This was roughly my thinking. When I was young, single, and had no responsibilities, I did the startup route and thrived in the stress, excitement, and ability to make a big impact. Now that I'm older and have a kid, a public company with RSUs that I can put a dollar amount on (vs. options), and some measure of stability are important. When I was 24, I could find a couch to crash on while getting back on my feet if the job went south. Now, I'm worrying about college, mortgages, and stability.