A Tight Ten Startup Pitch

TightTen2In the world of startups and venture capital, developing a killer elevator pitch can make all the difference. I’ve found that the somewhat parallel world of stand up comedy can provide valuable insights for crafting an engaging and effective pitch. In comedy, a "tight ten" refers to a perfected ten-minute routine that requires meticulous writing, practicing, and refining. Similarly, a venture pitch, whether it’s a quick two-minute elevator pitch or a more extensive 10-20 minute presentation with slides, can benefit greatly from these comedic principles. 

Many years ago, I decided to try doing a stand up comedy routine, mainly for the hell of it, but also, to see what this could teach me about how to be a better public speaker. There was an open mic night at the local comedy club. When I signed up, they put me at the very end of the list because they’ve never seen me before. I finally got on stage around midnight. Honestly, I was pretty terrified! I can still remember this one joke I wrote, “I just got back from Hong Kong, and you know I bought a suit there, because, well, everybody does.” My punchline was that the sizes in Hong Kong were funny, the suits came in "Japanese, Chinese, Samoan, and extra Samoan". People laughed, and at that moment, I realized that doing stand up comedy could be as addictive as heroin. The club asked me to return because I "showed potential", but I knew that this was fun, but wasn't my calling.

Anyway, I did learn from the experience, especially how to apply the rules of comedy to the elevator pitch, so here are "ten tips for how create a tight ten" for your business pitch:

 1. Start by brainstorming

A comedian knows that you need to produce a lot of ideas for material, to cut down to a few gems that form the spine of your tight ten. The same goes for designing your pitch. And it’s more than just articulating your value proposition, target market, business model, and unique selling points. It has to connect emotionally.

2. It is Crucial to Come up with a Strong Opening

In comedy, you need to capture the audience’s attention straight away, and the same holds true for pitching. It’s crucial to begin with a hook that draws investors in. This could be a startling statistic, a powerful quote, or a brief but engaging story that highlights the problem your venture solves. 

3. Vary Your Material, Volume, Cadence and Sense Dominance

A comedian uses different types of humor, and varies speaking volume and cadence, to keep the audience engaged. Similarly, a funding pitch should be dynamic - mix data with anecdotes, and use visuals or unique gesticulations to illustrate points… whatever it takes to keep the presentation engaging.

4. Timing via Breathing

They say that timing is critical in comedy, but I’ve found that it’s really about comedic breathing. The same is true for venture pitches: remaining centered and in your breath is vital. You have to keep it moving to hit the key points, but at the same time, allow moments for your audience to “get it” when you get to the punchline.

5. Test Your Material

Comedians test their material at open mics to gauge reactions and refine their delivery. Similarly, you should practice your pitch in front of various audiences—mentors, colleagues, friends. Remember tht the ability to hit home runs requires actually swinging a bat... a lot. I host a regular event, called a pitch practice party, once a month, so we all get to practice in front of supportive people.

6. Refine Transitions

Smooth transitions between jokes are essential for a cohesive comedy set. In a pitch, seamless transitions between different sections—problem, solution, market, financials—are equally important. Practice connecting these sections so they flow naturally and maintain a coherent narrative throughout your presentation.

7. Cut Until it Hurts

Comedy and pitching are subtractive media for creativity. Being concise is a hallmark of both a great comedy routine and an effective pitch. Eliminate filler words, jargon and irrelevant details that don’t contribute to your core message. This keeps your presentation focused and ensures every second counts, particularly in shorter pitches. If you need just a extra minute to tell your story, you don't.

8. A Big Finish

A stand up comic has to open strong and finish big. Similarly, your pitch should conclude with a strong closing that reinforces your key message and leaves investors wanting more. One tip is to reconnect to the beginning. The first time I heard the term “tight ten” was in the TV show, The Marvelous Mrs. Maisel. She begins her tight ten - one of the best comedy routines of all time - not being able to remember her kids names… and ends it by remembering. This allowed her audience to reconnect to the beginning for a sense of completion.

9. Be Genuinely Authentic

Successful comedians know that authenticity is vital, and the same is true for entrepreneurs pitching. It is crucial to be genuine and passionate about your venture, and without artifice in your presentation. So yes, include personal stories to build trust and connection at an emotional level. A great way to establish authenticity is by “laying pipe” during the initial chit chat or self introduction before the meeting starts in earnest. 

10. Rehearse the Hell Out of It

You have to practice your pitch to build confidence and familiarity with your material. Practice, practice, practice… in front of a mirror, recording yourself, or presenting to small groups of friends, so you can perfect your pitch. So if you want to hit a home run, practice. 

Special Bonus Tip: Handling Hecklers Gracefully

Stand up comics need to develop strategies for handling hecklers to maintain control of the room. I can still remember delivering a zinger to a drunk lady, “Ma’am, you really need to stop setting your vibrator on stun.” The equivalent of a heckler for the entrepreneur is the venture bureaucrat. That’s any VC who says “we’re looking for commercial traction” or “we’d be happy to co-invest when you find a lead.” You need to find a polite way to say, “Oh, my apologies, I didn’t know you had your testicles removed.” (But don't, no matter how much you want to, say this out loud to a VC.)

Conclusion

Applying the principles of comedy to venture pitching can transform your presentation from mundane to magical. Most importantly, it's not about being funny, or telling jokes, it's about accessing. your humility and humanity. It's about using these techniques to elevate your pitch, and then practice the hell out of it. Just as a comedian needs a polished tight ten, you know, in case they’re asked to fill a cancellation on the Tonight Show, you never know if you’re going to be stuck in an elevator with Richard Branson. 

My personal goal is to someday, somehow, present a venture pitch like a stand up comedy act. But like the character actor Edmund Gwenn, said on his death bed, “Dying is easy, comedy is hard.”

Well, he obviously never had to raise money for a pre-revenue startup!