IndieRails

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

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

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

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/

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

Justin
Twitter
Bluesky

Active Agents
Website
activeagent gem on GitHub (latest release: v0.4.0)
Documentation (new)
Discord Invite

Sea Foam Media
Website
Twitter

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

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.