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/

Wale Olaleye of Rails Fever joins IndieRails to talk about what it really takes to build a consulting business. The conversation spans everything from refining your message and brand, “I help founders with tech so they can focus on operations", to embracing marketing, sales, and networking as essential skills, not dirty words.

Wale, Jess, and Jeremy swap stories about outreach experiments, co-working spaces, local events, and the power of being visible in your own community. They explore how generosity, trust, and consistency can replace aggressive sales tactics, and why treating your freelance work like a business, not just a job, is the path to longevity.

It’s an honest and encouraging look at how independent Rails developers can build meaningful, profitable work by combining technical excellence with human connection.

Rails Fever
LinkedIn
Bluesky

In this episode, Jess and Jeremy catch up on life and work, and have a chat about the everyone's favorite topic these days.

In this episode we’re excited to be talking with Anthony Eden, founder & CEO of DNSimple.

For those who haven’t come across it yet, DNSimple is a service that makes managing domains and DNS simple and developer-friendly. Like DNS, DNSimple has been around many years. I first met Anthony years back at Less Conference in Atlanta, around the time DNSimple was just getting off the ground.

Jeremy and I also got to connect with Anthony recently at XO Ruby in Atlanta, where DNSimple was one of the sponsors.

There’s a lot of fun topics we covered, so hit play and get it started!

Links:
dnsimple.com
anthonyeden.com
X
Ruby Social

This special episode was recorded from the Buzzsprout podcast booth on Day 2 of Rails World 2025 in Amsterdam. Our guests (and fellow Rails World attendees) are Jesper Christiansen, Olly Headey, and Andreas Wagner. Together we have a roundtable discussion about our wishlist items as independent Rails devs toward the one-person end of the spectrum.

Thank you to Buzzsprout for sponsoring the Rails World Podcast program, and for providing us the opportunity to attend and record! 🙏

Jesper Christiansen
Twitter
Bluesky
Website
FormBackend
many.link

Olly Headey
Bluesky
Blog
Pagecord
Feedgrab

Andreas Wagner
Twitter
Bluesky
Website
Blog