Circle Live – Détails, épisodes et analyse

According to our survey of over 1,000 Circle partners, those using AI tools to build client sites report greater time savings and creative fulfillment. Yet, more feel pessimistic about these tools now. This mix of positive change and growing uncertainty begs the question: can you use AI to cultivate both your creativity and a thriving design business?

According to Andy J. Pizza, New York Times-bestselling author and illustrator: yes. In this episode of Circle Live, the free talk show from Squarespace for professional creatives, you’ll learn from Andy about:

• Balancing human imperfection with AI precision
• Andy’s strategies for delegating tasks to maximize joy in work
• How to move forward with confidence amidst rapid industry change
• Imbuing your work with feeling to stay creatively fulfilled while delivering sites that delight

Embrace AI-powered creativity more easily with fresh insights from Andy’s unique creative voice, as heard on his podcast, Creative Pep Talk.

Watch this episode on YouTube.

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

37% of web designers say the biggest barrier to getting new business is that they’re too busy working on current projects. Factor in shifting design trends, client demands, and industry circumstances, and even the most tenured designers may need help identifying effective ways to grow.

This month on Circle Live, the free talk show from Squarespace for professional creatives, we spoke to David Kennedy of Mediaspace and Chelsea Pimienta of 23&9 Creative. These experts with distinct career journeys explore the myriad paths and strategies pro designers can follow to find success for their businesses—and save time, too.

In this episode, you'll learn:

• Chelsea’s approach to passive income
• Ways to scale your business when you’re busy
• David’s model for generating recurring revenue through website management
• When to delegate or automate tasks so you can spend more time doing what you love

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

On this episode of Circle Live, we’re taking a look at ways to elevate client acquisition, retention, and satisfaction with Circle member, Squarespace educator, and author of Love is the Business Plan, Tanya Moushi.

Listen or watch to hear Tanya discuss her sales process, adding empathy and character into your client acquisition, creating engagement-driving websites, and more.

Discover key selling strategies like:

• Making client interactions more human
• Building trust that leads to more business
• Asking the right questions during client consultations
• Optimizing websites for engagement

Register now for the next episode of Circle Live, and in the meantime, watch or listen to last month's episode featuring Christy Price.

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

In this episode of Circle Live, we took a look at the past, present, and future of Circle with longtime Circle member, Squarespace educator, and cohost of the Somewhat Useful podcast, Christy Price.

Listen or watch to hear Christy and Squarespace’s Jeremy Schwartz discuss Christy’s career journey and the strategic choices she’s made to grow her career while partnering with Circle. We also shared some exciting news about how the Circle program is evolving to support and reward designers, agencies, and entrepreneurs at every stage of their careers.

Discover:

• Strategic decisions Christy made that grew her business
• What distinguishes web design professionals from amateurs
• Upcoming releases announced in our product preview, This Is Squarespace, on February 19 
• The advantages and benefits of Circle membership 
• Brand-new Circle perks and program updates

Then, check out Christy’s Web Designer’s Playbook, a step-by-step system for running successful custom website projects, watch her Circle Day 2023 discussion about crafting smooth client offboarding strategies, and listen to Jeremy's March 2025 appearance on Somewhat Useful discussing Squarespace and Circle's evolutions over time.

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

Get inspired to refresh your business by seeing how today’s top web designers get things done. For our first episode of 2025, we were joined by the co-founders of SquareKicker, Nick and Hannah Ippolito, to discuss web design in 2025 and Squarespace’s latest State of the Web Design Industry report. 

Based on a survey of Circle members from around the globe, the State of the Web Design Industry Report details how today’s web designers operate their businesses and the projects, milestones, and achievements they’re most proud of. 

Discover: 

• How the web design industry has evolved over the past year
• New trends, tools, and strategies to elevate your craft and achieve your goals 
• Inspiring Circle member stories 
• Motivating ideas to help you plan your next big project

Watch Nick and Hannah discuss which of the report’s findings were most helpful and surprising as well as how they plan on leveling up their business in the year ahead.

