I had a chance over the weekend to catch up with an old entrepreneur friend from school that I had not seen in while. He is not in the Flybridge portfolio, but rather someone who is bootstrapping a company he started a few years ago, about the last time I saw him. When he walked in I was struck by the fact that he looked older - less hair, more grey, a few extra pounds (maybe this is happening to all of us!)- and he looked a little tired. Most striking, though, was for a guy to whom everything - school, athletics, work success - had come pretty easily, was less of the air of confidence I was used to seeing.
After catching up on old friends and various stories from when we were in school, we turned to discuss his business. "It has been brutal", he said. He went on to add, "who knew it was going to be so hard." Taken aback a little by the candor, I asked for more details. "When we started out we were, in hindsight, too unfocused, trying to do too many things at once. As a result, we did not serve our initial customers as well as we should have and we lost ground to some of our competitors. To make things worse, we made a few hiring mistakes, which always takes longer to recover from than you would think. A little bit back, we took the chance to reflect on all of this and decided to go back to first principles: get our team in order and do more of what we were doing well, and less of what was not working. Always easy to say, but hard to do. Things are working much better now, we really have product market fit, our customers are happier and we adding a lot of value, but it has taken longer than I would like." As he described these improvements, the glint in his eye returned, but then he went on to add a few other thoughts. "I worry about our runway, I am ploughing all my savings into the business and the effort over the last while has taken its toll on all of us, including my wife and family."
As we brainstormed a bit, I suggested that maybe now was the time to look for an exit, peace with honor as they say, and that maybe he should reflect on this over a few days and we should get back together to discuss again. With this his whole body language changed. He pushed his beer to side and leaned across the table with a return of the confidence I had been missing earlier and a level of intensity I last saw when we played sports together and he said "No way. No reflection needed. We may have made some mistakes and I worry all the time, but we are not going to lose. We have a team I would match up against anyone out there - they are smart, driven, energetic and competitive and we are working super well together. If we were playing basketball, we could take the Miami Heat in a game of 5v5. What we are doing is important, we are changing our part of the world in fundamental ways, and we see this in what we are doing for our customers. Equally importantly, my wife is behind this 100%, so even if it takes longer, consumes most of our savings and requires sacrifices, we are going to make this happen. We are going to win." With that, he leaned back, took a sip of his beer, and said, "And let me tell you what we are going to do."
That, my friends, is the belief of an entrepreneur. A belief that what you are doing is important, a belief in your team, a belief in yourself and a plan to make it all happen. If you have those beliefs, I will have a beer with you anytime.