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It’s Monday! It’s July! Here’s a letter for Monday, July 6th. A Liminal Office Space If you’ve spent enough time around me, you’ve probably heard me ask, more than once, “Have you seen Office Space?” The 1999 film by Mike Judge (who also created the hit TV series Silicon Valley) follows a guy who wakes up one day and decides to stop going to work. Chaos follows, but at its core the movie is about rejecting the social contract and giving in to your (presumably) hedonistic inner voice: moving thro...

Hello! So much in the world of sports recently. Lots to chat about. Here’s the Monday Letter for June 15th, 2026. The World’s Cup Summer 2026 has arrived in style. The World Cup is in full swing, and it’s been a treat to watch the world come together in celebration. Folks in San Francisco’s tech scene are generally apathetic to sports, which is (in two words) extremely lame. I’m an avid sports fan. I rep my hometown Edmonton Oilers the most, but I also follow a handful of Bay Area franchises acr...

It’s been a while, happy Monday. This is the Monday Letter for June 8th, 2026. Physical Media Still Rocks My move to San Francisco was a bit of a whirlwind. I was lucky enough to get connected with my now-roommates (who are now some of my best friends) before the move, and they ended up securing our place. Only now do I appreciate what a gift that was, getting spared the gauntlet that is the San Francisco housing market. My only preview of our home was a brief Messenger video call where I could ...

Happy 4/20. Here’s your Monday Letter for April 20th, 2026. Geno Is Score I’ll start by saying something controversial: I like sports. You might think that is not controversial at all, but I’m not sure it’s safe to say in San Francisco. There’s a place called “Sports Basement” where you can, sure, buy hiking boots, but good luck finding a football (of any variety). I get visceral enjoyment, and real inspiration, from watching a bunch of sweaty dudes I’ve never met try to put an object into a tar...

It’s April. Did you get pranked on the first? My friend did, by a Waymo. The car told its riders to start humming to help the vehicle “calibrate” before the ride could start. Ha. Ha. Here’s the Monday Letter for April 6th, 2026. Line Dancing Line dancing is one of the best new things I’ve been doing this year. Every Sunday night, I stroll down to Lower Haight to join friends at the aptly named Lower Haight Line Dancing ("LHLD" from here on out, because that’s a mouthful). From 6 to 10pm, a handf...

And… we’re back! I’ve had a busy last couple of weeks, with trips to Whistler and New York. Lots to talk about. This is the Monday Letter for March 30th, 2026 (and March 23rd and March 16th). Give the agents an Autobahn Issue tracking is dead. Or so says the CEO of the hottest issue tracking company. As someone who works at another sort of issue tracking company (really, an everything tracking company), I don’t fully agree, but there’s some truth to it. What I think is dead is the how, more than...

Hello from thirty-four thousand, nine hundred and ninety-one feet. I’m on a return flight from Vancouver to San Francisco, and it is four hours to midnight, so it’s probably time for a letter. Slopes I spent this past weekend in Whistler, BC. It felt great to be back in Canada, and I felt great on the skis this time around. I’m a fairly average skier: comfortable on all blues, most blacks, and in solid conditions, I’ll occasionally attempt a double-black. I had the chance to ski with some great ...

Hello! It’s been a while. I hope you’re doing well. One of my big goals for 2026 is to create more, and one of my favorite ways to create is to write. It’s March, so it feels like high time to get started. To reboot my newsletter, I’ll be sharing some thoughts, plus what I’m reading, watching, or listening to, in a short weekly letter, on Mondays (though if I’m late for that, I’ll probably publish mid-week anyway). Here’s the first edition of The Monday Letter. Enjoy! Put yourself on the critica...

(And how I discovered—I think—the Google Messages Gemini assistant's system prompt.) Gemini is brilliant technology. As the first model to outperform humans on MMLU, with its million-token windows and impressive results on SWE-Bench 2.5—the talented team at DeepMind is achieving remarkable things. So, why hasn't this technical excellence translated into meaningful improvements across Google's product ecosystem? As a long-time Android user (from the HTC era through acquisition—I had the HTC One M...