was the right one.
The money lands. It’s the first time any of this has felt real.
The tax bill is also real, and it depends on the choices you made the year before in a window you didn’t schedule.
We did apply for this job.
We price the trade-offs, model the tax, and deliver a recommendation you can dissect before you have to answer. The decision stays yours. The rest of it doesn’t have to be.
A 45 to 60 minute phone call. If we’re not the right people for it, we’ll say so.
Book an Intro CallLong-form answers to the questions our clients actually ask.
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