Maybe because most banks prefer you pay all your mortgage every month. Any maybe he doesn't want to make up the difference doing freelance work at night because

Maybe because most banks prefer you pay all your mortgage every month. Any maybe he doesn't want to make up the difference doing freelance work at night because he'd rather spend time with his family. Very few startups actually get hocky-stick, rocket-speed growth. Six months later he's simply six months older. I have successful startups (by my standards but SV would probably call them "lifestyle businesses") so god willing I won't have to every look for real employment again. I never worked at a startup and I'm not sure doing so gives you a huge advantage. If anything, working at an established company or govt job gives you a bigger advantage because you're more likely to uncover inefficiencies and needs that can turn into startups.