Hi, I'm James Ledbetter the editor in chief at Inc. magazine and inc.com and I'm
thrilled today to be talking to Anthony Casalena the founder of Squarespace
Anthony thanks for having us here thank you for coming down
let's start at the beginning how was Squarespace born it started about we're
a little over 15 years old right now and it started back in my dorm room at the
University of Maryland I wanted to make a website for myself and I was really
unhappy with a lot of the a lot of the a lot of the tools out there on the market
you to get a website together that had a couple pages and you know a blog or a
photo gallery that was hosted you needed to combine all these different pieces of
software really yeah I mean we're talking 2003 yeah look you buy the
domain in one place and you have to like have to download this software and you
mush em all together the blogging software is different than the
page building software different than the statistics out like so you had up
put all these things together I thought that was really clunky but it was also
that you know I'm somebody who really cares about design and I care about the
way things look and I care about the way things are presented and how they work
and even if I could smash all the software together which I could do
because I'm admit it was an engineer it still wouldn't be cohesive and so really
those were the two reasons for starting Squarespace how did you raise money so
the first money to start it came from my parents they gave me 30 grand and as
they remember the story it's something that sounds like we've always supported
you we've always believed it cetera et cetera until I asked for 30 grand
yeah and then that's a couple hours did they see it or were they just kind of
humoring you or they knew I put a lot like I've been making I've been
programming so I was a kids making things putting it out there this is not
a completely crazy thing for me to do and you know I really put the entire
thing together except for the part that cost money right I mean I I needed the
money for servers like register back back at the time we were done in set of
servers initial hosting costs and actually a logo I couldn't draw the logo
but I could do you know the software I can make the website I pretended to do
the marketing you know it's I did all that I was just like I need this last
thing to to go presume you're out of the dorm at
this point I am out of the dorm at this point where is the office so I left
University from University of Maryland in 2005 I moved to New York in 2006 and
so before I added some people I was literally in my like ridiculous
apartment that I moved into here post college with complete strangers and
there was no office I would just run it from my from my like random five bedroom
apartment in Chelsea Wow yeah it's kind of crazy and then
eventually you know after doing that for a while it gets it gets tiring I mean it
gets it gets- makes it kind of crazy I mean you can wake up go to work
work is ten feet away from you go to sleep like that that's the rough so I
eventually got him and he's like before we were kids if I remember renting a
desk from architect who I met on Craigslist and moving into an office
downtown just to mix things up and then you know we when we started actually
adding people here in New York got a small small office to fit maybe seven or
seven or ten people on a Center Street yeah how long were you a one-man show
about three years I had some contractors at the time but you know it was it was
just me doing the majority the work for a while what was the moment where you'd
said it I've really got to hire somebody now I was very comfortable doing a lot
of the aspects of the business kind of myself it it just started to get
overwhelming I mean like at some point you start to set a goal for yourself you
you know spend three months working on something and you realize like well I
just spent the month doing accounting and them customer support and then you
know XY and Z and like I missed I'm not I'm not moving this thing forward and so
it was very clear I needed to I needed to grow the team out a little bit it
sounds a little bit like it's a it starts off like a kind of passion
project slash hobby slash mmm maybe there's a business here yeah but at some
point it becomes a genuine big thing and I'm curious what that felt like when
that period was for you by about 2010 I realized that the the software that I
had made that you know was primarily a blog centric piece of software
created an era that was you know five years in the internets forever you know
was probably not going to power the future of websites you know browsers
have gotten more sophisticated people you know this opportunity to use
JavaScript and hardware accelerated CSS on websites you know you could put big
fullscreen imagery on sites and a lot of the people here were really excited
about making sites like that and so what we did is we started rewriting the
entire platform around 2010 in our case rewriting was a really really positive
move for us really big deal we took the lessons of the past you know six or
seven years and built a system that really could create any kind of website
and really push the web forward we look at with Squarespace six we launched that
in 2012 and so with that platform we could go beyond just you know blog
centric websites and into portfolios and we had a focus around small business we
had you know we really were like hey like what are the categories to care
about and how can we do this and do you see demand for all these kinds of sites
so we evolved from just being a blogging platform to being a site building
platform in China tell me about the decision to advertise in the Superbowl
now what who made that decision presumably is you and what what was the
discussion like leading up to it so I think the idea of it had always kind of
floated around in in kind of culture here right they people joke it could be
a joke it's like well we should just do the Superbowl ad or whatever I mean so
I've done advertising we've done advertising from the moment I launched
it right I spent you know 200 bucks on AdWords and made a hundred bucks and
then spent 300 bucks on AdWords and made a couple more hundred bucks and like so
that was very natural and then you know when pot when AdWords sort of started to
top out it was like okay we reward we go next what ended up happening is we just
kept growing channels right and so you would go from AdWords to podcast to
radio to internet radio to Internet video to out of home to subways to and
you just you kind of to television you just kind of kept going and at some
point while it was a really big leap for us to do such a concentrated buy it was
like well how do we how do we how do we take a really big
step forward but I'm in there is a film about me being me is it a movie about
other people being inside you sure why not
what's really cool is it's 30 seconds that you're spending an immense amount
of money for and it really makes you think about what is your message and how
do you get that across in 37 yes and I'm not saying we've always nailed it with
every single spot and we've had different strategies year after year but
it became this kind of like rallying moment where it was like okay can we
really articulate what we're about in a way that resonates with people really
really really quickly are we confident enough with that message
also John you went from this long period of being kind of a one-man band yeah to
being the maestro of a very large order and and how how has that changed how has
it changed your day-to-day and how does it change you as a leader so it's
changed me as a person I think immensely and it's changed my day-to-day
substantially I mean you know 15 years ago I would have been doing programming
most of the day and then doing copywriting and running the AdWords and
installing servers and doing the uptime monitoring and network stuff I mean like
I did all that stuff answering the customer support which I
did for years and now you know my job is much more about communication hiring
having strategic conversations with people accountability you know just just
those sorts of things you're very different management which is different
it's a completely different skill set than everything I was doing before it's
literally you know going from an individual contributor right doing all
these different things to somebody whose main job is frankly dealing with people
yeah and how is that been I mean have you have you found what what what's the
biggest challenge that you found in that scaling up of duties people I mean like
you know it's it's a joke around about it but like I think just having I'm not
saying I've fully solved any of this but I think the moments of self-awareness
when things start to go wrong and you've realized you've made a huge structural
mistake or you've hired the wrong person you you know it neglected to do
something I think that I think that that stuff for me has been really you know
it's helped me grow a lot right because I mean things go wrong and really don't
have anyone to blame but myself and so when things go wrong I try to ask myself
why and what could I do in the future to not get myself in that kind of position