An interview with founder Anthony Casalena about leadership, how to manage growth, the challenges of success, and the winning lessons of failure.
Squarespace founder Anthony Casalena's story is so familiar it's archetypical: young developer nurtures an innovation from his dorm room, starts a company and moves to New York City, raises millions in venture funding, then grows an empire.
The company's long, quiet ascent also runs counter to the classic "grow fast, monetize later" startup strategy. Unlike other publishing tools like Tumblr and Wordpress, Squarespace keeps overhead low and does not offer a free version of its software. The slick, modern content management system built for creative professionals and SMBs has generated revenue since Day 1.
"I coded a blogging tool that I wanted to use," Casalena said in a recent interview with TechRepublic. "It wasn't until a friend said he'd pay for it that I realized I could also build a company." A few people did pay for the nascent product, and Squarespace was born.
Casalena constructed the first version of Squarespace in 2003 while enrolled at the University of Maryland. After graduation, with $30 thousand in seed funding from his father and a small grant from the state of Maryland, Casalena incorporated the company and relocated to New York City. "The city felt big," he said. "Squarespace benefits from the diversity here; the diversity of thought, the diversity of industries, the access to design, and to creativity. [Those values] are what we like as a company, what we stand for. [New York] was always a really natural fit."
Initially conceived as a blogging CMS, Squarespace went through several iterations. Casalena first hired a small team to handle design, coding, and support. As the company grew, the team remained a tight unit. "[Staying small] kept us efficient and focused on building a great product, but in retrospect I might have done things differently," he said "I stressed about every detail. I was coding during the day, then up at night answering support questions."
The team experienced some growing pains through product iterations and with early management shuffles. "I'm not perfect," Casalena said, "but Squarespace isn't a strict command and control structure, and we're still figuring things out."
Today Squarespace occupies a large building in Manhattan's SoHo district, employs over 500 workers, and raised over $78 million in venture funding to help, as CrunchBase noted, "build an empire."
The product has evolved to support a few target markets. The tool still supports the creative professional customer and recently launched a publishing partnership for Apple News. Small changes in the product allow the platform to be used as a robust CMS and manage a high volume of diverse content types.
The Squarespace e-commerce product has been particularly successful. The tool is targeted at small and midsize merchants and provides data that helps e-commerce SMBs successfully manage and display products, work with fulfillment vendors, and target customers. Spokesperson Natalie Gibralter recently explained, "there's often so much information to wade through that it can become overwhelming and time-consuming for small businesses ... our focus is to surface key data and actionable insights to help merchants make decisions that can drive more sales."
How did the startup grow from a handful of customers and few bucks in the bank to a half-billion dollar enterprise? Casalena spoke with TechRepublic about his history as an entrepreneur and the lessons of growing a successful technology company.
How have you evolved as a CEO and manager?
I'm very skeptical. I'm very nervous. I'm always worried something will break, and that I don't know what's going on, that something is moving in the wrong direction.
Put another way, the company is trying to solve the daily problems. My inclination is to get involved, but sometimes I have to step back, just for clarity. To move it forward.
The tendency to get involved comes from back in the 90s, when I was making products, I would give them to people, and I liked making things for myself. I would use the [thing I built] myself, then I would worry about problems with it. Bugs.
Now I want to get involved. I just need to get involved with the right things.
What lessons can entrepreneurs learn from your successes and failures?
There are two kinds of lessons: there are strategic lessons, where we've been late to put something out there that I should have known better on. Then the bigger failures, in hindsight, maybe it's not possible to avoid them.
I think I've had the wrong people in the wrong roles in the company sometimes. I don't know a single person inside of any company that gets hiring right all the time. My biggest issues have been knowing something is wrong, and actually pulling the trigger and taking an action to fix it.
One of the things I work on is trying to be clear about company culture and job roles.
When culture takes a long time, you incur what I call, "cultural debt."
For example, you make a change, you take a person out of a role, or you change the structure of the company. But if it was wrong for a while you are going to have huge problems piling up, and it is going to take a long time to clean that stuff up.
Now, contrast that with like, what if I made a bad hire and in Day 2 I know it is a bad hire, and in Day 3 they are gone. You know, that looks bad, that's dumb, we shouldn't do that to people, we shouldn't have that happen to us. But how much debt have you really incurred internally in your company a opposed to the first scenario? Nothing.
How do you juggle your time and various responsibilities?
As you grow, what becomes harder is kind of the demands on your time. You have to invest in communication as you grow.
When we were smaller, I didn't have any people management tasks to do. But because I didn't spend time on recruiting or people management, I was waking up all night having panic attacks, fixing servers, answering customer support things.
I think it feels better now that I have more freedom, but I also have more obligations to do certain things with the company. Over a million businesses and people rely on Squarespace to exist. So I have a responsibility to them to worry about things. But what I worry about had to change. If you don't change what you worry about as your company grows, you can quickly lose control of your time.
What lessons should aspiring entrepreneurs learn from how you run Squarespace?
It is dangerous to take anecdotes from certain stories to heart, but not really know the internal details of [the story].
People love to look at a company like in Apple and be like, 'Well, Steve Jobs is an asshole, so okay, it's good to be an asshole.'
That is wrong. That's just probably wrong. Is that true? Would the people around him say that? Yes, a company of how ever many zillions of people that Apple has employed, I'm sure over a hundred people in the world think the guy is an asshole. But it is dangerous to draw [leadership conclusions] on particular anecdotes.
[Our company] is run by 'doers.' People who accomplish what they set out to do. That's something I try to keep in the DNA. Having 'doers' is a predictive success factor for executives here. That applies to every single industry.