Outsider 🠒 Insider
Reflections after moving back to San Francisco
I have a confession to make.
For as long as this newsletter has existed, I have been an Outsider — living outside of San Francisco, hidden away amongst northern Michigan sand dunes and southern Georgia farm tracts. The conceit of this newsletter, of course, depends on my “Silicon Valley Insider” status. But to date, I’ve basically just been maintaining my virtual connections to the Bay, and otherwise pretending to know what people are talking about in Silicon Valley.
I shall pretend no longer! It took 11 days, 36 hours of driving, 24 apartment visits, nineteen trips up and down the service elevator, and too many of my hard-earned dollars, but I am now a proud apartment-renter in the Dogpatch neighborhood of San Francisco.
In the short-term, I’d kindly ask that you lower your expectations for this newsletter. Moving is crazy! But in the long-term, being back in the thick of things will help me bring some more truly Insider-y insights back to you all.
Even just being in SF for a week has reminded me of many things that I’d forgotten after nearly a year away:
San Francisco is an incredibly diverse city. My fiancée (the daughter of two Chinese immigrants) often noticed that she was the only non-White person in public places in Michigan; SF has put her in no such opportunities so far.
Startups are in the air. Nearly every billboard on Highway 80 heading into San Francisco is advertising a startup, and on a half-mile walk to dinner last week, we passed the offices for iHeartMedia, Envoy, Embark Trucks, Stripe, and Adobe. Truly unreal how everpresent startup life is here!
Eaze, a cannabis delivery startup, dominates the SF billboard scene. The weather is awesome, but turns chilly quickly at night. On the aforementioned walk, I was comfortable in shorts and a long-sleeve shirt on my walk to dinner, but nearly froze to death on the walk home. Rookie mistake!
The SF hills are not to be underestimated. After an attempted walk over Potrero Hill, I realized how much my calf muscles have atrophied from time spent on flat land. But I also remembered how beautiful the views can be once you (finally) make it up San Francisco’s massive hills.
📚 To round out this week’s Outsider, I have something a little unique for you: homework!
About two weeks ago, Evan Armstrong (who has spent his early career working exclusively at startups) published “You Probably Shouldn’t Work at a Startup,” a critical essay that makes two arguments: working at startups probably won’t make you rich, and working at starutps is stressful.
It gained some degree of notoriety as it passed around Silicon Valley Twitter, and prompted Nathan Baschez (interestingly, the co-founder of the blog platform Evan used to publish his piece) to reply with “Why I Love Working at Startups.”
I’d normally give you my thoughts on such a piece, and I will — next week!
For now, check out both of those pieces and develop your own opinion: it’s important to understand the pros and cons of startup life before diving in, so both are great reads for the startup-curious.
Thanks for reading!
My name is Christian, I’m the Chief of Staff at Astranis, and I’m a native Midwesterner. If you enjoyed this piece and want to join 340 folks in getting an email from me every Monday, I’ll help you understand Silicon Valley using normal-human words.