Anthony Casalena
Founder & CEO, Squarespace. On 2 shows, 3 appearances. The Shows tab opens the full record on each.
Anthony Casalena is the Founder and CEO of Squarespace, which he launched from his dorm room in 2003. He led the company to its May 2021 IPO after raising over $948 million.
2shows
3appearances
42statements
5resolved
5supported
0contradicted
100%fully supported
17said about them ↓ Everything Anthony Casalena said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Casalena: Websites are more relevant than ever because AI relies on them
“And I think that the website ends up being more relevant than ever for a number of reasons. One being, It's where the answer engines are finding their information. You know, they're crawling the web and using either old data or modern data or more relevant dat…”
Casalena: Rewriting core platform architecture takes 3x longer and is a disaster
“You never want to be in a situation where you're rewriting the core of your platform. It always takes three times longer than you would expect. You know, the people who originally wrote it are sometimes no longer there, and it's usually a disaster.”
Casalena: Squarespace is not threatened by AI coding tools
“Yeah, I mean, it's been a phenomenal tailwind for us. I mean, we're not particularly worried about the, you know, the idea that people could code a website where they couldn't code a website before because people haven't had to code websites for two decades us…”
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: Squarespace is a private business, not obligated to host every viewpoint
“We are a business, we're not the government, and we're not, you know, trying to protect every possible viewpoint on the planet, and so you know, we need to make sure that, you know, we're doing business with the right, you know, the kinds of people we need to …”
Casalena: Leaders consistently regret moving too slowly on decisions
“And I think that I would look back and go, you know, what decisions do I always delay on? And I'm always looking back and going, I wish I had done that faster. And I wonder why I've never gone to those decisions and gone, wow, I went too fast on that one. Righ…”
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…”
Casalena: Blogging sparked the DIY wave empowering non-technical web creators
“When blogging happened, I see it as the kind of beginning of this DIY, do-it-yourself wave, where people who would have otherwise been a little intimidated you know, it was this kind of like, oh, I can do this too, but then giving them something more powerful,…”
Casalena: Website builder customers have high retention and do not leave quickly
“Like, I mean, people are, they stay around, right? Like, they make a website, they're not leaving quickly.”
Casalena: Closing off critical feedback leaves companies vulnerable to breaking from seismic shifts
“To create an environment where you don't hear it is really the scariest thing for me, because I think that if you remain closed off to it, you become vulnerable to these big, like, seismic shifts where you just ignored something to the point where something's …”
Casalena: Podcast ads succeed through creator support and audience connection
“There's this really authentic thing around, like, you are supporting a show host. That show host has a connection with their audience. You are supporting the creation of that content, and you would never hide the fact that it's sponsored.”
Casalena: Squarespace 6 Launch, Not Outside Capital, Drove Growth
“The outside capital is not it. The main driver for it was Squarespace six launching, and that changed everything for us.”
Casalena: Growing on AdWords today is unlikely because consumers seek established brands
“I don't know if you could grow a business on AdWords the same way I did 15 years ago, because I think people look, they look for the brand now.”
Casalena: Paid subscription model naturally deters malicious online actors
“One thing that's great about Squarespace, frankly, versus other you know, situations other providers are in, is that it's a paid service, so we actually avoid the worst of this, right? Right, right. Very rarely is somebody like, I'm gonna post a bunch of bad s…”
The other half of the tape: Anthony Casalena's own voice is left out of every number here. Other people bring the name up 16 times in 6 episodes across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Harry Stebbings 8Guy Raz 4Tristan Handy 2Shervin Pishevar 1Sam Lessin 1
Statements about Anthony Casalena, by other people (1)
Every mention by year
tap a year for its mentions
20VC 12
How I Built This 4
2025 1 mention in 1 episode
2023 1 mention in 1 episode
2022 7 mentions in 1 episode
2021 5 mentions in 2 episodes 3 per episode
- 20VC: The Two Largest Changes in the Investing Market Today, Why The Scarce Resource in Venture is Access & Why Investors Are Acting Mostly Rational and Upside Scenario Planning Needs To Change with Anton Levy, Co-President @ General Atlantic
- Stacy's Pita Chips: Stacy Madison (2019)
- every mention in 2021, scene by scene →
2019 2 mentions in 1 episode
One line per show, most statements first. The link opens Anthony's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| HOW I BUILT THISLEDGER | Founder & CEO, Squarespace | 2 | 28 | 100% 2/2 | full record on How I Built This → |
| 20VCLEDGER | Founder & CEO, Squarespace | 1 | 14 | 100% 3/3 | full record on 20VC → |