Kelsey and Zack Gilbert-Kreiling are a husband-and-wife team from Chicago and the founders of Eventually, an event ticketing and commerce platform built natively for Squarespace. Kelsey shares how a fashion publication, restaurant websites, and a food festival led to her productized agency, Week of the Website, and Zack traces his path from PHP newspaper CMSes and Technori to Foursquare and fractional CTO work. They talk about how Eventually grew from a long-standing request in the Squarespace Circle community, why AI prototypes make great starting points for developers (and why designers feel differently), and how they built it as a Rails 8 + Inertia.js app on Squarespace's commerce and reseller APIs. We also get into scoping the first version with design partners, customers finding them through Claude, Instagram and marketing plans, and how they balance two businesses, two young kids, and a marriage while building together. Plus, how they met on Twitter, when Kelsey showed up to drinks thinking she was interviewing for a job at a hot new startup!

Related Links

• Eventually
• Eventually on X
• Zack on X
• Zack's website
• Zack on LinkedIn
• Week of the Website (Kelsey's Squarespace agency)
• Squarespace Circle
• Design OS by Brian Casel (Builder Methods)
• Inertia.js
• Bullet Train
• Technori
• 1871
• SEOSpace
• Explore Washington Park
• Bon Vivant Cakes

Chapters

00:53 Introductions
01:36 Kelsey's path: fashion publication, a ransomed domain, and restaurant websites
06:00 Producing a food festival and starting an agency
07:12 Week of the Website and productizing web design
13:58 Zack's path: PHP, newspaper CMSes, Technori, Foursquare
19:27 Fractional CTO work and rebuilding AI-built apps
20:58 How Eventually started: Kelsey's PRD and prototype
25:53 The value of prototypes for developers vs. designers
35:42 Working together, and how they met on Twitter
37:54 The idea: selling event tickets on Squarespace
41:16 The bigger opportunity: commerce for event-based businesses
44:48 The tech: Rails 8, Inertia.js, and Squarespace's APIs
47:04 Scoping the first version with design partners
53:56 Customer research and interviews
58:35 Growth: customers finding them through Claude, SEO, and Instagram
1:03:46 What's next: Squarespace extensions marketplace and styling rebuild
1:05:36 Balancing two businesses, two kids, and a marriage
1:11:54 Chicago's role in their story
1:15:36 Where to find them, and the Squarespace event in New York

After a 6-month hiatus, Jess and Jeremy return on a random Tuesday.

John Nunemaker is a Rails developer, entrepreneur, and indie hacker behind Flipper Cloud, Boxout, and Fireside. He joins us for a wide-ranging conversation about managing a portfolio of products at different stages of growth, how AI has transformed his development workflow, and the unique opportunity (and anxiety) that this moment in tech represents.

Related Links

• Flipper Cloud
• Boxout
• Fireside
• Momentum (South Bend entrepreneurship hub)
• John on X / Twitter

Articles mentioned:

• Something Big Is Happening
• AI isn't coming for your future. Fear is.
• 75 Years of AI Adoption