5 Pitching Lessons I Learned from a New York Stand-Up Comedian
5 Pitching Lessons I Learned from a New York Stand-Up Comedian
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5 Pitching Lessons I Learned from a New York Stand-Up Comedian
Yesterday, I attended a fascinating Creative Mornings talk titled "5 Lessons Being a New York Standup Comedian Taught Me About Winning Pitches" by Katherine "Billy" Williams. Her experience as a New York stand-up comedian provided fresh insights on how to approach pitching with authenticity, confidence, and a great delivery.
When she's not pursuing her dreams as a stand-up comic at night, Katherine works as a digital marketer during the day.
Here are the key lessons Katherine shared, backed with stories from her time on stage and in the boardroom.
1. Be Authentic: Know Your Personal Brand and Have Your Elevator Pitch Ready
Authenticity, as Katherine explained, comes from acknowledging your truths and vulnerabilities. In comedy, she said, being authentic means asking yourself the three big questions:
What annoys you?
What is your biggest fear?
What is your fatal flaw?
"From a comedian's point of view, being authentic is asking the three big questions and admitting your painful truths on stage," Billy shared during the talk.
Katherine’s Australian experience helped her connect with audiences in New York, even when the audience was rowdy and drunk. She emphasised that being authentic in pitching is just as critical as it is in comedy. When you're genuine, you build trust with your audience.
Katherine also stressed the importance of having your elevator pitch ready:
"You have to say, ‘This is what I do, this is who I am, and this is what I bring to the table,’ in less than 30 seconds."
2. Know Your Pitch Voice: Be a Pitcher's Pitcher
Katherine’s second lesson highlighted the importance of finding your pitch voice. Just like comedians aspire to be a "comedian's comedian"—someone beloved by fellow comedians—you should aim to be a "pitcher's pitcher."
Katherine explained, "I want my CEO to say, 'I want Billy on the pitch team. I know her voice, and I know she's authentic.'"
This is where storytelling comes in. A good pitch involves connecting with your audience through personal stories. Katherine described how she connected with a room full of drunk tourists in NYC through her authentic Australian stories and observations.
She referenced the James Joyce quote, “In the particular is contained the universal,” and shared how leaning into her personal experiences created a stronger connection with the audience:
"If you lean into the detail and into your personal experience, you'll have a stronger connection with them."
Her takeaway? “Capture the mind and shoot for the heart.”
3. The Difference Between Good and Brilliant is the Delivery
Delivery is everything, whether you're on stage or pitching to a client.
Katherine explained,
"Comedy is about rhythm. If you go too fast, you lose them. If you go too slow, you lose them. It's all about finding the right pace."
She talked about how she once had to adjust her delivery mid-set during a New York gig. The audience wasn’t responding, so she slowed down and made her setup clearer, which turned the set around.
The same concept applies to pitching. Reading the room and adjusting your tone, pace, and energy is key to keeping the audience engaged.
Katherine also introduced the Rule of Three, a technique in comedy where you build a premise, reinforce it, and then hit the punchline on the third point.
Here’s a comedic example:
When you die there’s a light at the end of the tunnel. When my father dies, he’ll see the light, make his way toward it, and then flip it off to save electricity. —Harland Williams
In pitching, this could look like setting up your message with two key points the audience expects, then delivering an unexpected third point that grabs attention.
As Katherine explained,
"The Rule of Three is a great way to convey information to an audience in a very clear, concise, precise way."
Here’s how the Rule of Three could be used in a pitch to sell a service:
Premise:
"When it comes to generating leads on LinkedIn, there are three key strategies that we focus on."
Reinforcement:
"First, we optimise your profile to resonate with your ideal buyers. Second, we create high-value content that addresses their specific pain points. And third, we use LinkedIn’s Sales Navigator to connect directly with decision-makers... without sending a single cold email."
Punchline:
"Instead of relying on cold email outreach, imagine getting leads coming directly to you through strategic engagement—because no one likes a spammy inbox."
4. Craft Your Act: Know When to Stop Talking
Katherine broke down the structure of a joke—premise, setup, and punchline—and how it applies to pitching. She shared how knowing when to stop talking is just as important as the punchline itself.
"We say the funny thing, and then we stop talking," she explained.
In a pitch, this translates to knowing when your audience has understood the core message and leaving it at that.
Katherine also shared the importance of editing, both in comedy and pitching:
"If I get to the third or fourth line and nothing adds value to my core concept, get rid of it."
Her advice? Edit ruthlessly. Every word should add value to the message, and you should know when to stop talking once your point has been made.
5. Post-Show Drink is a Must: Network and Build Relationships
Katherine wrapped up with an unexpected but crucial lesson—the post-show drink. In comedy, after a show, comedians gather at the bar to network and build relationships, and Billy stressed how important this part of the process is.
"After a gig, it’s not just about the laughs. You hit the bar, talk to your peers, and network. It’s where relationships form," she shared.
In business, this doesn’t necessarily mean grabbing a drink at the bar. If you don’t drink, find other ways to connect—grabbing coffee, going for a walk, or even staying back after the meeting to chat. The key is to make time to build relationships after the pitch. I’d add here that it helps to build rapport before the pitch.
Practical Tip: The "post-show drink" is a metaphor for staying engaged with your team or client before and after the formal presentation. You don’t need alcohol to network—what matters most is nurturing those connections.
My Personal Takeaway
Katherine talk reminded me that pitching, much like comedy, is about authenticity, storytelling, and connecting with your audience.
It was a timely reminder that whether you're in the boardroom or on stage, the skills you develop in one arena can always be transferred to the other.
Oh and I feel it might be time to get back out in front of audiences again.
How might you apply these lessons to your next pitch or presentation?
👍 PUBLISHED + WORK IN PROGRESS
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