Having worked at both a Fortune 500 software company, and a small valley startup with good funding, I can speak to this issue. On the matter of working at a st

Having worked at both a Fortune 500 software company, and a small valley startup with good funding, I can speak to this issue. On the matter of working at a startup: PROS: - You have a much larger impact on the product. Often times you may be working solo on a very significant part of the product. If you enjoy this feeling of autonomy, this is a major plus. I list this as a major PLUS because at the large company I worked for, I felt like a "cog in the wheel". I could easily be replaced. Despite doing good work, I was just one of many who could do the same work. I could only "own" a small portion of the application. - You have a chance to make money on the exit. Assuming you got stock options as part of your hiring agreement. CONS: - Jack of all trades, master of none. You will be asked to wear multiple hats. In my case that has meant I was hired to do one X, but actually ended up doing Y, and Z in addition to some X. Specifically, that meant learning new programming languages, new domains, etc. I list this as a major CON. While it can be very good to learn new languages / domains, I think you should do this on your own "track". Learning a new programing language on the job, especially at a startup, can be quite stressful when you're expected to also PRODUCE. On the other hand, learning it on the job can give you some of the most practical experience in the shortest amount of time. So this one can be a double edged sword. In general, if you are YOUNG in your career, this is GOOD. If you are middle, to late in your career, avoid a startup for this reason. (Don't stop learning. Rather, find a mastery of one domain, and make that your day job while keeping up your abilities in other areas). - On all the time. Your coworkers will be working weekends. That can mean that when you aren't working, you feel like you should be. - You'll never feel like you can take a vacation. Take them anyways. But you will feel guilty, and like you're asking a lot to take a week here or there. At a big company, this is "PTO" and you either have the days available, or you don't. Take the time if you have it, because you have a large team that can cover for you. - You'll never feel like you can leave, as the business hugely depends on you.