$100 Bill Sales Pitch

A unique sales approach used to overcome initial customer resistance in credit card processing sales by offering $100 for one minute of their time. Here's the detailed breakdown:

Context & Problem

• Credit card payment industry defined by deep distrust (circa 2007)
• Business owners receive complicated monthly invoices
• Providers intentionally make reporting complex
• Creates environment where sales people can be deceptive
• Walking into stores, customers immediately dislike salespeople

The $100 Bill Approach

• Offer $100 bill upfront for one minute of time
• Customer keeps money even if they say no
• Creates immediate interest and engagement
• Breaks down initial resistance and animosity
• Gets foot in the door for actual pitch

Core Sales Message

• Acknowledge industry problems

  • Highlight widespread deception
  • Address complexity of payments
  • Recognize customer skepticism

• Present simple value proposition

  • Be honest and transparent
  • Be clear about differentiation
  • Focus on reliability and competence
  • Emphasize trustworthy service

Key Success Factors

• System deconstruction and reconfiguration
• Focus on understanding how system really works
• No high-pressure sales tactics
• No manipulation of customers
• Build trust through transparency
• Create clear understanding for customers

Results

• Became company's #1 salesperson within months
• Generated $59,000/month in revenue after 11 months
• Built foundation for bootstrapping larger business (Braintree)