In my mid-20s (I’m 29 now), I was working in business development at WebMD. I liked my job and had become fluent in the language of CPMs and STDs. But in my free time, strangely enough, I increasingly found comedy a lot more interesting than chlamydia. I fed my appetite for consuming comedy by listening to comedians on podcasts, watching standup specials, and going to live shows in New York City. And I fed my appetite for creating comedy by writing a TV show (a half-hour comedy called Too Many Chiefs).
I’d tap bits of dialogue and story ideas into my phone while walking to and from work, nearly committing accidental suicide-by-cab as I obliviously giggled my way into oncoming traffic. At home, I’d work for hours at a time without even looking away from my screen. For me, this was unheard of; I’m well-known for having the attention span of a golden retriever.
Below is a photo of my living room wall in my old West Village apartment. Each big white sticky was an episode of the first season of Too Many Chiefs, which was about young douchebags living in New York City (write what you know!). Colored stickies within those were plot elements.
My protagonist was was an entrepreneur named Alejandro. He worked at a startup called Apartrents, and his nemesis was a co-worker named Sadie. This is my favorite exchange between them:
ALEJANDRO Sadie, I read your memo, but I think you might want to make one more round of edits before it goes out.
SADIE How come?
ALEJANDRO To be honest, it’s pretty sloppy. Lots of grammatical mistakes and run-on sentences.
Sadie’s face curls downward.
SADIE Really? Give me an example.
ALEJANDRO OK, take this line: “TheTime Magazine recently named Apartrents a startup to watch in the real estate space.“
SADIE What’s wrong with that?
ALEJANDRO It’s just “Time Magazine”.
SADIE You can do it either way. The “The” is optional.
ALEJANDRO No. It’s not.
SADIE Oh, really? Then why would I say that I read an article in “TheNew York Times” ?
ALEJANDRO Great question, Sadie! Maybe because the name of the fucking publication is “THENew York Times” !
Writing Too Many Chiefs was the first time I had ever been CONSUMED by the creative process. I found it intellectually stimulating and also intensely emotional — almost always in a positive way. I developed deep attachments to the characters I was bringing to life and dreamed about them most nights. With the exception of a small number of romantic relationships, there’s no experience I’ve had that has yielded anywhere NEAR the same exhilarating sensations of novelty and emotional gratification. Maybe I could make a career out of this?!
One Dream Dies, Another Arises
Becoming a writer was a pipe dream that didn’t survive its collision with reality; after writing a few hundred pages of my show, it became abundantly clear to me that due to a lack of both training and talent, I’d sooner become the next Dalai Lama than the next Judd Apatow, Tina Fey, or Conan O’Brien. But I was at peace with this, since all the writing I’d been doing was fun and helped me grow as a human being. Plus, I soon became entranced by a new kind of creative process that I found even more rewarding: inventing a company at the intersection of comedy and technology.
It was my continued attendance at live shows that inspired this evolution. The comics I saw perform routinely brought me to tears, and the people I brought with me — family members, friends, dates, co-workers — also doubled over in fits of hysterical laughter. I couldn’t get enough of the men and women on that tiny stage; to my mind, they were our modern-day poets and philosophers, mining humor from even the darkest of topics and drawing smiles out of even the dourest of audiences.
Nonetheless, most of these performers — some of the very best comedians in the world — remained unknown to the overwhelming majority of Americans. Very few people I knew could name more than 2 or 3 comics they really liked, and even fewer consumed standup or podcasts with any regularity.
As I learned more about the comedy world, the questions kept piling up: for instance, why was making a living as a comedian so damn difficult? I couldn’t believe it when I found out that “making it” as a comic was finding an agent who would ship you out to the boonies every Thursday through Sunday so you could make $1,500 for a weekend of shows.
A big breakthrough came when I realized that the issues facing consumers of comedy weren’t separate from those facing comedians — they were two sides of the same coin. Supply simply wasn’t finding demand very well.
Could I do something about that? What if I started a company whose mission was to fix these inefficiencies — to help consumers more easily find comedy they’d love, and to help comedians find more fans and make a better living?
I found the parallels between comedy and entrepreneurship endlessly fascinating. Both reward creativity, consistency, critical thinking, connecting ideas and concepts in new ways, and crafting a compelling, emotionally resonant narrative reliant on ~7 parts passionate truth-telling and ~2 parts exquisite bullshit. Both end in failure for all but the luckiest, most talented, and hardest working. And to succeed, both require you not just to create something you yourself think is remarkable, but also to find an audience that agrees with you.
Eventually, I took the entrepreneurial plunge. It’s been a maddening, humbling, frustrating, and demoralizing journey at times. The last time I was this poor was in the 9th grade. And there’s no guarantee we’ll make it in the long run.
So why am I still doing this?
Because more and more each day, we’re executing effectively on our mission to make both creators and consumers of comedy better off.
Because I still love building things and being creative.
Because this continues to be intellectually, emotionally, and professionally fulfilling in ways I didn’t know were possible.
Because I get to eat and breathe comedy.
Because I get to work closely with kind people who are way smarter and more talented than I.
And because there’s mounting evidence we might just pull this off in a big way.
Now all I want is a cover story on Laughable in T̶h̶e̶Time Magazine.
Thanks for reading — I welcome your feedback. Feel free to email me at email@example.com.