October 14, 2026
Your brokerage defaults to FIFO. That's almost certainly the wrong method. Here's how Anthropic employees should sequence ISO, RSU, and NSO share sales to minimize taxes.
October 12, 2026
The OpenAI IPO moved to 2027, and in September Sam Altman confirmed it on the record. This tracker covers the $852 billion valuation, S-1 status, the Anthropic comparison, and what OpenAI employees should do about their equity right now.
October 9, 2026
The default 22% withholding on your Anduril RSU settlement isn't a full tax payment – it's a statutory rate that likely covered two-thirds of your federal liability. One quarterly installment has already passed. This guide covers the safe harbors, the W-4 vs. estimated payment decision, and the eight steps to take before January 15.
September 28, 2026
Years of accumulated RSU equity can land in a single tax year at IPO. Here's the tax math, the withholding gap that trips people up, and what to do before November.
September 7, 2026
OpenAI's board answers to a nonprofit foundation that owns less of the company than Microsoft does. Here's how that's possible, what a Public Benefit Corporation actually means for shareholder rights, and what the open governance questions could mean for your equity.
July 30, 2026
You've worked hard for your Anthropic equity. Now comes the part most people don't warn you about – finding a financial advisor who actually knows what to do with it. Most don't. Here's how to find the one who does, and why waiting until November is already too late.
July 23, 2026
Most people focus on when to sell their SpaceX stock. The smarter question is which shares to sell first – because that single decision often determines more than timing ever will.
July 11, 2026
If you work at OpenAI and live in the Bay Area, your IPO payday comes with a California tax bill that most employees underestimate by six figures. Here's what to do about it – before vest day, not after.
July 7, 2026
If you work at Anthropic and live in the Bay Area, the November IPO isn't just a federal tax event. California's treatment of tech IPO income is among the most aggressive in the country – and several moves that work at the federal level either don't work here or actively backfire.
July 2, 2026
SpaceX is finally public. Your shares are right there on your brokerage screen. And you can't touch them yet. Make the most of the SpaceX lock-up period before it expires – so expiration day feels like a formality, not a fire drill.