The other day, during a workshop with Ukrainian and Moldovan founders, someone asked me a question I get all the time:
"Should I use jokes in my pitch?"
And I'll be honest - I love jokes. I think most people do.
There's something magical about laughter in a room full of investors. It lowers defenses. It creates connection. When a joke lands, it really lands.
But as I thought about my answer, I realized I needed to give her a warning.
Because humor is one of the riskiest tools you can use on stage.
And I've seen it go wrong more times than I can count.
The Joke That Killed a Pitch
A few years ago, I watched a founder open his pitch with what he thought was a clever joke about his competitors.
He delivered it. Paused. Looked around the room.
Silence.
Not awkward silence - confused silence. Half the room didn't get the joke. The other half was still processing.
He panicked. Started explaining the joke. Made it worse.
By the time he got to his actual pitch, his confidence was shattered. The investors had already mentally checked out.
That's the thing about jokes: when they work, they're magic. When they don't, they're poison.
What I've Learned About Humor on Stage
The timing is crutial.
A joke isn't just words - it's rhythm.
Where you pause.
Where the punchline lands.
How long you wait before continuing.
The founders who "kind of wing it" almost always fail. The ones who rehearse it twenty times usually nail it.
Test it outside your bubble.
Internal jokes are pitch killers. If only your co-founder laughs, it's not a pitch joke - it's a Slack joke.
Run it by people who don't know your industry. Ask: Is this actually funny? Could it be misunderstood? Does it require insider knowledge?
Hold your silence after.
This is the one most founders miss. After a joke, you must be quiet.
The audience needs time to hear it,
realize it was a joke,
decide if it's funny,
and then laugh.
That process takes longer than you think - especially in bigger audiences. If you start talking too soon, you kill the laugh before it happens.
The Deeper Issue
Nerves destroy humor faster than anything.
When you're nervous, your timing speeds up. You rush. You talk over your own punchline. What sounded hilarious in rehearsal suddenly falls flat - not because the joke is bad, but because your delivery crumbled under pressure.
That's why I tell founders: if you're not confident enough to hold five seconds of silence after your joke, you're not ready to use it.
The Bottom Line
Should you use jokes in your pitch?
Yes - if you've practiced the timing, tested it with outsiders, and you're confident enough to embrace the silence.
If not?
Clarity beats comedy. Every single time.
A clean, confident pitch will always outperform a risky joke that might land - or might crater your credibility.
So be honest with yourself: Is this joke serving the story? Or is it serving your ego?
If you can't answer that clearly, leave the joke out.
What's the best - or worst - joke you've seen in a pitch? Hit reply and tell me. I'd love to hear your stories.
See you next week.