Lessons from Messaging 300+ Investors or Potential Partners on X

Cold outreach is an art, a science, and, sometimes, a test of patience. Recently, I sent over 300 direct messages (DMs) to investors on X (formerly Twitter) to see what kind of response I could generate. The results were eye-opening.

Here’s what I learned:

1. Personalization Is Tedious but Essential

Copy-pasting the same message to hundreds of people doesn’t work. Investors (and people in general) can smell a generic pitch from a mile away. To improve response rates, I had to tailor each message based on their bio, expertise, achievments.

Example: Instead of saying, “Hey, are you open to new opportunities?”, I had better results with something like, “Hey [Name], your work in [specific industry] gives you a great perspective on emerging opportunities. We’re working on something that could reshape how businesses grow, and I’d love to get your thoughts.”

Yes, it takes longer, but the results are worth it.

2. Framing Matters: Ask for Thoughts, Not a Chat

One of the biggest takeaways? People are more likely to respond when you ask for their opinion rather than a meeting.

I initially asked, “Are you open to a quick chat?” and got minimal engagement. But when I changed it to, “I’d love to get your thoughts,” the response rate significantly improved.

Why? Because a request for a chat feels like a commitment, while asking for thoughts plays to people’s desire to share their insights without pressure.

3. Some People Are Just Mean

It doesn’t matter how well you craft your message—some people will be rude, dismissive, or downright nasty.

I received responses like:

“Stop wasting my time.”

“This is the worst pitch I’ve ever seen.”

“LOL. No.”

It’s easy to take this personally, but you can’t let it slow you down. For every negative reply, there are plenty of people who are open to genuine conversations.

4. It’s a Numbers Game

The truth is, no matter how great your pitch is, most people won’t respond. That’s just the nature of cold outreach. But the more you do it, the better your chances.

Here’s what I noticed:

A certain percentage will ignore you entirely.

Some will respond but won’t be interested.

A smaller group will engage and ask for more info.

And a handful will turn into actual connections or opportunities.

The key? Keep going. Outreach is about consistency, not instant wins.

5. Cool Side Effect: Your Following Grows

One thing I didn’t expect? Following people before messaging them led to a noticeable increase in my own followers.

Even if someone didn’t respond, many followed me back. That means the next time I post something relevant, there’s a chance they’ll see it, and possibly engage later.

Final Thoughts

If you’re considering cold outreach, here’s my advice:

Personalize every message. It’s time-consuming but necessary.

Frame your ask as a request for insight, not a sales pitch.

Don’t take rejection (or rudeness) personally.

Play the long game, outreach is about persistence.

Enjoy the side benefits, like an organic increase in your following.

Are you on X? Do you accept DMs? If so, how do you approach cold outreach?

find me on X.com @newdanielmorel