Best risk adjusted returns come from late stage startups - Series C or D typically - for VP level roles that get 1% grants ($4-$10m value over 4 years). Highly

Best risk adjusted returns come from late stage startups - Series C or D typically - for VP level roles that get 1% grants ($4-$10m value over 4 years). Highly de-risked. At year two or three the company will also likely top up the equity if they want you to stay... just negotiate a 10 year exercise window, so you're not writing a check on your way out the door. For whatever reason, why individual contributor equity grants fall off a cliff after Seed or Series A, the VPs remain relatively constant even as the value of the company goes up 20-50x while risk plummets.