IndieRails

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...

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

Articles mentioned:

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
...

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 st...

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<...

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...

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 ju...

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 o...

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
...

This special episode was recorded from the Buzzsprout podcast booth on Day 1 of Rails World 2025 in Amsterdam. Our guest, Mariusz Kozieł, is the CEO of Visuality, a Ruby on Rails agency based in Poland. We chat about Mariusz' career progression from developer, to engineering manager, to CTO, and now CEO. We also talk about his and Visuality's efforts to foster technical community with the Ruby Community Conference and Ruby Europe.

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

Related Links

Mari...

docs.search("indie, founder, rails, successful") => Jason Bosco / Typesense

In this episode, Jeremy and Jess sit down with Jason Bosco, co-founder of Typesense, an open source, typo-tolerant search engine. Jason shares how he and his co-founder committed to simply showing up every day, putting in consistent effort, no matter how small, and how that patience eventually compounded into success.

We dive into Jason’s journey from VP of Engineering at Dollar Shave Club to building his own company, why Typesense has chosen to stay customer-funded instead of VC-funded, and how open source has been central to...

In this episode, Jess and Jeremy chat with Matt Swanson, CTO of Arrows, author of Boring Rails, and host of the YAGNI podcast. In addition to his blog, Matt shares a lot of his knowledge about product development on Twitter. We talk with Matt about how Arrows builds software, what it means to be a product engineer, the easiest way for devs to get to $10K MRR, working with generative AI tools, and how and why he publishes technical content online.

Related Links
Matt's Twitter
Boring Rails
YAGNI podcast
Arrows

Rhiannon Payne and Justin Bowen are one of the very few couples working together in the Ruby and Rails ecosystem. Justin is a long-time Rails developer, consultant, and AI and computer vision specialist. Rhiannon runs Sea Foam Media and is the Marketing Director for Ruby Central. Together they are building Active Agents, an AI framework for Rails. We chat about their professional backgrounds (Justin's in software development, Rhiannon's in marketing), how they collaborate as a couple, the birth of Active Agents, and AI in the Ruby/Rails landscape. Oh, and we may have a cameo from a few cats! <...

In this episode we talk to Zeke Gabrielse, solo founder and owner of Keygen, a licensing and distribution API. We get deep in the weeds of running a solo business (much can be applied to any solo-type career working on the same project), how he handled the worst day(s) of his professional life, and much more!

Zeke's Links
Zeke on X

Keygen on X 

Keygen website: https://keygen.sh/

Jeremy's Notable Blog Posts

How to Build a Webhook System in Rails Using Sidekiq

That o...

In this special crossover episode, we make a slight departure from our typical format to chat with Adrian and Yaro from the Friendly Show and Jason from the Code with Jason podcast about a topic near and dear to our hearts: organizing regional Ruby conferences. Adrian is the organizer of Friendly.rb in Bucharest. Jason is the organizer of Sin City Ruby in Las Vegas. And as long-time listeners may know, Jeremy co-organized Blue Ridge Ruby in Asheville, NC back in 2023.

A few episodes ago, Garrett Dimon shared the story of how he sold his SaaS product Sifter. In this episode, we complete the story arc by catching up with JD Graffam, the buyer and current owner of Sifter. JD is an agency owner who started buying SaaS product companies in 2012. We talk about how his background, how he got started buying businesses, and his approach to making deals and finding the right people to work with.

Relevant Links

JD's website
JD's Twitter
Simple Focus
Audience Ops
Sifter
Ballpark
Metalab<...

In this episode, Jess and Jeremy chat with Radan Skorić, a long-time Ruby and Rails developer and team lead, co-organizer Ruby Zagreb, and author of the forthcoming book: Master Hotwire. We talk about Radan’s background in software, his discovery of Rails in the mid-2000s, technical blogging, writing a book, and technical aspects of Hotwire.

Related Links
Radan’s Blog
Radan’s Twitter
Book: Master Hotwire

This week, Jess and Jeremy get into the nitty-gritty of resource allocation for indie makers: how to make the most of your limited time, energy, and capital. As solo and small-team entrepreneurs, we constantly have to make tough calls about where to invest. It's not just about money; it's about what will actually move the needle.

They talk through the realities of running lean: how to balance building, learning, and staying sane along the way. From daily reading habits and favorite podcasts to managing information overload and keeping personal playbooks, they share the unpolished, behind-the-scenes strategies they...

In this episode of IndieRails, co-founders Ben Curtis and Joshua Wood share the origin story of Honeybadger, an application monitoring tool for Ruby on Rails applications (and many others).

They discuss their motivations for starting the company, the challenges they faced in the early days. The conversation also covers their approach to product development, marketing, pricing strategies, expanding into new markets and the lessons learned from their journey.

Honeybadger

Ben Curtis
Mastodon
Bluesky
LinkedIn

Josh Wood
Mastodon
Bluesky
LinkedIn

Our guest for this episode is Garrett Dimon. Garrett is a developer, author, conference speaker and multi time business owner. With some partners, he’s recently formed a company called “Very Good Software” where they own and operate several SaaS apps.
 
Garrett Dimon is a seasoned software developer and entrepreneur with a passion for front-end development and Ruby on Rails. His journey began in 1998, experimenting with HTML, CSS, and JavaScript before earning a Computer Science degree from the University of Texas at Dallas in 2000. Over the next eight years, he honed his skills in front-end development and informa...

Our first-ever IndieRails guest returns to the podcast just shy of two years later. Joe Masilotti shares about niching down on Hotwire Native, changes in the related open source libraries, the direction of his consulting work, his parental leave last year, and the process of writing his forthcoming book, Hotwire Native for Rails Developers. (Special discount for listeners in the episode!)

