ThinkInsideTheSquare

Hosted by Becca Harpain

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Aug 2026

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About the show

Ever wondered how to make your DIY website pop, turn your online presence into a client magnet, or transform your side hustle into a full-fledged business? You're in the right place! I'm Becca, content creator for InsideTheSquare.co. I've turned my career around, transforming myself from an unknown Squarespace designer into the worlds go-to expert on all things Squarespace in just a few short years. Every Thursday, I'm dishing out actionable advice, insider tips, and game-changing strategies that I've learned from years of hands-on experience in web design, digital marketing, and business growth. Whether you're a solopreneur juggling it all, a creative itching to monetize your passion, or a small business owner ready to level up your online game, Think Inside The Square is your go-to resource for all things digital entrepreneurship. We're talking Squarespace secrets, web design wisdom, content creation hacks, and business strategies that actually work in the real world. But this isn't just another "how-to" show. It's a community of forward-thinking entrepreneurs who believe that creativity thrives within boundaries. Together, we're redefining what it means to build a successful online business, one square at a time. So, are you ready to turn limitations into launchpads and constraints into catalysts for growth? Join me every week for a dose of inspiration, practical tips, and the occasional dad joke. Let's think inside the square and outside the ordinary. Your next big business breakthrough is just an episode away!

Listen to episodes

60 recent

September 8, 2026Episode 1008 min

Episode 100: When the Answers Get Easier, What Makes You Valuable?

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 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 hello@insidethesquare.co . 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

September 1, 2026Episode 9917 min

[99] Does AI-Generated Content Hurt SEO? The answer for Squarespace users, and well, everyone.

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

August 25, 2026Episode 9815 min

[98] Why I Stopped Selling Digital Products on Squarespace

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

August 18, 2026Episode 9715 min

[97] Can Squarespace Do That? How to Analyze What's Possible in an AI Design

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

August 11, 2026Episode 9612 min

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

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

August 4, 202612 min

[95] Saved Sections: The Squarespace Shortcut I Use on Every Site

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

July 27, 202610 min

[94] When Squarespace Adds a Feature: Should You Remove Your Custom Code?

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

July 21, 20266 min

[93] Vibe Coding for Squarespace

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 features 01:48 The real reason AI slop happens 02:32 My countdown timer experiment, live and unscripted 03:29 The one skill that makes or breaks vibe coding 04:26 Diagnose more, prompt less 05:19 Borrowing a framework from Will Myers on where AI's job ends and ours begins 06:19 Where to go next if you want to learn this for real Links mentioned: insidethesquare.co/beyond Will 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

July 14, 2026Episode 929 min

[92] Update on Squarespace Updates: July 2026

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 hello@insidethesquare.co 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

July 7, 2026Episode 919 min

[91] Five Things I Judge About Every Website I See 👀

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