How (And Why) I Went From Part-Time Startups To Full-Time Entrepreneur

I left my employer, of close to four years, on February 19th, 2015. I worked for an amazing software company called Decipher, which was recently acquired by Focus Vision.

Why did I quit my job? To pursue my dream, of course.

All my life, I’ve wanted to be an entrepreneur; I even studied entrepreneurship in college. I started my first company in my senior year after college, but it wasn’t paying the bills. So, I took a position at Decipher right before graduation.

Delayed Startup Gratification

Although I chose a great company to work for, I couldn’t help but feel a sense of disappointment. I felt as though I let my education and instructors down by becoming an employee after they worked so hard to teach me how to become an entrepreneur.

Even though I was now a full-time employee, it didn’t stop me from quitting on my dream. I became somewhat of a serial part-time entrepreneur. I started four ventures while working full-time during that four year stint.

I raised modest seed-funding for one venture and acquired thousands of users for two of the ventures, but none of this was enough traction for me to quit my full-time job.

It wasn’t until I co-founded my current venture, Benchmark Intelligence, that I took the leap of faith to become a full-time entrepreneur. Benchmark makes it easy for enterprises with 10 to 10,000 locations to monitor the health of their brick and mortar locations.

Incubating Startup Dreams

After working on Benchmark for six months part-time, we were accepted into a top tier accelerator, Boomtown. They offered us funding, mentorship and a place to work. My three amazing co-founders and I all quit our jobs, packed our bags and subsequently moved to Boulder, Colorado where the program is located.

“Success is never guaranteed. There is a chance that we will grow a multimillion dollar company in the next few years, but there is also a chance we may have to look for new jobs in six months.”

We’re about halfway through the program and we can’t wait for demo day. Although Boomtown is doing everything they can do to help us succeed with our company, success is never guaranteed. There is a chance that we will grow a multimillion dollar company in the next few years, but there is also a chance we may have to look for new jobs in six months.

Right now the future is scary, but I wouldn’t have it any other way. My team and I are hunting for our own food (money) and no one is spoon-feeding it to us anymore.

The best part is that I couldn’t have chosen a hungrier team to hunt with. The scariest part is that we don’t have it all figured it out yet. We’re learning as we go along and are constantly experimenting to find out what works and what doesn’t.

Figuring It Out As You Go

Here is why I decided to quit my job and pursue my dream, even though I don’t have it all figured out yet.

1. No regrets

   When you get older, they always say you’re going to regret the things that you didn’t do, not the things that you did do. Leaving my job to pursue my dream was one of the scariest decisions I ever had to make, but at the same time it was a one of the easiest decisions I’ve ever made.

   I was aware of what I was walking away from when I quit my job, but I was even more aware of what I would be walking from if I didn’t. I’d be walking away from the opportunity of a lifetime.

   Do your best to live without regrets. I know I am doing my best to do just that. Even if my company fails and I need to find a job, I will be happy in saying that I tried and gave it my all because at the end of the day, that’s all you can give.