From the founder

The IPO tax bill nobody warns you about

Congrats, Anthropic. Before the celebration, know your number.

Bola Akinsanya · Founder, Unlevered · October 27, 2026

I am so excited about this wave of IPOs. It is life-changing financial responsibility for so many people. Anthropic filing its S-1 is a big moment, and it won’t be the last one this year!

There is something special about watching an idea, and years of hard work from an entire organization, turn into life-changing money for the people who built it. Most of us only get a few earning years before retirement. Very few people ever get to live through an IPO from the inside.

So when it happens to you, you deserve to be ready for it. And the thing people are least ready for isn’t the stock price or the lockup. It’s the tax bill.

Why Unlevered exists

This is the origin story of Unlevered. I went through an IPO at Airbnb. It was nowhere near the scale of what Anthropic employees are about to see, but the feeling was the same.

There was a fun moment first. What am I going to buy? At the time it was a Tesla. Today it might be a Rivian.

What nobody talked to me about was the actual tax bill, and how I was going to pay it. If I could go back, that is the first conversation I would have with myself.

The bill shows up before you sell anything

RSUs are taxed as ordinary income the moment they vest. At an IPO, years of RSUs can vest at once. That income counts this year, even if you haven’t sold a single share.

Your employer withholds some of it at vest, usually 22% federal, or 37% on anything over $1M. The real bill runs closer to 47 to 54% in California. The gap is due when you file, often while the lockup still keeps you from selling.

Where everyone’s mind goes first

When the number lands, people think about the things we tie to wealth: a new car, or finally upgrading the primary home. Those are fair dreams, and you’ve earned them.

But almost nobody starts with the math on what they owe. In San Francisco the upgrade is also harder than it looks. The median home is around $2.2M, homes go $1M+ over asking, searches can take a year, and most of what you pay for is land, which never depreciates. A primary home does very little for your tax bill.

You have options: transfer the tax bill into real estate

Know your number first, then know your options. One of the strongest is a second home two to four hours out, run as a short-term rental: a ski cabin in Lake Tahoe, a getaway in Sonoma, a place at The Sea Ranch, Pacific Grove or Pismo Beach.

1. Buy a short-term rental. Average guest stays of 7 days or less, and you stay materially involved in running it.
2. Run a cost segregation study. It moves parts of the building into 5- and 15-year property instead of 27.5 years.
3. Take the deduction in year one. With 100% bonus depreciation back, those parts can be deducted right away, against the W-2 income your RSUs created.

Instead of a bill you simply pay, part of that money becomes an asset you own, use and rent out. The savings are federal only, since California doesn’t follow bonus depreciation, the rental and personal-use rules are strict, and depreciation is generally recaptured when you sell, so a good CPA matters. For the full picture, see offsetting RSU and IPO income with real estate.

The clock is short this year

To count against this year’s income, the home has to be bought and ready to rent by December 31, and you still need to meet the short-term rental and material participation tests that year. As I write this, that’s about nine weeks away.

If that feels too tight, you’re not alone. Many people get through the first wave, live through their first tax season, and then realize that vesting is the new normal. The second tranche is often when they act. Either way, we’ll be here.

Let us help

Figuring out your number, then your options, is the strongest move you can make right now. We’d love to help you do both. We can refer you to a great CPA who knows equity and real estate, connect you with realtors in the markets that work for short-term rentals, and work alongside both so the cost segregation is done right.

Start here: unlevered.io/hello. Congratulations to everyone at Anthropic. You built something incredible. Now let’s make sure you keep more of it.

Illustrative, not tax advice. Estimates assume a single California filer, 2026 rates, and RSUs as the only income. Talk to your CPA.