If the CEO has been a success before at a level you want to be: consider equity
This is an important point. I took a job at a startup where the founders have all been part of two 200M exits (1 IPO in the first internet boom and 1 acquisition in 2005). They all made out very well with their options (big house, small yacht, small plane kind of money). They definitely have the connections and the vision to repeat their success. They offered me 3 choices for compensation: high salary, low equity; low salary, high equity; medium salary, medium equity. I ran the numbers and figured based on previous exits that it would be more likely that the higher salary over 5 years would be a better payoff if the company doesn't have at least a 100M exit, and if we do have a much bigger exit, 2% vs 3% will just mean a smaller yacht and no plane.
This is an important point. I took a job at a startup where the founders have all been part of two 200M exits (1 IPO in the first internet boom and 1 acquisition in 2005). They all made out very well with their options (big house, small yacht, small plane kind of money). They definitely have the connections and the vision to repeat their success. They offered me 3 choices for compensation: high salary, low equity; low salary, high equity; medium salary, medium equity. I ran the numbers and figured based on previous exits that it would be more likely that the higher salary over 5 years would be a better payoff if the company doesn't have at least a 100M exit, and if we do have a much bigger exit, 2% vs 3% will just mean a smaller yacht and no plane.