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5 Ways Hecklers Can Prepare You for Pitching Investors

From improvisation to how to read a room, stand up comedy has a lot to teach entrepreneurs.
5 Ways Hecklers Can Prepare You for Pitching Investors
Image credit: Cindy Ord | Comedy Central

When I sold my second startup in September 2013, I found myself with the free time to pursue one of my greatest passions: Stand up comedy.

I’d always been fascinated by comedians and was deeply curious about the craft. So, I left Silicon Valley, where I’d spent years carving out a career in technology and entrepreneurship, and dove into the New York City comedy scene.

During the year I spent performing in New York comedy clubs, like any profession I had highs and lows -- sometimes during one performance alone. Once I followed Tracy Morgan on stage, bombed terribly, only to have him chase me down afterwards and offer words of encouragement.

Related: I Recently Made My Stand Up Comedy Debut. It Was Terrifying, But So Rewarding

Like any comic, I suffered through my fair share of hecklers. While it can be jarring and even a little painful at first, I eventually learned how to handle them on stage. And after moving back into the startup world, I quickly realized that if you know how to deal with hecklers at a comedy club, you'll be better prepared to deal with pitching investors on your next idea.

Here are five lessons hecklers taught me that have improved the way I pitch investors.

1. How to have thick skin

Stand up comedy is an incredibly vulnerable craft. You’re on stage alone, and there’s a literal spotlight on you. So when someone heckles, it can seem like a direct indictment of everything about you. Suffering through every insult imaginable makes you battle-ready.

Thus, when you realize you can survive hecklers, you gain the confidence to take risks in other areas of life and learn not be afraid of what others say. When a VC criticizes you or your idea, you take it in stride. And the good news is that investors aren’t nearly as obnoxious as hecklers and likely have a much lower blood alcohol level.

Related: 6 Tips for Perfecting Your Elevator Pitch

2. How to improvise

Comedians approach each show with an idea of what jokes they want to tell, and in what order. There’s a flow where you segue from one joke and topic into another. Heckling disrupts all that and immediately challenges the dynamic of stand up comedy. When this happens, the crowd will watch to see if the comedian can restore order. Some comedians will talk to hecklers and try to incorporate them into the show. Others will shut them down in ways that are clever, and sometimes brutal. Whatever the method, handling hecklers tactfully is an art. You have to make the heckler shut up in a way that’s funny, but doesn’t make the crowd turn on you -- all in a matter of seconds.

Investors aren’t all that different. They want to invest in people who can think on their feet, and who won’t buckle when things get chaotic. Investors look for and test qualities when they meet with entrepreneurs. You’re in the room because your idea has some merit but a VC is also investing in you and your ability to think strategically with great efficiency. Freezing up really isn’t an option.

3. How to read a room

When I performed at the People’s Improv Theatre, we used to say there’s no such thing as a good joke -- only good reactions to jokes. Stand up comedy is a relationship between the comedian and audience. Good comedians are always reading the room to see if they’re losing the audience, or to see if certain audience members look like they might start heckling. When the audience becomes bored, it not only stops laughing but shows it through body language and facial expressions.

Pitch meetings are similar. Certainly there are plenty of direct questions from investors. They want to know every detail of the idea being pitched to them. But nonverbal cues are critically important as well. If they’re not asking a lot of questions, chances are they’re not interested. In that case, it’s time to reevaluate the strategy behind your pitch.

Related: Unicorn Investors: The Top 5 Firms With the Best Records

4. How to cater to a diversity of worldviews

People heckle for a variety of reasons. Some jokes are simply bad and bomb. Sometimes a joke’s subject falls outside their realm of experience. Take Jim Gaffigan’s “Hot Pockets” routine. Some people have never eaten Hot Pockets, so a tiny percentage of this group might heckle Gaffigan because they can’t fully participate in the joke. They don’t have enough information. People also heckle when jokes are too obvious. Maybe they’ve heard the joke before, or they see the punchline coming. In these cases, hecklers are bored and choose to heckle because they have too much information.

Investors can evaluate ideas similarly. They come into each meeting with a unique worldview, and sometimes your idea won’t immediately resonate with them for a variety of reasons. Perhaps they don’t have enough information. Maybe the product is for young mothers but you’re pitching a 55-year-old white male who never married. Sometimes investors can be just like hecklers -- we’ve all seen Shark Tank. Yet sometimes it’s very hard to gauge what they really think, and you must pull their perspective out of them as otherwise, you gain nothing from the meeting.

Related: Want to Wow Potential Investors? You Have 19 Seconds.

5. How to pivot

One painful truth about hecklers is that they’re not always wrong. A heckler might hurl an insult your way that’s devastatingly spot-on. Even worse, it could be funny. But just because it’s true doesn’t mean it’s the only way to look at things. For example, most people would say that a hammer is a tool. But what is a hammer in the hands of a man being swarmed by zombies in The Walking Dead? It’s a weapon.

Good comedians reframe a heckler’s idea to work in their favor, and keep the audience on their side in the process. When launching a new business, your idea will more often than not have some shortcomings. Investors will inevitably point these out -- the almighty “pivot!” Instead of denying your shortcomings or trying to cover them up, take a note from stand up comedy and say to investors, “You might be right about that. But let’s look at it from this angle.” Particularly if it means getting that $1 million in seed funding. Either that or throw a beer at them.