Perfect people don't close deals
How I bombed my first keynote in front of 400 people and got booed off stage.
Everyone's worst nightmare happened to me on stage in front of 400 people.
Let me paint you this picture.
I'm a brand new executive at Anywhere and it was my first big trip. I was opening for our CEO at an event in Michigan.
Now if you know me, I bleed scarlet and gray – Ohio State Buckeye through and through. And if you know that rivalry, then you know Michigan is basically the worst place in the world for a Buckeye.
(Fun fact: I was in the marching band at Ohio State. So yeah, I'm THAT level of Buckeye.)
The night before, I watched the CEO make some college football jokes. He killed it. Room loved him.
So I thought, hey, I'll do the same thing.
I opened with: "Quick question – has it been 10 or 11 years since Michigan beat Ohio State?"
I didn't get silence.
I got boos.
Actual boos.
Someone yelled "Get off the stage!" Another guy shouted something about Ohio State that I can't repeat in this email.
My first big trip. 400 people. Hating me. 30 seconds in.
Here's what saved me:
Owned it (sort of): "Look, I'm a Buckeye – trash-talking Michigan is literally in my DNA. I couldn't help myself."
Made fun of myself: "This is what happens when you trust someone whose best college memory is dotting the 'i' in Script Ohio."
Kept moving: "Since we've established I went to a school only known for its football program, let me tell you why we're here today and how we're going to help you make this the best year of your life."
The whole room laughed. It was like air being let out of a balloon.
Tension broke and the speech went great.
Here's the thing:
People don't trust perfect. They trust recovery.
When you fall and get back up, people see themselves in you.
And here's the most important part: People buy from people they see themselves in.
This works for everything:
When your opener bombs
When the connection just isn't there
When your comment lands wrong
When the vibe shifts and you don't know why
Your safety net:
ChatGPT prompt: "I need help. I made an awkward [joke/comment] about [topic] and it completely bombed. Give me a quick self-deprecating recovery line that acknowledges it was bad but keeps things light and moving forward."
But honestly? ChatGPT's great, AI helps, but your natural reaction is probably way better.
The real secret: Recovering well beats landing perfectly every single time.
So take the risk.
If it bombs, you've got this.



