How to Connect with Your Audience with Deadair Dennis

Deadair Dennis, Ron Macklin & Deb Dendy

How to Connect with Your Audience with Deadair Dennis

Episode 52: How to Connect with Your Audience with Deadair Dennis

Ron opens by asking guest Deadair Dennis to introduce himself.

  • Dennis begins by noting that he is a podcaster, actor, and standup comedian.
  • He also says that he lives in Boston now, though he is originally from Baltimore.

Deb says that Dennis’ story about a “soul sucking fluorescent lit office” that she read on his website got her laughing, and asked what the story was in his head that he had to change about that story.

  • Dennis says how he realized at a young age that being a comedian was a job, the same as any other job that someone might get paid for.
  • He then relays a story of his previous job, and how he felt stuck in his previous job at a radio station.
  • He pushed all of his effort into becoming a standup comedian so that he could have personality and create for himself.

Ron asks how Dennis holds being creative in his mind, and then what is his stand for himself around being creative.

  • Dennis talks about how he views being creative as being an individual and expressing that to other people in a way that they can relate to.
  • He then shares one of his most popular bits and relates it to our own inner insecurities about how others view you.

Ron follows up by saying that people often struggle with opening up and being vulnerable, but realizes that Dennis does that to rooms full of people, and asks how he is able to do that.

  • Dennis describes why comedy almost always delves into being vulnerable, and how to get the audience to open up, he first has to open up to them.
  • He realized how good radio talk show hosts share about themselves so that their guest will share something similar from their life.
  • He then discusses how people are always looking to make connections with other people, and the best way to do that is to open up about yourself so they feel comfortable opening up about themselves.
  • Ron then relates Dennis’ story back to his own life and how he been able to make connections with people.

After a story from Dennis about being a standup comedian, Deb says from that story she can understand why that would be scary to someone.

  • Dennis takes the opportunity to explain what it feels like to do terribly while on stage trying to perform and help people enjoy their night out.
  • Ron discusses how everyone has moments when they feel that horror just going through different aspects of everyday life.
  • Ron and Dennis then relate to how different people connect with different stories.
  • Dennis then discusses how he has to acknowledge certain expectations based on peoples’ perceptions of who he is based on looks alone.

Deb notes that Dennis is able to keep an attention by discussing the story in his audiences’ heads, and realizes that he’s able to read peoples’ minds in a way.

  • Dennis says that he has to put people at ease quickly because a lot of his humor is dark, and the best way to do that is do open up about deep personal things.
  • Ron continues this line of thinking and asks Dennis what he would suggest people do if they want to connect with other people.
  • Dennis says that before you are able to open up to people, you first have to make sure that you are comfortable, but what that means is different for every person.

If you want to learn more about Deadair Dennis visit his website at

Join us to hear how understanding the idea of “self-talk” — and what you can do about it — could change your relationships and life for the better.


Episode Summary

How to Connect with Your Audience with Deadair Dennis
In this episode of “The Story in Your Head,” Ron, Deb, and guest Deadair Dennis discuss the struggles of opening up and being vulnerable to others. Dennis also describes his method for quickly connecting with his audience while on stage as a standup comedian.