What a teenager taught me about cold pitching

He cold pitched Mark Cuban (and got a reply) at 16. How's your outreach going?

I first met Shamus Madan the way I first meet a lot of people: by cold pitching him clients (in this case, for his podcast Clock Speed). When he was visiting San Francisco recently, we grabbed breakfast at Jane on Fillmore. Side note: can we normalize breakfast meetings over happy hours? Great energy for the day. Okay, back to the point.

Halfway through my latte, I realized this 19-year-old had sharper cold pitching instincts than most comms pros twice his age.

Case in point: he got Mark Cuban to respond to a cold email. At 16. No warm intro. No favors. Just a sharp, specific, well-timed note. The first pitch didn’t work. But the second one did. Because Shamus rewrote the email — not to make himself sound smarter, but to make it easier for Mark to say yes.

As comms pros we’re often asked about “who we know.” I can answer that, but I light up when instead asked about pitching people I don’t know. Relationships are great but they can only get you so far, cold pitching is an underrated superpower. I’d hire the person with great pitching skills over the person with great relationships any day.

Here’s how he landed the famous billionaire on his podcast, and five things every PR person should take away from it:

1. If the first pitch flops, write a better one. Yes, that means pitching the same person twice with a different note. Blasphemous, I know. Shamus’s original email started with a paragraph about himself. It was ignored. The rewrite? “Saw your tweet about Cost Plus Drugs. Want to come on and talk about it?” Same person. Same ask. New angle.

Use your judgment when applying this to media. I use email trackers, so if I see the first note was never opened and some time has passed, I feel totally fine re-pitching. We should always be A/B testing own our work and challenging our own assumptions around what is interesting!

2. Lead with what’s in it for them. Shamus’s revised email didn’t say, “Can I interview you?” — it said, “Want help getting the word out about something you care about?” Same pitch, different framing. Same goes for media: if your note is all about your client, you’ve missed the point. Use language that makes it clear your goal is to help the reporter — even if it’s not 100% true. That mindset will sharpen your writing every time.