Pitch Once Rule

A fundraising philosophy that emphasizes quick decision making and avoiding multiple pitches to the same investor. The focus is on finding enthusiastic partners rather than convincing hesitant ones.

Core Philosophy

• Fundraising should be informative, not persuasive
• First impressions are 90% cemented within 5 minutes
• True interest shows immediately - best investors/employees call multiple times after first pitch
• If you need to pitch twice, they didn't really want it

Why It Works

• Capital is relatively cheap if you have a great business
• Thousands of funds exist - no need to convince reluctant ones
• Enthusiastic investors will:
  • Call 12 times after first meeting
  • Show up at your door
  • Get on calls even during holidays
  • See it as a life-changing opportunity

Implementation Guidelines

• Give full attention during first pitch
• Be respectful of venture associates and fund structure
• Answer legitimate follow-up questions
• Don't try to "sell" after initial pitch
• Move on quickly to find truly excited partners

Exceptions

• Legitimate diligence questions are acceptable
• Follow-up with venture associates at large funds (like Sequoia) is okay
• Technical/clarifying questions don't count as "pitching twice"

Key Mindset

• Being on the persuasion side puts you in wrong negotiating position
• Focus energy on finding enthusiastic partners rather than convincing skeptics
• Trust that great businesses will find their investors
• Value your time and maintain leverage by moving forward quickly