 I'm Alexis Ohanian. I've started startups, invested in them, and met amazing people using the internet to change the world. Our generation has an opportunity unlike any other. We can create small empires without anyone's permission. We're back in Soho. Now there are three ways to make a website. Either you code it yourself, you hire someone else, or you use one of the many platforms available to get some help. Now, Squarespace has spent nearly the last decade focusing obsessively on making it as easy as possible to make a beautiful website so that you can spend your time doing what you love. Oh, hello. I'm Alexis. Hey, Anthony. Howdy. Awesome. So this is Squarespace. Welcome. Wow, I can already tell how much you guys care about design. Squarespace is a content management system that helps people make websites, blogs, and post them online. So you go to the website, you pick one of our designs, and you can manage the site yourself. Why did you want to go into the CMS space? So it was 2003, and I was in my dorm room, University of Maryland, and I wanted to make a website for myself. And really, at the time, everything seemed to be this $2.99, race to the bottom, like, bargain bin, you know, kind of service. And that really didn't appeal to me. It didn't fit with my personality. I, you know, I saw the website as sort of like, you know, my online clothing. It was like, this is going to be the thing that everyone sees when they look for you online. Not very many people were thinking about bringing A-game design to the internet. The CSS was there rounded corners were not a part of it back then. I remember that. There were no drop shadows back then. Yeah, to round a rectangle was, you know, four images. It's a total pain in the ass. Ridiculous. Ugly hat. Yeah, completely ridiculous. But like, why? There was no one else doing this. Right. So why you? Why were you the one in 03 thinking, you know what, design is going to matter? I just, I really wanted it for myself. Started in my dorm room, you know, built the software by myself in 2003, designed it, launched it in January 2004. I actually ran the company almost alone for the next three years. I was doing everything from customer support. I would answer all the tickets at a certain time every night and then wake up and answer some in the morning. And I just have that as a routine for years. To the server infrastructure, to the design, to everything, the writing, all of it. I was, as can be expected, completely and totally stressed out, like out of my mind, like problem stressed out. But good problems. Kinda. I mean, like, this is a level of stress where I'm walking down the street and a voice in my head, that voice in your head that's supposed to tell you like the good thing to do is telling me you can't do this anymore. Your own voice in your head is saying that. Yeah, it's saying that. And I push the voice aside. And you obviously told that voice, like, shut up, voice. I got this. I got this. You can find yourself in a position where it almost feels like you don't know how to get out of it. Or you don't know the step you need to take to kind of bring it to the next level. And that step actually was hiring. What I did in those early years kind of to a fault, and maybe ten years could have been eight or seven if I would have gotten some of this stuff right, is I really tried to do too much alone. And I was always really good at, you know, the engineering stuff and the creating stuff. And I could write and do all these different things. And so I would fall back on those skills. But what didn't come naturally to me is, you know, recruiting people to the company and figuring out how to determine if they're a good fit and if the relationship was going to work. And so I waited too long to do some of my initial hiring. And then after I waited all that time, the hiring is supposed to unstress you, not stress you more. And I actually made a lot of mistakes in my initial hiring. Because I was hiring... Hired the wrong people. Yeah, I was hiring some of the right people too, but I mean, not such a good ratio, let's say. You know, it's very, very dangerous when you get yourself into a position where you start to have a need, right? Like, I'm falling apart. I'm stressed out. I really want to hire people. I really want to hire people. I really want to hire people. I really want help. You start to make compromises and see the positives over the negatives, and you're not balanced in how you're evaluating things. During that phase, I think I could have done a better job there. So I stressed out the infrastructure. I didn't use the right litmus test when bringing certain people on. Frankly, I had never really worked in another company besides this one startup before us. I didn't really even know what things looked like. I didn't know what a manager looked like. I didn't know how much stress was supposed to be removed from me when hiring certain kinds of roles. It was just like, I'm just used to stress at level 10. So I guess if it goes down to level 9, that's pretty good. And yeah, it was hard. What is your stress level number at right now? Right now? Yeah. Maybe like a 6.5. And then if we shard the database properly, like 5. Main floor, big bookshelf. I love ladders on bookshelves. Cool, right? That's not a load bearing ladder, is it? Should I try to? You could try it. This is one of those offices. It's like there are certain apartments I walk into where I know I'm like, you're so much cooler than I am. Raise platform, yeah. So it's actually the same cost to rip up the floors, put all the wiring in the floor as it is to build this platform. And so we kind of used it as like a little bit of a design element to segment off the workspace. And it came out quite nicely. Hi, I'm Alex. I'm Alexis. I'm Derek. I'm Julius. Pleasure to meet you. Pleasure. So we do marketing. So Derek and I work on the podcast radio team. So if you guys hear us on Spotify, you guys hear us on Pandora, if you guys hear us on This American Life, that's our team. So this is definitely one of the best looking offices we have been in. Do you work with someone on this? Is there some interior designer, some professional cool person who picks all this stuff out or what? No, so actually all the stuff on the shelves is from us and employees and our designers and things like that are old things I have. Squarespace started out as one college student's blogging solution. And over time it came to be a platform for online portfolios and eventually an engine for e-commerce. We're here in Tribeca to meet with a design agency that is doing all of the above. Our backgrounds are both really strange and weird. I used to be a ballet