Nov 18, 2020My MonopoliesMost industries are dominated by monopolies. How we enforce antitrust law explains far more than you might think. Photo courtesy of BP Miller. My first monopoly was AT&T. I lived on a commune until I was eight. We didn’t have toilets, but we did have phones. We didn’t own them…6 min read6 min read
Jul 22, 2020Don’t Make Board DecksWhy and how my team built board reports instead of PowerPoint decks. Fifty pages, less work than slides, and more valuable. Image courtesy of Drew Beamer. Board meetings are a critical time of communication and reflection for a company. You have to share enough information that the people in the…Startup7 min readStartup7 min read
Jul 7, 2020Entrepreneur, Stage 1: Bootstrapping, Burnout, and BabiesHow I got here, how it went, and what happened along the way. I didn’t want to start a company. But I had no choice. I was a SysAdmin after college, because I tried everything else and got fired from them all. I had seven jobs in two and a…Founders11 min readFounders11 min read
Jun 30, 2020The First Two-Million-Dollar CheckA single drink perfectly captures the weirdness of raising money for the first time. Photo courtesy of Dylan de Jonge I found myself at a hotel with some friends. I was visiting Portland for a conference. Puppet’s first investment round — and mine! — was closing. …Founders4 min readFounders4 min read
May 21, 2020Member-onlyHow TechCrunch is like the IliadThe drive for social status created the worst, most important part of the Iliad. Now it’s filling up investment announcements. Picture by Mikuláš Prokop My fancy liberal arts school hazed me, like it does all students: I had to read The Iliad and The Odyssey. We did more than read…Founder4 min readFounder4 min read
May 24, 2019The Automator’s DilemmaAutomation is not to blame for all the job destruction and wage stagnation. But you can still do great harm if you build it for the wrong reasons. We’re told that automation is destroying jobs, that technology is replacing people, making them dumber, less capable. These are lies, with just…Startup6 min readStartup6 min read
Nov 29, 2018Review of the 2018 iPad ProThe sideways logo gets hidden, rather than fixed. Photo by eleven x. Yes, I know this photo is of the old model. But it perfectly captures what’s still wrong with the new one. The iPad has been my primary mobile computing platform since a couple years after it came out…21 min read21 min read
Nov 29, 2018Review of the 2018 iPad ProThe sideways logo gets hidden, rather than fixed. Photo by eleven x. Yes, I know this photo is of the old model. But it perfectly captures what’s still wrong with the new one. The iPad has been my primary mobile computing platform since a couple years after it came out…Apple21 min readApple21 min read
Published in NewCo Shift·Oct 16, 2018Hold On to Your WhyFounders need to retain their own mission while they build out the company’s. — Photo by Sharon McCutcheon Managing a high-growth company is the hardest thing I’ve ever done. One big reason is that I only received problems that no one else could figure out. …Startup5 min readStartup5 min read
Sep 7, 2018How to Neg a FounderIs that a compliment, or an insult? Photo by John Salvino My experience growing and fundraising for Puppet was full of inspirational-sounding phrases that cut like a knife. Aggressive goals got praise for wanting to “build a real product” and “really scale this thing.” These are some of my favorites…Advice2 min readAdvice2 min read
