An­thony Casalena, founder and CEO of Squares­pace

In 2016, his com­pany gen­er­ated more than $200 mil­lion in rev­enue, but the founder of web­site-build­ing plat­form Squares­pace doesn’t spend a penny he doesn’t have to

Inc. (USA) - - CON­TENTS - As told to KRIS FRIESWICK

How did you know your idea could be a vi­able busi­ness?

I started pro­gram­ming Squares­pace in 2003. Orig­i­nally, I wasn’t in­tend­ing to start a com­pany. I was cre­at­ing it be­cause I wanted to make a web­site for my­self, and I was re­ally frus­trated that it re­quired so many kinds of soft­ware. I didn’t un­der­stand why all those things weren’t in one place. I quickly re­al­ized that the thing I was making for my­self was some­thing other peo­ple could use.

You asked your dad for $30,000 to buy servers for the busi­ness. How did that con­ver­sa­tion go?

My dad re­calls some ver­sion of his say­ing to me, “We’ve al­ways sup­ported you. We’re al­ways ready to back your ideas.” I re­mem­ber it more like a huge fight. He didn’t un­der­stand why I needed two servers in­stead of one. I have to credit my mom a lit­tle bit for help­ing me talk him into it.

You boot­strapped the com­pany for the first six years. How can you tell when it’s time to take on in­vestor cash?

For Squares­pace, it was a num­ber of things. One, it was bal­ancesheet en­hanc­ing. We needed that money as a buf­fer, and to get loans against. Two, I don’t come from a wealthy back­ground, and I was able to sell some shares and sep­a­rate my per­sonal well­be­ing from the well-be­ing of the busi­ness. The other driver was I wanted to bring on bet­ter ex­ec­u­tives. To pro­vide some cor­po­rate struc­ture and get a stamp from great in­vestors would re­ally show peo­ple that this was an ex­cit­ing place to work.

How do you de­cide what to spend money on and where to rein­vest?

I at­tempt to op­er­ate to cash-flow breakeven. My mind­set is to make spend­ing de­ci­sions from a po­si­tion of pain. I don’t say, “I think we are go­ing to be able to hire 200 peo­ple this year. There is no ev­i­dence for that, but let’s just get this re­ally big of­fice and hope that it will be filled up.” We are a lot more an­a­lyt­i­cal than that. I try to be re­al­is­tic about growth pro­jec­tions and re­act to those in real time. Over the years, we’ve just kept ask­ing, “What can we do with this money to grow the busi­ness?” That’s how it’s al­ways op­er­ated.

Pho­to­graph by YAEL MALKA

PUB­LIC SPEAK­ING “We don’t have im­me­di­ate plans for an IPO,” says Squares­pace founder An­thony Casalena. “But I’m fo­cused on in­creas­ing our so­phis­ti­ca­tion so we could do that if we wanted to.”

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