Circle Live - Squarespace Circle

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https://support.squarespace.com/hc/en-us/articles/218890098
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Circle Live: Staying Creative in the Age of AI with Andy J. Pizza

Season 4 · Episode 3

Tuesday, March 24, 2026 • Duration 24:22

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/

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Circle Live: Profits and Process with David Kennedy and Chelsea Pimienta

Season 4 · Episode 2

Wednesday, February 25, 2026 • Duration 24:28

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 Live: Up Your Client Game with Tanya Moushi

Season 3 · Episode 3

Thursday, March 27, 2025 • Duration 48:22

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 Live: Strategic Growth with Christy Price

Season 3 · Episode 2

Friday, February 28, 2025 • Duration 45:52

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/eventsTo learn more about Circle, check out some resources below:

Circle Live: State of the Web Design Industry 2025 with SquareKicker

Season 3 · Episode 1

Friday, January 31, 2025 • Duration 44:55

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 Live: Design Trends 2025 with Dreyah Bohlen, Jen Maher, and Dorian Dreyfuss

Season 2 · Episode 12

Friday, December 13, 2024 • Duration 48:08

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/eventsTo learn more about Circle, check out some resources below:

Circle Live: Digital Alchemy with Omari Harebin

Season 2 · Episode 11

Thursday, October 31, 2024 • Duration 48:01

“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 Live: Ireland Edition with Teresanne O'Reilly

Season 2 · Episode 10

Thursday, September 26, 2024 • Duration 45:51

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/

Circle Live – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

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Latest published episodes

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Apple Podcasts

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Circle Live – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other75

Buzzsprout6

Youtube13

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Other75

Buzzsprout6

Youtube13