What I learned from getting rejected by 200 event planners
Before I had a speaking career, I had a rejection folder. Two hundred event planners who said no, didn’t respond, or said “we’ll keep you on file” which is the corporate equivalent of “don’t call us.”
I kept every one of those emails. Not as motivation. As data.
TL;DR: I got rejected by over 200 event planners before I built a consistent speaking calendar. Each rejection taught me something about my pitch, my positioning, or my ego. The speakers who make it aren’t the most talented. They’re the ones who keep pitching after the 200th no.
The first 50 rejections
My early emails were terrible. Long, unfocused, trying to cover everything I could possibly speak about. I pitched myself as a “leadership and resilience and advocacy and business speaker.” That’s not a pitch. That’s a word salad.
The first lesson was simple: pick one thing. I stopped pitching four topics and started pitching one. Resilience in leadership. Three words. Easy to remember, easy to refer.
Rejections 50-100
My pitch got clearer but my follow-up was nonexistent. I’d send one email, get no response, and move on. I assumed silence meant no.
It doesn’t. Silence means busy. Event planners are managing budgets, logistics, venues, catering, sponsors, and a hundred other things. Your email about a keynote speech is item number 47 on their list.
I started following up at 7, 21, and 60 days. My booking rate doubled. Not because my pitch got better, but because I stayed in front of people long enough for them to have a need that matched my offer.
Rejections 100-150
This is where I almost quit. A hundred nos will do that. I started questioning whether I was good enough, whether anyone wanted to hear what I had to say, whether the whole thing was a vanity project.
What kept me going was the occasional yes. One planner booked me for a chamber of commerce event. The audience feedback was strong. She referred me to two other planners. Those two became three bookings. Three became six.
The business didn’t build linearly. It built in clusters. One yes led to several, then a dry spell, then another cluster. Understanding that pattern kept me sane during the dry spells.
Rejections 150-200
By this point, my pitch was tight, my follow-up was consistent, and I had enough testimonials to fill my website. The rejections shifted from “we’ve never heard of you” to “we’ve already booked our keynote for this year.”
That’s a different rejection. That’s timing, not talent. So I started planning further out. Instead of pitching events three months away, I pitched events a year away. That single shift changed everything because now I was in the conversation before the decision was made.
What 200 rejections taught me
Your pitch is a product. Refine it constantly. If it’s not converting, the pitch is wrong, not the audience.
Timing matters more than talent in sales. Be in front of the right person at the right time, and a mediocre pitch beats a great one that arrives too late.
Rejection is information, not a verdict. Each no tells you something if you’re willing to look at it honestly instead of taking it personally.
The speakers who succeed aren’t the most talented ones. They’re the ones who kept pitching after the 200th no. I know because I’m one of them.
About Khary Penebaker
Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership experience in construction, operations, and civic engagement.
Frequently Asked Questions
How many pitches does it take to book a speaking gig?
Expect a 2 to 5 percent conversion rate on cold outreach. That means 20 to 50 pitches per booking. Warm referrals convert at 20 to 30 percent. Build relationships, not just a pitch list.
How do speakers handle constant rejection?
You separate your worth from the response rate. A no usually means wrong timing or wrong fit, not wrong speaker. Track your numbers and focus on improving your pitch, not taking it personally.
What makes a good speaker pitch email?
Three sentences or less. State the event name, the topic you would speak on, and one specific result a past audience got. Attach your one sheet. Do not write a novel.
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Last updated: March 13, 2026
