Dennis Menace Follow-Ups

A strategy for acquiring businesses by maintaining consistent, persistent follow-up with potential sellers, even after initial rejection. This approach was notably used by Andrew Wilkinson and Tiny Capital.

Core Strategy

• Regular, systematic follow-up with potential sellers
• Maintain professional demeanor even after rejection
• Stay in contact over long periods (sometimes years)
• Focus on building long-term relationships rather than immediate deals

Key Examples

• Letterboxd/Dribbble acquisitions
  • Emailed founders monthly for ~5 years
  • Eventually succeeded when timing was right
• Aeropress acquisition
  • Continuous follow-up with consistent interest
• Milk Road acquisition
  • Maintained contact after initial deal fell through
  • Showed continued interest without taking rejection personally
  • Successfully acquired company after timing improved

Best Practices

• Set up automated reminders for follow-ups
• Don't take rejection personally
• Check in every 1-3 months
• Keep message consistent: "Still interested if opportunity exists"
• Maintain professional tone even if initially rejected
• Be willing to be slightly "menacing" (persistent) in follow-up

Why It Works

• Timing changes circumstances for sellers
• Persistence shows genuine interest
• Creates opportunities when sellers finally ready
• Low downside risk to consistent follow-up
• Most responses are either positive or neutral
• Only small percentage (~0.2%) respond negatively

Implementation Tip

• For every 1,000 cold emails:
  • 998 will be positive or neutral
  • Only 1-2 might respond negatively
  • The upside potential outweighs negative responses