Do things that scare you

While this may sound like your standard Valley-speak BS, there really is something to it. The worst thing I can be is comfortable. I get complacent, I lose my edge, and I begin to underestimate my competition more than normal (this is something I’m working on…). I’m a perpetual optimist and when you couple that with any kind of ambition it turns me into someone with an almost unhealthy appetite for risk.

That first paragraph is essentially a long winded way of saying that I did something that was a bit scary at first, but in retrospect was almost REALLY fucking stupid. I’m writing this on 11/20/16 and Launch League’s Flight conference is about two weeks away. When we started working on it, about six weeks ago, it seemed like one of the craziest things we could try and pull off. Now as I think back over the decisions we made to try to create and host a regional startup conference in two months and I’m beginning to fully grasp just how insane I must have sounded when I’d tell people about the project.

The stakes for Flight are incredibly high. It’s essentially Launch League’s stake in the ground and our reputation with almost every startup organization from Cleveland to Pittsburgh to Columbus to Akron will flourish or die based on what we do in two weeks. We have raised a significant amount of sponsorship dollars for this and now we have to deliver on all the promises that come with that. We convinced 37 industry-leading professionals to spend a day sharing what they’ve learned over their careers with our community,and we have almost 40 organizations (startups and vendors) exhibiting who we need to make damn sure it’s worth their precious time and money. Finally, tickets sales are accelerating and it’s our job to make sure it’s well worth the price that everyone’s paying.

The only thing that’s keeping me from freaking out is the fact that I have some of the hardest working people to do this with. Courtney Gras is absolutely killing it with everything. She’s the driving force behind our sponsorship effort and was also responsible for securing about half the speakers. There’s zero way this conference gets done without her. Meghan Goetz is the other person making this possible. She’s handling basically all of the event setup, management, and marketing. While working with my wife can be tough sometimes, she’s so damn talented at marketing and event management that it’s worth it a million times over. These two are the reason I can risk a significant portion of Launch League, something I dreamt up and Rick and I built, and not lose my mind with stress.

I have a history of taking risks like this. In the first 12 months of owning OSC, I essentially bet the farm four separate times. Had the deal not gone through any one of those times, we wouldn’t have been able to stay in business. Since then I’ve taken my foot off the peddle a bit. I think I’ve only risked the entire business twice in the last 12 months. My point is, I really believe that you make your own luck. To really achieve anything and to learn anything about yourself, you have to go through some seriously stressful times. For me, I seek them out and I’d encourage you to do the same.


Well it’s now 12/3, the day after the conference, and it was an absolute success. When you start something, you typically have to make a number of compromises. The vision changes along they way, sometimes significantly, in order to accomplish the core goal. This is the first project I’ve dreamt up that turned out incredibly close to the original vision. It still hasn’t sunk in just how big of a deal this is. There are a few key times in life that were clearly turning points, but I typically don’t recognize them as such until much later. This time it’s different. I’m watching this area and this group of crazy ambitious people change and grow and this really feels like the tipping point. Launch League is reaching that critical mass that will allow it to take off (hence the name Flight…). So let this small piece of anecdotal evidence push you to take risks. It won’t always come out like this but that’s what keeps it interesting.