Ten years ago today, after a long lunch at a cafe in SOHO with my then business partners, I called The Company Corporation in Delaware and officially incorporated a start-up that had launched out of my Middlebury College dorm room the previous fall.

The spring of 2000 were heady times.  Everyone was full of optimism.  The NASDAQ was less then a month away from it’s all time high. Twenty-somethings like me were becoming multi-millionaires overnight on The-Emperor-Has-No-Clothes business models and we were going to be the next ones.  A Doonsbury Cartoon from that spring summed up the times, as one character said to the other “Just finished the business plan.  I’m off to get a Mercedes.  Want one?”

college xtra

Ten years later, the story didn’t play out that way for CollegeXTRA.com, Inc., but that’s just fine with me.  As a celebration of our tenth birthday, I’d like share a few things I’ve learned along the way, but first, a little history on how I got here.  If you want to fast forward through the “how we got here” part, my next post covers some of the things I’ve learned over the past ten years.

The business you start is not the one you end up in.
So how did we go from creating “for students, by students” web sites at college campuses to developing web sites for REALTORS?

Our original model was to develop sites like Middkid.com at campuses across the country.  Middkid, which is still very active today, is a hyper-local portal focused on the Middlebury College community and supported by advertising from the merchants in the town of Middlebury.  We have a local business directory with coupons from our sponsors, an offline printed discount card that can be found in the wallets many students on campus and a monthly special events email newsletter.  The site has a database with thousands of course evaluations written by students over the years, sharing their experiences about the classes they took and the professors that teach them.  There is a Middlebury student who is our Campus Manager each year that resubscribes the businesses during the summer and the updates & markets the site through out the school year.  It’s an awesome, paid internship that is one of the best hands-on run-your-own business jobs I’ve seen for college students.

With all the success we had (and continue to have) at Middlebury, why didn’t this go national? The answer there is a blog treatise in itself, but the quick points are as follows

  • Ideas are great.  Implementation is really, really hard.  At 33, I don’t know much.  At 23, I knew nothing.  We experienced a lot of the challenges that faced most start ups.  Partners that didn’t always see eye to eye.  Lack of infrastructure.  A frenetic pace that wasn’t sustainable.  Insufficient skill sets in key areas of the business.  Some bad timing (we launched our expanded campus platform in September 2001).  The list goes on.
  • As we chant at the hockey games “there’s only one Middlebury.”  The town:gown ratio in Middlebury turned out to be the perfect balance.  Businesses counted on students, but students had options so the businesses need to advertise.  When we went to smaller communities, like Hamilton, NY, home of Colgate University, there was only one pizza place.  When we went to larger ones, like Syracuse, the students were drowned out by the population of the community.
  • We were only as good on each campus as the student that was representing us (and the student turnover was every year).  The priorities of college life require that you drink with your friends, hang out with your significant other, go to class / complete your assignments and sleep.  Managing a business came fifth, at best.  Only a select few of the students were as passionate about their campus site as I had been about Middkid.  It was a job for them, not their baby, and it took me a while to come to grips with it.
  • We were ahead of our time.  Sounds like a cop-out, but in 2000, we were selling online advertising to College-town merchants who had no web site.  In order to get the sale, we ended up building a web page on the college site for the merchants and those pages were becoming their de facto web sites.  Since you follow the money in business, we went to where it was (web development) and left behind what wasn’t working.

When we decided to put the college student business model to bed, we looked around and saw another opportunity, which is the story of Union Street Media.  We had developed a great content management system that let the campus managers update their site.  We were able to leverage that tool for business clients who needed a web presence.  However, when you’re literally going door-to-door selling web sites, you’re competing with the most precious assett in business, and life: people’s time.  We were having marginal success at it, when our then advisor, now board member and long time mentor, David Bradbury, set us up with meetings at three different trade associations in Vermont.

We established partnerships with the Vermont Bar Association, the Vermont Lodging and Restaurant Association and the Vermont Association of REALTORS.  With each partnership, the association paid us to develop their web site.  We then discounted our services and they marketed us to their members as a benefit of joining.  As it turned out, lawyers were too smart for the internet in 2002, lodging & restaurant establishments in Vermont couldn’t afford it, and the real estate industry was about to be fundamentally changed by the “Internet Data Exchange” (IDX), which is the sharing of brokers’ listings online.  Previous to the internet, if you wanted to buy a house you needed to walk into a broker’s office and look at the “black book” of listings.  The book was printed monthly and out of date the moment it left the press.  It made for an extremely inefficient process, but let REALTORS control the information.  The tug-of-war that ensued with in the real estate community was vicious.  One Vermont REALTOR virtually accosted my brother at their annual convention in 2003 “Scooby-Doo” style for ruining his businesses (“if it wasn’t for your rascally kids…”)

From the early days of developing web sites for local Burlington VT real estate clients like Century 21 Advantage and Brian Boardman, we expanded to NH, MA, NC and Chicago (we’re White Sox fans).  We are now developing web sites and providing internet & social media marketing for hundreds of agents, brokers, teams and real estate offices all over the country.

Now that you know the history, check back tomorrow for the lessons I have learned over the past ten years running a business.