What's missing here is the idea that you want to be able to grow with your startup over time. Being solely involved in startups -- especially since most fail -

What's missing here is the idea that you want to be able to grow with your startup over time. Being solely involved in startups -- especially since most fail -- only lets you see how an organization is run up to the size of the startup. It's the organizational equivalent of the Peter Principle. A larger organization is going to let you see more sizes (since they are typically organized as subunits) and the issues that arise in each size. As examples: 1. Do you know how to manage a team of 3? 10? 50? 2. Do you know how to hire 10 engineers (ie, after you've asked all of your friends)? 3. Do you know how to budget/spend $100k? $1M? $5M? If not, then investors may be less willing to put money into your venture. Gaining those skills, especially the first two, has you situated to more successfully manage growth. I believe that spending some time at a large, successful company can be very beneficial. Disclosure: I recently joined TripAdvisor for just this reason. And I'm hiring into my team, thereby gaining experience in 1, 2 and 3!