PODCAST · business
Somewhat Useful
by Will Myers and Christy Price
Welcome to Somewhat Useful, the show where we explore the world of entrepreneurship and web design. We'll discuss topics that are shaping the world around us and tackle your questions from the mailbag. From Will Myers, Squarespace Developer, and Christy Price, Squarespace Designer.
Episodes
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We Are the Weirdos
Half of U.S. adults use an AI chatbot now. Only 4.5% pay for ChatGPT, Gemini, or Claude. (Guess which group we're in.) In this episode, we go through two new reports on how people use AI, then ask what the numbers mean if you build websites for a living. We discuss: Would you give an AI agent…
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Our Real AI Workflows for 2026
We're back after a three-month break, catching up on what we've been building, how AI has (and hasn't) changed our workflows, and continue the ongoing conversation about how AI is impacting web designers. Squarespace Circle Day: https://circleday.squarespace.com/ Tools Mentioned in the Episode:...
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Should We Be Building Websites for Humans or Robots?
AI bot traffic is projected to surpass human traffic by the end of 2027. In this episode, we discuss how web design is changing and what we can expect for the future. We talk about whether the extra SEO effort is worth it, adding AI clauses to design contracts, and why we still believe we should...
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Practical Ways to Use AI for Client Work
In this episode, Will sits down with Becca Harpain from Inside the Square and Dave Hawkins from Made by Dave to discuss all things AI: vibe coding, what they will and won’t use AI for, how their workflows have shifted now that AI tools are widely available, and the main skills Squarespace…
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Kill Your Darlings: When to Let Things Go
In this episode, we discuss the concept of "killing your darlings" — letting go of products, processes, or tools in your business that no longer serve you to make room for what's next. Will shares how he’s rethinking his plugin strategy and Christy reflects on services she’s no longer offering.…
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Building Eventually with Kelsey Gilbert-Kreiling
Today we're joined by Kelsey Gilbert-Kreiling (of Week of the Website and Eventually) to chat about launching the new event ticketing platform she built with her husband Zach. We learn about the origin story, how they use Claude in their build process, and discuss how AI is shaping the future of...
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If We Had to Start Over in 2026
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...
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Building on Your Own Terms with Gavin Zuchlinski
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...
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Making Your Business Less Miserable
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...
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Standing Out in an AI World with Jacq Fisch
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 author and writing coach Jacq Fisch to talk about: Writing in 2026 and…
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It's 2026. Now what?
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's YouTube Growth Lab Sponsor: Breely is modern scheduling software with...
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BONUS EPISODE: State of the Web Design Industry Report with Squarespace Circle
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 the report: https://pros.squarespace.com/web-design-industry-report…
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BONUS EPISODE: Circle Day Recap for Squarespace Pros
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, copy and paste styles), the new custom fonts workflow, Circle dashboard...
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How AI is Impacting our Businesses as Web Designers & Developers
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 possibilities? In this episode of Somewhat Useful, Christy and Will have an...
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Entrepreneur Maternity Leave while Building an Agency with Kelsey Gilbert-Kreiling
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, founder of Week of the Website, to talk honestly about what it’s like…
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What Dogs Can Teach Us About Squarespace Web Design with Kristine Neil
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 the internet. We get into what dogs can teach us about web design, using...
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Creative Inspiration and Storytelling with TOP Squarespace Designer Hoyd Breton
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 of minimalism, story driven design, and the tools to support it. Hoyd...
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Time Saving Tips, Intentional Business Practices, and Community Through Summits with Liz Ellery
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 their voice, bringing a sense of spirituality into her business, and what to...
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Squarespace Feature Requests, AI Tools, and Business as a New Mom with Dreyah Bohlen-Harrington
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 with Dreyah Bohlen-Harrington about how becoming a mom changed the way…
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Make ADHD Your Superpower, Our Favorite Chrome Extensions, and Charging Your Worth, with special guest Jen Maher
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 business. She gives her take on the common advice of charging your worth and...
