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.

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.