My brother Andrew is an award-winning standup comedian with fifteen years of experience on stage.
He has never cold called anyone in his life.
I asked him which was harder: cold calling or standup? Without flinching he said, "standup."
So we put it to the test. I handed him a list, walked him through the basics, and we dialed for an hour.
Now, I spent the first 7 years of my career teaching teenagers how to write.
One thing that experience drilled into me:
If you really want to learn something at a deep level, try teaching it to somebody else.
Unsurprisingly, teaching my broski to dial also taught me.
Here are 3 things he learned, and 1 thing I learned:
- Takeaway #1: Earn their attention by naming a problem they actually have
- Takeaway #2: Keep dialogue flowing by always “serving it back”
- Takeaway #3: Use "worst case" to sell the meeting
- Takeaway #4: Keep them laughing
Takeaway #1: Earn their attention by naming a problem they actually have
Sellers talk A LOT about cold call openers. But verrrrry little about the next thing you say, which in my opinion is far more important.
Once you've got someone’s permission to pitch, the next thing out of your mouth should be a problem you believe they're experiencing, based on what you know about their business.
DO NOT start talking about yourself. That way lies hangups.
Hypothesizing a specific problem shows you've done your research and you understand the buyer’s world. It is far more likely to get their head nodding and earn you enough interest to talk about how you help.
Here’s an example we use at 30MPC:
"Given how fast you're growing, I'm guessing your enablement team is stretched too thin for tactical coaching on the skills that actually win in 2026. Have some ideas for how we could help, but not sure if that's actually what you're dealing with."
Here’s an example of Andrew selling comedy show tickets:
"Most companies are hybrid or remote right now and are looking for fun ways to bring people together in person, but corporate events just aren't that fun. Looks like your team is part-remote. Is that right?"
One of two things happens from here: the prospect nods along because you've named a real issue they’ve been thinking about. Or they tell you that's got nothing to do with their business and kick rocks.
So you either keep talking or you learn they’re not a good fit.
Win-win.
Takeaway #2: Keep dialogue flowing by always “serving it back”
Every sentence you say on a cold call has the goal of earning the right to say one more sentence. You never want the flow to fizzle.
The easiest way to keep earning more sentences is to end each statement with a question or a statement that puts the ball back in your buyer’s court:
"Tons of ACME sellers are fans of 30MPC. Have you heard that name tossed around?"
"Usually that means reps are struggling to get executives' attention, but not sure if that's true in your case."
"Had a couple ideas for how we could help if you're open."
Nothing is guaranteed, nothing is granted. Andrew described it better than I could: "It's like waterskiing. You have to hold onto the rope and stay up."
Every time you let a statement just hang there, you're letting go of the rope. Ask a question. Make a statement that invites a reaction. Keep it moving.
Takeaway #3: Use "worst case" to sell the meeting
Your only job on a cold call is to get agreement for a longer conversation.
One of the best ways to do that is "worst case" framing.
Instead of just asking for time, make it clear why that time is going to be valuable, even if they never talk to you again:
"Want to talk more when I'm not calling you out of the blue? Worst case, you share some areas the team is struggling with and I'll point you to some free resources that'll make an impact right away."
"Any interest in learning more about that another time? Worst case, I’ll tell you a couple jokes you can use around the office."
If the meeting itself feels valuable, that's a much easier yes.
Takeaway #4: Keep them laughing
My favorite moment from the whole day came after Andrew got shut down hard.
A woman picked up, heard what he was calling about, and immediately said she was not interested. Not even a little.
She chuckled a bit, though.
Andrew caught it immediately: "Well, you sure? Because you're already laughing."
She cracked up and then immediately spilled her guts about the state of the business. I was kinda shocked. It was still a no, but a “good no.”
Not every cold call ends in a booked meeting. But if you learn something that sharpens your POV for the next conversation at that account, that’s a win.
So no matter what happens, if you can stay light and loose, and especially if you can get them laughing, you stand a great chance of having a meaningful chat.
Conclusion: Success isn’t always a meeting
Cold calling is harder now than it maybe ever has been. The AI noise is deafening, buyers are fatigued, and most reps are one bad quarter away from convincing themselves it doesn't work.
It does work. But you need to get really clear about how to define success.
Success is not always a meeting. Sometimes it's learning something real about the account, or having an actual conversation that warms up a relationship worth coming back to.
And if that still doesn't work out, well, maybe try standup comedy. According to Andrew, it's way easier.
Check out the full video of me teaching my standup comedian brother how to cold call here:
