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My Entrepreneurial Full Circle (Part III)

My Entrepreneurial Full Circle (Part III)

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Where do I begin talking about WhyGoSolo?!? I honestly still can’t talk about WhyGoSolo without feeling some pain, remorse, sadness and disappointment which is why I decided not to go into too many details.


From February 12th, 2007 to August 15th, 2009 – WhyGoSolo was at the core of everything I did, although it was much more intense in the first year.  You can find out a lot about the start of WhyGoSolo at the original blog I started in May of 2007 – unfortunately, when I  canceled the hosting for the remainder of the story was deleted except for the last blog post which is on this blog: WhyGoSolo Coming Offline.

Looking back I’m still baffled by what we were able to accomplish with basically no resources. We created what I considered to be an excellent web startup that was ahead of it’s time. It actually stings to think about it.  We were a well oiled machine driven by a big dream. I wished the story would have had a happy ending.

The one question I still can’t answer to myself is “Why didn’t I move to San Francisco?” Why did I choose to waste my time in DC when WhyGoSolo would have had a better chance in S.F.   Given the opportunity to go back in time; the first thing I would do is move. Not moving is the only regret I have about the whole thing. I otherwise feel I did everything I knew to do and could think of doing.

Anyway, the first year or so working on WhyGoSolo was a total roller coaster ride.  Surreal good things would happen that would end up leading nowhere – it was tough to bounce back from the disappointments and always put on a strong face for everyone.  It was also tough to talk to investors who didn’t understand the web and where it was heading (where it is now).

I went completely broke while working on WhyGoSolo – I had been living off my savings since the summer 2005 and hadn’t really made any income. As I was losing my house and trying to get back on my feet; I got hit a few more times with two heartbreaks; one romantic and the other from a business partner. The pain and disappointment I lived through because of WhyGoSolo created a small black cloud of anger and hatred in me towards a lot of the things I believed in.  I still have to cope with the leftovers of that cloud today.

I did not easily bounce back from failing and letting people down this time around.  Thankfully, the opportunity to get away from DC and recover presented itself in the form of orders to Marine Forces Reserve, in New Orleans.

But in the end, besides all the lessons I’ve learned, what I take away is that I hope someday I can have as an exciting and fun time with another venture as I did with WhyGoSolo. I was blessed to work with amazing people and be part of a wonderful startup community…so although it didn’t end well and it was overall tough as hell – I can only wish I’ll get to do it again and have a happy ending this time. I really got to live the entrepreneurial startup life with WhyGoSolo.

Next blog post…I’ll do a quick mention of BeFitNOLA and get into what I’m working on now and why I say I’ve gone full circle.

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