What's the worst that can happen if you send the email?
They don't respond. That's it. That's the whole downside.
This fall, I'm running the Executive Speaker Series for the Ole Miss Business Club. 615 members, 2nd largest org on campus, built in one year. Every speaker confirmed started as a cold message to someone who had zero obligation to reply.
I've gotten a letter back from Donald Trump. I've landed the CEO of Glo Tanning. Last year the club brought in Scott Wapner from CNBC and five CEOs and founders.
None of those felt realistic when I was staring at a blank draft.
I reached anyway.
Here's what actually gets responses:
Make it impossible to misunderstand. I send a full briefing packet with who's in the room, the format, the time commitment, and a proposed date range. Vague asks die in inboxes. Specific ones don't.
Lead with their relevance, not your need. Nobody responds to "I'd love to connect." They respond to "here's exactly why this room is the right one for what you've built."
The second message converts. Not a "just following up." A real one with a new angle and a genuine reason to re-engage. That message has worked more times than the first.
The real barrier is almost never the other person. It's the story you tell yourself about whether you're worth their time before you ever hit send.
You're not too small. The reach isn't too far. The worst outcome is already survivable.
So send it. Make it count. And let it play out.
It never is too far.
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