Becoming an entrepreneur. Again. And again.

About four years ago I had a meeting with Dr. Todd about a business idea.  During that meeting, I discussed with him two options I had as I finished my graduate degree from UK.  Down one path was a steady programming job, a solid income, and all the comfort that comes with a safe career choice.  Down the other path was launching my own software company.  No clear sight of a paycheck, an extremely blurred vision of my future, and no real clue on where to even start.  He gave me advice in that meeting that had a lasting effect.  He said, “Brian, do you want to try to start your own business or not?  Because you can always get a job in a year or two if that doesn’t work out.  You may not always be able to start your own business.”

That quote influenced me to make a series of decisions that led to where I am today.  I basically interpreted that as “Go big today…play it safe tomorrow”.  I decided that day to run my business full time.  I recruited two of my engineering friends (one being my brother) to run my software company, APAX Software.  Within two years we were doing over a million in revenue and had 20+ employees.  Through the success of APAX, I was given another opportunity and therefore another decision to make about how to reinvest my share of our profits.  I reflected on his advice again and thought, “I can play it safe and enjoy this situation of moderate success…or I can go big again and try to leverage this success and start something even riskier.”  My conclusion – I can always play it safe in a year or two.

The outcome of that conclusion is Awesome Inc.  I reinvested all of my money into building Awesome Inc.  It’s been a roller coaster of an experience, including several instances of not only almost closing the doors of Awesome Inc, but I also nearly lost my original software company from lack of focus on it.  I’ve spent countless nights working until 2, 3, or 4:00 am down at Awesome Inc putting sweat and tears into our passion and mission that is – to help other entrepreneurs do what they are passionate about and support themselves and the people around them.  I wouldn’t trade it for anything.  A few of the highlights have been – launching the KY Entrepreneur HOF  (hearing stories from John Y. Brown, Pearse Lyons, Dr. Todd, & Davis Marksbury), building a high tech startup culture of communities and events that include Startup Weekend, a series of mobile technology conferences that have featured speakers from Facebook, Yahoo!, PayPal, and AT&T (brands that would normally have no reason to step foot in KY), and a monthly pitch contest that gives away $500 to the winner of each event.  Most importantly, we’ve assisted in the launch of dozens of companies including our most successful and highest potential startup, AwesomeTouch.

This leads to another crossroads that I faced as recently as a few months ago.  I had finally built Awesome Inc to a sustainable break even state (we weren’t paying ourselves anything, but we could at least cover the rent and the staff it took to run it).  My software company was back on track and has been profitable for 15 of the last 17 months.  About this time, Nick Such and the AwesomeTouch team were starting to gain significant traction.  We had three paying customers on reasonable sized contracts and a couple of very large opportunities in the healthcare space that were interested in purchasing our solution.  We knew we needed some investment to take it to the next level.  So we started applying to the top seed stage accelerators around the world.  If you aren’t familiar with a seed stage accelerator, it is kind of like grad school for entrepreneurs.  It’s generally a 3 month boot camp that is intended to accelerate your startup to the next inflection point, often leading to investment.  Not long after applying we were accepted into a program in Providence, RI called Betaspring (read the story here).

Another decision had to be made – continue making a moderate to strong impact on Lexington with the initiatives at Awesome Inc or go all out again and potentially risk losing the foundation I’d built for the past four years.  This time, the decision wasn’t as difficult…I can play it safe in a couple years, right?  Nick and I decided pretty quickly that we had to do this.  We had to do it to excel AwesomeTouch to the level it needed to be at.  We had to do it to put Awesome Inc on the national map, and we had to take the chance of winning really big for Lexington and UK to be able to point to our company as a success story that would encourage others to follow in our footsteps.

…And now we’re back in Lexington.  AwesomeTouch launched another company, Buildinglayer (an even more ambitious endeavor).  Nick, founder of AwesomeTouch & Buildinglayer, had to decide between creating ‘google maps for indoors’ (the basic premise of Buildinglayer) or going to Standford to get his MBA…guess what he chose?  Having the confidence, the nerve, or the naivety to think that you can create a better opportunity than the one you currently have is a huge part of being an entrepreneur.  In fact, it’s necessary.  The question is, how often will make that decision in your life, in your company…or when the opportunity to solve a problem in the world by creating a company, comes along?  My answer, I hope, is ‘every time’.