While I appreciate that my response might sound just a wee bit wistful, it’s worth noting that you have to want to grow past 50 employees for a very specific reason.
The most fun I ever had, as a company, was when I had under 50 employees.
There was singular management. It was a spoke system where everyone, ostensively, reported to me even though there were several individuals who had certain areas of responsibility. We shut down for birthday parties for as long as 2 hours at a time, we had activities inside and outside the office that were a blast, and so forth.
In those days, we didn’t think about HR-related matters; we didn’t think about potential liability; we didn’t think about employment claims; we just didn’t think about them because they didn’t happen.
We were a group of people who enjoyed being around each other and we had fun in the process of creating.
As I take a look back, now that we have 580 people, and I hear about those companies out there that are doing really neat things, chances are very strong they have under 50 people. There’s a lot of reason they may want to stay there.
When you scale your company, you need to make a decision that it’s what you want to do. And you also need to decide, that as much as you’ll attempt to keep the small company mentality in lots of different ways, you are also going to have to recognize there are some things you’ll have to do differently. Federal law requires it. State law requires it. And most importantly, the nature of human interaction makes it almost impossible to create the bonds of friendship and the relationships you have in a small company when in fact you’re not.
There will be a time in which we have 1,500 employees. When that time comes, it’s going to be based upon an affirmative decision I make, at some time in the process, to scale the company recognizing, all along, that the chances are pretty strong that I will not be able to preserve, as much as I’m going to try, the wonderful benefits and quality of life I had in the business when we were all so very young and few in number.