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!
Rhiannon
Twitter
Bluesky
The Remote Work Era Book
Active Agents
Website
activeagent gem on GitHub (latest release: v0.4.0)
Documentation (new)
Discord Invite
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
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
Garrett's Episode
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 use to grow without burning out.
If you’re bootstrapping, juggling roles, or just trying to make smarter bets with your time, this one’s for you.
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.
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 information architecture through consulting roles with organizations of all sizes. During this time, he also shared his expertise through a column on front-end design and development for Digital Web Magazine.
In 2008, Garrett started his entrepreneurial journey and launched Sifter, a bug and issue tracking application built with Rails, which he ran until its successful sale in 2016. His experience building and selling Sifter inspired him to write and self-publish Starting and Sustaining, a book about building and running SaaS applications. After Sifter, Garrett took some time off from entrepreneurship and joined Wildbit and then egghead.
Eventually he went back on his own independent consulting where he helped clients Fireside.fm and Flipper. Little did he know that later on, he'd become part owner of these companies. In the fall of 2024 the one time business seller became the buyer. He, John Nunemaker, and Kris Priemer are operating Very Good Software, where fireside.rm and Flipper are core products.
Links:
GarrettDimon.com
BlueSky
Fireside.fm
Flipper
Very Good Software
Recent podcast appearances:
Taking Over Fireside with John Nunemaker & Garrett Dimon
Master of Generators (with Garrett Dimon) | Dead Code
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 discusses building companies like Bendyworks and Flagrant, emphasizing how design and professional connections shaped his career path. The conversation follows his path from running Adorable to launching Flagrant, including the personal challenges he faced—health issues and navigating business during the pandemic. Jim reflects on the vital role of personal growth, team empowerment, and maintaining human connections in a remote-first world. Drawing from his agency experience, he shares how taking initiative and self-authorization were crucial to his entrepreneurial success. Throughout the discussion, Jim offers valuable perspectives on consulting and collaboration, emphasizing his core belief in actively supporting others' success. He explores the varied landscape of consulting work, industry uncertainties, and the power of personal mission statements. The conversation highlights how meaningful connections, purposeful work, and courageous leadership intertwine. Jim's guiding motto reveals how generosity and community-building shape his professional approach.
Show Links:
Socials
https://bsky.app/profile/jremsikjr.bsky.social
https://www.linkedin.com/in/jremsikjr/
Flagrant
https://www.beflagrant.com/team/
https://www.beflagrant.com/blog/author/jim-remsik/
Conferences
Posts
https://www.beflagrant.com/blog/2024-predictions-2024-01-30
https://devops.com/the-ruby-on-rails-resurgence/
https://devops.com/the-ruby-on-rails-resurgence-2/
Other Podcasts
https://shows.acast.com/dead-code/episodes/all-those-letters-that-you-do-with-jim-remsik
https://www.codewithjason.com/podcast/14444689-211-jim-remsik-ceo-of-flagrant/
XO Ruby
https://bsky.app/profile/xoruby.com
Readalong - Practical Object-Oriented Design: An Agile Primer Using Ruby
https://app.thestorygraph.com/readalongs/5983b152-bf48-4ff3-aeb0-976ea67d0d08
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 challenges, and the value of brainstorming unconventional ideas. Through it all, they emphasize the importance of community, sustainability, and creating software that should exist in the world to make a meaningful impact.
Links:
Good Enough
Jelly
Pika
All Products
Good Enough Socials:
Newsletter
Mastodon
Bluesky
Threads
X
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 role to develop a custom app.
More About Becky
Becky Searls is definitely not another influencer, and she’s more than a personal trainer. Her experience in education, embrace of evidence-based research, and personable judgment-free approach sets her apart in an industry famous for baseless hype and scammy practices.
Spending over a decade as an accomplished foreign language teacher, Becky truly has the heart of an educator. When she learns something important, her first thought is always how to best share it with others. She also knows life's greatest lessons are found outside of the classroom. So as she dives deeper into research papers spanning health, fitness, nutrition, and psychology, she can’t imagine keeping all the useful things she discovers to herself.
That's what Better with Becky is: the place she translates cutting-edge science into practical tools and everyday advice for the rest of us.
That may explain why, as her debut product, Build with Becky doesn't look like other exercise programs. Yes, it will give you a great workout. But you won't believe how much you'll learn along the way, without even realizing it. And yes, you'll probably see progress toward your fitness goals. But don't be surprised if you also gain deeper insights that connect with other parts of your life. That's just part of what you get with Becky!
Training and certifications include:
• Master of Arts, Education (The Ohio State University)
• National Strength and Conditioning Association Certified Personal Trainer (NSCA-CPT)
• Mindfulness-Based Behavior Change Facilitator
• Precision Nutrition Level 1 Certified Coach (PN-L1)
• USA Weightlifting Level 1 Certified Coach (USAW-L1)
• Pain-free performance specialist (National Academy of Sports Medicine)
Relevant Links
Beckygram (which syndicates her Instagram)
Becky's YouTube
The Empowered Programmer (Justin's Rails World talk, featuring Build with Becky)
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 challenges in maintaining open-source libraries. Throughout the conversation, they emphasize the value of transparency in product development and the need for community support. They wrap up with thoughts on the importance of events like Rails Hackathons and the continued evolution of Rails for solo developers. Hit download now to hear more!
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.
Buttondown
Website
Twitter
Changelog
Stack
Open Source
Third South Capital
Website
Twitter
Relevant Links
Markdoc
babelmark
Curtailing the free plan
Work on what matters