dancer in a former life. I've always been really interested in technology. My father is a photographer, so at a certain point I got injured and those interests kind of came together in a new way. I went to school for computer science and art. My career has been in marketing and web design and all that kind of stuff. But we really found our sort of energy in terms of working with outside clients was making films about brands and telling their stories. And that's really like what we really like to do, using a documentary style to tell stories. Squarespace is a CMS built around helping people create beautiful things and tell their stories on the internet. But what does it do for your business? We found Squarespace working on a project. We were commissioned by Wiley DeFrain to design his new restaurant brand and website. And we decided to use Squarespace for that. And it was right around the time when they started to offer commerce. And we as a small design studio, it's just us and we have a couple people helping us, we're looking for something that allowed us to create really quickly and really beautifully. And we created photography and a logo and a simple type treatment. And very quickly we were able to get our clients assets into the site and make it beautiful. We have a store that we work on now which is called General Store, which is our old studio, which was a storefront. And people started coming in and asking us if they could buy things from our conference room, which was really weird. Yeah, but a good sign. You're probably onto something. Well, it was kind of, yeah, it was weird. So we had like, I don't know if you guys can see that, but that's Paul Francis, our white buffalo. He has his own website, also paulfrancis.com. He's prolific. Yeah, he's like all-knowing, all-seeing. But he was on our wall in our storefront and people would come by and say like, hey, how much? How much for this thing? And we're like, it's just ours. We're not really selling it. Paul was not for sale. Yeah, he was. He tried to pull them away. What ended up happening there was we started to have a desire to curate things people could actually buy, which I think is a really strange way to start an e-commerce slash retail business. Our hope is to sort of help reduce the choices that you need to make to find really great things to surround yourself with. First off, how old are you? I heard a rumor that you were like 15 and a prodigy. I'm not 15. One of those is true. No, I'm 21 recently. I joined this company when I was like 18. You joined the company when you were 18. Shouldn't you have been in school? Yeah, maybe. Why weren't you in school? I went to art school for six months, and that was a lot of fun. Okay. So I left, and then I was running an agency with a rent of mine for like two years. LLCs and signing them when you're 16 doesn't really work too well. So that was a little iffy, but I turned 18, and I was like, all right, I'm going to finally sign my LLC papers. And then we ran an agency, and then Squarespace hired us for some contract work. And then I spent more time here than my own office. And so I was like, well, I'm going to join this company. What do your friends think about what you guys do for a living? They think that being in a startup means that I'm naive, being that I'm inexperienced, that I'm just chasing a, what's it called? What's that? A dream? Yeah, just a dream. And I don't want to just ruin their perception of it or tell them because I'm ahead of the curve. And we're doing things that are very exciting. We're growing at rapid paces for the company ourselves. And we're just learning new advertising techniques that are not used by any other company. What if a professor shows up day one, first semester, and says, all right, you guys need to start a web design consulting agency. Yeah. Report back to me in a year and have at least three clients. Yeah. Do you think that is perhaps a future for how one might look at education? Yeah. I mean, you learn more about relationships between people, right? Because you're working with this client, and it's like you have to sustain a relationship with them. And that was like, how do you email clients? You can't say certain things. And at first, I would just be like, yeah, check this stuff out. You can't say that. You can't just drop a link on them and be like, just give me some feedback. You've got to be constructive about it. So there's stuff like that that you really learn on how to communicate with people and then figure out what people need and want and all that other stuff. That really teaches you something that I don't think you get to learn anywhere else. There seems to be a kind of more mainstream appreciation for design. And what do you think that means in the future if more products are being thought of more thoughtfully with how they're designed? Better lives, I think. People's lives would be better if all of the products that we use every day. So what do you mean by that? I'll give an example. There was an older gentleman that came into our store, and he saw that we have a toothpaste that's $10. Which, when you think about toothpaste, $10 seems like a lot of money. He was kind of hemming and hawing about who in their right mind would pay $10 for a tube of toothpaste. And the toothpaste happens to be, it's made by this company, Marvis, and they have these really awesome flavors. And it's actually kind of more of an experience. And if you think about it, you're brushing your teeth hopefully at least two times a day. And if that experience could be something that's really special and great as opposed to just this thing that you have to do, wouldn't that extra little bit be really nice just in your general life? And so I told him that. And he came back. And he bought it. And he was like, okay, you know what, I'll take you up on this. Let's try this toothpaste. And he came back the next morning and was so excited. He was like, the toothpaste is amazing. He brought his wife back with him. He was really excited about it. Honey, you've got to try this toothpaste. He did it in Old Man Boys too. He was like, the toothpaste is great. I could see him shaking his cane and just be like, this is incredible. All right, so I really need to see what this toothpaste is all about. Looks like normal toothpaste. Oh, my God. That's incredible. Wow. I could brush all day. Am I allowed to swallow this? I don't think that's a great idea. You're not the boss of me. What's some of the more random or just interesting stuff that you've seen people use Squarespace for? The sites that get traffic are never the ones you expect, like the big name brand sites that are using Squarespace right