I’ve been at Zillow for just about three and a half years. I haven’t tackled accounting, but I’ve been on almost every business team we have (sales, partner relations, customer service, marketing) at one point or another since starting as an intern in September of 2005. Working at a start-up that has gone from “stealth” to 8.9 million unique users a month in 3 years has been quite a journey. Here are a few lessons I’ve learned along the way:

  • Pick your battles — I’m an opinionated guy, sometimes too much so. But it’s because I’m passionate about what I do — if I wasn’t, quite frankly, I’d be doing something else. But regardless of how badly you want to, you can’t fight every battle.  Know when to push, let up, escalate, concede, etc. Know that some battles are not worth fighting. This lesson could also be “Be strategic about using your political capital – you only have so much of it”
  • Don’t use social media marketing if your product sucks — If you have a crappy product, no amount of social media marketing will work regardless of how many resources you throw at it. After all, social media marketing is REAL; expect your audience to puke all over you if they don’t see value in your product.
  • Persistence is key — This is a biggie. Everyone is busy, myself is included. To get things done, you have to be persistent and confident what you are advocating for is the correct decision/course of action. Follow up, follow up, follow up.
  • Partnerships are like friendships — they take time and effort to nurture. If both sides aren’t willing to put in equal effort, the partnership is not going to be a success in the long run.
  • Choose the right technical solution from the get-go — yes, certainly this is easier said than done, but if at all possible, make sure the technical solution you go with is right from the start. For instance, migrating Zillow Blog from typepad to wordpress was a nightmare that I would have rather not had to do (we should have just picked wordpress to start with). However, realize that sometimes the wrong decision is made initially and that’s okay. My advice in those situations is to migrate over to the correct solution as quickly as physically possible once you realize that you should be using another technical solution. The longer you wait to migrate, the more time and effort you’ll likely spend doing the migration.
  • LISTEN — I can not stress the importance of this one enough. There are so many people/companies who are GREAT at talking, but horrible at listening; don’t be one of them.
  • Take advantage of public speaking opportunities — If you’re given opportunities for public speaking engagements, take them. It’s such valuable experience to have in the long run that will make you a more confident person. Plus, just as blogging puts you in a spotlight that often results in unexpected opportunities to arise, public speaking will lead to opportunities in a similar fashion.

I’m sure there are a few others I’m missing, but this is a start. Maybe I’ll do a Part 2 on this topic at some point in the future.