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

Rémi is a former stained-glass master turned freelance Ruby on Rails developer. He writes extensively on software topics on his blog, and he recently wrote a reflection on his return to freelancing this past year. Rémi joins us to share his journey into software development, and the recent transition back to freelancing.

Related Links

Rémi's Website
Newsletter
Work
Ruby.social
LinkedIn

Reflecting on 2025

In this episode, Jared Norman joins us to talk about his journey from aspiring game developer to founder of Super Good Software, an agency specializing in e-commerce and Solidus. Jared shares the story of how Spree evolved into Solidus, the role his team played in that transition, and what it's like to build a specialized consultancy around open source e-commerce. We also get into branding, business development, the complexities of e-commerce beyond product management, and his podcast Dead Code.

Related Links

Jared's Website
LinkedIn
Dribbble

Super Good Software
Solidus
Dead Code Podcast

In this episode, John Athayde joins us to chat about how a student of architecture ends up in software, finding the Ruby and Rails community, working at the intersection of design and development, consulting in user experience, and his work on the Rails Guides refresh project.

Related Links

Website
Twitter
Bluesky
LinkedIn

Meticulous (John's consultancy)
Sfumato Farm (John's farm)
Ocufii
Knightsbridge Research

Rails Guides get a facelift
How They Work Better Together: Lean UX, Agile Development and User-Centered Design

Jeremy and Jess turn the corner on a new year with an unedited one-on-one discussion, reflecting on 2025 and looking ahead at 2026.

In this episode of IndieRails, Jess and Jeremy interviewed Jared Brown, co-founder and CEO of Hubstaff.

The conversation began with a serendipitous meeting at XO Ruby, where an early-morning parking deck encounter turned into a deeper discussion about SaaS, engineering, and long-term company building. What started as a casual conference conversation ultimately led to this episode.

Jared shared the story of Hubstaff’s journey from a two-founder startup in 2012 to a globally distributed company with more than 130 employees and roughly $33 million in ARR. He reflected on the importance of strong co-founder relationships, early technical decisions, and finding product-market fit in a competitive space.

The discussion covered long-term thinking, data-driven decision-making, and the realities of scaling a SaaS business over more than a decade. Jared also spoke candidly about the sacrifices required in the early years, the role of mentorship, leadership transitions, and the self-awareness needed to grow alongside the company.

This episode offered practical insights into networking, virality, engineering-led leadership, and what it really takes to build and sustain a successful independent software business over the long haul.

Links:
Jared's LinkedIn
Hubstaff.com