Cold Outreach Sequence

Here's what I've learned about cold outreach: the word "cold" is the problem.

If you're sending messages to strangers who've never heard of you, with templates you copied from some guru — yeah, that's cold. And it doesn't work.

But if you've done even 10 minutes of research, found something specific about them, and have a genuine reason to reach out? That's not cold. That's just... reaching out.

This skill helps you do the second thing.

Before You Write a Single Message

The research is the work. Skip it and you'll sound like everyone else in their inbox.

For each prospect, find:

• Recent news — Funding, launches, hires, press
• What they're posting about — Their content tells you what they care about
• Their likely pain — Given their role and stage, what's keeping them up?
• Your connection point — What can you genuinely comment on?

Where to look:

• Their LinkedIn activity (posts, comments, shares)
• Company news (Crunchbase, TechCrunch, press releases)
• Their website (about page, blog, careers)
• Podcasts they've appeared on

Time investment: 10-15 minutes per high-value prospect.

This is what separates you from spam.

The Connection Request (LinkedIn)

You have 300 characters. Don't waste them on a pitch.

The formula:

[Specific observation] + [Simple reason to connect]

Examples:

"Following [Company]'s growth — the [specific thing] is smart positioning. Would love to connect."

"[Their recent post] resonated. Been thinking about the same thing. Happy to connect."

"Congrats on [news]. Impressive trajectory."

The rules:

• No pitching. At all.
• Be specific (prove you looked)
• Keep it human
• No "I'd love to pick your brain"

First Message (After They Accept)

Wait 24-48 hours. Then:

The formula:

[Thanks] + [Bridge to relevance] + [Light value] + [Soft question]

Example:

Thanks for connecting. I've been working at the intersection of [relevant area] — [one-line credibility].

Curious if you have someone owning [relevant function] as you scale, or if that's still founder-led?

Either way, happy to share what I'm seeing work in the space.

The rules:

• Still not a hard pitch
• Demonstrate relevance, not desperation
• Ask a question that invites dialogue
• Offer value without strings attached

First Follow-Up (If No Response)

Wait 5-7 days. Then:

The formula:

[Light nudge] + [New value or angle] + [Easy out]

Example:

Bumping this up — know you're slammed. Came across [relevant thing] and thought of your situation at [Company]. Worth a look if helpful.

Or:

Following up — been seeing [trend] hit companies at your stage. Happy to share what's working if useful. If not, no worries.

The rules:

• Don't just say "following up"
• Add something new
• Give them an easy out (takes the pressure off)

The Break-Up (Final Attempt)

Wait 7-10 days. Then move on gracefully: