Latest Episode
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:
SquareKicker Compose: https://squarekicker.com/compose
Base44: https://base44.com/
Fathom: https://www.fathom.ai/
Kit: https://kit.com/
vidIQ: https://vidiq.com/
Instinct: https://instinct.com/
Pangram:
Recent Episodes
1
Oct. 5, 2026
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: SquareKicker Compose: https://squarekicker.com/compose Base44: https://base44.com/ Fathom: https://www.fathom.ai/ Kit: https://kit.com/ vidIQ: https://vidiq.com/ Instinct: https://instinct.com/ Pangram:
9
May 28, 2026
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 build for humans first. Mentioned in the episode: Internet traffic composition: https://blog.will-myers.com/post/internet-traffic-composition Phone stand: https://www.moft.us/products/invisible-phone-t
8
May 20, 2026
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 designers should be focused on right now. Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notificat
7
April 24, 2026
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. We also discuss the shifting landscape of the web design and development industry and debate the creativity (or lack thereof) of LLMs. Thank you to our sponsor, Breely! Breely is modern scheduling softwa
6
April 14, 2026
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 reshaping the future of in-person gatherings. Will explains why he moved Code Curious off of Squarespace, and Christy shares an update on her wine education journey. Try a free month of Eventually at eventuallyticketing.com
5
March 31, 2026
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 about SEO, YouTube, AI search, email lists, Instagram, digital products, client work, and the slow reality of growing something that lasts. Plus, Christy shares the story of winning $5,000 at Sponsor
Join the Email List
Listen On
Sponsors
