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Back to PlaybookChapter 05

Cold Outreach That Converts

The funnel math, email templates, and follow-up sequences that work.

The Warm Intro Hack

The most effective outreach hack: get a warm introduction. Warm intros convert at 2–3 times the rate of cold emails. Before writing a single email, spend 30 minutes per target searching LinkedIn for intro paths.

Where to Find Warm Paths
LinkedIn 1st/2nd degree connections. University alumni networks. Former employer alumni. Shared communities (Slack groups, Discord, industry associations). Friends of friends.

The 800-Email Rule

To get 1 customer, you might need to send 800 emails:

800
Emails Sent
50% open rate
400
Emails Opened
10% response rate
40
Responses
25% demo rate
10
Demos
10% close rate

You need dozens of emails per day — 50 is a good target for early-stage founders. Block 2–3 hours daily for outreach.

The 7 Principles of Cold Email

1
Focused specific goal
One ask per email. Don't ask for a demo AND an intro AND feedback.
2
Be human
Write like you talk to a friend. Use 'hey' not 'Dear Sir.' Typos are okay — they signal a human wrote this.
3
Personalize deeply
Go beyond name swapping — reference their product, a recent launch, a LinkedIn post.
4
Keep it short
75–125 words gets 5–15% higher reply rates. Most people read on mobile.
5
Establish credibility
Mention YC, ex-Google, past companies. Share customer logos.
6
It's about them, not you
Reframe every 'I' as 'you.' Tell your story as solving their problem.
7
Clear call to action
End with a standalone sentence: 'Reply to let me know.'

Follow-Up Sequences

Day 0: First Email
Your initial outreach with the 7 principles.
Day 3–4: Second Email
New angle or value. Share a relevant article or case study.
Day 7–10: Third Email
"Break-up" that closes the loop. Add final value.

Current best practice: 2–3 emails maximum. More than that triples spam complaints. Each follow-up must add value, not just ask "did you see my last email?"

Common Mistakes

Bad targeting — perfect email to wrong prospect is waste
Generic personalization — 'Love what you're doing at [Company]' feels templated
Making it about you — 'I I I' emails get deleted
Too many asks — one CTA per email
Automating too early — write 100 emails manually first
No follow-up — 80% of sales require 5+ touchpoints