July 12, 2025 | Read online​

Scroll through Linkedin for 5 seconds and you’ll see “influencer” talking about the importance of personalization when it comes to your outbound efforts.

I’ve been teaching/preaching about the importance of personalization AND relevance for years.

I also get about 250-300 emails a day and about 300 inmails a week.

Do you know how many of those are actually personalized?

Almost none.

I ask almost every executive who comes on my podcast how often they get a truly personalized and relevant message. Most of the time they can’t remember the last time they got one.

That’s why, when someone does it right, it stands out by a mile.

Case in point, meet James Hewitt from Drip.

He prospected me this week and put together what I would consider a 10/10 when it comes to his approach and contact strategy.

Here’s why:

1. Every email was brief, timely, personalized AND relevant
2. Great use of using resources to learn my tech stack
3. Highlighted specific pain points that others like me might have
4. Leveraged social to find more info
5. None of it was pushy at all
6. Used the mails to build and tell a story

Oh, and guess what HE DIDN'T USE AI TO WRITE THEM!!!!!!!

Another thing, this also proves that you don't need 16 touches to get a response. I forwarded his first email to my COO to see what she thought. I responded to his second email to schedule a call.

(full disclosure, I asked if he would send me what he would have sent as the third email if I didn't respond just to see what it would have been 😉 )
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Please read through these with my comments and share with your team. This is how you do prospecting right.

By the way, this is exactly what I teach in my Membership training. You can either buy a single module on email personalization here for $79 or a full membership that we just dropped down to $420).

Bonus: Join Me Live – Free Training Thursday (July 24 @ 12pm ET)

Topic: The Dangers of Personalization at Scale and the Importance of Relevance

James nailed it because he did the work, he made it personal and relevant. That’s rare.
Most reps automate the wrong things and end up with templated garbage that gets deleted on sight.

In this live session, I’m going to break down:

• Why bad personalization does more harm than no personalization
• What true relevance looks like—and how to deliver it consistently
• A step-by-step framework you can plug into tools like Regie.ai to make your outbound actually worth reading

If you’re using AI, sequences, or “personalization at scale” and still not getting replies, this one’s for you.

Reserve your spot here – it’s free, sharp, and built for modern sellers who give a sh*t.

SIGN UP NOW

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How did I do with this edition? Amazing - can't wait till next week It was okay Needs work