In my first post, I referred to myself as an entrepreneur. It has taken me many years to be comfortable with that title, and I am still not fully on board with it. Whether I am an entrepreneur or not has been a popular discussion topic for many years with a great friend of mine (who truly is an entrepreneur in every sense of the word). Out of respect for my friend’s opinion and my credibility in writing about entrepreneurialism I do, at this point, kind of have to own that descriptor, so reluctantly I will accept for now that if not an entrepreneur I display tendencies. And the tendency that I probably display the most is a complete and utter disregard for risk. I know plenty of folks who have better business acumen than I do and would love to run their own business, they talk about it all the time, but they never take any steps toward making that happen. Why?  In short – Risk tolerance. As I brought on partners in companies I started, the one common thread that they all seemed to have was the absolute inability to tolerate risk. It made for a good counterpunch to my complete disregard for it but it was painfully obvious that they would never have started anything on their own. They wanted 40-hour weeks, a cell phone allowance, a closed-door office, and a company car. I still have the terms of employment one of the first senior partners I brought on emailed me and it reads like he was focused on trying to start an employee union and not becoming a profit-sharing owner; 40-hour weeks with every Friday off, cell phone, and home internet covered by the company, company provided home office equipment, and of course the ever-present request of a company car. It was maddening. None of that has ever mattered to me and my summation is that it also doesn’t to true entrepreneurs. 

My discomfort with describing myself as an entrepreneur stems from the fact that my first venture was not a result of years of planning and a burning desire to venture out on my own. It was simply the result of my employer’s downsizing. The thought of starting a company had literally never entered my mind.  But in early 2009 I found myself unemployed at the age of 36 with massive debt, no savings, and expecting our third child. All while in the middle of the worst recession in a generation. So when a past colleague offered 2 weeks of consulting work overseeing one of his projects it was actually the last thing I wanted to do, I wanted to find a real job that lasted more than 2 weeks and felt my time would be better spent looking for it. What I really wanted to do was bury myself with Cheetos on our old worn-out couch and not come up for air for a week. However, with nothing in the bank, I had little choice but to take the job so the caveat that I had to start a company in order to invoice my time over those two weeks seemed, at that moment, like an annoying administrative chore.  

During the evenings of that 2-week project, I spent a lot of time in a nearby bookstore reading all I could on “how to start a business” and I can honestly say I did the opposite to almost every piece of advice I read. I registered the company myself online, I didn’t write a business plan; I didn’t know what my plan was. I didn’t get an accountant; I tried to teach myself QuickBooks. I didn’t get a lawyer, insurance broker, banker, or bookkeeper. Although I eventually did engage all these entities when the company grew in size, I will say that had I followed the advice I was reading, particularly the number 1 piece of advice all the books preached, writing a business plan, I would not have seen the company grow to over 200 employees with offices in 5 States and close to $50MM in annual revenue. There simply would not have been any flexibility to take on projects outside of the scope of the business plan that I would have written (unless that business plan clearly stated “do whatever you can to make money even if you have no clue what you are doing”).

The lessons learned in those early years led to the creation of five more companies in the ensuing years, some solely by me, and others with partners. And with them, I have experienced almost the entire range of human emotions. I have secured my family’s financial future but have also had the indignity of being dismissed by a board I created for a company I founded; I have made lifelong friendships but have also been betrayed by business partners and colleagues I loved. Most of all I have learned that high reward does not always stem from high risk, after all, I had little to risk in starting my first company as I had nothing to lose, and it was that company that was the catalyst for all that followed. On the flip side, I have certainly experienced little reward from high-risk ventures. If my experience as an accidental entrepreneur has taught me anything, it’s that risk does not always result in reward, but it is certainly good for an assist. 

At some point, I will embrace the title of entrepreneur wholeheartedly but today I still just feel like a lucky idiot.