From the Vault: Uber in Q1 ‘15
Below is an essay I wrote in February of 2015. Other than some minor cosmetic edits, I’m publishing the blog post now, in full, as it was when I first wrote it.
Context:
When I wrote this essay I was basically two years out of college. And I was just a month shy of my one-year Uberversary (read: about to vest for the first time). I was still recovering from my first Q4 at Uber—Halloween and NYE 2014 were intense, to say the least. A mere nine days into the new year, Uber announced a sweeping price cut across US cities, putting front-line Ops teams like mine in the hot seat with drivers.
My title at the time was Marketing Manager, and I was on the spry, eight-person Maryland Operations team, sharing responsibility with two others for all rider acquisition, engagement, and advanced support in both Baltimore and Annapolis. On the driver side, when the team and I weren’t hosting in-person onboarding sessions in our Baltimore office or in a suburban hotel conference room, I was co-managing and executing a text+email conversion campaign that Max and I created and scaled to 90% of the East Coast cities where Uber operated at the time. The entire team was hustling hard to bring ridesharing to the entire state—I wrote this piece in the evening after our team had hosted a luncheon to showcase Uber to the Maryland Assembly.
I ALMOST TURNED DOWN UBER
February 15, 2015
Some of you don’t know me. Those of you who do of course know that I did mock trial in college. What you might not know is that I tried rather hard to join an a capella group — both before and after I made the mock trial team. Mockers, Uberettos, family, and friends have called me passionate…what I actually am is obsessive.
But when I was offered the job of Baltimore Community Manager at 11:54pm — six minutes before my other (and only) offer would “explode” and ten days before March’s theretofore-unpayable rent was due — I paused. I called my parents and asked,
Is Uber going to be a repeat of mock trial?
You see, fake law dominated my life for four years. Through Mock, I formed some of my strongest bonds and deepest animosities. I experienced high-like joy and recognition at the national level, along with deep disappointment, even depression at the personal level. Today, when Mock memories come up, I usually change the topic pretty quickly because the ups and downs still evoke such strong emotions. From managing events and people; from the art of presentation to the science of persuasion, mock trial contributed the lion’s share of shaping [high-school-senior Jay] into [college grad, entry-level-work-applicant Jay]. One year into Uber, [working-professional Jay] can’t help but reflect.
My first job application process was an extension of my other obsession: Iran. In seven semesters, I took every single class Penn had to offer on the subject. I studied the country’s politics, its peoples’ history, the Persian language, poetry, and prose. I was a final-round candidate for a job with the Intelligence Community. But when I got the paper-thin envelope from some nondescript address in Northern Virginia, I knew without opening that I didn’t get it.
Fast forward to an unpaid fall internship at a DC think tank that for some reason didn’t magically pave the way to employment. Happy Christmastime quickly turned into Unemployed Februarytime. Sixty applications to the public-ish sector later, doubt started to erode my obsession. Granted, I could always fall back on my loving parents, for either cash or for lodging. But then, one night, in the aftermath of a Philadelphia blizzard and two (…alright four) glasses of wine into a lovely French dinner at my favorite restaurant, I announced with great pride that I would be requesting an UberSUV to safely get all my friends home. That pride continued to vocally fester to the point that, as my friends disembarked, one suggested over her shoulder:
If you love Uber so much, why don’t you work for them?
Five weeks later I was hired.

My first Uberversary is coming up on March 10th. It’s about this time that, relatively speaking, I was a year into college mock trial and I secretly tried out for a capella a second time. My history with obsession induces high anxiety over the opportunity cost of it all.
I’m not the only Uber employee who regularly works from 8:30am to 10:30pm (on a good day). I’m not the only Uber employee who feels frustrated not irregularly with choices being made that are equal parts out of my control and immensely impactful on my ability to do my job. And so surely, I’m not the only Uber employee who wonders, Is it worth it?
It’s funny. For a technology company, our work is incredibly tangible.
I help build hundreds of small businesses every month, and I shake hands with several of those entrepreneurs. No matter where I am, simply saying that I work for Uber is sure to get me an earful; whether it’s about a terribly long pickup time or about the PhD Syrian refugee who — thanks to the promise of partnering with Uber — was able to quickly and securely transition his family away from daily horror. I create pure joy when delivering ice cream and puppies on-demand. I love when I not only learn new coding languages and software but playbook, scale, and teach others. Longer-term efforts like supplying the city on Halloween and New Year’s Eve ultimately save lives by re-directing drunks from the front seat to the back seat at the push of a button. It’s an incredible opportunity, and at times feels incredibly important. Our CEO has compared Uber to a political candidate. And just as inner members of a presidential administration must feel, I tell myself, I might not get another chance like this.
But at what cost? Friends are at parties meeting future spouses when I’m still at the office. Staring at a computer screen all day has made falling asleep a Herculean feat. Other healthy habits like picking up a new instrument or an old book aren’t afforded to The Uber Faithful. If cults are said to drink the proverbial Kool-Aid, then my lips are deep, deep red.
#OhYeahhh // #SuperPumped // #Hustle
My thoughts and feelings about Uber are — like the company itself — ever evolving. This is the current state of affairs: I firmly believe that in no other capacity of employment could I contribute (both to the company and to the world) so much at this point in my life. Nowhere else would as many important people listen when I speak. Quite frankly, I probably wouldn’t define as many peers as “important” at any other company. If I had turned down this job I do believe that I would be worse off.
But the most beautiful part of working at Uber is that good enough is never good enough. We disrupt the status quo within Uber with as much gusto as we fight antiquated regulations. So I can’t help but feel a similar discontentment with how some things are, no matter how good the absolute state of things is. I am Uber, through and through. Which means that as much as I love what we do and why we do it, I’m going to keep pushing that boulder higher and higher up the hill — no matter how many times it rolls back down or how many people tell me it’s impossible.
After all, there are no easy jobs at Uber. The amount of work that needs to get done exceeds the cumulative number of waking hours across the 2,000ish employees we have. Long nights and weekend shifts come with the territory of history’s fastest growing company. If you’re interested in solving truly new problems while riding this bucking tiger with me, get in touch. And/or if you happen to be recruiting for an adult a capella group, let me know. My personal goal for these next 12 months is to insert more artistic expression in my work/life blend.
