Squarespace

“I realized that our old Saster AI Day websites were still on Squarespace, not Replit, because we built it, you know, in 2020 and just kept refreshing it. So first I was like, okay, I've got to just move this from Squarespace to Replit, find the agent, and then…”

“I think it says the pre-AI business is terminal. That's what the public markets are saying, right? And they don't think that the AI play is enough to rescue it from terminology, right?”

“Shopify destroyed them all. There's no reason to use. This is another category where the low end was destroyed by Shopify, who amazingly went up market and down market successfully at the same time. And there's just, it's not worth it. You can't save enough mo…”

“We acquired the assets from Google Domains, and so we met, we're one of the by brand, probably the third biggest domain registrar out there.”

“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…”

“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…”

“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…”

“And like Vimeo and Squarespace were our two first adopters, but they're recovering 13% more revenue on disputed charges from adopting it, and they're doing that with zero extra labor.”

“I also kind of predict that that's going to Be a very shaky space to build on... It might be that they're the next Squarespace. Squarespace, you know, eventually become a public company, but I don't personally think so. I think that that's going to be just lik…”

“We were charging 2000 dollars a month as a website builder around driving dine in and reservations. Which, to put that into perspective, typical website builders that restaurant owners use are Wix and Squarespace, and they're like, 49 a month products. So we w…”

“Which ends up giving us customer acquisition costs in the future that look more like Squarespace or Shopify with lifetime values that are even greater than toasts over time because the attach rate is so high once you earn the trust on free products.”

“But those businesses will clearly disrupt the square space and the web flows and et cetera.”

“What we just released is that you can actually edit this. Like this is a fully functioning product, but you can edit it visually. Like you can edit, like you do in Squarespace and Wix and so on. So I'll just change the text to buy now. And then it instantly ch…”

“I could no longer be charging 10,000 dollars to build a website when people were just going to Wix or Squarespace, and they could create a website for 10 dollars a month. So all of a sudden my business collapsed pretty much overnight.”

“So for Stripe in that first camp, this was back in 2017 that we started our foray into enterprise, and it was the Shopify's, the Lyft's, Squarespace's were all growing up, bringing in adult CFO's, contemplating IPOs, and so they had a bunch of demands.”

“The challenging thing in that environment that nobody really likes to talk about is that it is, it's like an unbelievably high level of personal stress when you're a leader at an organization that is not winning. It brings stress into your home life. You funda…”

“And a lot of VCs, you not included, but a lot of investors are like, but the TAM is too small. You're just focused on blogs or you're just focused on selling surfboards. Like, you know, it's not that tends to not actually be an effective long-term strategy. Ca…”

“We'd raised forty million bucks during my time, and I'd gotten to, I would think, a pretty meaningful product market fit. It was more than ten million in a revenue standpoint.”

“The fact that you could do it yourself was an educational sell, so we had to find long formats. And true, this format was one of our keystones to success, but we found podcasters and that ability for someone to actually share their experience with it really he…”

“The lesson that I learned from Squarespace, and I probably should get much closer to my heart, was we originally had, or during the cycle time, like a thirty-day trial, and so you get to, you build your site and everything else, and we quickly discovered that …”

“I would say, no, don't use funding. Don't use hiring. Don't use your pretty box as your symptoms of success. Those are all number of employees, worst one possible. It really should be something where you can feel the impact.”

“So, from that, so I got my initial seed, and I went on squarespace.com, and I created a one-page website called youprobablyneedahaircut.com, and it was a way that connected barbers in Williamsburg Primarily with people who needed haircuts, because at this poin…”

“The analogy that I sometimes like is that on the early days of the web, you could use kind of like something that would Create a website for you, right? You could use the equivalent of a Squarespace or for weeks, and that would make you feel good, right? Becau…”

“Just make money first and just use like a, you know, store name dot squarespace.com for like the initial like a hundred bucks in sales and then go and get the domain name.”

“And so the stock is down, you know, 50% since the IPO. They're at this, like, kind of nine hundred million revenue run rate now. It's a subscription business with more than four million subscribers.”

