Video Transcript

00:07 Anthony Casalena: And that was just horrible [chuckle] I remember thinking that I was just completely and unbelievably screwed.

In 2003, Anthony Casalena founded Squarespace, which helps individuals and businesses make websites.

For the first two years, Anthony didn't hire a single employee--even as Squarespace grew to thousands of users.

00:31 Casalena: I had set up Squarespace because I was basically running the whole thing. There were these series of system set-up that where whenever there was a server problem or if something was down or anything, I would get an alert on my phone. And so, I'm used to getting these alerts and having to go scrambling and running sometimes to a computer to fix things. So, it's Friday night, I'm in SOHO and at about 12:30 or 1, I get an alert on my phone that essentially, shouldn't have even been able to reach me because it's like, is the "Everything is completely down, it's so screwed" alert. So, I didn't even know that left the data center to get to me, but in some sort of miracle it did. I remember my heart sinking 'cause I had never seen a problem like that, and I immediately just left and I got into a cab and went down to Wall Street where our data center is, and my friend's texting me, going, "Are you okay? You just left and it's kind of weird." And I'm like, "No, I'm not okay. It's messed up."

Anthony confirmed that every website Squarespace hosted was down.

01:41 Casalena: And so, it's Friday, it's 1:30, I go in there. I go to Squarespace's cabinet, and I see, basically, the traffic chart to Squarespace is now just like this little line at the bottom, and then this huge spike up. And before I could really even register what that meant, all of the machines just turned off. They just turned off. And so, I'm sitting there in the data center, after two drinks on a Friday night at 1:30 AM and I'm just like, "Holy shit! What [chuckle] what?" And so I call, I call the network, I call the network technician to send somebody. It takes about 30 minutes from the com. Guy comes, pretty clear, within a couple of minutes of meeting him that he is not in the most fit of mental states here, now at 2, 2:30 on a Friday. So we see each other and we're like, [chuckle] "Oh my God, this is gonna be fun!"

Anthony figured out that Squarespace had been hit by hacker 'robots' that were after a site it hosted on its servers.

Even with the network technician, the problem took more than six hours to troubleshoot and fix.

03:08 Casalena: "Why am... Why is... Why is this even happening?" I mean, this isn't what I signed up for. This is crazy. My entire livelihood, my days are tight, so whether I'm getting text messages in the middle of the night, and robots are attacking Squarespace and it's just completely and totally, and utterly exhausting. I think that when I'm honest with myself, again, I can think back then and think, "Okay. Well, I was always really good of being the engineer and being a programmer and building this thing, getting it running and doing all the jobs myself." And eventually, there was a point in the company's history where that that skill to do all that wasn't a strength, it was a weakness, and what I really needed to be doing is not falling back on that engineering strength, but actually, going out there and trying to build a team and get redundancy in place from a personnel perspective. And that's a really hard thing to do. And I think getting pushed outside of your comfort zone and dragged forward and realizing that you can't do it all yourself is really an important time.

Today, Squarespace has 90 employees, and offers 24-hour tech support to users in 120 countries.

In 2010, Squarespace received $38.5 million in funding, led by Accel Partners and Index Ventures.

Published on: Aug 16, 2012