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Contemplations of an indie SaaS founder

I love the craft of making software and I occasionally share my insights here.

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Changelogs For Everything

Changelogs are underrated. We software developers get some of them for free, courtesy of our Git logs and issue tracking systems. But the usefulness of a changelog extends beyond just code changes! When building Drip, Rob and I used to maintain a Marketing Changelog. It was nothing fancy, just a Google Sheet with timestamps and descriptions of various marketing activities (changes to the website…

Ship Small, Ship Fast

Big, long-running feature branches are the worst. They’re challenging to tame, and they slow you down. The odds of bugs slipping in under the radar are high. Each time you return to the project, you need to load an increasing amount of information in your mental RAM to return to flow. Merge conflicts stack up. Over time, you feel less and less confident in the code. When you ask your teammates for…

10 Questions for Teasing Out Market Opportunities

What successful companies are resting on their laurels? What products have gone so far up-market that a broad base of customers can no longer afford them? What successful products have critical flaws for a subset of users? What products are people using for a different purpose than originally intended? What popular products are extensible and could be augmented to work even better for a particular…

Finding My Next Bootstrapped Business Idea

Most business ideas are neither objectively good nor bad. The quality of an idea for you (as a founder) depends on your goals, your skill set, and your risk tolerance. Even the quintessential lousy idea of trying to “build the next Facebook” is not necessarily a bad idea. Someone will eventually pull it off – it just comes with an enormous amount of risk and requires one hell of a skill set. So…

I’m Walking Away From the Product I Spent a Year Building

Here I sit, in a cabin on Lake Superior by the fire, with late-season snow pelting the windows and ominous waves crashing against the rocky shore. Despite the treacherous terrain that surrounds me, I feel at peace with the decision I’ve been weighing. I’ve decided it’s time to take a step back from building Level as a standalone alternative to Slack. I’ve become comfortable sharing the…

Choosing Your Technology Stack

Nothing quite compares to greenfield software development. The canvas is blank and you finally have the opportunity to do it “The Right Way” from the ground up. If you’ve been building web apps for a while, you’ve undoubtedly found yourself working with technologies that you’d never use again, given the luxury of a blank canvas. And if you follow the open source world, there’s probably a…