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 Moore

Atomic Habits by James Clear

Kit Conference

Web Designer's Playbook

Will's Toolkit

Will's email list

Christy'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 OpenClaw

Final Surge app

Die with Zero book

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.

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 Circle

The 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.