ThinkInsideTheSquare

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AI has become an essential part of my workflow as a Squarespace designer. So when I came back from maternity leave, I added a new question to every potential client call: How comfortable are you with me using AI as part of this project?

In this episode of Think Inside the Square, we're talking about the awkward part of using AI professionally: disclosure. What should your Squarespace clients know? Do you need to tell them every time AI helps you write CSS or troubleshoot JavaScript? And what happens when a potential client says they don't want AI involved at all?

CHAPTERS
00:00 How I Disclose AI to Clients
01:44 AI in the Squarespace Workflow
04:17 AI Tools vs. Designer Expertise
06:04 When Clients Don't Want AI
07:50 AI, Client Data & Transparency
09:18 Why Your Expertise Still Matters
13:18 Setting AI Boundaries With Clients

Support the show

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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Your next web design client might already have an AI-built website.

AI can help someone get surprisingly far into a website project. They can create layouts, generate copy, choose images, and build something they're genuinely excited about.

And then they hit the part where the website actually has to work.

In this episode of Think Inside the Square, I'm talking about what I think is an emerging service opportunity for web designers: taking an AI-built website and getting it across the finish line.

Because the real problem isn't necessarily that an AI-generated website looks like AI. The bigger opportunity is improving the parts AI hasn't finished: functionality, accessibility, responsiveness, maintainability, design judgment, brand personality, and the overall structure of the website.

For Squarespace designers especially, this may mean entering the project much later than we're used to. The client has already started;  our job is to finish it.

In this episode:

• Why making a website “look less like AI” shouldn't be the main goal
• Why familiar AI design patterns aren't necessarily the biggest problem
• How clients are starting website projects differently
• What it means to finish an AI-built website
• Why designers may start entering projects at the 60–80% mark
• How Squarespace can simplify an unnecessarily complicated AI-built setup
• Where accessibility, usability, branding, and design judgment still matter
• Why this work starts to look more like consulting than traditional website design

If clients are starting to bring AI-built websites into your inbox, I'd love to hear what you're seeing. Email me anytime at [email protected].

Full episode transcript & resources: insidethesquare.co/podcast

Hire me to build your AI design on Squarespace: insidethesquare.co/hireme

Questions or something interesting happening in your own Squarespace business? [email protected]


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

#SquarespaceDesigner #AIWebDesign #WebDesignBusiness

Support the show

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

Send a message to InsidetheSquare

I built a Squarespace membership site, even though I’m definitely not a fan of Squarespace Member Areas. 😂

In this episode, I’m sharing why Squarespace was still the right choice for this particular project, plus the parts of the member experience that continue to drive me bananas: the avalanche of signup emails, the limited control over the account interface, and the surprising lack of search for paywalled content.

We’ll also talk about the bigger question I think matters more than Can Squarespace do this?

That question is: Should you use Squarespace to do this?

Because the best platform isn’t always the one with the longest feature list. It’s the one that gives your specific project what it actually needs.

In this episode:

• Why I chose Squarespace Member Areas for The Archive
• Where the signup and account experience falls short
• Why I had to create my own search workaround
• When Squarespace can be a great fit for membership content
• When you should probably use a dedicated membership platform instead

Mentioned in this episode:
The Inside the Square Archive: tutorials.squarespace.com

Support the show

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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For years, Inside the Square was built around answers.

Someone had a specific Squarespace problem. They searched for a solution. I made a tutorial that helped them solve it.

That model worked incredibly well, until the way people found those answers started to change.

Squarespace can now handle many customizations that once required code. AI can generate code, layouts, copy, ideas, and technical answers in seconds. But just because the answer is easier to get doesn't mean the decision is easier to make.

And that's the shift I'm exploring in episode 100.

The problem I built my business around hasn't disappeared. People still want more control over their Squarespace websites. But the way they solve that problem is changing — which means the way I help solve it needs to change too.

In this episode, I'm sharing what that realization means for the future of Inside the Square, why I think value is shifting from knowing the answer to knowing what to do with the answer, and how you can use the same idea to think differently about your own work.

In this episode:

• How one tiny CSS tutorial accidentally became Inside the Square
• Why the business model that worked in 2019 doesn't make as much sense today
• The difference between the problem you solve and the method you use to solve it
• Why easier access to answers doesn't automatically lead to better decisions
• Where experience, judgment, taste, and perspective become more valuable
• What the next chapter of Think Inside the Square will focus on
• Three questions to ask when technology starts changing your industry

AI is already showing up in Squarespace client projects in some pretty unexpected ways. My new resource, Now What? walks through six real situations I've encountered — from AI-generated code and mockups to questionable copy and complicated client expectations — and how I'm thinking through my response.

→ insidethesquare.co/nowwhat

Have a weird AI/client situation of your own? Send it my way at [email protected].

Most importantly, have fun with your Squarespace website.

Support the show

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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Will Google penalize your Squarespace website because you used AI to write your content or code? Not automatically, but what you actually publish still matters. In this episode of Think Inside the Square, I’m breaking down what Google currently says about AI-generated content, how to review AI-written copy before adding it to your Squarespace site, and why AI-generated CSS and JavaScript deserve an extra layer of scrutiny. We’ll also talk about the SEO features Squarespace already handles for you, AI-powered search, llms.txt, and the three questions I ask before publishing anything AI helped create.

