Day 0: Initial outreach
Lead with thesis context and a clear ask—15 minutes, not 'would love to connect.' Include traction in one line. Keep under 150 words.
Day 3: First follow-up
Only if no reply. Add new information—a customer win, metric update, or relevant news—not 'just bumping this.' If they opened the first email, acknowledge the space without being creepy.
Day 7: Second follow-up
Shorter. One paragraph. Different angle on why this fits their portfolio. Some founders share a one-pager link here.
Day 14: Final touch
Graceful close. 'I'll assume timing isn't right—happy to reconnect if your thesis shifts.' This often triggers replies from investors who were busy, not uninterested.