The Worst DM I Ever Sent (and what you can learn from it)

Heyy frieend,

Let me take you back to 2021.

Early days. I was running on hope, instant coffee, and YouTube advice.

And one day, I decided to “go all in” on cold outreach.

I picked a dream client.

Spent 40 minutes crafting the “perfect” message.

You know, the kind that starts with:

“Hey there! Big fan of your work. Thought I’d reach out and connect…”

😬 Cringe.

The rest was a confusing cocktail of compliments, vague value, and a link.

No real context. No real reason. Just vibes.

They saw it.

They didn’t reply.

And I immediately deleted it like a guilty text.

But here’s the plot twist:

That same person replied… 7 months later.

Not to my message, but to a new one I sent.

This time, I skipped the pitchy energy.

I referenced something they had posted.

Said what I was working on.

And ended with:

“Happy to show you. Might be useful, or not. Either way, no pressure.”

📩 They replied in 12 minutes.

Same person.

Different energy.

Completely different outcome.

That’s when it clicked for me:

🔑 People don’t ignore you because you're unknown.

They ignore you because you're unfamiliar.

Familiar feels like a friend.

Familiar feels like “this person gets me.”

So now, I obsess over 3 things:

💡Context. If your message could be sent to anyone, it shouldn’t be sent to anyone.

⏱️Timing. Not everyone will be ready. But if you stay consistent, the reply will come.

🗣️Tone. No one wants to feel like a lead. Talk like you’d talk to your favorite cousin. But, y’know, professionally.

Anyway, I still think about that first message sometimes.

Not with regret… but with a quiet laugh.

Because without that awkward DM, I wouldn’t have figured out what works today.

Talk soon,

Piyushh (Founder, xAutoDM)

Better DMs don’t start with “Hope you’re well.”
They start with real context, real timing, real you.

Try xAutoDM for free, and never send a boring DM again.