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Send a message to InsidetheSquare 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

Send a message to InsidetheSquare 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 goalWhy familiar AI design patterns aren't necessarily the biggest problemHow clients are starting website projects differentlyWhat it means to finish an AI-built websiteWhy designers may start entering projects at the 60–80% markHow Squarespace can simplify an unnecessarily complicated AI-built setupWhere accessibility, usability, branding, and design judgment still matterWhy this work starts to look more like consulting than traditional website designIf 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 ArchiveWhere the signup and account experience falls shortWhy I had to create my own search workaroundWhen Squarespace can be a great fit for membership contentWhen you should probably use a dedicated membership platform insteadMentioned 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

Send a message to InsidetheSquare 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 SquareWhy the business model that worked in 2019 doesn't make as much sense todayThe difference between the problem you solve and the method you use to solve itWhy easier access to answers doesn't automatically lead to better decisionsWhere experience, judgment, taste, and perspective become more valuableWhat the next chapter of Think Inside the Square will focus onThree questions to ask when technology starts changing your industryAI 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

Send a message to InsidetheSquare 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

Send a message to InsidetheSquare 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

Send a message to InsidetheSquare Everyone thinks vibe coding means handing AI the wheel and walking away. I've got a countdown timer that proves exactly why that's wrong, and what happened when I wasn't specific enough while vibe coding it live on YouTube. In this episode, I get into what separates a designer who vibe codes well from someone who just generates AI slop, why "diagnose more, prompt less" is becoming my new rule, and how knowing Squarespace inside and out is the actual unlock, not the AI itself. Chapter Markers 00:00 What vibe coding really is (and isn't)01:04 Where AI fits alongside Squarespace's native features01:48 The real reason AI slop happens02:32 My countdown timer experiment, live and unscripted03:29 The one skill that makes or breaks vibe coding04:26 Diagnose more, prompt less05:19 Borrowing a framework from Will Myers on where AI's job ends and ours begins06:19 Where to go next if you want to learn this for realLinks mentioned: insidethesquare.co/beyondWill Myers (Squarespace coder, referenced for his take on AI's role in the design process)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 never stops changing, and in this episode I'm breaking down five recent updates, two I love, two I'm not thrilled about, and one that might not affect me but could matter for you. Recorded from my porch this week (long story), with an assist from Adobe Podcast's audio enhancement tool. Chapters: 00:00 – Intro: 5 Squarespace updates you need to know 00:27 – Why I'm recording from the porch today 01:16 – Automatic customer tagging in Squarespace Campaigns 02:00 – New: individual page sections on product pages 03:16 – Squarespace raised prices again (here's what changed) 05:00 – New AI visibility feature and confusing pricing 06:38 – Animations and transformations expand to more blocks 08:27 – A word of caution on using animations 08:58 – Wrap-up and what's next Full show notes and links: https://insidethesquare.co/podcast/92 Got a Squarespace question you want covered on a future episode? Email me anytime at [email protected] 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 Season two of Think Inside the Square continues! With two decades of web design experience—ten of them focused entirely on Squarespace—I’ve seen a lot of trends come and go. In this episode, I’m breaking down the exact five-point checklist I use whenever I review a website. We'll be covering how to audit your homepage copy, optimize your site for mobile visitors using Fluid Engine, declutter your typography, and structure your buttons for maximum impact. Whether your site has been live for years or you're preparing for a new launch, these practical fixes will help you elevate your design and build a polished online presence you can be proud of. Chapters: 00:42 Why your homepage headline needs a strict check (and the robot voice trick) 02:03 How to optimize your mobile experience using Squarespace 7.1 Fluid Engine 03:39 Why font consistency matters and how to avoid the "too many fonts" trap 05:25 Understanding primary, secondary, and tertiary buttons inside Squarespace 06:54 Why your About page shouldn't read like a resume and how to rewrite it for your audience 08:35 A sneak peek at next week's episode covering the biggest Squarespace updates of 2026 Full show notes: insidethesquare.co/podcast/91 Learn how to use Squarespace: insidethesquare.co/start - - -    The term "Squarespace" is a trademark of Squarespace, Inc. This video was not approved or endorsed by Squarespace, Inc. I just really love their platform ♥ 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 Season two of Think Inside the Square is here! In this kickoff episode, I'm sharing what's changing, what you can expect from the season, and why we're focusing entirely on Squarespace. We'll be covering website design, customization, platform updates, AI tools for Squarespace users, launch strategies, and practical tips to help you build a website you're proud of. Whether you're creating your own website or designing sites for clients, this season is packed with actionable advice you can put to work right away. In this episode: Why season two has a new, Squarespace-only focusWho this season is for (DIY website owners and designers alike)How AI will fit into future episodesUpcoming topics including design, customization, updates, and launching your websiteHow you can help shape future episodes by submitting your questionsFull show notes: insidethesquare.co/podcast/90 Learn how to use Squarespace: insidethesquare.co/start 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 you've ever watched your website traffic drop, your strategy stop working, or your momentum disappear, this episode is for you.  In this episode of ThinkInsideTheSquare, I'm sharing exactly what happened when I lost 80% of my website traffic overnight and how I’ve spent the last six months rebuilding my business in a smarter, more sustainable way.  From SEO struggles to strategy pivots and launching my own AI assistant, you’ll hear what worked, what didn’t, and how I’ve shifted from chasing metrics to creating content that truly connects. Whether you’re a Squarespace designer, content creator, or small business owner navigating your own digital curveball, this episode will give you real-world insights and encouragement to help you keep moving forward. You’ll learn how to embrace change, rethink success, and start building something better, especially  when things don’t go as planned. Important Links 📝 Full show notes: https://insidethesquare.co/podcast/89 🎧 Past episodes: https://insidethesquare.co/podcast 🤖 Chat with Custom Codey: https://customcodey.com 👯‍♀️ Follow me on Instagram: https://instagram.com/thinkinsidethesquare 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