Watch Wil Reynolds on Circle Live, where he reveals how to succeed in AI search by focusing on delivering clients your brand’s unique value.

Watch three Circle partners pitch real client sites, from a kids’ art camp to a wellness retreat, and learn their approach to landing the deal.

Watch Fiona Humberstone on Circle Live as she breaks down how to build a design business on your own terms, from client work to online courses.

Sam Crawford built Six-Figure Design Club to teach web designers how to earn from their expertise and build high-revenue businesses. In this Circle Live episode, he walks through how he built and markets the course, how he runs it entirely inside Squarespace, and what it takes to turn your expertise into something that sells.

Web designer and Yangu Web Studio founder Marya Nguyen gets real about what it actually takes to run a sustainable design business—rigid routines, confident pricing, and knowing when to walk away from a prospect. Watch Circle Live to hear how she structures her days, shifts her mindset around rates, and spots the early signs of a "vampire client" before saying yes.

Watch Andy J. Pizza, host of the Creative Pep Talk podcast, share how human creativity and AI can coexist in the modern web design business.

Watch the February 2026 episode of Circle Live featuring David Kennedy and Chelsea Pimienta. The two join us to discuss how web designers can maximize profits through process.

Watch the latest episode of Circle Live featuring Christy Price and Will Myers. The two join us to discuss Squarespace Circle’s State of the Web Design Industry 2026 report.

The Circle community has achieved so much in 2025. Watch this episode of Circle Live to see our favorite guests share those wins and the lessons that inspired them throughout the year.

In this episode of Circle Live, Becca Harpain shares the SEO and AEO best practices she's currently implementing. Discover actionable insights to elevate your own content strategy.

Discover how to develop and uplift your own web design process in this episode of Circle Live, featuring web design educator Hayley Fedders of Studio Seaside.

Learn to use color and design elements to create deeply resonant work that your clients will say "yes" to in this episode of Circle Live, featuring brand stylist Fiona Humberstone.

During Circle Day 2023, Squarespace CEO and Founder Anthony Casalena joined a special edition of Circle Live, Squarespace’s monthly talk show for web designers, entrepreneurs, and other creatives. Attendees tuned into a candid conversation about Squarespace’s mission and trajectory.