Related Links
Twitter
Bluesky
Website
Hotwire Native for Rails Developers
Pragmatic Bookshelf page
Hotwire Native docs
Rails World 2023 Talk: Just enough Turbo Native to be dangerous

In this episode, Jeremy & I are excited to share a mic with Jim Remsik. Jim is the Founder and CEO of a digital agency called Flagrant. He is also a conference organizer…he created and hosts the popular Madison + Ruby conference. Jim has held many roles:  MC, speaker, developer, CEO, conference organizer, writer and many more, but I imagine most people know him as someone who is an all around awesome human.

Jim Remsik shares his journey through the tech industry, from his early days in software development to his transition from government work to agency life. He...

Jess and Jeremy kick off the first recording of 2025 with a recap of 2024, and a look at their plans and goals for the new year. We chat about the importance of celebrating milestones, time management, financial planning, scaling development with business growth, and the cycles of sowing and reaping in our work.

Paul Campbell is a Rails developer (since v0.13), conference organizer, and the CEO and co-founder of Team Tito. Paul joins us to talk about his career building software, companies, and events. We chat about Paul's journey into programming, the risks and rewards of running conferences, finding his co-founder, and the opportunities that led to building Tito, Vito, and most recently, IO.

Relevant Links
Paul on BlueSky
Team Tito
Tito: event registration
Vito: online communities
IO: bespoke RSVPs

In this episode, we are joined by Barry Hess, James Adam, and Matthew Lettini from the Good Enough team to discuss their journey in creating a self-sustaining business built around meaningful, user-focused software. We explore the inception of their company and their latest product, Jelly—a shared inbox for teams. We dive into their experimental approach to business, their year of experimentation known internally as "Cosmic Maelstrom," the rollout of other products like their blogging software, Pika, and the decision to offer free tools. The team shares their insights into maintaining a human touch in customer support, navigating marketing ch...

In this episode, we're excited to introduce our guest, Becky Searls. We recently met Becky at Rails World and learned about her business, Better with Becky—a fitness training program focused on people with a growth mindset. Over the past year, she worked with her husband Justin to build her first product, Build with Becky, a personalized workout program and fitness app built in Rails, which launched publicly during the conference! We chat with Becky about her professional journey starting as a K-12 educator, becoming a fitness instructor, building her own business, and now moving into the product owner ro...

In this episode, Jess and Jeremy chat about leveling up professionally, the importance of community and personal growth, and the challenges of starting new things. Jess shares several things that have inspired him recently, and Jeremy gives an update on Liminal and shares some ideas he has around discoverability challenges in the Rails ecosystem.

Referenced

In this episode, Justin Searls (open source author, speaker, and co-founder of Test Double) joins us in-person at Rails World to talk about his career, speaking, consulting, the One Person Framework, and building a web application for his wife's fitness business, Better with Becky.

Follow Justin
Website
Twitter
Mastodon
LinkedIn

Relevant Links
The Empowered Programmer talk
Test Double
Breaking Change podcast
Fred Brooks
RubyKaigi
The One Person Framework

On Day 2 of Rails World, Jess and Jeremy join with Drew Bragg of Code and the Coding Coders Who Code It and Adrian Marin and Yaro Shmarov  of the Friendly Show to chat about the conference. Enjoy!

In this crossover episode, Jeremy and Jess join up with Chris & Jason from Remote Ruby podcast to discuss Ruby programming, indie development, and the challenges of building and maintaining software as solo developers. We dive into the origins of Indie Rails, share our individual career journeys, and explore Jeremy's project, Liminal, which aims to replace traditional forums and Slack with a more modern solution. The group reflects on the frustrations with current platforms, their experiences with indie development, and the importance of marketing alongside coding. They also compare Rails and Laravel, talk about the "one-person framework" concept, and the...

Justin Duke is the founder of Buttondown, an email platform with first-class Markdown support. Justin is also a partner at Third South Capital, where he and his partners buy and grow existing software products. We chat about his background in marketing and software development, bootstrapping Buttondown while working at Stripe, the Buttondown tech stack (Django, a cousin of Rails and Vue), and his latest endeavors with Third South.

Justin
Website
Twitter

Buttondown
Website
Twitter
Changelog
Stack
Open Source

Third South Capital
Website
Twitter

Landon Gray is a Rubyist, speaker, strategic advisor, and AI engineer. In May, he left Test Double to found Identus Consulting, where he helps companies with generative AI and machine learning. We chat about his love for consulting, how he got into AI, and how he's working with clients these days, using a blend of technical and project management skills.

Follow Landon
Twitter
LinkedIn
Ruby AI Twitter
Identus Consulting
Curious Centroid
Forecasting the future: Intro to Machine Learning for weather prediction in Native Ruby

Relevant Links
Test Double<...

Our guest will be no stranger to most of our listeners. He’s been around the Ruby community for many years. He’s spoken at conferences, hosted conferences, hosts a "pretty good" podcast, author of courses, a staff engineer at Podia and more recently the co-founder of a successful SaaS: Job Boardly. Enjoy the show with Jason Charnes!

Related Links
Personal Website

X

Job Boardly
Podia
Remote Ruby

In this episode, we are thrilled to host Nate Berkopec, a renowned author, speaker, trainer, and consultant. Nate runs Speedshop, his Rails performance consultancy, and is the author of "The Complete Guide to Rails Performance." He also maintains Puma, the most popular Ruby web server, and somehow finds time to be an avid cyclist. Nate's journey from a junior Rails developer to a leading performance expert is nothing short of inspiring. Join us as we dive into his story, insights, and expertise.

Links:

In this episode, Jeremy shares his latest product idea (Liminal, a fresh take on old-school forums) with Jess and gets his raw, unfiltered feedback. At the end, Jeremy makes a commitment to Jess to launch an MVP by November 1.