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CSS, Content Marketing, and Growing a Web Design Business with Chris Schwartz-Edmisten
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 journey from coding to photoshop mockups to helping clients customize…
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Newsletter Longevity, Community Building, and Independent Journalism with Lex Roman
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 to web design, to growth and monetization, and now community building…
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State of Web Design Report, Setting Deadlines, and Doing YouTube Right with LaShonda Brown
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 about her YouTube channel growth strategies. She explains that fun is...
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Email Marketing Tips, Squarespace's Evolution & New Circle Tiers with Jeremy Schwartz
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 Squarespace over his 12 years there, including ongoing efforts to…
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From Client Work to Selling Templates and Courses with Kate Scott
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 successful Squarespace educator and template creator. Kate discusses the...
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Growing a Software Business - Inside Weglot with CMO Eugène Ernoult
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 Eugène’s journey into marketing and his transition from being a founder to...
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Algorithms, AI, and Adaptation with Becca Harpain
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 Square. Becca shares the challenges she faced with Google’s new algorithm...
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[with Omari Harebin] From Corporate Dropout to Digital Alchemist
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 shares his thoughts on adapting to changes in the web design landscape,...
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Behind the Scenes of Squarespace Circle with Sarah Greisdorf and Sam Zelitch
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 Day, now in its third year, which celebrates the work of professional...
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The Story Behind Ghost Plugins and What’s Next with Cody Juhnke
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 of the largest resource for Squarespace websites, offering over 500 free...
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A Peek Behind the Curtain of a Web Designer's Process with Tony Howell
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 The ins and outs of running his agency from Bali, Indonesia His process…
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Will AI Kill Web Design and Creating Brand Partnerships with Phil Pallen
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. Phil shares with his: His evolution from personal branding consultant to...
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Growing your Website Business the Agency Way, with Kelsey Gilbert-Kreiling
Ever wondered what it's like to run a successful web design agency? In this episode of Somewhat Useful, we sit down with none other than Kelsey Gilbert-Kreiling, co-founder of Week of the Website, a Squarespace agency celebrating its 10th year in business. We get into it all in this episode.…
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Can Squarespace REALLY Do E-Commerce, With Kristine Neil
Welcome back to another season of "Somewhat Useful," where we explore digital entrepreneurship and web design with a particular focus on Squarespace. In this episode, we have a special guest, Kristine Neil, an ecommerce expert who shares her insights into using Squarespace for ecommerce. Kristine...
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Surviving Burnout With Special Guest Monica Kovach
In this final episode of season 2, Will and Christy check in about the seasonality of web design and give some tips on reviewing your online bios. Then, they hear from Monica Kovach of Hold Space Creative about identifying burnout, how self care doesn’t address the root of the problem, and…
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Working With Your Spouse, Value of the Circle Forum, and Special Guests Nick & Hannah from Squarekicker
Today Will & Christy talk specifically about working with your spouse. They chat about the value of the Squarespace Circle forum, and then Will’s wife Ren joins the podcast to share the pros and cons of working together. We also hear from Hannah and Nick of Squarekicker about their experience...
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Working With Outside Experts and 3 Tips on Collaboration from special guest Henry Purchase
Are you a solopreneur wondering how to expand your team or project scope? In this episode, Will and Christy talk about the expected scope of a web design project, how to best work with outside experts, and how to package and manage complex projects. They also hear from Henry Purchase of SEOSpace...
