Pros
The two main reasons I love working at Thumbtack: 1) We're actually having an impact on the world. A lot of people use Thumbtack to fuel their small business. Some wouldn't exist without Thumbtack and some would, but just be smaller. To be able to empower people to pursue their entrepreneurial passions is really cool. 2) The people at Thumbtack are great. It's not always common to find a culture that prizes ambition, intelligence, AND kindness, but all three are definitely present among those working at Thumbtack and this makes working at Thumbtack much more enjoyable.
Cons
It's scary to not be an established player like Google or Facebook. While we're doing well financially, there's no guarantee that Thumbtack will be around in 10 years. Having said that, this is also an opportunity. Everyone can make an impact at Thumbtack and leave their mark here in a way that wouldn't be possible at one of the aforementioned companies.