I was asked recently in a networking event to talk about the hardest and the easiest challenges we faced starting VCSonline.com 10 years ago this summer.  The question caught me a little off guard and I starting thinking back to those early days (queue stereotypical harp music soap operas use!).

Back in 1998 I had a lot more hair up top and lot less wrinkles around my eyes.  What we lacked in startup funding, customers, and employees we more then made up in hope, desire, and pure potential.  There was no doubt we would set the world on fire.  It was a magical time of creative ingenuity.  The web-based software was an embarrassment by today's standards but back then anything data driven over the web that helped teams manage projects and report to management got 'ooos' and 'ahhhs'.

Fast forward 3 kids, 10 pounds, and 30,000 clients later to today.  Finally (thank you God) things are really taking off.  Our VPMi Express and Professional SaaS resource and project management software have seen a 300% increase in the last 6 months.  We are having to schedule demos around the clock to meet the sales demand.  I guess the old joke is true, it does take 10 years to be an overnight success!  

Back to the present and the question at hand.  What was the single hardest challenge (that seemed easy) and the single easiest challenge (that seemed hard).  Lastly, if you had a time machine would you go back in time and warn yourself of the challenges you would face and the mistakes you would make?

Easiest thing that seemed hard

The #1 easiest was finding our first enterprise customer to believe in us and take a big chance on a startup.  We were so scarred when we started that no one would hire us as "2 men and a truck" building project portfolio management software.  We were working from our basement and making cold sales calls till 5PM and then working till 3AM on development EVERY DAY.  We had no funding, no employees, and you could here my babies crying every now and then on conference calls.  We were motivated by fear of failure as much as anything.  Eventually we got through to an executive at BlueCross BlueShield who saw the passion and domain knowledge we had and it was contagious.  They actually threw out the software we had at the time and paid us to model and develop it "right" using our knowledge and vision as cornerstones. 

After the VPMi went live was asked them why they picked us.  They admitted they were always complaining how expensive Microsoft, CA, SAP, HP, and some of our other competitors are and how bad the service often was.  They had a vested interest to try new suppliers (at a lower cost) to stimulate alternatives in the marketplace.  If they didn't invest in companies like ours they reasoned they have no room to complain about the price and service the large software houses provide.

Hardest thing that seemed easy

As for the "what was harder" that is easy to answer too. Nearly everything was harder then we originally estimated!  When you start a new business you are by nature optimistic.  You overstaff, over commit, and under estimate everything!  Then you make up for your sins by working days, nights, and weekends to deliver. 

On top of that you never say "no" to a potential customer, even when you know you are not a perfect fit.  You end up making a lot of software changes and customizations to appease each customer and it hold you back from growth of your main product.  The more a company can focus on what it does best, sell the vision you are reaching for (even if you don't have 100% in place today), and say "no" when you have no business getting involved you will actually reach your goals sooner!  Ask me how I know...

What message would I sent back in a time machine to myself?

So the $20,000 question is, "if I could go back to the beginning and give myself some advice, what would I say?".

For me the answer was "nothing". I have made thousands of huge mistakes.  I have delivered products I wish I could do over.  I have said some things I later regretted.  Yet in the end we always did our best to hire good people and incented them to deliver great service/products regardless of profit.  We didn't sell out to the venture capitalists during the DotBomb and didn't sell out during the last merger years.  We will never be the biggest SaaS project management solution, but for customers passionate about project management, we will be the best.

At the end of the day, we control our own destiny and have the best jobs on earth - helping companies big and small reach their full potential through project management solutions.  I would hate to mess that up as I have learned 100x more from my many mistakes then the few times I got it right the first time!

I hope this inspires a few of you closet entrepreneurs out there to do the same some day.  Let me know if any of this rings true from your experiences or if any of you have the itch to start your own company.  I would love to hear your stories too.

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