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[96] Before You Cancel Squarespace: What It Really Takes to Host a Site Yourself

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In the middle of 2026, Squarespace raised prices, adjusted the increase a few days later, and set off a wave of "I'm leaving" posts across Reddit and the Squarespace forum. One comment kept coming up: I'll have AI build my site and host it somewhere cheaper. For some sites, that's a reasonable call. In this episode I walk through what you'd be taking over yourself if you did it, and who I think should go anyway.

You'll learn the difference between a website builder and a website platform, why AI can help you build a site but not run one, and the three categories of work Squarespace handles behind the scenes: security, including SSL certificates and where your form data goes when someone hits submit, discovery, including sitemaps and 404 pages and why an invisible website never throws an error, and functionality, including everything around a blog post and everything around a checkout that isn't the page itself. I also get honest about the price increase, the strange second email, and the switching costs that make leaving harder than it looks.

Timestamps
00:00 The price increase and the comment that started this
02:56 Website builder vs. website platform
04:08 SSL certificates and why they fail quietly
05:10 Where your form data goes when someone hits submit
06:00 Spam protection you never see working
06:30 Sitemaps and the invisible website problem
07:05 404 pages, the one everybody forgets
07:54 Blogs and stores are systems, not pages
09:33 Who should leave, and who should stay
10:22 What you're really paying for

Show notes & resource links:
insidethesquare.co/podcast/96

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The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

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