What's up, it's Zayd.

Running a sales company means I get sold to constantly.

All day I get LinkedIn DMs, cold emails, and the occasional cold call…to a number I didn't know was public.

I read most of them.

Partly out of professional curiosity.

Partly because you can learn more about what's wrong with outbound by being on the receiving end of it than from almost anything else.

Most of what I receive is bad in exactly the ways I'd predict. Some of it is bad in ways that still manage to surprise me, which is an achievement of its own. And occasionally, something lands in my inbox that makes me actually stop.

This week we’re talking about those.

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My favorite finds of the week

I feel like I always go back to this example, but it’s the easiest one to reference. A while back I got a message that opened with something like: 'Hey Zayd, noticed you're based in NYC, have you tried Blue Bottle Coffee? Anyway, come join our webinar.'

Sure, that was technically personalized, but…useless.

The sender thought they were doing something smart. In theory they had a local hook that made sense for me, but the problem is that personalization without relevance is just decoration. It makes the message look like it's about me without actually being about me, and people can feel that gap immediately (especially now). We are remarkably good at distinguishing between someone who has thought about our actual situation and someone who has just run our name through a template.

I see versions of this constantly. The compliment that could apply to anyone. The observation about a company milestone that has nothing to do with why they're reaching out. The “I was impressed by your recent post” opener followed by a pitch that has zero connection to what that post was actually about.

The messages that make me stop share a few key qualities:

To be fair, my AI-detection instincts are probably better tuned than most people's, given what I do all day, but I also think those instincts are becoming more common across the board.

Certain phrases have become signature tells.

“I was impressed by,” “that resonates with me,” “I noticed you're doing incredible work.”

These have become the signs of someone who hit generate and didn't edit.

It's not that AI-assisted messaging is inherently bad. We literally built Valley around it. The difference is in the training and the editing.

A message that went through a thoughtful approval process, that got shaped by someone who actually knows how to sell, that got reviewed by a human before it hit send can be genuinely good.

A message that got generated and shipped as-is almost always reads like a message that got generated and shipped as-is.

If you're using AI in your outreach and you haven't spent serious time teaching it to sound like you, you're just producing mediocrity faster.

The Ultimate LinkedIn Hook Writing Guide: A Complete System for High Performing Content:

A few weeks ago I got a message from someone who had clearly read a few of my newsletters. They referenced a specific point I'd made about the difference between personalization and relevance, said it changed how they'd been thinking about their own outreach, and then made a connection to something their company was working on that was genuinely adjacent.

The ask was simple. They wanted to know if I had thoughts on a specific problem they were running into.

I responded within the hour.