1. Many individuals at OfferUp are stuck in the mentality that they got there because they're amazing individuals. While this is true for a lot of people, you can't escape the ego. It's a road block in literally every org, and every avenue of the job. VP's and managers will make incredibly important decisions because they think their position makes them more qualified to do that then you are, even though they just hired you to make those decisions. Prepared to be ignored, and when you're not ignored, to have your input (valuable or otherwise) brazenly dismissed.
2. While parties and events and the like are super fun, there's a certain point where you realize that half the people around you are just passing time until the next excuse they have not to work. These events are not for all people in the company - its either first come first serve, or you need to be on someone's "favorites" list to make it.
3. Unless you're in the CS org, and then none of this applies. The listed job description, all the way up to the official description given in the job offer, specifies all these wonderful perks. Upon signing on, you're informed that none of that applies to you because you're in CS. Whoops. Sorry not sorry.
4. There are people from all over the world and all walks of life at OfferUp. That's great, except the company frequently fails at accommodating religious requests. While I can't speak for the (I think two other) people at OfferUp who identify as part of the LGBTQ community, I didn't feel safe here. I was frequently harassed and stereotyped, and on more than one occasion, cornered after hours by employees who were uncomfortable with who I am.
5. This actually refreshing and incredibly empowering.
6. What's more important - letting people order as many alcoholic beverages as they want at the restaurant you rented out for another unnecessary party, or putting some extra funding into teams that are woefully under-budgeted?
7. If you like doing shots at 9am, I guess this is cool. Nobody will give you a hard time about it (to your face).
8. They company is often lovingly referred to as a rocketship. I chuckle to myself every time I hear this, because there are simple asks from departments (like can we have this feature configured in Zendesk) that have been languishing as internal tickets for over a year. Nothing goes anywhere, development stalls constantly, and every suggestion made to any department comes with the caveat that it isn't a priority item.