My Life as an Accidental COO of a Tech Startup (Part 1)

This is the first installment in a four-part series. See part 2, part 3, and part 4.

Note, names have been changed for privacy.

I was in Gold Rush Territory(1), and it was a strange place. I had heard about this place, of course. It advertised itself everywhere — billboards on the Bay Bridge, seemingly constant articles and whispers about 22-year-olds becoming millionaires. I had an uncle who spent a lot of time in Gold Rush Territory, and a few people I knew from high school, and a lot of people they knew. But I had never been here myself.

I walked into the flagship office of General Assembly (2), a company whose tagline is, “We are the Future of Work”. One of the walls was exposed brick, which I had to assume was fake because brick has not been a sanctioned building material in San Francisco since 1906. Attached to the brick was a neon sign that had some saying like #Hustle or Follow Your Dreams written in bright, curly pink. I was greeted by an iPad and it’s person, and directed into the main room. This room boasted an open floor plan, with a long reclaimed wooden table on one end and a couple of Working Nooks with hard couches, coffee tables, and brightly colored Ergonomic Sitting Cubes (3).

When about 20 or 25 of us had trickled in, we were herded to the stack of pizzas on the kitchen island, across from the Working Nooks, where I had already positioned myself and grabbed a slice so I would have something to do other than introduce myself to people.

At some point in the preceding weeks, someone had told the folks in the GRT that there weren’t enough techies working on actual problems that real people had; that the GRT had — at some unknown point — become a smidge disconnected from the real world, but that it had the power to save itself and everyone around it from continuing down this path. We were all there for a hackathon (4) sponsored by an entity calling itself SFTech4Good. The groundbreaking concept of this particular hackathon was to invite non-techies and see what they might contribute. They put the bat signal out to non-profit leaders, policy wonks, academics, activists, and anyone else who wanted to use the power of Design Thinking (5) to solve issues related to crisis response, democracy, immigration, media, and society. We were to break out into teams based on our interests, shuffle off into separate rooms equipped with whiteboards, power outlets, and our imaginations, and work for the next day and a half before pitching our ideas to Important People. They encouraged us all to drink as much kombucha (6) on tap as we liked.

I think it’s time for me to explain where I was in life and how I came to be here. I was 24. I had finished grad school in London just over three months earlier, gone on a 200 mile bike trip from London to Wales, broken up with my British sweetheart, visited friends in New York and DC on the way back to San Francisco, moved back in with my dad and brother, and had begun the arduous process of Starting My Real Life. Like many of my friends, the field I saw myself in was interdisciplinary and could go in hundreds of directions. Armed with my degrees in Human Services & Social Justice, Political Science, and Urban Economics, I knew I wanted to be back in the Bay, working toward bettering the systems in which we operate, centering the needs of people who have less power in our society. What I actually wanted to do though was very, very up in the air. I was applying for any job that sounded remotely interesting, going on as many informational interviews as I could schedule, interning (7) with a Supervisor in City Hall, doing a short-term gig for a transportation planning non-profit in which I distributed free Clipper Cards to people I walked up to on the street, and continuing my copywriting gig to rebuild the meager savings I had eviscerated in grad school. All in all, I was very busy and very unemployed. I dreamed about a job in which I got a paycheck that was predictable enough to pay rent for a shitty apartment and move out of my dad’s house. A job in which I was doing something worthwhile, at least vaguely related to what I had spent the past six years studying, and that was challenging enough that I wouldn’t scream of boredom.

I had heard plenty of stories of friends and colleagues in exactly my position, spending six months, eight months, a year applying for jobs before they were hired. Surely not me, I thought. I have experience in lots of different jobs. I graduated in the top 5% of my class from a prestigious university. How arrogant I was. Nobody had heard of my university (8), nobody cared about my slew of three-month internships in college, nobody was interested in my “potential”. They wanted hard skills, they wanted demonstrated experience, they wanted 2–4 years of project management and supervision, they wanted me to have already been doing the work they were hiring for.

Three months into this in-between stage and I found myself deeply humbled by my lack of immediate dream job offer. So I decided I would try anything, everything. I had no idea what was going to pan out. Would it be a cold application submitted for a job posting? Would it be by volunteering for who knows how long and eventually getting hired? Would it be a connection I made through attending some event?

So here I was, on a Friday evening, at a hackathon in General Assembly’s San Francisco campus, surrounded by people who spoke an entirely different language than I did, Design Thinking around the issue of homelessness. I had submitted my brief application, checking my “areas of expertise” as nonprofits, academia, and policy, because I had dabbled in them all for the preceding six years though I would be the first to say I was no expert.

Except for myself and one other person in the room, nobody else actually knew people who were or had been homeless. Most had never had a conversation with someone who was homeless. And yet, here we were, trying to design some app that would benefit people who were living on the streets of San Francisco. There are plenty more details I could share about how we spent the next day and a half, but they’re not important.

What is important happened the next day, and took less than a minute. We were at the Pitching portion of the event, and shortly after our team pitched our idea, the Democracy team pitched theirs. Their team was two boomer guys and a young, shy woman. Their idea was an app that helped enthusiastic voters turn out the vote among their personal and social networks, with the overall goal of increasing voter turnout among progressives in the 2018 midterms. The overall idea was rough around the edges, as all of ours were, but as they walked back to their seats, I leaned toward one of the team members and said, “I really like your idea”, with some earnest but mainly out of politeness. He leaned toward me and said, “Thanks! Any suggestions?” Yeah maybe a couple! “Let’s talk about it” Uh, ok. “What’s your instagram, I’ll message you”.

I could have ended it there. I could have said I didn’t have an instagram. I could easily have given him my instagram and not replied to his message. I could have even given him my instagram and replied saying I wasn’t interested but good luck. But two days later I was sitting in a mom and pop cafe on Polk Street, talking to this guy named Ben from Texas, who wore a cowboy hat and tiny circular glasses. Because, as I mentioned, I was taking any avenue I came across, hoping something would stick.

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End Notes

(2) Now with 30 campuses around the world, General Assembly is an education provider for the tech industry. They have sent me emails with headlines such as “Alexa, Change my Career Path in 12 Weeks” and “Become a Web Developer. Increase Your Worth”.

(3) Also known as an ottoman stool, these are uncomfortable to sit on for more than 30 minutes and range from $65 to $479 each on Wayfair

(4) I grew up understanding the word “hacking” to mean something the bad guys did in sci-fi and action movies, in order to break into some government or bank’s servers and steal something. Apparently this definition is a gross misrepresentation, and true hacking means “finding a way to do something more efficiently”. A hack-a-thon, then, is an event in which a group of people gather to generate ideas about new ways to do something specific in a short amount of time. Generally with pizza provided, apparently.

(5) Design Thinking is when you put ideas on a whiteboard and draw circles around them with different colored markers.

(6) A modern stand-in for Kool-Aid

(7) Answering the phones of constituents who were pissed off about their parking tickets and the fact that there were homeless people on their block, fixing the printer, and starting a Twitter for another volunteer who was a boomer, interested in tweeting @ companies he thought were ripping him off.

(8) I attended University College London (UCL), which is one of the newer universities in the UK (founded 1826). Most who asked me where I went subsequently asked if I meant UCLA.

My crowning accomplishment is that I once came second-to-last in a pun competition.

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