Here is how I closed a 6-figure deal with humor | Kevin Hubschmann - 1967

Sometimes all you need is the right personality to close a deal. When you hold back, play it safe, or fail to fully show up, prospects notice and engagement suffers. In this episode, my guest Kevin Hubschmann shares why suppressing your personality can cost you in the long run and how using comedian techniques can help you close a six-figure deal.

Blending Humor and Professionalism in Sales

· Kevin shares how he balanced his life as a standup comic and improv performer with his full-time sales role.

· Like many reps, he struggled to merge his personality with his professional image. Once he stopped separating the two, he began building stronger connections and seeing better outcomes.

The Six-Figure Meme

· Kevin walks through the real story behind a six-figure deal that started with personality.

· After sending nine standard, scripted emails with no response, he tried something different.

· His tenth message included a relatable meme, and it finally got a reply. That moment highlights why being yourself and taking smart risks can cut through the noise.

· Humor and authenticity help humanize sales and open conversations that traditional outreach often misses.

Improv, Listening, and Leadership Support

· We talk about how humor in sales is not about telling jokes. It is about listening, reading the room, and responding with empathy.

· Kevin shares improv-based techniques like “yes, and,” listening exercises, and reframing ideas to create more engaging conversations and build trust with prospects.

· We also discuss the role leadership plays in this process. Sales teams perform better when managers create a culture where reps feel safe showing their personality, trying new approaches, and learning from mistakes.

Key Takeaway

· Sales is about real human connection. When you combine your personality with professionalism, focus on active listening, and allow room for creativity, better conversations follow. Those conversations lead to stronger relationships and long-term success.

“Be yourself, because yourself is what's going to get you loose. It's going to create new ideas. You're going to take more risks..." - Kevin Hubschmann

Resources

Do you want to learn more about Kevin’s laughing and development classes? Check out laugh.events and join his newsletter Laugh Rx Laugh Events.

Join my Sales Mastermind to get real-world feedback, accountability, and proven sales strategies. Visit Blue Mango Studios for help in creating podcast production content.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

2. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

3. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.