A whole bunch of SpaceX/Anthropic/OpenAI people are about to get completely destroyed by this sort of insanity, aren't they?
Sheesh... go talk to AQR and get some nice ways to diversify while generating capital-losses, this plan is absolute insane.
I spoke with a member of the technical staff at Anthropic yesterday who is about to make $17 million.
He's been there less than 2.5 years and is blown away by his equity value. His biggest worry now is tax strategy.
His CPA told him to "max out his 401(k) and consider a donor-advised fund."
While that's a great starting point, here's what makes even more sense:
He's acquiring a 48 unit apartment complex in Phoenix for $14.5 million.
We're running a cost segregation study to reclassify approximately 30% of the depreciable basis into 5, 7, and 15 year property.
Here's the math:
• $14.5M purchase price
• ~$12.3M depreciable basis (excluding land)
• ~$3.7M reclassified to short-life assets via cost seg
• 100% bonus depreciation under OBBBA = $3.7M accelerated to Year 1
Plus standard Year 1 depreciation on the remaining basis adds another ~$315K.
Total Year 1 deduction: approximately 4M.
His wife is qualifying as a real estate professional 750 hours, more time than any other activity. The loss is no longer passive. It offsets ordinary income.
At a 37% federal bracket plus 13.3% California, that's a combined rate just over 50%.
$4M × 50% = 2M in tax savings. Year 1.
Layer in operating expenses, loan interest, and startup costs on the property, the total offset against his Anthropic income crosses $3 million.
Not deferred. Not spread over 27.5 years.
Meanwhile, the property cash flows. He's converted concentrated tech stock into a real asset producing monthly income. And he's done it all before he files the return on his equity windfall.
This is what real tax planning looks like for tech liquidity.
If you're an engineer, exec, or early employee sitting on a meaningful equity position and your CPA hasn't mentioned cost segregation, bonus depreciation, or REPS qualification, you're probably leaving seven figures on the table.