The Ledger
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Casalena: Squarespace reached a $10M run rate on $30K seed capital
“It was about 30 people, maybe, run rate of around, around ten million. So we got from nothing to there, you know, with 30,000.”
Casalena: Capital cannot directly solve usability or engineering management problems
“I think my problems were not exactly money dependent back then as much as they were making the product easier to use or, you know, engineering management or things like that, that money can't just directly fix.”
Casalena took secondary liquidity in 2010 to avoid selling Squarespace
“Back when I took some secondary, I would say it was, and this is 2010, it was very much not the norm, and I was looking to do it for a very specific reason, because I didn't want to sell the company, and at the time I basically owned all of it.”
Casalena: Squarespace chose a direct listing to avoid unnecessary IPO dilution
“So for us, because the company did not need to raise money, right? I mean, we've raised very little over the years. We had that primary round we did before doing the direct listing, which was done for A number of reasons, but otherwise we didn't need to raise …”
Casalena: Squarespace monetizes GMV via a revenue-share partnership with Stripe
“We do monetize all of the payments flowing through the e-commerce platform. Long ago, we made a, we were one of the, I think, first large companies to do it. We partnered with Stripe to enable the, our merchants to get online and to accept payments. And as par…”
Casalena: Squarespace has spent up to $1B on brand marketing
“We've also spent hundreds of millions of dollars, probably a billion dollars on brand”
Casalena: Focus on design was Squarespace's main early differentiator
“There was an uphill battle along the way, obviously, selling people on, frankly, the importance of design and what it could do for them, and, you know, we look at it now, and it's obvious that was a huge differentiator in the company, and it really set us forw…”
Casalena: Squarespace ran break-even for seven years on a $30K investment
“I started the company with a 30,000 dollar investment from my parents and ran it through Break even for seven years.”
Casalena: Squarespace raised under $50M in primary capital over 17 years
“Squarespace has grown up with about fifty million dollars in primary capital invested, save the round we did right before going public, which was a couple months ago and had a different use. But for 17 years, it was essentially under fifty million in primary c…”
Casalena: Breaking even gives founders control and fundraising leverage
“If you are break, even you are more in control of your destiny and it puts you in a better negotiating position for when, you know, you do need to go or want to go and raise money because you can take it or leave it.”
Casalena: Direct listings cause near-term trading choppiness due to missing models
“It's just in the near term, it's a bit choppy. I mean, your volume can be low, it can It could be because direct listing, you know, people don't have the same modeling capabilities because you haven't been out there for a while. You don't have a lot of quarter…”
Casalena: Public investors track up to 80 portfolio companies simultaneously
“I think the other thing I started to realize is I spend every day thinking about Squarespace, but for public market investors, they have their own portfolio. Maybe they're looking at 70 companies, 80 companies. You're one sliver of their time, and, you know, w…”