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 EventuallyEventually on XZack on XZack's websiteZack on LinkedInWeek of the Website (Kelsey's Squarespace agency)Squarespace CircleDesign OS by Brian Casel (Builder Methods)Inertia.jsBullet TrainTechnori1871SEOSpaceExplore Washington ParkBon Vivant CakesChapters 00:53 Introductions01:36 Kelsey's path: fashion publication, a ransomed domain, and restaurant websites06:00 Producing a food festival and starting an agency07:12 Week of the Website and productizing web design13:58 Zack's path: PHP, newspaper CMSes, Technori, Foursquare19:27 Fractional CTO work and rebuilding AI-built apps20:58 How Eventually started: Kelsey's PRD and prototype25:53 The value of prototypes for developers vs. designers35:42 Working together, and how they met on Twitter37:54 The idea: selling event tickets on Squarespace41:16 The bigger opportunity: commerce for event-based businesses44:48 The tech: Rails 8, Inertia.js, and Squarespace's APIs47:04 Scoping the first version with design partners53:56 Customer research and interviews58:35 Growth: customers finding them through Claude, SEO, and Instagram1:03:46 What's next: Squarespace extensions marketplace and styling rebuild1:05:36 Balancing two businesses, two kids, and a marriage1:11:54 Chicago's role in their story1:15:36 Where to find them, and the Squarespace event in New York
