Category / Comedy

by ruchirwp

Standup Comedy: Lessons from Entrepreneurship

Before business school, I spent four years starting a company. The best way to describe entrepreneurship is a nonstop roller coaster. There are days you are extremely happy, and then there are days you are extremely sad. Entrepreneurship brings you the closest to life’s most extreme emotions: depression, anger, fear, and pure happiness.

This summer, my experience as a budding standup comedian has felt extremely similar to entrepreneurship. Every day brings with it a roller coaster of emotion.

My life right now combines two very different skills: writing and performance.

Whenever I think of something interesting, I write it down. It might be a time I felt really frustrated (My parents trying to set me up with girls), it might be a random thought (The Venus Flytrap would be a great gift for an enemy), or it might be a time I made my friends laugh (The time I went skiing without goggles and burnt my eyes). Writing comedy is a challenging, difficult to define art. I start with these interesting ideas, look at a blank Google Doc and try to create something funny.

At night, I go to as many open mics in the city as possible. Standup comedy is incredibly democratic. Anyone can pick up a microphone, go to a coffee shop or bar, and get a few minutes of time to make an audience laugh. This is called an open mic. Every comedian, from Jon Stewart to Eddie Murphy, has gotten their start with open mics.

Often, in New York, open mic audiences are made up entirely of other comedians who are very hard to make laugh. They have high standards, they are thinking about their own material, and they are often depressed. But, through this brutal cycle, I get immediate feedback on everything I spent the day writing and editing. Feedback is a complex term for a simple concept: laughter. The more laughs I get, the funnier a joke is.

There are few better feelings in the world than writing a joke that just absolutely kills, when the entire room just erupts in laughter. After spending hours and hours writing and editing and performing the same chunk of 50 words, suddenly one day it magically works. It’s a beautiful, truly incredible artistic process and the reason so many people love standup comedy.

Just yesterday, my friend Cason was visiting New York, and I did my best set ever at a dive called Mama’s Bar. Everyone laughed! I doubt anyone at that mic even remembers my name, but I spent the next few hours with a huge smile on my face, skipping all over the subway. I’m still happy thinking about it.

My favorite performance so far was a musician open mic I went to at Sidewalk Cafe in the East Village. It was all incredible musicians except for me and a comedian friend. I went up on stage, pretended to be a professional singer from Juilliard, and sang “I Feel Pretty”. I got such a rush from going up and just being ridiculous. I love open mics for moments like this, when you can really connect to the audience, surprise them, and slowly win them over.

Other times, it seems like the entire world is collaborating to crush my dreams. I’ve sometimes traveled miles across the city (one day, I walked 17 miles), only to find that the mic has been cancelled or is full. Sometimes, I may make it into a mic but be slotted dead last. The same room that was roaring in laughter earlier may now be full of much fewer, burnt out audience members.

One time, I got up second- arguably the best time to perform. I was ready and pumped up for my material. And then I got on stage and saw a pretty girl in the audience. I completely lost my nerve and did terribly.

Every time I do awful, the next hours are spent in misery and self contemplation. What went wrong? I spent hours writing and re-writing but nobody laughed. Did I seem nervous? Do I have what it takes?

As I struggle in the comedy world, I find myself coming back to the lessons learned from starting a company. Here are three key lessons that apply to both entrepreneurship and comedy:

1. Don’t compare to anyone but yourself

When starting a company, one of the biggest challenges is self-doubt. You constantly question yourself, and you invariably compare yourself to others: your friends, your family, and your competitors. When you are working on a project that could take years before you see real results, it is easy to compare and feel like you are completely failing.

My budding standup career has been full of self-doubt. I have performed at almost 60 open mics in the city. I have done terribly at the vast majority of them.

Human instinct, whenever you do badly, is to immediately compare yourself to other comedians. This is how you drive yourself crazy. Everyone’s circumstances are completely different. Maybe they’ve been doing comedy for a lot longer than you. Maybe the bits they tried today have had years of practice. Maybe they have close friends in the audience. Maybe they are just having a really great comedy day.

When fighting it out on the open mic circuit, it is critical to compare to only one person: yourself. If you feel yourself getting better, if you feel your writing and performance are improving everyday, you are doing okay. You are on the right path to eventually being a successful comedian.

2. Community is critical

Entrepreneurship can feel extraordinarily lonely. When you first start a company, you might be the only person involved. Even when you have a team, it remains extremely lonely at the top; you are the only person who is completely, 100% obsessed with the company being successful.

Just like entrepreneurship, standup is, ultimately, a solitary act between you and your audience. You create and perform, alone. You fail and succeed, alone.

When I felt the loneliest as an entrepreneur, having a community helped me tremendously. Mentors, especially experienced entrepreneurs who had once gone through the same experiences, helped inspire that there is truly light at end of the tunnel. Fellow founders, who were experiencing the same craziness, were an incredible sounding board to discuss problems and often just vent.

