The seed to move to San Francisco was planted during an hour-long commute to my first (and last) corporate job down in sunny San Diego. It was 2016. I had made this drive countless times, headbanging to Pierce The Veil, but this day was different. A coworker suggested I listen to a “podcast.” I thought, “What the hell is that?”
I grew up in small-town Ohio—no, not Springfield—and back then, no one was listening to podcasts. We were more of a Kiss FM crowd. Curious, I opened the app, clicked on technology, and there it was: a podcast by Jason Calacanis, one of Uber’s first investors. I became obsessed, listening religiously from episode one during my daily commute. Eventually, I sent Jason an email and, to my surprise, not only did I get a response, but I was invited to join his syndicate and attend a pitch meeting in San Francisco.
I found myself sitting one seat away from Jason, watching his founders pitch to a room full of investors. They even let me, the guy who had been a product manager for all of six months, ask questions. This was the quintessential San Francisco experience for any technologist. In this city, any idiot is welcome—all you have to do is ask and be somewhat interesting.
That spirit extends online too. You can DM almost anyone on 𝕏 (née Twitter) and meet them in person, sometimes the same day. I was hooked. I quit my job before reaching the one-year mark, packed everything into the Tesla, turned on Autopilot, and made my way up to San Francisco.
So, what am I still doing here seven years later? I’ve worked at a handful of startups, started my own, and made lifelong friends. San Francisco has shaped so much of my life.
Now, I’m starting my family and thinking about what to work on next. My son, Mayu, will be one next month. We take advantage of San Francisco’s perfect weather every morning. We live in Nob Hill, where Baby turns his head to watch the cable car pass by, then looks up at the giant American flag flapping in the wind atop the InterContinental. We keep going, the Bay Bridge peeking out between the skyscrapers, until we arrive at the best filter coffee you’ll ever have at The Coffee Movement on Washington.
Baby enjoys a banana muffin, smiles at everyone in line, and screeches at every dog that passes by. Once he’s finished, we have our pick of five playgrounds, all within walking distance, each with different steps and ropes for Mayu to climb. Also, did you know we have pizza now? Give the guys at Outta Sight some love next time you’re in the Tenderloin.
Speaking of, yes, we have problems. Everything good about this city is God-given: the best geography on earth and the lovely people of San Francisco. Everything bad about the city stems from City Hall. Luckily, we can all feel the warm glow of moderation and common sense washing over this charming place, but it’s far from guaranteed.
The most important votes you’ll cast on November 5th, aren’t for president—they’re these local decisions that will directly impact your daily life:
Yes on San Francisco Prop D – Cut and cap the number of commissions. We currently have over 130. Drain the swamp.
Yes on California Prop 36 – Repeals Prop 47, which allows theft under $950. Let’s make crime illegal again.
For the rest of this year’s very long ballot, check out the Pirate Wires Voter Guide, which I had the chance to help write!
If you enjoyed this post, please subscribe and share it with a friend who lives in SF or is thinking about moving here. I’m happy to show them around!
love this!