Last year I wrote an end-of-year update for 2021, and really enjoyed writing and sharing it.
I thought I’d do so again, but break it into parts to make it easier to read.
Part 1 -
SF, Startups, Visa’s
2022 began for me in San Francisco. I’d gone there in December, to explore building a startup with someone. He had offered to let me rent one of the bedrooms in his rent-controlled house for a very modest amount. In my mind, I was moving to SF!
However, almost immediately things began to awry, both on the housing and work front.
It was a pre-war house in the mission - the electrical system so dainty you could only turn on one appliance in the house at a time - it was either the water heater, space heater, or the stove. The whole space had an uncared-for and slightly grimy feel to it, and I was cold the whole time I was there. No matter how low the rent, it never felt anything like home.
With the cofounder too, it just turned out we were in very different places in life. He was older and more settled, fairly far along in his career, and had little financial incentive for wanting to start a company. Whereas I was doing this because I couldn’t get a job, wanted to build to bolster my skills and resume, and to create a product I could be proud of. Very soon it become obvious that it wasn’t going to work.
A week in, I was already thinking about what to do next, when some friends said they were going to India for the winter, and offered to let me stay at their place.
Never refuse a good offer, my mother always says.
I spent the next 5 weeks there, till the end of January when I found a place to rent in the mission. I had little intention of going back to Toronto, because a series of conversations with lawyers led me to believe that getting a visa would be trivial, allowing me to stay and work in the US.
In hindsight, those weeks in January were the highlight of my year.
Without the structure of a job or a manager, I was making money through independent consulting, meeting founders in SF, giving product talks, and coaching product managers and students. I was also swimming regularly, doing yoga, and had a bunch of awesome people to hang out with.
Back to Toronto
By the middle of Feb though, all the visa promises evaporated. It turns out everything was more complicated, required more time, and came with more restrictions than initially promised.
Having precarious legal status in the US immediately made it a lot harder to figure out everything else - work, romantic partners, finances. I had a deadline of when I had to leave, and when I gave up the visa fight, it didn’t make sense to stay on.
And so, although I didn’t really want to, I came back to Canada in Feb, leaving my new apartment after only 15 days.
Toronto was a big change. Sunless, cold, covered in snow, devoid of the bustling SF social scene. I immediately felt a huge sense of disconnection. Whereas in SF the struggle was to stay at home and work till at least 5, in Toronto, it was to find somewhere to go.
I was still riding the high of SF, but suddenly, all my energy and focus had nowhere to go.
Ideas come together, a move foments
I had to figure out what came next. At some point, I plastered my walls with all the startup and work ideas I’d been thinking about, and eventually, found a way to tie them all together.
It would be a company to help young people build careers and companies, something like a venture studio. This would allow me to teach all the things I’d learned over the past few years, continue to work with people 1:1, and explore specific startup ideas.
This idea appealed to me on many levels, and over the next few weeks I became convinced that it was what I was meant to do. I felt a profound sense of certainty and inspiration and had no doubts that I would do it, and that it would work.
It became more ambitious too, and I created folders and folders of all the ideas I had on how it would work. These included a publishing arm, a venture fund, a digital public library, a tv show, a board game division, an immigration business, and many, many books.
India seemed like the right place to start building this idea. I couldn’t go back to the US just then, and Canada was not fun or big enough. I figured the market would be huge in India, and I could live cheaply and afford to hire people there.
Within a few weeks, I had sublet my apartment, packed up, and bought tickets to India with a short visit to my brother in New York.
New York was brief but exhilarating. I met lots of people, talked about all my plans, went to the Met (where I documented my visit), and tried to soak up every last drop of NY. My brother was moving away shortly after, and I sadly and silently bid adieu to that whirlwind of a city, catching a one-way flight to India on the 25th of March, shortly before my 32nd birthday.
That’s all for now, part 2 here. :)