My First Year of Entrepreneurship - What I Think and What I've Learned

Just over a year ago, I left my job at the Washington Capitals to become an entrepreneur. It's been a valuable learning experience and a great ride, but like any other job, there have been ups and downs. I wrote a post last August about what I learned after one month on my own, and this article augments those thoughts.

While I've learned a ton over the past year, I think I've broken even in terms of progress. In the corporate world, that's unacceptable. In the entrepreneurship and startup worlds, depending on the situation, it may be a bit more common. Regardless, it's kinda depressing.

Consulting

On one hand, the independent consulting work I've been doing has been going really well. I currently have three core, long-term clients for which I hope I'm doing a good job and we're making solid progress toward our goals. I've also successfully executed two other short-term projects. Additionally, I have a couple of other potential clients in the pipeline. The best part is that all of these clients and projects have come through referrals, with no formal sales or business development processes. I can't complain one bit about my consulting work.

Startup Stuff

But consulting is not why I became an entrepreneur. I want to build a technology startup, and on that front, I haven't done much at all.

I wrote about what happened with my first startup, Dokkit. Since then, I've made only a little progress in my second at-bat. But a big takeaway I learned was that ideally, the startup team should come first, then the idea (for other opinions on this, see here and here). I am working with a couple of developers on a startup, and one of the team members is a consulting client of mine, so we know how each other functions and work really well together. We've thrown around a ton of ideas but haven't been able to agree with one that we all want to execute. This process can be really frustrating, but I think the hardest part, assembling a founding team that you know you can work well with, is out of the way. We're taking our time with developing the concept and being really diligent about pursuing an idea that we're all passionate about and has the potential to be a real business. Though it's moving slowly, I think we're going about it the right way.

An exciting endeavor I'm involved in is volunteering as an Up Global (formerly Startup Weekend) DC Organizer, where I coordinate events and workshops that help entrepreneurs get their companies off the ground, learn about startup frameworks and resources, and connect with fellow entrepreneurs. I've only been doing this for a few months but it has allowed me to give back to the DC entrepreneurship community and meet many smart, talented, and driven entrepreneurs who may build the next great company.

Overall, there's been a lot of activity but not so much progress. I'm working to change that.

The Struggle

Yeah, I'm going through ups and downs, but I'm not yet going through The Struggle. The Struggle sounds horrendous, but part of me wants to feel that stress and have that kind of responsibility. I am lucky to be in the situation I'm in - I have a really supportive wife, family, and friends and stable consulting work - but those blessings may be hiding the urgency that many startup entrepreneurs face that forces them to move at 100 miles per hour and really get shit done. Don't get me wrong, I count my blessings everyday, but sometimes wonder about the other ways they impact my work.

One year in, it's been an amazing ride so far. But I stress out everyday thinking that I'm not moving fast enough, learning enough, or making enough progress. Regardless, I wouldn't change a thing. And when I write another post like this in a year, hopefully I'll have a lot more to say about the technology company I'm building.