Episodes

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, ...

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 a...

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 conference Sponsor Games Christy'...

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 ...

We break down the biggest updates from Squarespace Circle Day, why this year felt different, and what matters for your client work. We cover Finish Layer in ProTools (animations, layers, grouping with Stacks, hide on mobile, ...

AI is transforming everything, from how we work to how we build businesses. But what does that actually mean for entrepreneurs and creatives like us? Are we on the brink of losing our jobs… or stepping into a new era of possi...

In this episode, Will and Christy touch base about wrangling code updates, keeping up with Squarespace’s ongoing changes, and the debate between live and pre-recorded marketing. Then they bring in Kelsey Gilbert Kryling, foun...

In this episode, Will and Christy talk about everything from big Squarespace updates (especially around e-commerce), to taking real sick days (or not), and why it’s actually okay if your website isn’t the prettiest thing on t...

In this episode Christy and Will debrief the Kit conference and weigh the pros and cons of doing live and pre-recorded content. Then they bring on Hoyd Breton, principal product designer at Squarespace. They discuss the power...

In this episode, Will and Christy review the tips from their last Circle Day talk, “ 7 Ways to Save Time as a Web Designer ” and discuss which are still relevant. Then they talk with Liz Ellery about helping clients find thei...

Will and Christy kick off this week’s episode talking about the fun industry events they recently attended. They share their top three feature requests for Squarespace as well as a couple Squarespace updates. Then they talk w...

In this episode Christy and Will talk about their favorite chrome extensions and share the latest Squarespace update. They are joined by Jen Maher who discusses her ADHD diagnosis and how it impacts the way she runs her busin...

In this episode of Somewhat Useful, Will and Christy talk about how they are using AI in their workflows and share a couple platform updates from Squarespace. Then they chat with CSS expert Chris Schwartz-Edmisten about his j...

In this episode, Will and Christy chat about the pros and cons of social media for their business and discuss how they manage their social media usage. They are then joined by Lex Roman, who talks about their journey from TV ...

In this episode, Christy and Will debrief Squarespace’s State of the Web Design Industry report, and share their thoughts on setting deadlines and shipping products. Then they talk with LaShonda Brown of Bootstrap Biz Advice ...

In this episode, Christy and Will chat about email marketing and how it fits into their business. Then they talk with Jeremy Schwartz, General Manager of Channel Partnerships at Squarespace. You’ll hear about the evolution of...

In this episode, Christy and Will talk about whether or not you need a website copyright and share their Somewhat Useful tips for your business. Then they talk with Kate Scott about her journey from WordPress book blogger to ...

In this episode, Will and Christy discuss getting past perfectionism and give their Somewhat Useful tips. Then they talk with Weglot CMO Eugène Ernoult about the company’s innovative translation solution. You’ll hear about Eu...

In this episode, Will and Christy talk about the intersection of Google and AI. They share the big projects they’re currently working on and give some tips for your business. Then they talk with Becca Harpain of Inside the Sq...

In this episode, Christy and Will share their words for the New Year and tips for your business. Then they talk with Omari Harebin about his journey from a struggling freelancer to a successful entrepreneur and coach. Omari s...

In this episode of "Somewhat Useful," we get to speak with special guests Sarah Greisdorf, team lead for Squarespace Circle, and Sam Zelitch, Squarespace senior community events manager. Our conversation centers around Circle...

In this episode of "Somewhat Useful," we dive into the world of Squarespace plugins and digital entrepreneurship with Cody Juhnke, the founder of Ghost Plugins . Cody shares his journey from freelance web designer to creator ...

In this episode of Somewhat Useful, we get to pick the brain of Tony Howell, a personal brand strategist and web designer for award-winning artists. Join us as we discuss: Tony's journey from Broadway actor to web designer Th...

Ready to dive into the world of AI, personal branding, and digital nomad life? In this episode, we're joined by the wonderful Phil Pallen, a brand strategist, speaker, Adobe ambassador, author, and just all around great guy. ...