“I'd love to buy it because I think it's a great company that's super undervalued. It's not being run to maximize profits. So it's being run in a way that keeps it at breakeven.”

“And the first partner that we worked with, who we still work with today, is Squarespace. They did a three-episode deal with us, and that was enough for me to, like, get champagne for me and Sawyer.”

“MailChimp, like Squarespace, doesn't get me audience. It's just a tool.”

“To date, Anthony has raised over nine hundred and forty eight million dollars for the company from the likes of General Atlantic, Index Ventures, Tiger Global, culminating in their IPO in May 2021.”

“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…”

“I started the company with a 30,000 dollar investment from my parents and ran it through Break even for seven 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…”

“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.”

“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.”

“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.”

“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 …”

“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…”

“In the private markets, we did a four and nine A, we were doing it monthly, but you know, it's kind of, it's not that volatile.”

“The ability to sell things on Squarespace has been the most requested feature for a decade. We started investing in our e-commerce platform. That's basically physical goods, digital goods, eight years ago.”

“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…”

“We've also spent hundreds of millions of dollars, probably a billion dollars on brand”

“Wix and Squarespace and web flow. All of these other platforms have, you know, the inherent problem of being proprietary closed systems. So when you are building a site on Squarespace, number one, you don't own your website. Squarespace owns your website. You'…”

“I can't tell you how many Websites. I've had to migrate from Wix and migrate from Squarespace because the business gets to a point where it's like, well, we're big now. We want to do this and this and this. And it's like, ah, well, you can't do that on Squares…”

“Substack is in this kind of interesting place in the middle where, like, on one level they are squares, they are a Squarespace or MailChimp, they're a tool, and you pay them, or if you're charging, you pay, if you're not charging, it's free, and that's it, whi…”

“I can put a Squarespace website and print business cards, and we can go and talk about this and see if people would like it. And that's how I got my first investor meeting.”

“So our goal was basically to build Squarespace or a Webflow or a Wix or one of those products, but that could actually build enterprise level applications.”

“I still think WordPress is better for blogging and for podcasting because of the serial nature of it and just how many good plugins it has.”

“Because our first round of applications was an embedded Squarespace form that went into a Google spreadsheet that pretty soon had 900 rows in it with 30 columns, and then we had to hook into Zapier to send a confirmation.”

“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,…”

“So, the original version of it, I started programming it in 2003, April 2003, a little bit before that. And it took me until November, December, I was kind of like done and ready to launch it. So, let's say eight months.”

“So I went to my parents who, you know, I don't know how to calculate, but I needed 30 grand. And, you know... I needed these servers. I needed two of them, right?... And, you know, they eventually I eventually won that fight, and they were the first investor i…”

“So I remember Googling it at the time, and there were zero Google results for Squarespace.”

“I bought like 200 bucks of Google AdWords under like build a website, make a blog, like all these different things.”

“So, little known fact is, actually for the first year, we did have a free plan. You could actually use it for free. We always had a free trial. We still have a free trial. But back then, I actually had a free plan.”

“Like, I mean, people are, they stay around, right? Like, they make a website, they're not leaving quickly.”

“And so I actually stayed on, instead of graduating in four years, I waited and graduated in five, and kind of took some, like, Let's just say pretty light workload classes on that fifth year. I was buying myself time, right? I was buying myself out of, like, m…”

“I mean, so in the first year, I think we were like a run rate of like 50 grand. And in the second year, I think we were at a run rate of like 200 grand.”

“Yeah, so I had at some point along the way a part-time, towards the end of this, somebody who was doing part-time customer support, and then I had contracted out somebody to do some of the, helping me with the template designs, but there were no, no full-time …”

“I would put it 100% back in as much as I could. If I made 20 bucks on AdWords, I put 20 bucks back in AdWords. If I made a thousand bucks on AdWords, I'd send a thousand more bucks on AdWords. If I spent You know, I keep a little bit of a balance in case I nee…”

“You know, Squarespace always had enough money to Yeah, we always had enough money to pay people salaries. That kind of wasn't an issue.”