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I Failed as a Stand-up Comic. Here's How It Made Me a Better Entrepreneur. Here's what I learned from a failed career in stand-up comedy.

By Justin Vandehey Edited by Chelsea Brown

Opinions expressed by Entrepreneur contributors are their own.

In the middle of a quarter-life crisis, I began evaluating my professional career choices. While working a day job as a sales executive at a very large and successful tech company, I became jaded by corporate jargon, acronyms and daily standups. So, to spite my professional career, I started a personal blog as an attempt to go out on my own and build an audience. The premise for my blog, a.k.a. Justin's Live, was that every weekend, I'd visit a new restaurant or bar with friends in San Francisco and write up a comedic review of the weekend shenanigans.

My thought was that the reviews would be informative and hilarious. What I learned was that my reviews were in fact useful, as I observed readers cross-posting on their travel blogs; However, no one thought the content, or the producer of the content, was funny or entertaining.

So, in an attempt to become a more entertaining writer for the blog, I decided to sign up for stand-up comedy classes in San Francisco. Every week, I began writing jokes and standing up at open mics throughout San Francisco. While I don't believe I got that much funnier, I believe every entrepreneur should try stand-up comedy at some point in their lives. Here are a few ways that a failed career in stand-up comedy made me a better entrepreneur.

Related: This Comedian Breaks Down Stand-Up, Startups and Entrepreneurship

Farts aren't always funny

The first time I stood up at SF Comedy College for an open mic, I delivered the perfect fart joke. It involved my grandparents, a church pew and the act of confession. Not a single person in the room laughed. Not one.

Fart jokes aren't unique or special. They're funny when the actual fart happens, but someone talking about a fart isn't all that entertaining.

It's no different when you're a valuable startup that solves a real customer problem. My former investor, Phil Libin, uses the analogy of building new apps into a developing ecosystem. When Apple launched the concept of mobile apps, there were hundreds of fart apps, but none of them stuck. It took years to build quality experiences that solved real customer problems. Farts are a shortcut. Same as the F- word. Go deeper to find substance versus relying on cheap laughs.

The blinking red light

Whenever a comedian bombs on stage, they get the flashing red light indicating that their time on stage is over. The quicker you fail on stage, the faster that red light flashes in the back of the audience. I became really accustomed to seeing that flashing red light, or in other words, experiencing rejection from an audience that didn't think my aforementioned fart jokes were funny.

It took six months of visiting late-night open mics before my sets progressed beyond two minutes. What's more, throughout the process, my skin thickened. I noticed my performance in my day-to-day selling career improving. I was able to manage more difficult conversations, and I didn't take "no" personally. The blinking red light taught me how to deal with rejection and failure in a very public manner. No matter how bright or fast that light blinks, don't be afraid to face the red light.

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

Riffing and reading the room

On several, if not most, occasions, my written material bombed. So, during many of those sessions, I was forced to "riff," or improvise, by engaging directly with an audience.

As every improv purist knows, stand-up comedy and improv are two very different things; However, there are a number of skills from applied improv that carry over to stand-up comedy. The ability to take cues from an audience, accept their offer and riff on it, is one of the most important and valuable skills I've obtained as an entrepreneur.

Whether it's handling sales objections, defusing conflict or collaborating on a whiteboard, the ability to listen to a group of people, take what they give you and build upon it is a superpower.

Nailing the punchline

With every open mic set, I made it a goal to get at least one joke to land. It took months to get a full two- to three-minute set where I was stringing a handful of decent jokes together to avoid the blinking red light.

These were a couple of things I learned in the process of nailing my punchlines:

  • I found that the more specific I got into the details of real-life scenarios and problems, the more those stories resonated with my audience.

  • I learned to use hard consonants because words with letters like K, B and P are just funnier.

  • By using the foundations of joke structure, I could take an audience's preconceived opinions and expectations about everyday scenarios, like going to the grocery store, and break those expectations by injecting an unexpected outcome to make them laugh.

  • The more life experience I acquired, like getting married and having kids, the more relatable my material got.

Coincidentally, this process and these insights were identical to the work that was required in finding product-market fit and crafting stories that resonated with investors, partners and customers. More specifically:

  • The more I focused on the specific pain of our customers and understood their business and lives, the better my "material" got.

  • During my startup pitches to VCs and customers, I learned to focus on the language I used to communicate my ideas.

  • In scenarios where venture capitalists or prospective customers had established beliefs about a problem area, I could break their expectations by showing them a better way forward.

  • The more work experience I obtained, the more I could speak to real-life business problems and tell a story about how to fix them.

Related: How Amit Tandon Turned Comedy Into Serious Business

It goes without saying that I'll likely never become Dave Chappelle or Chris Rock, nor will I sell out an entire stadium to hear my legendary church pew joke. There isn't a blinking red light big enough for my stand-up comedy career; However, not to "toot" my own horn, but I'm confident those late-night open mics helped me put the gas on my entrepreneurial endeavors. So, entrepreneurs, what are you waiting for? Let 'er rip! (Ok, I promise that was the last one).

Justin Vandehey

Entrepreneur Leadership Network® Contributor

Cofounder of Disco. Producer of the Bridge podcast

Justin Vandehey was the cofounder of Disco, the first company built on Slack & Microsoft Teams. In 2021, Disco was acquired by Culture Amp. He currently leads partnerships and business development for Culture Amp. He is an advisor for the Alchemist Accelerator & invests in early stage B2B startups.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

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