Making Your Business Less Miserable

We just got back from Squarespace Circle Day, and we have thoughts. Squarespace unveiled some new updates for 7.1 as well as their new AI builder, Forma. We share our honest first takes.We also cover what’s been going on in the industry, including a PHP security leak, Claude Duet, whether or not this is an AI bubble, and the parts of web design that are not changing.Watch the Circle Day replay here:https://www.youtube.com/@squarespacecircle Offerings from Will & Christy:christyprice.com/wdr toolkit.will-myers.com 

Half of U.S. adults use an AI chatbot now. Only 4.5% pay for ChatGPT, Gemini, or Claude. (Guess which group we're in.)In this episode, we go through two new reports on how people use AI, then ask what the numbers mean if you build websites for a living.We discuss:Would you give an AI agent your credit card? Meta's Muse, OpenAI's Dots, and how much permission each of us hands over.Why web designers are the weirdos. The median AI subscriber pays $25 a month. The top 1% pays about $903.Search is the #1 thing people use chatbots for. 44% of Americans use ChatGPT and 6% use Claude, so check where your client's customers are.Lovable, Canva, Figma, Claude Design... the build is getting crowded. Taste isn't.71% of Americans think AI makes their personal info less secure. "Built by a human who answers your email" is a selling point.Lightning round: a bathtub injury, a 4th grade spelling bee grudge, and our walk-up songs.We skipped sponsors this season to share our own things:Christy's is Web Design Roundtable, her community for Squarespace web designers. More info at https://christyprice.com/wdrAnd you can find Will's plug ins at https://www.will-myers.com/productsSources:a16z, The Top 100 Gen AI Consumer Apps, 7th Edition: https://a16z.com/100-gen-ai-apps-7/Pew Research Center, Americans and AI 2026: https://www.pewresearch.org/internet/2026/06/17/americans-and-ai-2026-chatbots-smart-devices-and-views-on-impact/ Hosts:Christy Price: https://christyprice.comWill Myers: http://will-myers.com/Editor: Rikki Gunton

We're back after a three-month break, catching up on what we've been building, how AI has (and hasn't) changed our workflows, and continue the ongoing conversation about how AI is impacting web designers.Squarespace Circle Day:https://circleday.squarespace.com/Tools Mentioned in the Episode:SquareKicker Compose: https://squarekicker.com/composeBase44: https://base44.com/ Fathom: https://www.fathom.ai/  Kit: https://kit.com/ vidIQ: https://vidiq.com/ Instinct: https://instinct.com/ Pangram: https://www.pangram.com/ Lovable: https://lovable.dev/ Figma: https://www.figma.com/ Codex: https://chatgpt.com/codex/ Resend: https://resend.com/ Github: https://github.com/  Offerings from Will & ChristyChristy’s Two Day Website System: https://learn.christyprice.com/template-buildout-system Christy’s Client Process Checklist: christyprice.com/client Will’s Step Flow Timeline plugin: https://www.will-myers.com/products/p/step-flow-timeline 

AI bot traffic is projected to surpass human traffic by the end of 2027. In this episode, we discuss how web design is changing and what we can expect for the future. We talk about whether the extra SEO effort is worth it, adding AI clauses to design contracts, and why we still believe we should build for humans first.Mentioned in the episode:Internet traffic composition: https://blog.will-myers.com/post/internet-traffic-composition Phone stand: https://www.moft.us/products/invisible-phone-tripod-stand?variant=43898583056471Computer stand: https://www.amazon.com/Roost-Laptop-Stand-Adjustable-Portable/dp/B01C9KG8IG/ref=sr_1_18 Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.Sign up for Will's NewsletterSign up for Christy's Newsletter

In this episode, Will sits down with Becca Harpain from Inside the Square and Dave Hawkins from Made by Dave to discuss all things AI: vibe coding, what they will and won’t use AI for, how their workflows have shifted now that AI tools are widely available, and the main skills Squarespace designers should be focused on right now. Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.Mentioned in the episode:Dave’s course: squarehead.co.uk (use code somewhat10)Becca’s Custom Codey: customcodey.comWisprflow: https://wisprflow.ai/ The Lean Start Up book: https://theleanstartup.com/Find Dave: https://madebydave.org/ Find Becca: https://insidethesquare.co/ Sign up for Will's NewsletterSign up for Christy's Newsletter

In this episode, we discuss the concept of "killing your darlings" — letting go of products, processes, or tools in your business that no longer serve you to make room for what's next. Will shares how he’s rethinking his plugin strategy and Christy reflects on services she’s no longer offering. We also discuss the shifting landscape of the web design and development industry and debate the creativity (or lack thereof) of LLMs. Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.Sign up for Will's NewsletterSign up for Christy's Newsletter

Today we're joined by Kelsey Gilbert-Kreiling (of Week of the Website and Eventually) to chat about launching the new event ticketing platform she built with her husband Zach. We learn about the origin story, how they use Claude in their build process, and discuss how AI is shaping the future of in-person gatherings. Will explains why he moved Code Curious off of Squarespace, and Christy shares an update on her wine education journey.Try a free month of Eventually at eventuallyticketing.com/somewhat-useful Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.⁠Sign up for Will's Newsletter⁠⁠Sign up for Christy's Newsletter⁠

If we had to start over today, with no audience, no email list, and no reputation, what would we actually do?In this episode, we break down what still works for building a web design business, what we'd skip completely, and where we'd focus if we had to rebuild from scratch in 2026. We also talk about SEO, YouTube, AI search, email lists, Instagram, digital products, client work, and the slow reality of growing something that lasts.Plus, Christy shares the story of winning $5,000 at Sponsor Games, and Will talks about how he's in his Claude era.Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.Mentioned in the episode:Sponsor Magnet by Justin MooreAtomic Habits by James ClearKit ConferenceWeb Designer's PlaybookWill's ToolkitWill's email listChristy's email list

In this episode, Christy and Will discuss recent and upcoming conferences, Squarespace updates, and Will’s evolving opinion on OpenClaw. Then they chat with Gavin Zuchlinski, founder of some of the best scheduling tools on the market, including this season’s sponsor, Breely! You'll hear about how he created Acuity as a side hustle, the Squarespace acquisition, and why he wanted to build yet another scheduling platform. Mentioned in the episode:Will’s article about OpenClawFinal Surge appDie with Zero bookThank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

AI tools are moving fast, client work gets messy, and some days, business feels heavier than it should. In this episode, we talk honestly about what makes entrepreneurship feel miserable, how AI is adding new anxiety (hello, OpenClaw), and the boundaries that actually help.You'll also hear a few timely Squarespace updates (and bugs), plus what the next year might look like for Squarespace designers and developers as AI keeps changing the workflow.Mentioned in the Episode:Squarespace CircleThe Web Designer Summit (March 5)Thanks to our sponsor Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.