The genuine opener, the value-led follow-up and the one line that gets a reply. If you’re trying to reach that one CEO, investor or partner who could move your business forward in one conversation but has never replied to your messages, sounding like everyone else isn’t going to cut it.

Jason Luboyera runs 360 DigiSales and has spent close to a decade growing businesses through LinkedIn. He once landed a meeting with the MD of a major UK asset manager, from South Africa, off a cold message. Here’s the approach.

The mistake is treating the first message as the pitch. Jason’s framing is the opposite: you give value first, signal you’re not desperate, and earn the conversation before you ask for a thing.

“Buy the person a drink up front, and never assume they’re not busy.”

The difference between a pest and a peer is research. Before you message, read something they actually did: an article they were in, a post they wrote, a talk they gave. Reference it genuinely, not as a hook you bolt on.

Jason opened his asset-manager message by referencing the actual article the MD had appeared in. That one move signals you’re not blasting a hundred identical messages — you came for them specifically.

Desperation reads instantly and kills the message. The counterintuitive move is to signal that your time is valuable as well; you’re reaching out because it’s worth it, not because you’re short of options.

“My schedule’s full, but maybe we could grab a coffee.”

Never assume they’re not busy, and never act like you’re not either. Two busy people finding time to read as a meeting of equals. A free person begging a busy one reads as a pitch.

One message rarely lands. The follow-up is where most people turn into a pest: by asking for the meeting again, and again. Jason’s rule: follow up as many as seven times, but every single touch has to add value to their life, not chase your meeting.

Find something tied to their goals and give it for free: a useful article, an introduction, a relevant insight. Each touch should make them glad to hear from you, not brace for the ask. Chase, and you’re a pest. Give, and you’re someone worth replying to.

Around the fifth touch, if there’s still silence, there’s one line that consistently gets a response from founders and CEOs.

“Everybody’s busy and so am I. I had two things I wanted to share, but it seems we won’t get to them. My door’s open when you’re ready.”

It works because it’s the opposite of pestering; you’re respectfully stepping back, with a hint of value left on the table. But it only lands if you’ve shown genuine intention first. Fire it off cold and you’re just another pest with a clever closer.

You stop waiting for warm intros and start opening the conversations that move your business, with people you’d have written off as unreachable. Done right, a cold message reads as a peer reaching out, not a stranger begging.

It costs you ten minutes of research per person. It can open a door that a hundred networking events wouldn’t.

This play is one piece of LinkedIn 101, Jason’s full masterclass inside the Founder Collab that shows you how to use LinkedIn as a real business-growth tool:

You’ll also get access to 40+ other masterclasses from SA founders and operators on sales, fundraising, UX, paid media and more inside The Founder Collab.

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