It’s August! It’s Monday! That means it’s time for a Monday Letter.

About a year ago, I read this article about drinking coffee on your stoop. It’s a simple, brilliant idea: if you’re going to have a morning coffee anyway, why not take it out to your front step and say hello to the neighbors? And while San Francisco has the right population density for this (it’s 1/6th the land area of my hometown, with the same population), it can feel surprisingly insular. Everyone’s enamored with their devices, building the next billion-dollar business. And regardless of where you are, community has to be built. It doesn’t come for free.

After reading it, I immediately knew I had to try it in my neighborhood. I live in a prime location to host, and I love coffee. I texted my roommates, and we were set. On the occasional weekend when the weather has been nice, we drag a few IKEA LACK tables out to the street, pull up our Wayfair dining room chairs, and start gabbing.

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 through life in a Camus-style Absurd way, doing and saying whatever you feel like. All because you’ve been asked to include a cover sheet on your TPS reports one too many times.

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 across the major leagues, adopted the Vancouver Whitecaps as my MLS club in college, and keep up with a bit of F1 and UFC as well. For me, elite competition is a steady source of inspiration, both for my own play in soccer and hockey and in life. With the World Cup, it’s been fun to see that energy spread far and wide, so casual fans can get a taste of how great the atmosphere can be. Look no further than the Dutch fans marching through Dallas in a sea of orange on their way to AT&T Stadium. Everyone’s getting involved.

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.

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 target. I’ll never forget waking up at 7am Pacific to watch Lionel Messi take his final step and earn World Cup glory. Or the heartbreak of rolling out of bed at five in the morning to watch Team Canada get crushed in this year’s Winter Olympics. There’s nothing like sport.

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

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.

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.

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 critical path

Early in your career, optimizing for learning matters more than optimizing for comfort (don’t take this too far, but still). Critical-path work tends to maximize learning because it sits closest to what really drives the business.

Happy long weekend! I’ve been in a good writing mood recently, so I’m back again. This time I have a short-ish piece, reviewing Google’s various attempts to integrate Gemini into its products, from a long-time Android user. (tl;dr It is… not good.) My point being: there’s still lots of room for great, AI-enabled products. Whether they come from Google (or Apple) or not remains to be seen.

Feel free to give it a read on my blog, here. And let me know what you think! (I’d normally copy it here, but there are a lot of screenshots, so I think it’s best viewed on my website.)

That being said, I don’t want to leave you empty handed. As a fun snippet, I might’ve stumbled across Google’s system prompt for it’s Google Messages assistant thing?

Happy Saturday. As life would have it, I’m graduating very soon. And I have the privilege of giving of speech!

I was stumped on what to say for a while, but have finally put pen to paper. I’d love to share the speech, and some context around it, with all of you. (If you’d prefer, this piece is also available on my blog.)

Enjoy.