ThinkInsideTheSquare

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

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 focus
• Who this season is for (DIY website owners and designers alike)
• How AI will fit into future episodes
• Upcoming topics including design, customization, updates, and launching your website
• How you can help shape future episodes by submitting your questions

Full 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

Send a message to InsidetheSquare

Did you know more than half of your website visitors are probably on their phones? In this episode, I'm sharing my expert advice on how you can make your Squarespace site look fantastic on every screen size. Hint: It all starts with how you edit.

We're diving into mobile-first design (and why it matters SO much), how to use the mobile preview to customize your small-screen layout, and the top three issues that trip up most Squarespace users (text overwhelm, tiny buttons, and broken layouts).

I'll share my favorite tricks for creating mobile-friendly designs, including the secret to perfect button sizing, how to fake layered images that look great everywhere, and a simple 3-question test to make sure your site delivers an awesome experience for phone users. 

Important Links
📝 Full show notes: https://insidethesquare.co/podcast/88
🎧 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

Send a message to InsidetheSquare

Wondering how to turn your expertise into an AI tool that helps others and generates income? In this episode of Think Inside The Square, I'm sharing the straightforward process I used to create Custom Cody, my Squarespace code AI assistant that's now helping hundreds of users with their website customization questions.

I'll walk you through my entire journey, including the complicated detours and technical rabbit holes that cost me months of development time, before sharing the much simpler approach I discovered. You'll learn exactly how to evaluate your AI idea, train your custom GPT on your unique knowledge, test it effectively, and share it with your audience using a pricing model that makes sense for your business.

This isn't about creating "passive income" (I spend hours every weekend improving Custom Cody!)  This is about extending your reach and helping more people with your knowledge. Whether you're a consultant, coach, designer, or specialist in any field, this episode gives you the practical blueprint to package your expertise into a valuable AI tool your audience will happily pay to use.

Important Links
📝 Full show notes: https://insidethesquare.co/podcast/87
🎧 Past episodes: https://insidethesquare.co/podcast
💌 Check out Custom Codey: https://customcodey.com
👯‍♀️ Follow me on Instagram: https://instagram.com/thinkinsidethesquare

CHAPTERS
00:00 - The AI assistant I never thought I could build
01:00 - What exactly IS a custom GPT? (Simpler than you think!)
03:00 - The essential "intelligence test" your AI idea must pass
05:00 - My costly over-engineering mistakes (don't repeat these!)
07:00 - The OpenAI feature change that changed everything
09:00 - Training Custom Cody to speak "Squarespace" fluently
12:00 - Real-world testing: The secret to reliable AI responses
14:00 - Simple pricing strategies that make everyone happy
18:00 - Weekend optimization routine for continuous improvement
20:00 - Is creating a custom GPT right for YOUR expertise?

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

🔄 Is your online business ready for the NEXT big industry shift? Learn how to spot trends BEFORE they impact your bottom line!

In this episode, I'm sharing my decade of experience weathering digital disruptions. From the decline of Myspace to AI design tools threatening to replace designers, I've seen how quickly things can change—and how to position yourself to thrive regardless.

🔥 What You'll Learn:

• Discover 3 powerful sources for spotting trends months before they hit mainstream
• Learn which big tech investments signal the future of web design (and what Adobe's moves tell us)
• Create strategic income diversification that protects you from industry volatility
• Recognize the 3 clear signals that it's time for a business pivot
• Implement my weekly 30-minute trend-monitoring system anyone can follow

⭐ New: Try my Squarespace AI assistant Custom Codey at customcodey.com - your 24/7 code helper specifically designed for Squarespace users: customcodey.com

💡 PRO TIP: "Don't try to follow every trend—focus on identifying the underlying patterns that signal where the industry is truly heading."

Important Links
📝 Full show notes: https://insidethesquare.co/podcast/86
🎧 Past episodes: https://insidethesquare.co/podcast
💌 Join my email list: https://insidethesquare.co/email
👯‍♀️ Follow me on Instagram: https://instagram.com/thinkinsidethesquare

#SquarespaceExpert #WebDesignBusiness #FutureProofBusiness #OnlineBusinessTips #SquarespaceDesign #WebDesignTrends #AIandDesign #DigitalProducts #BusinessStrategy #PassiveIncome #RecurringRevenue #PivotStrategy #BusinessDiversification #TrendSpotting #SquarespaceTips

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

🏠 Confused about domains, hosting, and CMS? In this episode, I break down exactly what you need to know about domains, hosting, content management systems, and professional email addresses - the essential building blocks with no fluff, just practical information to help you understand what's happening behind the scenes of your Squarespace website.

By the end of this video, you'll understand the difference between domains and hosting, know which CMS is right for your needs, and learn how to create a professional email address that matches your domain.

⭐ Check out my Blueprint AI tutorial to build your prefab digital home super fast: insidethesquare.co/blueprint

⏰ TIMESTAMPS:
00:00 Website Basics: What You Need to Know
02:00 Domains Explained: Your Digital Address
03:00 Hosting: The Land for Your Website Home
04:00 Content Management Systems Compared
05:00 Squarespace Blueprint: Build a Site in 30 Minutes
06:00 Professional Email: Level Up Your Business Credibility
08:00 Connecting External Domains to Squarespace
09:00 Next Steps: Secure Your Digital Real Estate

Important Links
📝 Full show notes: https://insidethesquare.co/podcast/85
🎧 Past episodes: https://insidethesquare.co/podcast
💌 Join my email list: https://insidethesquare.co/email
👯‍♀️ 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

Send a message to InsidetheSquare

 Want to turn your Squarespace website into a thriving membership community where people connect, engage, and happily pay for your expertise?

In this step-by-step tutorial, I break down exactly how to use Squarespace Member Areas to create an exclusive space your audience will love. I'll show you my favorite workarounds for Squarespace's limitations and the third-party tools that take your membership to the next level!

Building a successful membership doesn't require a huge following or complex tech - just Squarespace plus the strategies I'm sharing today. Let's transform your audience into a genuine community!

🔥 What You'll Learn:

• The exact structure of a successful Squarespace Member Area
• Creative content ideas that keep members engaged (beyond just courses!)
• My clever workaround for community features Squarespace doesn't have
• How to properly integrate Slack/Discord with your membership
• Email strategies that dramatically increase member retention

Important Links
📝 Full show notes: https://insidethesquare.co/podcast/84
🎧 Past episodes: https://insidethesquare.co/podcast
💌 Join my email list: https://insidethesquare.co/email
👯‍♀️ 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