My experience in standup has been exactly the same. When you’re really struggling, other comedians are the greatest source of support. My friend Joe Nehme, an experienced comic and really funny guy, is always around when I’m feeling down. No one but a fellow comedian really understands the ups and the downs, the agony and the joy, of why aspiring comedians put themselves through this roller coaster. Sometimes all you need is a “You have potential!” and you can make it to another day.

Failure is totally okay, and can even be fun, when you have friends by your side.

3. You need to be a little arrogant

To be successful as an entrepreneur, you need a certain degree of arrogance that you are one of the best. This is even more the case as a standup comedian. In the traditional corporate world, you can spend your life as a moderately successful middle manager. With standup comedy, it’s essentially be CEO level or be out.  There are just not enough spots for everyone to make it.

If you don’t believe in yourself, if you don’t believe you are truly funny and clever enough to be among the best and most successful comedians, you will give up. The struggle is too challenging. Too long. Too fraught with uncertainty.

I am not sure if I will continue with standup comedy my whole life. Despite having a little bit of arrogance, I’m not sure if I’m really good enough to make it. But I’m going to try. I’m going to fight for the high of an entire room bursting into laughter. Because it really is the greatest feeling in the world.

by ruchirwp

Performing in Times Square

For me, the hardest part of doing standup is not caring what other people think. When you bomb terribly during a standup set, or even when you do well, there are always people who will judge you. The less you care what other people think, the better a comedian you will be.

To help tackle this fear, I spent Friday afternoon with my fellow comedian friend Carter performing comedy on the New York City subway and in Times Square. It went terribly, but it was a great learning experience.

As a new stand up comedian in NYC, you are always trying to get stage time. You’re not good enough for people to pay to see you, so it’s always hard to get a real audience. Enter: performing in public.

Legally, public performance is protected in the friendliest of terms by the First Amendment. In New York City, anyone is allowed to perform (and ask for money) in the city’s subway stations. The same right applies to the city’s streets. Performing in the subway cars themselves is illegal, but that may be for the safety of the performer more than for the commuters.

So, we decided to give it a shot!

First, we bought a big, blue bucket to ask for donations. Our goal was to make enough money to pay for the bucket. We bought the bucket for a lavish $4 and walked into the Times Square subway station, New York City’s busiest. We had our blue bucket, a cardboard box that could be made into a sign, and the wit of two of the city’s most confident comedians.

This was apparently not enough.

First we went to the mezzanine area- the part of the subway people walk through to go downstairs to the trains. Nobody stopped. We tried yelling, which got curious glances, but no one actually stopped to even say hello.

Then, we went down to the platform- right next to the trains. Here, we finally should have had a captive audience- people who have absolutely nothing else to do with their time. They could either wait for the subway in silence or they could listen to us. They all chose to wait for the subway in silence. We would walk over and start performing near a large group of people. Within a few seconds, before we even got to get into any jokes, everyone would move over to the other side of the platform.

After 30 minutes of this, we finally go these two teenagers to pay attention to us: two foolish individuals who were truly enticed by the prospect of a free comedy show. We finally got a chance to practice our material! And then they didn’t laugh at anything, politely leaving a few minutes later.

As we continued to experience complete and utter failure in the Subway, we went upstairs to Times Square and found a beautiful spot to harass the world’s tourists.


So many people walk through Times Square! It’s really something to behold. So many people completely avoid making eye contact- no matter how loudly you yell. A vast majority of people would make very quick eye contact, look away, and then read the writing on our box as they walked on by.

One guy was waiting for someone in the same area we were performing. Instead of coming by to watch us, he stayed as far away as humanely possibly – observing from a distance while apparently making a conscious choice that we weren’t good enough to observe close up or become engaged.

After about an hour of this, we decided to call it a day. Carter took the cardboard, I took the bucket, and we took the subway to an open mic. I’m definitely just a little bit more famous than I was before I did this.

What did I learn from this experience?

First and foremost, there is literally zero reason to care what strangers think about you. This is a great life lesson as well! Strangers – and even people you may know well – are wrapped up in their own problems, their own challenges, and their own busy lives. They think about you way less than you think about them; sometimes, they might not even notice you! Live life the way you want to live it without worrying about what others think.

Secondly, when performing comedy- or when doing any sort of presentation- it is critical to get people hooked extremely quickly. People have very short attention spans and, while it may have been an extreme in a subway station, a hook at the beginning is critical. You need to get people hooked before they make a snap judgement about what you’re offering them.

Lastly, I’ve gained a tremendous amount of appreciation for artists and musicians who are passionate beyond anything else about achieving their dreams. It was super challenging to do standup in a public location for one hour- I can’t imagine doing it day in and day out for years.

Next time I see a street performer, I’m definitely gonna stop and listen. And maybe even laugh. Just by being there, they are doing something truly incredible.