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 LinksJD's websiteJD's TwitterSimple FocusAudience OpsSifterBallparkMetalabGarrett's Episode
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58:10
Radan Skorić - Mastering Hotwire
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 LinksRadan’s BlogRadan’s TwitterBook: Master Hotwire
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1:01:49
Time, Energy, Capital...LOL
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.
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39:35
Ben Curtis & Josh Wood - Kids These Days
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.HoneybadgerBen CurtisMastodonBlueskyLinkedInJosh WoodMastodonBlueskyLinkedIn
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1:04:37
Garrett Dimon - A Long Winding 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.comBlueSkyFireside.fmFlipperVery Good SoftwareBooksRecent podcast appearances:Taking Over Fireside with John Nunemaker & Garrett DimonMaster of Generators (with Garrett Dimon) | Dead Code
Jeremy and Jess interview indie developers who have a passion for the Rails framework and bring their hustle and creativity to building a business. They strive to understand the challenges these developers face and how they are overcoming them to create successful businesses.
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