I often hear that people would love to have a business like ours and I personally hear “Man, you are living the dream”. And while I totally agree – I also think that most people, if given the opportunity to have the same thing would change it – quick. They would be bored. They would feel lonely. They would also have the feeling that they could do much much more. Anyone could do what we are doing – but they probably won’t and here are 5 reasons why:

1. It’s too unconventional. If we are growing with no sales team and not much marketing and no trade shows – imagine who much more we could grow if we had/did those things!
2. We choose to have a really narrow focus – which means we say no all the time. We say no to integration with other systems. We say no to partnerships. We say no to more features. We say no to selling to other industries. We are happy when people outgrow us and need more features and need to leave. Imagine how much more we could grow if we added more and clawed and scratched and tried to please everyone!
3. The owners of this business don’t live in the same city and don’t report to an office – still – 6 years into it – with solid growth. So we don’t get together every morning to talk about what we are going to do next or what we are going to build and add and sell. Imagine how much more we could grow if we got together more and came up with more ideas!
4. When presented with free time, we spend it with our families and doing the other things we love. We don’t fill it with more software building or more ideas or more work. Often, to this day, with 3,000+ paying customers and 7 figure revenue – I still hear “Is Schedulefly your full time job?”. I used to get irritated by it and try and explain – but I don’t any more. I think it’s because the people who ask don’t see me at an office or headed to the airport. I’m not wearing a tie and handing out business cards. The see me in a t-shirt dropping my kids off at school or on a jog at 10:30am or with an 8 day old beard at a coffee shop and a laptop. Imagine how much more we could grow if I shaved and went to a real office and traveled and sold and worked 80 hours a week!
5. It takes a very very long time to get legs beneath you when you don’t take capital and you don’t hire people and you don’t partner with other companies. It takes years. It also takes a relentless confidence that one day you will wake up and “be successful” – having done it on on your own. Just imagine how much more successful we could be if we took that investor’s money and hired a team of software developers and partnered with bigger companies and sold, sold, sold. Imagine!

Well, given the talent of our team of 5, it’s easy to imagine how much more business we could go get if we did things differently. It’s easy to imagine how much more money we could earn if we did more. Sure, I know we could build dozens of valuable tools and sell to a bunch of different industries and partner with big companies and take over the world.

Nah. If we did that, I’d be wearing a dress shirt and dress pants and in meetings all the time and worst of all – I’d stop hearing – “Hey Wes, is Schedulefly your full time job? What else do you do?”

Wes