From an outsider point of view, we executed our well-defined business plan beautifully from founding to eventual exit and our decade-long entrepreneurial journey was smooth. Except that it wasn't.
As soon as we launched the company after our series A venture capital financing, many of the real estate brokerages whose property listings lived on our site said "take it down!" leaving us with an empty website.
Similarly, when late 2008 rolled in and we were in a fragile point of our evolution and starting to scale our early business, the global economy crashed, bankrupting many of our customers and nearly Trulia.
As I have spoken with other founders and CEO's who have built companies from scratch to dominate or create a whole new category, practically everyone goes through frequent "sausage factory" moments--unexpected twists, turns, and existential crises--despite the perception of linear success that most outsiders perceive.
Why is tumultuousness the default and not the exception? First, a startup trying to create or dominate an industry, by definition, needs to do something nobody has done before. It is the same as sailing unchartered waters, every day. You simply don't know what's around the corner.
Secondly, rapid growth means everything is always a bit messy. Organization, processes, and people need to evolve all the time. There is no time to optimize every detail, and it never feels like things are neatly in order. Even in the best-run startups the experience feels like organized chaos.
Luckily, there are concrete steps you can take to tackle the seemingly insurmountable obstacles you'll face.
Build a resilient, flexible team.
Even before obstacles arise, you can help yourself by identifying people with the right disposition for facing a never-ending stream of challenges. Hiring renaissance people--individuals who can simultaneously make sound decisions and execute and iterate extremely fast in multiple areas--helps. Look for clues in someone's background, too. Have they worked in a startup or high-growth environment before? What challenges did they face in the past, either at work or their personal life, and what was the result?
Identify the critical path, and communicate clearly.
Don't worry about solving every bit of minutia. With each challenge, only a few details will be important, and finding and addressing those as fast as possible should be your primary task. Communicate the path forward to your team, and then remove obstacles for them and trust their execution.
At times almost every new challenge appears to have trajectory-altering consequences. While the challenges are many, not all of them will ruin your company. Taking a breath to spend a moment isolating the ones that truly matter will not only keep you focused on the right things, but will also help you keep your emotions in check and provide mental clarity.
The flip-side of facing and tackling these obstacles is that they provide massive personal growth for you and your team that you're likely not going to acquire elsewhere. Once you learn to handle chaos, it becomes an invaluable tool to help you navigate the rough waters of startup life.
Are you contemplating joining a growth company that looks rosy from the outside? Good. But be prepared to embrace and enjoy a sausage factory.