Squarespace CEO well worth $2.4 billion immediately after world-wide-web business retains NYSE debut

The New York Inventory Trade welcomes Squarespace, Inc. (NYSE: SQSP), on Could 19, 2021, in celebration of its Direct Listing.


By 2010, Anthony Casalena was seven many years into bootstrapping his begin-up Squarespace, which he’d developed from a dorm home job at the University of Maryland into a enterprise with $10 million in earnings.

That is when Getty Illustrations or photos approached him to see if he wanted to market.

Casalena deemed the provide prolonged and tough, but he didn’t want to give up control. As a substitute, he opted to remain independent and carry in outside buyers for the 1st time, permitting him to accelerate selecting and products enhancement and also sell some of his stock.

He failed to know it at the time, but in elevating a $38.5 million funding round, Casalena was building a billion-greenback final decision for himself and a highly worthwhile one for undertaking firms Index Ventures and Accel Associates.

Squarespace, which sells instruments for easy website generation and publishing, debuted on the New York Stock Exchange on Wednesday with a sector value of $6.6 billion. Casalena, the company’s most important stakeholder, owns shares worth $2.4 billion, though Index and Accel regulate holdings valued at $944 million and $750 million, respectively.

Simply because Squarespace went community by means of a immediate listing alternatively than boosting money in an IPO, insiders can start off promoting ideal away and never have to hold out for a lock-up expiration. Their stakes stated previously mentioned involve some revenue that they registered to trade proper away, which include 6.2 million registered by Casalena.

“A immediate listing match for us mainly because Squarespace has been a lucrative firm for a quantity of years and we will not will need to raise dollars in this event,” Casalena informed CNBC’s “Squawk Box” on Wednesday. “Our considering was go after the direct listing, give people the solution to invest in if they want to obtain, offer if they want to provide. What’s fantastic about the direct listing is no one’s struggling pointless dilution today.”

Squarespace experienced a tough debut, opening at $48, down below its $50 reference value on the NYSE. In March, the organization lifted a personal round at $68.42 a share, valuing the small business at $10 billion. Shares have been broadly down on Wednesday, and cloud software program shares have been poorly underperforming the sector this year, as traders rotate out of possibility.

Nonetheless, at 38 many years outdated, Casalena is the most up-to-date tech entrepreneur to be a part of the billionaire ranks as high-development corporations that had stuffed up the IPO pipeline in latest years hit the current market with major valuations. The founders of Affirm, Roblox, Coinbase, Bumble, UiPath and AppLovin have all entered the 3-comma club this year.

Squarespace competes most straight with corporations this kind of as Wix, Automattic’s WordPress, Square’s Weebly and Shopify. The firm has 3.7 million subscribers.

Revenue previous 12 months rose 28% to $621.1 million. Internet earnings narrowed to $30.6 million from $58.2 million a calendar year earlier, as the corporation boosted paying out on income and advertising and marketing by 40% “in mild of the accelerating traits in the total of time and money customers are paying on-line through the COVID-19 pandemic,” Squarespace claimed in its prospectus.

From faculty to CEO

The Squarespace story began in 2003 at a student condominium advanced identified as South Campus Commons in College or university Park, Maryland. While in university, Casalena was wanting for a site that enabled straightforward online publishing, but he identified the present solutions this kind of as Blogger insufficient. He coded alongside one another his possess and shortly discovered that someone wished to pay back him to use it.

“The weblog was the anchor, but it was usually about undertaking much more with it,” Casalena advised the NPR podcast How I Created This with Person Raz, in 2019.

Casalena inevitably persuaded his father to give him $30,000 so he could get a few of servers and property them in a data middle in New York. Just after school, he drove to Manhattan and took up home in a fourth-flooring walkup condominium that he’d observed on Craigslist.

More than the next several decades, Squarespace grew steadily with a skeleton crew and very little construction. In 2007, Casalena commenced attempting to professionalize operations and even hired a far more seasoned govt as CEO. He realized that approach was not heading to do the job.

“I acquired a lot of lessons the hard way, by practically making, I imagine, fairly substantially each and every achievable oversight a single can make,” Casalena informed Raz. “I failed to know what I was having into.”

