IndieRails

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 LinkedInHubstaff.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 EpisodeStanford research on dev productivity w/ AI tooling (video)The Automated RoadmapBonsai ServiceA Tech Debt Fighting Champion For DevelopersGet DXPhilly.rbCanopy

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/@briancaselpanelpodcast.comhttps://briancasel.com/https://x.com/CasJamhttps://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 FeverLinkedInBluesky

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.comanthonyeden.comXRuby 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 ChristiansenTwitterBlueskyWebsiteFormBackendmany.linkOlly HeadeyBlueskyBlogPagecordFeedgrabAndreas WagnerTwitterBlueskyWebsiteBlog

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 LinksMariusz on TwitterMariusz on LinkedInVisuality websiteVisuality on TwitterVisuality on LinkedInRuby Europe websiteRuby Europe on TwitterRuby Community Conference

docs.search("indie, founder, rails, successful") => Jason Bosco / TypesenseIn 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 BoscoCEO & Co-Founder at TypesensePreviously VP of Engineering at Dollar Shave Club Previously VP of Technology at Verishophttps://x.com/jasonboscohttps://www.linkedin.com/in/jasonbosco/https://www.crunchbase.com/person/jason-boscohttps://github.com/jasonboscoA 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/jasonboscoFeatured Videoshttps://www.youtube.com/watch?v=1cdH1F6zbIghttps://www.youtube.com/watch?v=ER8FDiCMPCYhttps://www.youtube.com/watch?v=QymF4NUmALMhttps://www.youtube.com/watch?v=QNLA8RCrYwkhttps://www.youtube.com/watch?v=u4Z3BYwizzwFeatured Linkshttps://typesense.org/abouthttps://typesense.org/blog/To Raise VC, or Not. Choosing The Road Less Travelled.The unreasonable effectiveness of just showing up everydayWe bought HUNDREDS of billboards in San Francisco, for our open source producthttps://gorelay.co/t/pursuing-an-open-source-bootstrapped-long-run-path-towards-serving-the-fortune-1-million-with-typesense-s-co-founder-jason-bosco/915https://livecycle.io/blogs/dev-x-project-jason-bosco/