> at a strong price (the latest valuation is already 2x the strike price I would get) By "latest valuation" do you mean their valuation based on the most recen

> at a strong price (the latest valuation is already 2x the strike price I would get) By "latest valuation" do you mean their valuation based on the most recent round? Remember that valuation is for preferred shares, and you will receive common shares. Preferred shares are usually valued significantly higher than the common share (IE 409A) valuation. (Investors are paying for the potential growth, employees pay the 409A price which is what is company worth right now) Edit: also get a warm referral to a good attorney, they may review your paperwork and give you advice for free. In my case this free consultation led directly to an easy $10K cash swing in my favor, on top of a professionally reasoned plan for managing my equity. The attorney is an invaluable aid in negotiotation because they can play the bad cop hardass and also call the company's bluff (assuming the company isn't hoping to pull one over on you, in which case bringing in an attorney might conceivably make the company behave defensively and thereby risk your offer).