Somewhat Useful

Hosted by Will Myers and Christy Price

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May 2026

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About the show

Welcome to Somewhat Useful, the show where we explore the world of entrepreneurship and web design. We'll discuss topics that are shaping the world around us and tackle your questions from the mailbag. From Will Myers, Squarespace Developer, and Christy Price, Squarespace Designer.

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46 recent

May 28, 2026Episode 91 hr 0 min

Should We Be Building Websites for Humans or Robots?

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

May 20, 2026Episode 81 hr 1 min

Practical Ways to Use AI for Client Work

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

April 24, 2026Episode 755 min

Kill Your Darlings: When to Let Things Go

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

April 14, 2026Episode 650 min

Building Eventually with Kelsey Gilbert-Kreiling

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

March 31, 2026Episode 553 min

If We Had to Start Over in 2026

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

March 17, 2026Episode 457 min

Building on Your Own Terms with Gavin Zuchlinski

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.

March 2, 2026Episode 348 min

Making Your Business Less Miserable

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.

February 20, 2026Episode 241 min

Standing Out in an AI World with Jacq Fisch

We start this episode by reviewing what’s new with Squarespace, including the retirement of the Amazon block and our thoughts on search functionality. We also discuss Squarespace’s recent Super Bowl ad. Then we’re joined by author and writing coach Jacq Fisch to talk about: Writing in 2026 and how to stand out in a sea of noise and AI-written contentWays to use AI without selling your soulFind Jacq at:https://theintuitivewritingschool.com/https://jacquelinefisch.com/https://jacquelinefisch.substack.com/https://www.instagram.com/theintuitivewritingschool/Mentioned in the episode:Monacle searchVoxerOtterThank 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.

February 9, 2026Episode 150 min

It's 2026. Now what?

In this episode we chat about what 2026 looks like for web designers and developers. We'll share what we're leaning into this year and what we're leaving behind.Mentioned in the episode:Kit conferenceSponsor GamesChristy's YouTube Growth LabSponsor: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.Follow:⁠⁠Follow Christy on Instagram⁠⁠⁠⁠Follow Will on Instagram⁠⁠⁠⁠Sign up for Will's Newsletter⁠⁠⁠⁠Sign up for Christy's Newsletter⁠

January 21, 202642 min

BONUS EPISODE: State of the Web Design Industry Report with Squarespace Circle

Want to know how web designers feel about AI? In this bonus episode, Christy and Will dive into the new 2026 State of the Web Design Industry Report with Sam Zelitch and Sarah Greisdorf from the Squarespace Circle team.Read the report: https://pros.squarespace.com/web-design-industry-reportFollow Christy on InstagramFollow Will on InstagramSign up for Will's NewsletterSign up for Christy's Newsletter