What are the key takeaways from this The Sales Evangelist episode?

Key insights include: **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.

What did Kevin Hubschmann discuss on The Sales Evangelist?

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 topics include: **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..

How long is this episode of The Sales Evangelist?

This episode is 40 minutes long. SignalCast provides an AI-generated summary so you can get the key insights in about 3 minutes.

The Sales Evangelist

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

January 12, 2026

40 min episode · 2 min read

Kevin Hubschmann

Episode

40 min

Read time

2 min

Topics

Health & Wellness, Leadership, Sales & Revenue

AI-Generated Summary

Published Jan 14, 2026

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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Episode Transcript

This episode is brought to you in part by the following TSC sponsors. You don't become the world's most valuable women's sports franchise by accident. Angel City Football Club did it with a little help from HubSpot. When it started, data was housed across multiple system. HubSpot unified their website, email, and fan experience in one platform. This allowed their small team of three to build an entire website in just three days. Three days. The results? Nearly 350 new sign ups a week and 300% database growth in just two years. Visit hubspot.com to hear how HubSpot can help your team grow better. Finding the right lead can feel like an endless search for sellers. What if you could get to the right conversations faster? From finding new leads to strengthening existing relationships, LinkedIn Sales Navigator is your strategic AI powered partner. It cuts through the noise with real time data and insights backed by LinkedIn's network of over 1,000,000,000 professionals. Try it for free for sixty days at linkedin.com/tse. Terms and conditions apply. Imagine using your humor to actually close big deals. I mean, make tons of money in sales. Is that possible? My guest today did exactly that. Check it out. Hey. Hey. Hey, everyone. Welcome to another great episode of the Sales Evangelist Podcast. I'm your host, Donald c e Kelly, the sales evangelist, and I'm so excited for another great episode. I'm so excited to be here with you today. On this episode, I have Kevin Hauptschmidt. And, Kevin and I got a chance to connect. He uses humor all the time. He used humor to close a 6 figure deal, and you won't believe what he did. Some of you might say, man, I don't know about that. But I feel there's many different ways you can use your personality to find success without compromising your professionalism. And Kevin is gonna give us some breakdown of that today. If this is your first time listening to our podcast, I appreciate that because this show is designed to be able to help you to improve your sales skills no matter where you are. We want you to build that to get that $6.07 figure career, and we wanna give you ideas and strategies that will help you build pipeline and accelerate deals to the pipeline. As we dive into this episode, I want you to listen to what Kevin shares. Like, listen. You're gonna hear some things on this. One of the third points on how you can actively listen on a day to day basis and see how this can apply to your life. He starts off we go into the story about his experience with this company after we set up the episode. And, man, I was like, you can't believe how many emails this man sent. Check it out. Kevin, welcome to the show. Thanks for having me. Excited to be here. Of course, man. I'm really looking forward to this conversation. …

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