Here's a long and thoughtful article by Charlie O'Donnell, offering some insight into startup career paths. The article breaks things down into three axes:
- Risky company vs de-risked company
- Role you get vs role you want
- Own business vs someone else's business
And an important quote about running your own business:
Prove something to yourself about your potential for success before you raise enough money to get stuck in the idea for two years. Launch, sell a customer, or de-risk something important, because, in this environment, your biggest cost is opportunity cost.