now. The highest traffic site for a while, and this was like four or five years ago, was a, it was a knitting site. It was actually a yarn store in Soho called Pearlby. And she's got this great following of people that love the store and love what she's doing. And I was like, that's the most high traffic site on the system? That's crazy. What is the coolest thing you've seen someone do using Squarespace? It's the coolest thing. I mean, there's tons of nice websites, which is amazing. There's tons of amazing stuff that come out of the developer platform that I'm just like, people did that? No way. Someone figured out how to use that thing and I only thought that would be in my dev box and never appear in production. And then there's like beautiful artwork that goes up. Like I'm just, we like go through like all the sites that we have and it's just amazing to see like the different types of people that are on the platform. Like amazing artists and then these huge bloggers and then, you know, someone like selling some weird junk on us in their store and all that other stuff. It's like, where did all these people come from? You must know that hearing all of this stuff sounds like a just total success parade. Like from inception to present, it has just been amazing. And I think in a lot of ways it probably has been, but you got to give some of us out here just a taste of the worst moments of it. Yeah, sure. Moments of terror and panic and fear. Yeah, there's a lot along the way. Here's the quick version of the Hurricane Sandy thing. Our data center is on Wall Street. We know Sandy's coming and the data center flips over to backup power, you know, 24 hours before they've got enough fuel for a week. They've gone through multi-day blackouts before. It's totally fine usually. I think like the cell towers and stuff weren't completely dead at this point. I somehow get like one email through to my phone and it's from our head of systems. And it says something along the lines of massive problem. Basement of the data center is flooded. The fuel tank's gone. We have 12 hours of electricity left. Essentially what comes out, there's a fuel header for the building. That's going to run out of fuel. But we at the data center have this separate fuel tank that has like a couple hours worth of fuel in it. And it's determined that we can carry fuel to the fuel tank, 17 flights of stairs up the skyscraper. And if we do that, we can keep the thing online. And we did that for three days and it stayed online the entire time. It did not go down. And I mean, there were like barrels of like diesel fuel on the roof and we set up systems and people would like be at every stairwell and carry it up and all this stuff. And it is one of the worst experiences of my entire life. And I cannot believe that we actually made it through that like that. But it was just crazy thing where I'm like walking down there with my backpack on in the morning and I'm like, really? Really? After nine years, after ten years, really? I'm walking to the data center? I'm walking to the data center. What are some of the values that you share with Anthony? A passion for universal building blocks. The idea of creating structures that are reusable, that you can build upon. I do think that also, you know, he has tried in his product to create something that is simple and elegant and beautiful. And he's trying to make something that everyone can enjoy and share. It's almost like you don't have to focus so much on the design of your website, but more so on the content of your website. It's awesome to know, I guess, that there are humans behind the product. It's a technology product. But knowing their dedication to it is really awesome. There's humans behind the code. They're making it happen. There are a lot of people who watch this who are either thinking about starting their own company or are running one right now. And they want to know, here's someone who's clearly had a ton of success. How did he get there? I think there's always this feeling early on where people... There's almost this expectation that you have to have in your mind, this sort of, I'm going to change the world, sort of make a dent in the universe kind of ambition. But it's actually okay early on to just kind of solve small problems in layers until you actually get to a point where you have the capacity to do that. I was having a conversation with one of my friends recently. I was like, you know, if I went back and explained to myself when I was 13 years old, you know, you're not going to be a fighter pilot, you're not going to make Star Wars. But instead you kind of have this passion for content management systems. It's really weird, but somehow I just fell in love with it. Code is the electricity of the 21st century. Back in the day, people were like, electricity, we can do some wondrous things with these. We don't have to worry about steam and worrying about pressure differences to get things to move. Code is like the new platform to really invent things and make new things with. And so it's like if you really do love creating things in this century, code is the way to do that. I think to be a creator and an inventor of this century, it's like you've got to know code. Let's be real here. Yeah. There are smarter, less stressful ways to make money. It was to make a living. Yeah. Right. So why keep putting yourself through that? It's a great question. What was the thing where you were finally like, all right, fine, I'm just going to do this. I love programming, right? So I got to do that and I got to make things, which was always something I had done since I was younger. I felt like the thing was having an impact. People loved it when they used it. And that's a really, really cool feeling to give somebody a platform where they use it. They didn't think they could get that thing done before. It makes them look really good. And they put their ideas on this thing and sometimes it changes their life. And you get those stories sometimes. And it sounds cheesy, but it really is a great feeling. It's a good, like, honest thing. I made this thing, give it to you, spend a little bit of money, and you're winning too. It's cool. One person alone cannot build an empire. And it took Anthony three years to realize that he needed help. And when he finally got it, even though things kept going well, they were extremely stressful. So it seems only fitting that Squarespace has grown to be a really impressive company, now building a platform that makes it easy, trivial really, for countless entrepreneurs to make beautiful websites so they can focus on what really matters. Am I still in the frame? Thanks, man. Thanks, man.