Casey & Chloé Living the Dream

My San Francisco experience was vastly different from Chloé’s.

We were both neuroscience majors at Northwestern. We had met before in a couple classes, did shots together once at the one local Evanston pub, but we didn’t really become friends until a couple of crazy life choices made us both end up in the Bay Area.

I had “concentrated” in Computation & Systems Modeling in college, which basically means I know how to code. So immediately out of college, in June 2019, I began work as a software engineer at JP Morgan in Chicago. In the meantime, my nights and weekends hobby was my brain drill startup. 

Chloé double majored in Theatre, which in the most condescending definition, means she knows how to sing and dance. Chloé bought MCAT books and planned to spend the year after college working in her undergraduate neuroscience lab while applying to medical school. Her side gig was auditioning for shows. In July, Chloé booked the Broadway Hamilton San Francisco Tour as an ensemble cast member. She stopped studying for the MCAT, and in October, moved to a shitty apartment in the Mission. 

Near simultaneously, my startup got accepted into a prestigious business accelerator program in Palo Alto, which included significant investment and free office space in San Francisco’s financial district. I quit my job in November, and moved to my family friend’s house in Oakland. I had hardly known these people, but my dad had gone to college with both of them and continued to go on an annual ski trip with Phil, so they happily agreed to let me stay rent-free. Their house was gorgeous, and they had an extra car they let me use. They were also walking distance from a bus stop which dropped me off directly at my new office space. 

Two science majors on track to be a software developer and doctor, respectively, managed to exchange the Chicago winter for sixty-degree days at the beach. We were each getting paid to work on our life passions, and our future careers were set.

I lived amidst the obscene wealth of San Francisco venture capitalists. Every day, I arrived at my office where the two draft beers on tap (switched out each day) and cappuccino machines provided unlimited choice between free depressants and free stimulants. I also had weekly ginseng health shots delivered there for free from a startup CEO I had met.

I usually had my first couple of meetings at the office before having to sprint up the San Francisco streets to make my next meeting. I almost always got free catered food at these lunch meetings. Belly full, I’d often Uber to my next location. In one Uber pool, the two strangers in the back found out they were both email marketers. They discussed how they coded algorithms to scrape not just LinkedIn, but Tinder, to automatically flirt with recruiters and try to get jobs. In another Uber, the driver told me he had discovered unified field theory and subsequently coded a language that could destroy the world.

After my daytime meetings, I usually had a nighttime networking event. Once at a Northwestern alumni happy hour, a group of men in their 30s and I decided to leave the event to get Indian food. After ordering and eating an obscene amount, one man passed the bill to his friend. “He’s got it, don't worry,” he said. “He IPO’d last year.” At another event for Women in Robotics, I met a kind robotics engineer in his early twenties who offered to drive me home since he also lived in the East Bay. Outside, he unlocked his 2019 Maserati. Apparently he began a startup in college that was basically DoorDash, got acquired by DoorDash for a million dollars, and then IPO’d the year prior. 

On weekends, I hiked with Phil and Beth who were now my best friends. I also got work done on my laptop from their house in Oakland. Sometimes, I had weekend events. One time an angel investor in his late twenties called me up on Sunday morning. He liked meeting me at that one event, he said, and he’s potentially interested in investing. Do I want to meet him in Chinatown for coffee?

I drive to the city (it’s easier to find parking on weekends) to meet him at his designated café. He orders an espresso drink mixed with gin and tonic. He pays for my cappuccino. We’re only halfway done with our not-to-go drinks when he asks, “Hey, are you hungry?” Before we can discuss logistics or I can mention I have a car with me, he has already ordered the Uber. Suddenly we’re at a Michelin star restaurant. He orders two appetizers, two entrees, and two desserts. We eat three bites of each while I pitch. Suddenly, he says he has to get going and orders me an Uber to my parking garage. I start to ask for to-go boxes and he says “Nah, this won’t taste good reheated.”

Another weekend night, I had an accelerator event at a tequilaría. It was an open bar, and after the actual dinner and business portion, I spent the rest of the event chatting with the bartenders about how crazy my new startup life was. I accidentally left my jacket there and vomited in Phil and Beth’s basement shower until the wee hours of the morning.

Outside of the draft beers, ginseng shots, Indian food, and espresso gin and tonics (I’ll learn months later that I’ve gained 15 lbs), I worked completely alone as a sole founder. It won’t be until late January that my first intern starts working for me, and late February when I hire my technical co-founder. I was astounded every day by the beauty of the Bay Area and how movie-like my life had become, but I missed my boyfriend. We had been dating for over two years by that point. I had graduated in three years, Chloé being the year above me, so all my closest friends were still finishing their senior year. I didn’t envy them, but I did miss them. 

Chloé’s and my friendship worked because we both had weird schedules. She had shows throughout the weekend and rehearsals all week, her only day off being Tuesday. I had events most nights and meetings most days, but my schedule was mostly up to me. I could see her weekday mornings before rehearsals or late Monday nights, giving myself Tuesday morning free. We went on night hikes and got drinks and splashed our feet in the freezing Pacific. 

Chloé made 4x the money working for a Broadway national tour than I did on my budding startup. Yet my life was spent living in a big house in a lovely area of Oakland, working in the wealthiest area of San Francisco, and attending weekly events in Palo Alto. The people I passed on my commute were largely multi-millionaires in T-shirts and mom jeans. 

Chloé lived in the Mission and worked at the Orpheum Theatre in the Tenderloin, often going to the Polk Gulch for dinner with her cast members. It wasn’t unusual for Chloé to see a homeless person taking a shit on the BART station stairs or shooting up in Dolores Park. I got to watch Chloé in Hamilton on a discounted ticket, and she gave me a backstage tour afterward. She talked about how she loved San Francisco, but it took such a toll to see drug addiction and homelessness every day. I agreed that it was terrible. I was about to say that it is unfortunately like that in Chicago too, when outside the theatre I stepped on three needles littered in a row.

Chloé loved her job. She was intellectually challenged learning all new choreography and harmonies and performing three to four nights a week. She was astounded every day that she got to walk onto the set of Hamilton and get paid to do it. Strangers asked for her autograph.

Like me, Chloé was also a little lonely. She learned that unlike college, the cast and crew treated the show like a job, not a family. When work ended, they packed up and went home to their real families. She had two roommates in a very small apartment. Having met them online before moving, she loved one and was lukewarm toward the other. Her schedule was too unconventional to see either of them much anyway. She had started dating a guy from our neuroscience class that summer, but he hadn’t wanted to continue dating long distance. So she started dating again. She met friends of friends and used a dating app. She realized that dating strangers… sucks. It was much easier in college when you dated people you already knew. 

I travelled a lot to abate the lonesomeness, and because I could. I took a short flight to Vegas for my JP Morgan friend’s elopement. It was another insane and fun weekend, but this time with more friends and without investors or free drinks.

Chloé had to keep working throughout the holidays, so I said goodbye and took an even shorter flight to Orange County to spend Christmas with my dad’s side of the family. I flew from there to Evanston to spend New Year’s with my boyfriend. I had a conference in Boston the first week of January, so I figured a short pit stop halfway made sense. During the conference, I stayed at Harvard with two of my high school friends. 

In the meantime, Chloé updated me on her tragically hilarious dating woes. She was jealous I got to escape the dream for a couple weeks, seeing family, boyfriend, and old friends. I was jealous of her for becoming a “real San Francisco resident,” which evidently to me was defined by spending holidays there. But I returned to her and the Bay shortly, and I was back to living my dream as well. That is until COVID-19 hit.