When to message someone cold

I got my job at Replit that began with a cold DM to a Penn classmate.

We recently signed a deal with the CIO of a Fortune 100 company that began through a meeting set up by a cold email.

I've made friends through cold Twitter DMs - and these friends have helped me immensely in a professional capacity.

However, cold messaging doesn't always work. In fact, it works only in select cases.

Here's where it works:

A shared background helps: past employer, school, or city. The smaller the circle, the higher the reply rate. Mutual connections that actually know you signal social proof, showing you could have asked for an intro but chose to reach out directly. For example, I will often message people from Pune cold because it's a small enough city that they are likely to respond - and we likely have many real LinkedIn mutual connections.

Pune FTW

You're not "asking for something" per se (e.g. as a job seeker) but instead have an opportunity that could be mutually beneficial (e.g. sharing deal flow or partnering together).

How I slid into Anmol's DMs.

A bit of common reputational surface area helps. If your name or work has shown up in their circles, replies jump. I'm not saying that you have to be SRK level famous, but instead just known in certain circles.

This ended up leading to a small investment.

In conclusion, you can most certainly cold DM almost anyone you want. However, to be successful, try and be selective about how you go about it.