When I was 15 I got a job at an internet company. They were trying to recruit my Dad. He already had a job. He told them to talk to me because I was good programmer.
[The idea for Squarespace]: I wanted to make a website for myself. At the time you had to put all these different software programs together to make a website. Blogging software, page building software, software to tell you who is visiting the website etc. Then you’d go somewhere else to find hosting. I didn’t want that. I didn’t want this missmash of things.
I wanted more than just a blog. I wanted a full functioning website. The blogging services didn’t let you do that.
I made this for myself. I showed it to one of my friends and he said, “I’ll give you $200 for that.” That made me realize other people could use this. It evolved into a business. [Read Derek Siver’s essay: Don’t start a business until people are asking you to.]
[How Anthony thought about the potential market for Squarespace]: When blogging was taking off I saw that as the beginning of the do-it-yourself wave. People realized they could publish too. I thought people should have a more powerful tool. I wanted them to be able to publish whatever they wanted. With Squarespace you could publish a blog post, a page, a photo gallery etc. It was always about doing more.
[How Anthony funded Squarespace]: I needed money for servers. My parents were the first investors. They lent me $30,000.
[How Anthony came up with the name Squarespace]: I needed a name that was available. The domains had to be for available for purchase. I didn’t have enough money to negotiate for a domain. There were zero Google results for Squarespace.
I purchased two servers and put them on the floor of my dorm room. They were so loud. The sound was intolerable. At the time I was reading a lot about software development. One of the blogs I read was by Joel Spolsky. His blog was hosted by a company in New York. I knew I wanted to be in New York so I drove my servers there.
At the beginning Squarspace had a free plan. There were plenty of examples at the time of giving away software for free and getting millions of users. Blogger, MySpace etc. Everyone told me give it away for free and people would upgrade. I realized there were a lot of people who were never, ever going to upgrade. I didn’t have any other money. I needed to focus on the people who would pay for this. I didn’t want to be the next LiveJournal or Blogger. I priced it at $5 or $15 a month so it was really inexpensive.
After the first year Squarespace had a run rate of $50,000. I started to think I could double or triple that. I needed to buy myself more time. I stayed an extra year in college. I took a light class load so I could work on Squarespace.
The first year we had $50,000 in revenue. The second year was $200,000 in revenue. It wasn’t $1 million overnight. [He was the only employee until 2007. Squarespace reached $1 million in revenue as a one person company.]
I reinvested as much of the revenue back in Squarespace as I could.
Google AdWords was the initial distribution channel.
It took me a few years to understand what the stress was doing to me. I’d have panic attacks. My heart would race. My throat would close up. I’d have trouble breathing. Nothing would trigger it. I’d just be sitting there thinking about it and start to get stressed.
I teamed up with a more experienced person. He wanted to help me hire and expand. He offered to join Squarespace as the CEO. I didn’t know what titles meant at the time. I felt like I was still running the company. This created more stress for me than I realized. I was 24 or 25 years old. This didn’t work for me.
I leaned a lot of lessons the hard way by making every mistake imaginable.
We launched a huge update to the platform called Squarespace 5. It was a total disaster. We flipped it on for every customer at once. It was full of bugs. Everyone in the company had to do customer support. At this time we had 85,000 customers and were doing around $10 million in revenue.
Around this time Getty Images offered to buy the company. I was struggling with this decision. I never started Squarespace to sell it. But I didn’t have a lot of money. At the same time some investors contacted me. They told me I didn’t have to sell. The offered to invest money into the company and buy some of my shares. I liked that idea. I could get liquidity, a board for accountability, and the ability to keep running the company.
You need to create an environment where you hear feedback even if you don’t agree with it. If you create an environment where you don’t hear feedback you become vulnerable to a seismic shift where you ignored something to the point where it is going to break.
I’ve made so many mistakes in the past it would be silly for me to think I’m not making any now. I have to be. Hopefully I’m just faster at resolving things.
Squarespace experienced a lot of success from advertising on podcasts. The first podcast ad was on This Week In Tech. It was $30,000. That was our whole AdWords budget for a month. We decided to try it. It immediately worked for us. There is a really authentic thing with podcasts. You are supporting a show host. You are supporting the creation of this content.
The core of Squarespace is entrepreneurial success. To help you put the site online that you want. To sell online. To help you be successful.
