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Today, I’m talking to Anthony Casalena, the founder and CEO of Squarespace, the ubiquitous web hosting and design company. If you’re a podcast listener, you’ve heard a Squarespace ad.
I was excited to talk to Anthony because it really feels like we’re going through a reset moment on the internet, and I wanted to hear how he’s thinking about the web and what websites are even for in 2023.
If you’re a Vergecast listener, you know I’ve been saying it feels a lot like 2011 out there. The big platforms like Facebook and TikTok are very focused on entertainment content. Twitter is going through… let’s call them changes. People are trying out new platforms like Instagram Threads and rethinking their relationships with old standbys like Reddit. And the introduction of AI means that search engines like Google, which was really the last great source of traffic for web pages, just don’t seem that reliable anymore as it begins to answer more questions directly. It’s uncertain and exciting: a lot of things we took for granted just a couple of years ago are up for grabs, and I think that might be a good thing.
Anthony founded Squarespace in his dorm room in 2003 — and over the past 20 years, he’s seen a lot of web ideas come and go. My questions were pretty simple: why would anyone even make a website in 2023? He told me that right now, a lot of Squarespace clients think of Instagram and other social sites as their homepage — and they bring people to their websites just to complete transactions because they have more payment options on the web. That’s a pretty huge shift in thinking about the web and what it’s for.
The other huge shift is thinking about where all the content on a website might come from and how much AI-generated content might pollute the web. It’s already happening — and Squarespace is in the mix, with new AI tools for generating sites and copy with OpenAI tools. Is that good for the web? Is that good for business? Is it good…
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