Weird Money-Making Icebreaker

A unique icebreaker question that helps avoid pretentious networking conversations and gets people to share more authentic stories.

Why This Question Works

• Avoids typical "what do you do" conversations that lead to scripted responses
• Prevents one-upmanship in rooms full of successful people
• Gets people to share vulnerable, interesting stories instead of achievements
• "Nags the whole group" - brings everyone down to a more relatable level

Example Story Shared (Ramon's Story)

• At 18, started advertising as a general contractor despite no experience
• Took an electrical job without knowing anything about electrical work
• Showed up wearing a vest trying to look like an electrician
• Couldn't understand technical terms client was using
• Came clean the next day about having no experience
• Client respected his honesty and taught him about subcontracting
• Led to successful contracting business making significant money

Key Takeaways About Storytelling

• Best stories often involve self-deprecating elements
• People who only tell stories about their successes tend to repel others
• Good storytellers understand how to make themselves relatable
• Stories about mistakes or learning experiences connect better than success stories
• The CIA operative's rule: "Only tell stories where I look like an idiot"

Impact on Networking

• Creates more authentic connections
• Leads to people helping each other out
• Gets people excited to share their own stories
• Makes successful people more approachable
• Builds trust through vulnerability