Important Chapter Timestamps
00:00 Does AI-Generated Content Hurt SEO?
02:07 What Google Actually Says About AI Content
04:19 What to Check Before Publishing AI Content
05:24 Is Your AI Content Original Enough?
06:52 Does Your Content Actually Answer the Question?
07:50 AI-Generated Code on Squarespace
10:05 What Does the Website Visitor Experience?
11:15 Does Squarespace Already Have a Solution?
12:32 Squarespace SEO in the Age of AI Search
14:10 llms.txt + My Final Answer

For a full transcript, resource links, and summary, visit insidethesquare.co/podcast/99

Support the show

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

Send a message to InsidetheSquare

If I teach people about Squarespace, why don't I sell my digital products on Squarespace? It's a fair question — especially considering digital products have been at the center of my business for years.

I actually did start on Squarespace. In this episode, I walk through why I eventually moved my digital products somewhere else: the customer experience after purchase, the amount of support and follow-up the system created, and the costs that started adding up as my sales volume grew.

We'll talk about expired download links, the three-email membership experience, and why something can technically work while still not work well for your business.

I also cover where I think Squarespace is a great choice for selling, including physical products, services, limited releases, and simpler digital downloads. And if you're deciding where to sell your own product — or helping a client make that decision — I'll give you the three questions I think you should ask before choosing a platform: What are you selling? What's your volume? And what happens after the sale?

Plus, in the show notes you'll find three alternative platforms worth exploring for digital products: Flodesk (my personal favorite), SendOwl, and Payhip.

Full show notes, transcript, & resource links: insidethesquare.co/podcast/98

Timestamps

00:00 Why I don't sell my digital products on Squarespace
01:00 The 34-page PDF that started it all
02:20 Expiring download links and the support problem
03:38 When something technically works but creates a bad customer experience
05:21 Follow-up emails and digital product delivery
06:20 The Squarespace membership experience
08:03 The hidden cost of a system that requires constant effort
08:42 When fees started changing the equation
09:25 Squarespace can still be a great selling platform
09:47 New Squarespace tools for limited releases
10:53 When Squarespace might still be the right choice
11:14 Three questions to ask before choosing a selling platform
11:28 Question 1: What are you selling?
11:48 Question 2: What's your sales volume?
13:05 Question 3: What happens after the sale?
13:49 Retiring the digital product that started it all

Support the show

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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A client sends you a link to a website they generated with AI and asks if you can "just" build it in Squarespace. That one word is doing an enormous amount of work. In this episode, Becca breaks down what actually happens when an AI-generated design lands in your inbox — why AI tools design for how something looks rather than how it gets built, and why they're not thinking about Fluid Engine, page sections, content blocks, or the fact that mobile isn't just a smaller version of desktop. You'll learn the three-category system Becca uses to translate any AI mockup into a real Squarespace build before she replies to the email or quotes a price: built in (what Squarespace already does), built custom (possible, but it needs CSS and a judgment call about whether that detail is worth two hours), and built somewhere else (functionality like booking systems that isn't a design element at all — it's an entire platform hiding inside a pretty rectangle). Plus: how to explain all of this to a client without ever saying "Squarespace can't do that," and why the most valuable thing you sell now isn't your ability to recreate every pixel — it's your judgment. Your client has the idea. You create the plan.

Chapters:

00:00 The "Can You Just Build This in Squarespace?" Email
02:59 What AI Design Tools Are Actually Doing (And What They Ignore)
04:43 Why Squarespace's Structure Is a Feature, Not a Limitation
05:52 Built In: What Squarespace Already Does
06:58 Built Custom: When Custom CSS Is Worth It
08:46 Built Somewhere Else: Hidden Functionality and Integrations
10:33 How to Quote an AI-Generated Design and Explain It to Your Client

Support the show

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

Send a message to InsidetheSquare

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

Support the show

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

Send a message to InsidetheSquare

In this episode I walk through the three sections saved to my Squarespace account, so they're one click away on any site I work on, and the three sections I build into every client site's template page, ready to duplicate and restyle.

You'll learn the difference between fluid engine, list, and gallery sections, including where Squarespace moved list and gallery after retiring the old menu name, why a blank gallery section saves you from deleting demo content every single time, and the mini footer and mini header setup I build to keep landing pages compliant and consistent without dragging in a full site nav.

Timestamps
00:00 Why saved sections save so much time
01:12 What a page section is in 7.1
01:37 The three sections I save to my account
02:59 Gallery sections and the demo content fix
04:00 List sections, my favorite for organizing content
05:56 Element sections, my old WordPress habit
07:35 The three sections I build into every client site
08:00 Mini footer and mini header (with my fav accordion trick)
10:16 Hero section & recap

Show notes & resource links:
insidethesquare.co/podcast/95

Support the show

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

Send a message to InsidetheSquare

Squarespace keeps absorbing the things designers used to hand-code.So when a feature ships that replaces code already sitting on a live client site, do you rip it out or leave it alone?

In this episode I'm sharing how I decided if the code should stay or go.
I also cover the customizations I have no intention of giving up, and the small branded details I call Disneyfying a website.

Full show notes: insidethesquare.co/podcast/94

00:00 — Squarespace added the feature. Do you remove your custom code?

01:21 — The first question: how many pages does this code affect?

01:36 — Hiding the header and footer on a Squarespace landing page

02:15 — Two columns of products on mobile: remove this code and use the setting

02:59 — Uploading a custom font to Squarespace instead of coding it

03:55 — Button hover effects: when to keep your CSS and when to use the editor

05:27 — Mobile menu customizations that still need custom code

07:58 — The rule: sitewide stays in code, one-offs go native

Support the show

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