November 17, 2019
How Squarespace Went From a Dorm Room to a $200 Million Company | Inc.

How Squarespace Went From a Dorm Room to a $200 Million Company | Inc.

Hi, I’m James Ledbetter the editor in chief at Inc. magazine and 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

33 thoughts on “How Squarespace Went From a Dorm Room to a $200 Million Company | Inc.

  1. Parents are a huge part of the success of a person, mentorship, capital seed, etc and the right mentality… If you have toxic parents you are fucked, at least if you wake up fast

  2. I've heard all forms of rags to riches tales. And the methods change as the eras pass.
    Would Squarespace still be possible or even as efficient if he- let's say: saved paychecks while living with his parents or still attending college?
    Anyone have an idea?

  3. My cousin did the super bowl ad thing. Best move he ever made even though they used Captain Kirk lmao. Today HULU is pretty dam big.

  4. I dnt respect people who grew up with money..his family..parents have money to give him to start his business…..i dnt respect dat
    ..if it was a poor guy dat grew poor..parents dnt have money to help with business..poor nigga would start out of scratch tryin

  5. interview is great but the camera work is terrible. it's just distracting to try to watch as the camera is unnecessarily zooming in and out every couple of seconds.

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