Pros
Free drinks, flexible hours, typically nice coworkers, projects can be interesting (but probably not very useful and/or well-adopted).
Cons
The company is stuck on a path to mediocrity and obscurity if Stephen keeps running the company the same way he always has. If you are so lucky to find yourself in a highly-visible position or on a project that is on SW's radar - be prepared to take some flak, grow thick-skin, or find another place of employment every time he runs into a small bug or his expectations aren't met (which is very, very often). There are very few people that he trusts them at their word, so be prepared to endure the temper tantrum of an adult man with a hairline trigger if you and your manager are not one of these few people. Project management is always in disarray as well. Resources are stretched thin so depending on the week (or even day), people will probably be working on another project and making little progress due to the CEO's ever-changing desires. One could imagine how difficult it is to make progress or even finish a project when people are being pulled left and right and developers are being forced to work long hours. In terms of culture, you will probably get along with your team/coworkers, but I've noticed that there is an "every-man/team-for-himself" type of atmosphere. This is no doubt due to the fact that managers are afraid of spending their team's time and resources on work that Stephen has either indirectly assigned them or wants them to help another team with. This results in certain teams being cut-off and insulated. Who can blame them though? Everyone has so much work to do already, if you are too receptive to your coworkers then you will take on an unbearable workload and you will never meet expectations - thus resulting in being pulled randomly into a meeting just to be yelled at by Stephen and be seen by him henceforth as "unreliable and incompetent". All this being said, if the company were doing great things or if the pay was adequate then you might be able to see past all these major flaws. But that is unfortunately not the case. You will most likely not have very many friends that know what the company does or have ever used one of their products. They are interesting in theory but the end product is never really well-adopted besides by a small, niche following. If you are straight out of college then this might be a good starting point for your career, but know your worth once you gain some experience and move on to a bigger town/city for much better pay.