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

After more than two years, Ernesto Tagwerker returns to IndieRails to chat about the changing industry landscape and running an agency in the age of AI. Ernesto is the founder of OmbuLabs, makers of FastRuby.io, and maintainers of many open source projects in Ruby and Rails. We talk about upgrading Rails apps with the help of LLMs, their fixed-cost maintenance service Bonsai, new AI-related offerings (from assessments to greenfield buildouts), and championing DX (developer experience).

Mentioned in the Episode
Stanford research on dev productivity w/ AI tooling (video)
The Automated Roadmap
Bonsai Service
A Tech Debt Fighting Champion For Developers
Get DX
Philly.rb
Canopy

In this episode, Brian Casel joins IndieRails to talk about how AI is reshaping the day-to-day reality of software development and why full-stack Rails developers might be uniquely positioned to thrive in this new landscape.

The conversation digs into the blurring lines between developer and product manager. When you can build the whole thing yourself, you're not just writing code you're making product decisions, understanding customer needs, and wearing multiple hats by default. We explore how that generalist mindset, the one Rails devs have been cultivating for years, is becoming more valuable, not less, as AI tools change what it means to "build."

They also get into the practical side: how AI is actually showing up in their coding workflows, what's working, what's overhyped, and what skills matter most when the tools keep shifting under your feet. Plus we detour into YouTube as a channel for building an audience and the dynamics of showing up consistently, sharing your work, and connecting with people who care about the same stuff you do.

It's a wide-ranging conversation about adapting, staying curious, and leaning into the advantages that come with being a builder who thinks like an owner.

Links:
https://buildermethods.com/
https://www.youtube.com/@briancasel
panelpodcast.com
https://briancasel.com/
https://x.com/CasJam
https://www.linkedin.com/in/briancasel/