Running a startup is definitely an emotional roller-coaster ride. You are going to have really good days (like when you are featured on The Today Show) and a bunch of down days as well.
Your product development will always be much slower than you want; you’ll put your heart into product changes you think are great but the customer balks at (or even worse, doesn’t notice). You’ll put in an experiment “destined to win” until it meets the real world where it promptly loses by a large margin. And as you go through the meandering customer development process of learning what exactly the customer wants, it will feel like your company is going nowhere. Add that all up and if you are only waiting for the end goal it will feel like it will never come.
So how do you stay optimistic and keep moving forward?
At Shop It To Me, instead of only celebrating the final goal, we make an effort to celebrate the little things. We release new functionality weekly, and with every weekly release comes a mini-celebration (“Beer-Thirty”) — reveling in what was accomplished that week, the hard work that was put in, and the fact the product is (almost always) better than the week before. We celebrate that we put the experiments in and found out the results even if they weren’t the results we actually wanted.
And we’ve been experimenting with another way of celebrating too — the “mini-milestone”. Each product team comes up with a set of small milestones that are achievable in about a month’s time. The milestones are not guaranteed to happen, but likely if everyone works hard ( examples include a set of features or experiments included or a metric goal that shows we are making some progress.) Each time we achieve a milestone. the team is given a small allotment ($250 or $500) to spend on the company and celebrate that milestone — they get to pick how. The celebrations are usually not that big — examples include a fancy brunch for the company or a Nespresso machine — but so far the result has been super positive. The team gets recognized for the work they have done, the entire company sees that progress is being made towards reaching our bigger goals, and after each celebration the teams are more motivated than ever to be hosting the next one.