Here is how I closed a 6-figure deal with humor | Kevin Hubschmann - 1967
Episode
40 min
Read time
2 min
AI-Generated Summary
Key Takeaways
- ✓Cold Email Persistence: After nine conventional cold emails failed, the tenth email containing a Titanic meme asking "can anyone hear me" broke through and started a six-figure deal conversation, proving humor creates human connection when traditional approaches fail.
- ✓Active Listening Framework: Eliminate words "no," "but," and "or" from discovery calls and replace with "yes, and" to validate prospect pain points. Apply the "F Your Good Idea" principle—suppress interrupting with clever responses until prospects fully express their problems.
- ✓Psychological Safety Culture: Managers must create environments where failure becomes normalized and expected, not just verbally permitted. Conduct team-building activities in the same boardroom used for serious meetings to signal that authentic personality belongs in professional spaces, not just off-sites.
- ✓Last Letter First Word Exercise: Practice active listening by playing a game where each person must start their sentence with the last letter of the previous speaker's final word. This trains the brain to fully listen before responding, preventing premature interruptions.
What It Covers
Kevin Hubschmann shares how he closed a six-figure SaaS deal by sending a Titanic meme after nine failed cold emails, then using comedy skills like active listening and empathetic communication throughout the sales process.
Key Questions Answered
- •Cold Email Persistence: After nine conventional cold emails failed, the tenth email containing a Titanic meme asking "can anyone hear me" broke through and started a six-figure deal conversation, proving humor creates human connection when traditional approaches fail.
- •Active Listening Framework: Eliminate words "no," "but," and "or" from discovery calls and replace with "yes, and" to validate prospect pain points. Apply the "F Your Good Idea" principle—suppress interrupting with clever responses until prospects fully express their problems.
- •Psychological Safety Culture: Managers must create environments where failure becomes normalized and expected, not just verbally permitted. Conduct team-building activities in the same boardroom used for serious meetings to signal that authentic personality belongs in professional spaces, not just off-sites.
- •Last Letter First Word Exercise: Practice active listening by playing a game where each person must start their sentence with the last letter of the previous speaker's final word. This trains the brain to fully listen before responding, preventing premature interruptions.
Notable Moment
A sales manager told Kevin to stop being so salesman and start being more Hubschmann, explicitly giving permission to blend his comedian personality with professional work, which transformed his approach and led to authentic client connections that closed larger deals.
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