Essay · 5 min read

How to Cold Email Investors

Aaron Harris · Y Combinator Startup Library Free Beginner

This is the canonical structure for the investor cold email, written by a YC partner who reads them from the other side. It is short and prescriptive: what to say, in what order, and why brevity beats a long pitch. Treat it as the skeleton you fill in, not a script to copy word for word.

  • The goal of the email is a reply, not a term sheet, so keep it short and easy to say yes to.
  • Lead with real progress relative to how long you have been building; traction reads as confident, and confidence is the opposite of desperate.
  • Research the person first so the email shows you know why you are writing to them specifically.
Open on ycombinator.com ↗

It answers 6 questions

  1. How do I write a cold email that people actually reply to?
  2. How many times should I follow up before giving up on a cold prospect?
  3. What should my very first cold email subject line actually say?
  4. How do I personalize cold emails at scale without making them feel fake?
  5. How do I write cold emails and LinkedIn messages that founders actually get replies to?
  6. What are the most common cold email mistakes that make people delete on sight?

Read with it

  1. Once you have a list of people to reach cold, this shows you how to write emails they actually answer. Seven concrete... Y Combinator Startup Library Video · ~33 min How to Convert Customers With Cold Emails Aaron Epstein
  2. A tactical follow-on covering the channels and motions top B2B startups scale after the first ten. Grounds distribution... Lenny's Newsletter Article · ~15 min read How to win your first 10 B2B customers Lenny Rachitsky
  3. An Indian founder story where the early demand test was manual, cold emails and direct outreach to find the first customers... Prime Venture Partners Podcast Podcast · ~50 min How Khadim Batti Built Whatfix Into a Global SaaS Leader Prime Venture Partners
  4. The permission slip to recruit users by hand, do things manually, and deliver 'insanely great' experiences to your first few... paulgraham.com Essay · ~15 min read Do Things That Don't Scale Paul Graham
  5. This is the rare cold email piece written by someone who has actually sent thousands of them (Steli Efti built Close, a sales... Close Article 15 Best Cold Email Templates That Actually Get Replies (Proven Examples) Steli Efti
  6. A short, direct conversation between two founders on when cold email works, who to send to, and how to write the subject line... The Startup Chat with Steli and Hiten Podcast · 18 min The Startup Chat, Episode 014: Cold Email Steli Efti and Hiten Shah
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