Culture

Most of what we use online feels free. Search engines, maps, email, video. All the things we reach for without thinking. They’re not really free of course. They’re funded by advertising and by siphoning off our attention and our data. You already know the line: if you’re not paying, you’re the product. In a world of user pays - what would you pay for? But what if that model never existed. What if every service had a price tag. No ads, no data harvesting, no “free tier”. Would you pay for YouTube. Would you pay for it and Spotify and cloud storage and messaging apps. At some point you’d run out of money and you’d have to choose. ...

I’ve worked in places where the fire never stops, and in places where the fire went out years ago. Neither is healthy. One will burn you out. The other will quietly let you rust. These are two faces of the same problem: a culture that’s failing its people and its purpose. It’s not just the productivity of the company the suffers. It’s the toll on the people inside the company, and how those patterns get built in. ...

Originally published on September 20, 2022 I was lucky. One of my first real gigs was at a startup that actually understood agile—not just the part where you stand around at 9:30 reciting what you did yesterday. No, I mean real agile. The founder believed in it. Not just the words, but the mindset. And in 2007, that made them look a little unhinged. Estimates in points instead of hours? Delivering small, usable increments? Developers writing tests on purpose? Teams interviewing and hiring their own teammates? It was weird. It was new. And it worked. ...

Originally published on August 26, 2022 In my last post, I described the arc most software companies follow—from chaotic startup to process-heavy bureaucracy. If you missed it, check it out here: An Evolution of a Software Company. Spoiler: there’s a pendulum, and it swings hard. Today, we’re talking about what happens next—and how to stop the pendulum from turning your team into a JIRA-powered approval queue. From Chaos to Control By the time the dust settles, you’ve landed in a company that’s seen one too many outages and decided that the cure is process. Lots of it. ...

Originally published on August 15, 2022 Let’s start with a story. It’s one you’ve probably lived through in some form, if you’ve spent more than ten minutes in the software industry. The Origin Story (and Its Inevitable Sequel) A company forms. There’s an idea, a goal, a dream. Usually it involves building the next great thing—a widget, a platform, a barely differentiated SaaS for onboarding PDFs. The founding team is small and experienced. They might be well-compensated, but more often they’re paid in the warm, fuzzy promise of equity. ...