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4 Tax Strategies to Diversify Your Anthropic Equity Without Triggering a Huge Tax Bill

4 Tax Strategies to Diversify Your Anthropic Equity Without Triggering a Huge Tax Bill

by Tom Lo | Aug 26, 2026 | Tax

Key Takeaways: Direct indexing enables you to strategically sell shares at a loss (tax-loss harvesting) so you can offset the tax on the gain in your Anthropic shares. When one of your investments drops, you can sell it to lock in a loss, which erases the tax...
How to Minimize Your Taxes on Your Anthropic ISOs, NSOs, and RSUs

How to Minimize Your Taxes on Your Anthropic ISOs, NSOs, and RSUs

by Tom Lo | Aug 15, 2026 | Employee Equity Compensation

Key Takeaways: With ISOs, you have a huge opportunity to save on taxes. If your ISOs qualify for the lower long-term capital gains tax rate, you can save up to 17% in taxes on your Anthropic gains. With NSOs, exercising is the taxable moment. The spread between your...
How Much Anthropic Equity Should You Sell After Your IPO

How Much Anthropic Equity Should You Sell After Your IPO

by Tom Lo | Aug 12, 2026 | Employee Stock Purchase Plan

Key Takeaways: Fund known near-term needs first. Sell to raise the cash required for taxes and identifiable expenses in the next year, so you have cash when you need it; then allocate beyond the price movement of one company. Choose a long-term Anthropic allocation. I...
Should You Sell Your OpenAI PPUs After Your IPO?

Should You Sell Your OpenAI PPUs After Your IPO?

by Tom Lo | Jul 2, 2026 | Employee Stock Purchase Plan

Key Takeaways: The timing of the Profit Participation Unit (PPU) sale depends on your documents and lockup period. Your sell decision starts with what your PPUs became, when they can be sold, and which restrictions still apply. Your concentration and goals after an...
What OpenAI Employees Should Do Before Your IPO

What OpenAI Employees Should Do Before Your IPO

by Tom Lo | Jun 25, 2026 | Employee Equity Compensation

Key Takeaways: Determine how concentrated you are in OpenAI equity. A large share of your net worth may sit in legacy Profit Participation Units PPUs, converted OpenAI Group stock, restricted stock units (RSUs), or future grants, and sizing that up is the first step....
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Recent Posts

  • 4 Tax Strategies to Diversify Your Anthropic Equity Without Triggering a Huge Tax Bill
  • How to Minimize Your Taxes on Your Anthropic ISOs, NSOs, and RSUs
  • How Much Anthropic Equity Should You Sell After Your IPO
  • Should You Sell Your OpenAI PPUs After Your IPO?
  • What OpenAI Employees Should Do Before Your IPO

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