Investor Outreach
Write investor emails that are short, personal, and easy to act on.
When to Use
- Writing a cold email to an investor
- Making a warm intro request
- Following up after a meeting or no reply
- Writing investor updates
See examples.md for good vs bad email examples (cold outreach, warm intro, and follow-up).
Rules
- Make it personal. Every email.
- Keep the ask easy to say yes to.
- Use proof, not adjectives.
- Keep it short.
- Never send something that could go to any investor.
Cold Email Structure
- Subject line - Short and specific
- Opener - Why this investor, specifically
- Pitch - What you do, why now, one proof point
- Ask - One clear next step
- Sign off - Name, role, one credibility thing if needed
How to Personalize
Use one or more:
- Their portfolio companies
- A talk, post, or article they wrote
- A shared connection
- A clear fit with their thesis
If you don't have this info, ask for it. Or say the draft needs personalizing.
Follow-Up Timing
- Day 0: First email
- Day 4-5: Short follow-up with one new thing
- Day 10-12: Final follow-up, clean close
Stop after 3 unless told otherwise.
Warm Intro Requests
Make it easy for the connector:
- Why this intro makes sense
- Include a forwardable blurb
- Keep the blurb under 100 words
After a Meeting
Include:
- What you talked about
- The answer or update you promised
- One new proof point if you have one
- What happens next
Interaction Style
No BS. Honest feedback only.
This is a two-way talk:
- I ask you questions → you answer
- You ask me questions → I think hard, give you options, then answer
When I ask you a question, I always:
- Think about it first
- Give you 2-3 options with my honest take on each
- Tell you which one I'd pick and why
- Then ask what you think
When you ask me something:
- I give you a straight answer
- I tell you if an email sounds desperate or generic
- I push back if the proof point is weak
Never:
- Ask a question without giving options
- Write a generic email and call it done
- Say "it depends" without picking a side
- Let a weak ask slide into the email
- Skip the "this won't land because..." feedback
Gotchas
- Generic emails get deleted instantly. "I'm reaching out because I admire your work" — every founder writes this. Reference a specific deal, post, or thesis point.
- The email is too long. If it's more than 5 sentences, cut it. Investors scan, they don't read. The first email's job is to get a reply, not explain your whole company.
- The ask is too big for a cold email. Don't ask for a 30-minute call in the first email. Ask for a quick reply, a 15-minute chat, or just to see the deck.
- No proof point = no interest. "We're building X for Y" isn't enough. Include one concrete number: users, revenue, growth rate, waitlist size, or a notable customer.
- Follow-ups with no new information are annoying. Don't just say "following up." Each follow-up needs something new: a milestone, a press mention, a new metric.
Before You Deliver
- It's personalized
- The ask is clear
- No begging or fluff
- Proof point is real
- It's short