This is a post I have been meaning to write for a while.  It’s one of those topics that I go back and forth on whether or not to share.

Entrepreneurship has best been described as a roller coaster.  The are ups, downs, corkscrews, and loops.  Sometimes there are days when you feel you will conquer the world and two minutes later you believe you are going out of business.  Needless to say the highs are high and the lows can be low.

4/22/2010 is the date when my entrepreneurial journey began in earnest.  In some ways I was all ready an entrepreneur since I was a 1099 contractor for about 1.5 years but this was my first time building a company.  A previous client of mine wanted to build a national chain of healthy restaurants and asked me to join him on the journey (BHAG: Change the way America eats).  Restaurants?  What the heck do I know about that?  I like to eat in them but beyond that never gave thought to running one.

With complete ignorance in my mind, I of course jumped in with two feet.  He was a very, very senior executive and when a guy like him gives you an opportunity to do something big, you take it without question.  I figured I building a company with him would be a hell of a ride and I would learn a lot along the way.

Was I right.

Over the next four years, I learned entrepreneurship in the school of hard knocks.   I learned all about creating something completely new, the challenges of replicating it, how to raise money (and how not to), how to hire hundreds of people, how to run a business, I learned all about construction, and learned many other things I never thought I would ever know (and can’t write about).  This was the hardest thing I have ever done in my life and I loved it.

Then there were the not so great parts

There was a five month period where I didn’t get paid, I saw my bank account go down to a few weeks of cash, had arguments that were the most intense I have ever had, got completely screwed over by vendors, caught employees stealing, was lied to on a regular basis, and traveled so much that I was rarely home.

Looking back on it, the whole experience was insane.  From the outside, everyone thought success was assured.  We won award after award, were in six states within 36 months of opening our first restaurants, created amazing food, built up a in-restaurant culture that respected staff (rare in fast casual or fast food restaurants), and everywhere we went people wanted to help us grow.  It was amazing.  I tell people all the time that I didn’t work a day in four years.  I lived and breathed the mission and what we were trying to accomplish.  I loved what I was doing.

So why did I leave?  After four years of running hard, I was burnt out.  We were also taking in a lot of money from a strategic and the writing was on the wall with respect to the team.  So, I got ahead of it and decided it was time to transition.

Over the next 12 months I tried three different things; tried to start a restaurant tech company (went no where after a few months), joined on demand food startup as a co-founder (bad team mismatch), and joined a medium sized outsourced executive assistant company as interim COO (discovered they were insolvent after 3 weeks).  Objectively speaking, I failed at each one (3x in one year!).  However, I believe that I simply discovered a few paths that weren’t going to work.  Somewhere along the way, I come upon the idea of building a small business internet portfolio and went on the journey I am today.

What kept my resolve going?  Maybe it is stubbornness and dogged determination to control my own destiny.  Maybe its like Steve Jobs said:

I’m convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance.”

About that time when I was a multi-millionaire.   Unfortunately, my bank account didn’t have lots of zeros in it but it was all paper wealth.  When I left the restaurant company my equity and options were worth a few million.  After I left, I learned all about cram downs, repricing, and all sorts of things that financial people can do when giving a company money.  In the end my investment in the restaurant company was worth 15% of the original amount with no real hope of getting to even 50% and my options were so underwater that there was no hope for any value.  The only saving grace is that we ended up starting a frozen food business as well and the value of that investment gave me enough cash to cover my original investment and a bit more to parlay into another business.  A single, nothing more….and I got lucky to make it happen.

After four years of dedication and hard work, I came out with poorer than I would have if I took a high paying job with a steady paycheck and great benefits.  What did I gain?  A four year degree in how business really works.  This isn’t something they teach you in business school (GO BLUE!) but something you learn by jumping into the deep end of the pool and figuring out how to swim.

Why am I sharing this now? I think that it’s important for others who are on the journey or about to embark on it that it’s a rough road but if you stick with it long enough, you will get where you want to go.

The question people ask me is “knowing what I know now, would I do it all again?”  My response?  I am about to.

I close on next Friday