Anthony Casalena: The best web entrepreneur you've never heard of

Back in March of 2006, nextNY held it's second social gathering--that time it was at Dewey's Flatiron.  This guy comes up to me and says he works at a company called Squarespace.  I had heard of it--they were big buyers of Google Adwords and I felt like I had checked out the site before.  It seemed like a pretty comprehensive publishing tool.  I asked him how many people he had working with him.  The answer?

"None.  It's just me."

Honestly, I wasn't sure I believed Anthony Casalena at the time.  It just seemed like a lot for one person to build.  He did say something about having hired a contractor once to do some small stuff, but still, I was throughly impressed.  

Since then, I've only grown more and more impressed.  He has grown the team and they've just moved into an awesome new office.  This year, I finally became a Squarespace user after admiring the product for a while.  I love it.  

Apparently, I'm not the only one.  After taking no more than just 20k from his dad way back when, Anthony and his team just raised $38 million from Accel and Index.  Not only was it nearly twice as much as Foursquare just raised--and probably at a higher valuation.  Given that he's actually profitable and making money, why would he bother giving up more than a third of the business?   Probably wouldn't, so I have to imagine that this was a $100 million pre deal.  

And yet, no magazine covers for Anthony.  Maybe this news will change that--but I doubt it.  He seems more focused on just building a great business.  Good luck to him and his team!

All in all you were all just bricks in the wall...

This is a pic of literally the first moment I met Anthony--back in March of 2006.  It may be the back of his head, but now we know how much potential he had going in that noggin.