My Entrepreneurial Journey

I wasn’t sure whether to call it my “Journey” or my “Roller-coaster” but since all roller-coasters end at some point let’s go ahead and call it a journey.

Reid Hoffman, co-founder of LinkedIn, is attributed with saying that an “entrepreneur is someone that jumps of a cliff and builds an airplane on the way down.”

Wow! Can you imagine how scary that would be if it were really the case?

Well… I’ve been there (three times) and it does feel pretty scary. I’d have to jump of a real cliff someday to tell you if it’s really possible to build something that can fly at all while you’re on the way down – but for now let’s stick with this metaphor.

I said three times because I’ve had three failed businesses in the past. Pardoned me, I’ve had three very expensive and emotionally-draining business educations. That sounds better.

I will elaborate on each past failed-business experience on future posts because there really are some really good nuggets of information there that could potentially save some younger entrepreneurs from committing the same errors I’ve made.

My first business,, was born as a result of me getting laid off back in 2002 (right after the events of 9/11 lead us into recession).

Starting was like jumping of a small cliff and eventually landing on some trees with some very minor injuries to my body. I din’t quite get to build the plane on the way down, but I did manage to “glide” for a while (4 1/2 years to be exact) until it was time to get grounded.

In 2011 I left an incredibly successful corporate job of five years to start another business, WebForce1, which was a Microsoft Partner firm that focused on helping small businesses move to the cloud. That business lasted close to two years and somehow I manage to again “glide” into safety. I actually glided into another plane (another Microsoft Partner firm that needed my skills) and provided some safety as I was still learning to build a plane.

Then in 2016 the entrepreneurial bug bit me again. This time I started a company called PingMomo, which was developing a mobile app and service to help working parents find safe and reliable transportation for their children when they were stuck in situations where they couldn’t do it themselves. Although the app was never fully built (another plane that didn’t get built) I have to say this was one of the most amazing experiences I’ve ever had as an entrepreneur. I’ve never been more grateful about a failure as I was with PingMomo. Why is that you say?

Well… You’ll need to come back to my blog soon to learn why. 😉

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