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

Circle Live is the monthly series featuring conversations with guests from the Squarespace Circle community on how to build a business, enhance your design skills, and create unique experiences for clients using Squarespace.

In this episode featuring Dorian Dreyfuss, Squarespace’s Senior Brand Designer, and Squarespace Experts Jen Maher and Dreyah Bohlen Harrington, we discussed the most-anticipated designs your clients will ask for in 2025:

• Typefaces and web design: a love story 
• Incorporating the human touch into your designs
• Bringing inspiration from nature into the digital sphere
• How to design joyful online experiences
• Creating impact with a chaotic clash of vibrant colors

Take the quiz to discover which 2025 design trend best defines you!

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

“Digital alchemy follows a very simple formula: turning problems into content, then turning the solutions that you come up with into products. It’s a compounding thing that makes up a very simple but no less impactful content flywheel.”

While each web designer’s journey looks different, there comes a time in every career when it’s necessary to change destinations or forge a new path forward.

Discover how to recognize when it’s time for a career pivot at October’s Circle Live with one of Circle Day’s most popular speakers, Omari Harebin. We discussed Omari’s journey to becoming a Squarespace web designer and the decisions he made along the way to work toward a more flexible, fulfilling, and profitable career.

Omari Harebin is a Squarespace mentor, marketing expert, and self-described digital alchemist. In his new book, The Corporate Dropout, Omari tells his story of his experience embracing discomfort to drive forward toward success.

During our October episode, we discussed:

• Omari's new book, The Corporate Dropout
• The journey toward Squarespace web design
• Benefits of working for yourself
• Benefits of working on yourself
• What's digital alchemy? 

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

For the first time ever, we brought Circle Live to the Squarespace office in Dublin, Ireland, for a special episode with Teresanne O’Reilly, founder and managing director of The Forest. 

This special episode featured the best advice and insights we learned at Circle Day 2024. 

Highlights:

• Teresanne’s journey creating a strategy-first website design company
• How to position your brand more strategically 
• Actionable advice from Circle Day sessions

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

A positive client relationship is the foundation of every great web design project. But with so much work to support every step of the way, creating an effortless client experience takes a whole lot of effort. 

Get the tools to strengthen and streamline your client relationships in this episode of Circle Live featuring the team from ChowNow. We discuss how ChowNow extends the delight of in-person hospitality into digital experiences and how you can deliver better service by finding the right clients, curating your customer journey, and ensuring success once your project is complete.

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/

After working as an executive at companies such as PepsiCo and Old Navy, Philip now works as a creative entrepreneur and shares his business expertise with over 290,000 YouTube subscribers. In this episode of Circle Live, Philip joins hosts Sam Z. and Sarah G. to share how entrepreneurs and businesses of all sizes can grow their following and client base by creating smarter, more effective, and refreshingly human lead magnets. 

Conversation highlights: 
00:00 Intro
05:33 First steps to a lead magnet
07:06 Best performing lead magnets
08:06 Measuring conversions
09:30 Reusing content
11:20 Not doubling up efforts
13:44 Finding your customer avatar
16:56 Automation
20:11 Keeping content fresh
24:32 Philip's career journey
31:43 Balancing content creation with client work
33:35 YouTube conversions workflow
34:28 Lead magnets in Squarespace
35:15 Content pillars and topics
38:27 Closing clients on Zoom

If you use a podcast player (like Overcast), use this link to subscribe to Circle Live: https://feeds.buzzsprout.com/2299108.rss

Already a Circle member? Check out the events calendar to see what’s coming soon! ➡️➡️➡️ https://forum.squarespace.com/events

To learn more about Circle, check out some resources below:

• Circle overview: https://www.squarespace.com/circle
• Getting started with Circle: https://support.squarespace.com/hc/en-us/articles/218890098
• Circle member benefits: https://support.squarespace.com/hc/en-us/articles/218890098#toc-circle-member-benefits
• Circle blog: https://pros.squarespace.com/