I've worked at Stitcher for 6 years, and it's been a great experience. We've had many ups and downs during that time, but the core team has remained intact and is now more productive and together than ever before. I think the reason that the core team has stayed intact is that there is a genuine love of the product, a flexible home/work balance, and a friendly vibe in the office. The best is still to come.
Cons
We are a small team, so everyone has to pull hard in the same direction to make progress. This sometimes means we have to forego, exciting/interesting innovation opportunities in order to focus on the core product. Though as we grow our team in 2017/18 we plan on being able to innovate in the podcasting space once again.