IndieRails

Rails World 2026 - The Lost Recording

On Day 2 of Rails World 2026 in Austin, TX, Jess and Jeremy sit down with Matt Swanson of Arrows and Robby Russell of Planet Argon to reflect on a conference where pencils and rust were on everyone's mind. Thank you to Buzzsprout for providing us the opportunity to record! 🙏 (00:00) - Teaser and intro (00:30) - Welcome from Rails World 2026 in Austin (01:32) - Thumbs up, middle, or down: David's keynote (03:01) - Rails is extracted from real businesses, so apply it to your own context (04:36) - What Matt is taking back to Arrows, and what conferences are for now (06:11) - Robby's keynote: the workshop where people and agents build (09:22) - Who's accountable when Claude wrote it? (11:22) - If it's painful, do it more: letting designers ship (13:33) - "The most valuable engineer is not shipping features" (15:22) - Rethinking PRs and verification (16:35) - You don't have to throw out your practices (18:06) - Taking responsibility vs. "just blame the bots" (19:39) - Is it just tech debt, accelerated? (21:07) - The bigger picture: problems way beyond Rails (23:29) - It's not just the speed, it's the scope (24:08) - Grateful for a career that started as a hobby (25:14) - When customers can't keep up with the features (27:17) - Arrows: starting a new product this year (28:57) - Planet Argon: retainers, clients as bottlenecks, and showing it working (31:23) - A vibe-coded MVP that won a client (32:16) - Translating AI into business value (33:45) - WUTS: wonder, unpack, tinker, share (37:37) - Telling Claude (and your team) which patterns not to copy (38:47) - Custom dev tooling is cheap now, and still engineering (40:11) - The squished middle: product thinking vs. verification (41:26) - Losing flow, and finding it again (42:51) - Architects, portfolios, and pride in the finished product (43:39) - Thanks, and thanks to Buzzsprout

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• Chapters

Kelsey & Zack Gilbert-Kreiling - Eventually, Someone Had to Build It

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

A Random Tuesday

After a 6-month hiatus, Jess and Jeremy return on a random Tuesday.

John Nunemaker - The Conductor

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

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Rémi Mercier - The Stained-Glass Master

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

Jared Norman - Building Super Good Software|Teams|OS|companies|.*

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

John Athayde - Guiding Design in Software

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

Turning the Corner (Unedited)

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.

Jared Brown - From Indie to 33 million in ARR

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

Ernesto Tagwerker - OmbuLabs on AI

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

Brian Casel - Teaching Devs to Build with AI

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 - Helping Founders with Tech

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

The Obligatory AI Episode

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

Anthony Eden - Making Business Look Simple

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

One Person Wishlist - Rails World Roundtable

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

Mariusz Kozieł - Wizards and Kings

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 Mariusz on Twitter Mariusz on LinkedIn Visuality website Visuality on Twitter Visuality on LinkedIn Ruby Europe website Ruby Europe on Twitter Ruby Community Conference

Jason Bosco of Typesense - From Shaving Faces to Shaving Milliseconds

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 their mission of democratizing search. Along the way, Jason offers insights on perseverance, product focus, and the long game of building an indie software company and how it can all good and difficult can take a toll on health. Jason Bosco CEO & Co-Founder at Typesense Previously VP of Engineering at Dollar Shave Club Previously VP of Technology at Verishop https://x.com/jasonbosco https://www.linkedin.com/in/jasonbosco/ https://www.crunchbase.com/person/jason-bosco https://github.com/jasonbosco A good way to describe Typesense is that it's an open source alternative to Algolia and an easier-to-use alternative to ElasticSearch. https://github.com/jasonbosco Featured Videos https://www.youtube.com/watch?v=1cdH1F6zbIg https://www.youtube.com/watch?v=ER8FDiCMPCY https://www.youtube.com/watch?v=QymF4NUmALM https://www.youtube.com/watch?v=QNLA8RCrYwk https://www.youtube.com/watch?v=u4Z3BYwizzw Featured Links https://typesense.org/about https://typesense.org/blog/ To Raise VC, or Not. Choosing The Road Less Travelled. The unreasonable effectiveness of just showing up everyday We bought HUNDREDS of billboards in San Francisco, for our open source product https://gorelay.co/t/pursuing-an-open-source-bootstrapped-long-run-path-towards-serving-the-fortune-1-million-with-typesense-s-co-founder-jason-bosco/915 https://livecycle.io/blogs/dev-x-project-jason-bosco/

Matt Swanson - The Product Engineer

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 & Justin Bowen - Agents of Change

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 Justin Twitter Bluesky Active Agents Website activeagent gem on GitHub (latest release: v0.4.0) Documentation (new) Discord Invite Sea Foam Media Website Twitter

Zeke Gabrielse - Build for Your Users Without Obeying Them

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 one time Keygen went down for 5 hours (twice) Keygen is now Fair Source No calls In defense of linear Self-promotion Steering the ship