My Entrepreneurial Full Circle (Part III)

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.

Establishing a Foundation: My ‘SOB Moment’

Everything I write about in this blog is gathered from personal experience and having lived through it – I know there’s nothing like a story to help people realize the importance of what I’m recommending you do. So here goes…

A couple of weeks ago I had a ‘SOB moment’. It came the morning after TECH Cocktail DC 2 at the Hangover Breakfast hosted by Micah Baldwin of Lijit.

A few of us were sitting around shooting the breeze talking business, business models and investment options. One of the guys sitting in the crowd was Eric Olson…and the fact that he delivered my ‘SOB moment’ is unbeknownst to him. Eric is an associate at DFJ Portage. He ran through a few scenarios of the entrepreneurs they see at DFJ Portage and the type of investments they make and why.

As he kept talking the main theme about the people they invest in was very clear: “They invest in the most knowledgeable and qualified people within their fields in relation to the startup they aim to start.”

They invest in the most qualified of the people/teams; I obviously knew that and had heard it many times before but it hadn’t really sunk in the way it did that morning. The way Eric explained things, clearly parted the clouds for me to have my ‘SOB moment’. It made me think about what we’ve been working to establish and what our qualifications were to pull it off. I realized as I walked away…”Fuck – We’re not quite there yet.”

In our case, the qualifications have nothing to do with how well I can lead a team and be the CEO, how awesome our tech is or how sharp our sales team is – the qualifications have everything to do with the market…our contacts, knowledge, and background of our market.

Forgetting About Our Target Market

When I started WhyGoSolo – I knew that I needed to establish a foundation by having a strong presence on the web, the startup community and within the social media circles for when WhyGoSolo would be ready to launch. I did that and I did it well.

I just happened to overlook a major key foundation over time – Our Market. Granted, our market has shifted, but I hadn’t caught just how much of a disadvantage we were getting ourselves into, until that morning.

Going To Skin that Damn Cat

It’s a crappy time to realize you’re on first base when you’re suppose to be on third base and you’ve got a lot of skin in the game.

Side story…

This kinda reminded me of The Basic School. “What now Lieutenant? We’ve lost communication with second squad, first squad took two causalities and they need a medical evacuation for two others; we’re low on ammo and completely surrounded. What now Lieutenant? What are your orders?”

The Situation

What now boss?? We’re exposed to the market, the competition is moving in our space and we don’t have the contacts, knowledge or background needed to address our target market…

It took me a few days…but than I gathered the team and said “Gents, here is what we’re going to do” (Sorry – not going to divulge the specifics just yet).

We’re going to skin this damn cat – we might not have had the best foundation in place when it comes to our current target market, but we’re building it now in a strategic fashion off of the foundation that has been put into place.

Hello, McFly!!

I can’t go back in time but I can ask myself “WTF, Hello McFly…how did you miss that?” (My internal dialogue has more cursing than my external dialogue) I missed it because this is my first go-round and I’ve had to learn on the go; it’s painful to learn things first hand. I did however, try to avoid that.


For the past year I’ve been looking for a good advisor/mentor but haven’t found him/her. That’s a huge part of establishing your foundation. Find someone who has been there before, so they can help to guide and direct you in order to avoid making mistakes as much as possible. (Will do a blog post on what to look for in an advisior)

Do Keep Reading This Blog

I will continue to pass on what I’ve learned and know. Hopefully you’ll listen to it and avoid some setbacks…particularly if you’re not strong at thinking on your feet when bombs are coming your way.

The One Truth You Must First Accept

We’re going to thoroughly discuss how to be successful entrepreneurs in this blog and how to overcome situations by being innovative and creative but before we start there is one harsh truth you must accept upfront:

In Business: You Can Do Everything Right and Still Fail

Why is it that you can do everything right and still fail? It’s because you don’t know what you don’t know. You will do everything right according to your abilities and knowledge within your particular scope at the time being. You don’t know what limitations will arise, what circumstances will come into play or what resources you will need and not have. Time and resources are continuous ticking time bombs.

This is obviously why the Vision, Plan and Foundation are critical to have but even with all of those in place – a startup business is a land mine of unknowns.

If you can accept that you can do everything right and still fail then you will save yourself a lot of agony along the way. This truth exist for one main reason.

For You to Always Give It Your All

Let go and give it all you’ve got…it doesn’t matter if it’s enough or not. Whether you succeed or fail those who go into business know the journey is well worth it – you learn and discover so much about yourself, other people, business and the ways of the world.

The key to the journey is to not give up. Whatever piece you were missing the first time…you’ll have the second time and that will take you further.

When I got my first motorcycle people told me “There are two kinds of riders. Those who have gone down and those on their way down.” I didn’t want to accept that…than I went down and realized it’s a truth every rider must accept.

I’ve always had the mindset that failure isn’t an option…well guess what? I failed at my first business.

When I finally accepted the truth that I can do everything right and still fail – I became a much better, smarter, wiser and successful entrepreneur.

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