How I'm Skirting the Rules

How I Learned to Spot Talent and Create a Comedy Empire

Caroline Hirsch followed her gut instincts and has built a comedy empire in the heart of New York City.

In 1982, about nine years before the cable TV channel Comedy Central even existed, Caroline Hirsch had a feeling that stand-up comedy was going to become popular. So she trusted her gut and opened up a small cabaret club in the Chelsea neighborhood of New York City. Ten years later, she relocated the club to the heart of Manhattan’s Times Square neighborhood and named it Caroline’s on Broadway. The 300-seat venue is open seven days a week and continues to draw big-name comedians and large crowds who come to wine, dine, and laugh. In 2004, she also created the annual New York Comedy Festival, a five-day festival that features more than 200 comedians who perform in more than 60 shows at more than 20 venues all over New York City. Below, Hirsch reveals how she spots talent, reels it in, and juggles the many tasks of running her own business.

I or my company is Skirting the Rules by going with my gut. Now there are cable networks doing comedy, but when I started my club 37 years ago, comedy was not a big deal. I was working in retail out of college, and I had friends that wanted to open a club. At first it was cabaret, and then we wanted to do comedy.

Around 1982, in the club’s early days, we had seen Jay Leno on TV doing comedy and we tracked him down through his agent and hired him. Over the years, we went on to hire comics like Billy Crystal, Garry Shandling, Sandra Bernhard, Kevin Hart, Norm MacDonald, Whitney Cummings, Chelsea Handler, Jerry Seinfeld, and many others.

A time when I found the possible (a creative solution) within the impossible (against incredible odds) is… What I did was an original thing and there were certainly not that many women in New York doing it. I faced a lot of challenges when I was first starting out. How do you convince people to come work with you?

Sometimes you ask for a favor. When it came to Billy Crystal, for example, I had a friend of mine put in a good word. My friend told him, “You should work at this club that just opened. It’s really good. I know the people.” So Billy came and he sold out.

Another key was paying the performers well. A lot of clubs in New York, even today, don’t pay the performers much, if at all—maybe $20 or cab fare. The comics go do 15 minutes at those places just to try out new material and practice their jokes. We were the first club to headline these people that were kind of known and that got us a national presence. The performers come and do their whole act and people come to see them. That’s why Caroline’s is different and why no one in New York City does what we do here.

An example of how listening to my intuition has helped me is… I can watch a comedian for about 10 minutes and get a good or bad feeling about the person. I look for originality and delivery. I listen to my gut and make a decision quickly.

My secret talent is… When I make a decision, I stick with it. I say yes or no fast and I’m not wishy-washy. It’s instinctive. I either like something or I don’t, and I never waver. It comes from years of experience and age.

A lot of people like to use the word “pivot” now. But I say: If you come up with an idea and you think it’s great, stay with it. People are going to slap you down, but if you can stay with it and give it a try, you may achieve your vision.

 A woman is most powerful when she knows her own mind. It means having a certain amount of confidence in what you do. I make too many decisions in a day to second-guess myself.

I remember feeling more confident when I finally got over the hump in business. In the beginning, you might make some money, then lose some money, and then break even, etc. It may vary from month to month. But once you start consistently making money, that’s a good feeling—when you feel steady and stable in your company.

What I wish I had told my myself when I was starting out is… I probably should have been a lot more aggressive earlier on and I should have branched out more in the beginning. For instance, in 2004 I created the New York Comedy Festival. And maybe I should have created that sooner. It has been very successful. When I was younger, I wasn’t as confident as I am now.

My favorite skirt (a.k.a a life hack or life rule) is… I try to get one main thing accomplished each day. That’s my goal. I keep it simple. The job can be overwhelming, because I wear many different hats. I manage about 40 to 50 people all together. I have a talent director, a COO, a social media manager, a public relations specialist, servers at the club, etc. I manage the club all year long, and I oversee the comedy festival each year. I have to switch back and forth between management, going to parties, doing public relations and advertising, and other things.