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Pricing Your Website Offers and The State of the Web Design Industry Report (with Special Guest Rache from SquareStylist)
In this episode, Will & Christy talk about their respective approaches to pricing and give their thoughts on the recent “State of the Web Design Industry Report” released by Squarespace. We also, we hear from friend-of-the-podcast, Rache from Standout Squarespace (one of the best Squarespace…
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To Membership or Not To Membership & Staying Focused (with special guest Liz Wilcox)
Let’s talk about Memberships; should you build one, or should you not? In this episode, Will & Christy share their Somewhat Useful thoughts on when and why to start a Membership. Also, we hear from friend-of-the-podcast, Liz Wilcox who has a fantastic Email Marketing Membership, about what…
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Pivoting Your Business & New Years Resolutions (with special guest Kerstin Martin)
It’s difficult to know when you need to make a pivot in your business. In the first episode of 2024 season, Will & Christy discuss the times in which they pivoted their businesses and what made the pivot successful. They also hear from friend-of-the-show Kerstin Martin who has recently pivoted…
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How to take time off as a digital entrepreneur
It’s hard to take time off when you’re always connected. In this episode, we share our strategies and thoughts about how to take some much needed time off to unplug that you can return to work fully-charged. Timestamp: 1:00 - How long it took before we could take a real vacation. 5:30 - When…
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Networking as a Digital Entrepreneur & Squarespace Circle Day
This episode was recorded before Circle Day 2023, BUT we talk about our experience at Circle Day 2022 and share our advice on how to network as a digital entrepreneur when you don't have co-workers. Timestamps: 0:45 - Circle Day 2022 3:25 - How to get the most out of Circle Day or any other...
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Work Less & Earn More: Some Strategies on Raising Your Prices and Hiring Help
We discuss: 0:30 - how Christy increased her revenue over the years 2: 15 - some strategies to increase your prices with new AND current clients 9:40 - when it's important to hire someone to help you out 14:05 - how Christy makes income with affiliate marketing 19:00 - how to be strategic &...
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Creating Delight: surefire ways to make sure clients spread-the-word about you
In today’s episode, we’re going to talk about “Creating Delight” with your customers. This is a term that we heard from Kelsey over at Week of the Website, or maybe Ben Manley from Knapsack Creative, at Circle Day last year, we’re not sure tbh we didn’t create it, but we love the phrase and…
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The Right Tool For The Job
There are dozens of different website builders, email marketing platforms, invoicing systems, course platforms, podcast hosting platforms, and membership softwares. How do you decide what is the right one for you, or better yet, how do you advise your client on which one to use? In today’s…
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Why is marketing so hard?
Marketing and building a business is hard work. We are right there in the trenches with you. In this episode, we chat about our marketing strategies, including organic SEO, blog writing, and email marketing. Sign up for Will's Newsletter: https://www.will-myers.com/newsletter Sign up for…
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Imposter Syndrome
On this episode of Somewhat Useful, Will and Christy discuss imposter syndrome, the ways it manifests itself in business, and how to overcome it. They also talk about the importance of admitting "I don't know". Listeners will get useful tips for overcoming imposter syndrome and building a...
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7 Ways to Save Time in your Business
On this episode of Somewhat Useful, we explore productivity hacks and time-saving tools for busy business owners. We discuss the benefits of email templates, scheduling emails, and tools to manage clients and leads. Join us for insights that will help you work smarter, not harder. Sign up for...
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ABOUT THIS SHOW
Welcome to Somewhat Useful, the show where we explore the world of entrepreneurship and web design. We'll discuss topics that are shaping the world around us and tackle your questions from the mailbag. From Will Myers, Squarespace Developer, and Christy Price, Squarespace Designer.
HOSTED BY
Will Myers and Christy Price
CATEGORIES
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Frequently Asked Questions
How many episodes does Somewhat Useful have?
Somewhat Useful currently has 48 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Somewhat Useful about?
Welcome to Somewhat Useful, the show where we explore the world of entrepreneurship and web design. We'll discuss topics that are shaping the world around us and tackle your questions from the mailbag. From Will Myers, Squarespace Developer, and Christy Price, Squarespace Designer.
How often does Somewhat Useful release new episodes?
Somewhat Useful has 48 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Somewhat Useful?
You can listen to Somewhat Useful on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Somewhat Useful?
Somewhat Useful is created and hosted by Will Myers and Christy Price.
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