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 fght. 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 frst 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 balance-sheet enhancing. We needed that
money as a bufer, 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 well-being 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-fow
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 ofce and hope that
it will be flled 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.
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
“We don’t have
immediate plans for an
IPO,” says Squarespace
so we could do that if
we wanted to.”
As told to KRIS FRIESWICK Photograph by YAEL MALKA
THE LAST WORD 104 - INC. - APRIL 2017