Meanwhile, Accel experienced been retaining a close eye on Casalena. The organization, which was greatest acknowledged for an early wager on Facebook, had started seeking for world wide web and application organizations throughout the world that ended up getting considerable traction with out undertaking funding. Someday, Accel’s imagining went, these founders may well want to raise revenue to make an acquisition or seek funding to employ some more expensive expertise.

“In these conditions, we want to do our finest to make a partnership and consider to be there when most likely they evolve their contemplating,” Andrew Braccia, the Accel husband or wife who ended up foremost the Squarespace financial investment, mentioned in an job interview.

Accel utilised a equivalent tactic to commit in Atlassian, an Australian software package business whose products have been well-known with builders, and Qualtrics, a household-run cloud application business enterprise in Utah. Atlassian now has a current market cap of $54 billion, and Qualtrics was obtained by SAP in 2018 for $8 billion, in advance of spinning out this calendar year into a publicly traded business worth $17 billion.

A 10 years back Accel’s advancement investing system was just a thesis, but Braccia explained it’s now distinct that “you can create enterprise-type returns out of later on-stage bootstrapped firms.”

Braccia, who’s dependent in Silicon Valley, flew out to meet Casalena in 2010. He and fellow Accel associate Ryan Sweeney had breakfast with the Squarespace founder at Mercer Kitchen area downtown and then spent a pair several hours at the Squarespace place of work, where Casalena walked them by means of his eyesight for the following iteration of the firm’s publishing procedure.

“I recall viewing Anthony take us by way of the new model of his products,” Braccia reported. “He was maniacally centered on the smallest of information.”

A blessed eruption

Around the exact time, in July 2010, Index’s Dominique Vidal was in New York to satisfy Casalena. He was introduced by Jonathan Klein, Getty’s CEO at the time, and flew in from London to consider to land the offer. Vidal, who was also friends with Braccia from their pre-venture days performing at Yahoo, ended up caught in New York for a lot for a longer time than envisioned since of the volcanic eruption in Iceland that spewed ash across considerably of Europe and disrupted global journey.

Vidal was not readily available for an interview, but Nina Achadjian, yet another lover at Index, relayed the story to CNBC on his behalf.

“Dom’s flight was canceled, and he hung out with Anthony a ton much more,” Achadjian said. “The additional time he invested with Anthony, the extra he was blown absent.”

Casalena instructed Raz on his podcast that he was not absolutely sure how Index and Accel heard that Getty experienced manufactured an offer you, but by some means they “caught wind of this,” he said. They experienced a counterproposal for him.

They stated, “You don’t have to do that. You never have to sell it all if you want some liquidity,” Casalena advised Raz. “Why don’t you accept an financial investment from us? We are going to place some revenue into the business. You can provide some of your shares to us. You can retain running it. We will put a board in position, we’ll support you recruit executives and all that. I favored that.”

Vidal and Klein joined the board along with Braccia. Casalena resumed as CEO.

Squarespace went on to elevate one more $40 million in 2014 in a spherical led by Common Atlantic, which is now the most important outdoors trader, with a $1.3 billion stake. The enterprise lifted $200 million at a $1.7 billion valuation in 2017 and $300 million in March ahead of the immediate listing.

The New York Stock Exchange welcomes Squarespace, Inc. (NYSE: SQSP), on Could 19, 2021, in celebration of its Immediate Listing.


By ready so extensive before elevating his first exterior capital, Casalena maintained a even larger stake than a lot of founders of venture-backed organizations.

He also has an outsized quantity of management more than decision-building. Squarespace has a twin-course voting composition, and Casalena owns most of the Class B shares, offering him handle of about 68% of the overall voting energy.

While that framework has develop into widespread in Silicon Valley between founder-led firms, critics say it results in poor methods for accountability and limitations the skill for the board and shareholders to get action when required.

IPO analysis agency New Constructs, in a report this week, explained the company construction is a single of the reasons that investors should really be cautious. The firm reported Squarespace is well worth “at ideal $4.2 billion,” in component for the reason that it operates in a extremely competitive current market with much less expensive alternate options.

The consolidation of energy won’t help.

“A chance of investing in Squarespace’s immediate listing, and other new IPOs, is the actuality that the shares bought provide tiny to no say in excess of corporate governance,” the agency wrote.

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