How to Tell a Captivating Story like a Stand-Up Comedian!

Great comedians say standup skills are like muscles. They’ll atrophy if you don’t use them. If an athlete wants to win the gold medal in swimming, they get in the pool every day. Want to win “the gold” at standup? Get in the pool.

Welp, I hadn’t been in the proverbial pool since 2019. This was my biggest in person crowd since pre-covid – roughly 125 folks in the room.

At the last minute I got hit with a bit of stage fright that came in the form of dry mouth. I couldn’t help but smile while thinking my lips are so dry, I could do an amazing Fire Marshall Bill impression right now.

As always, big thanks to John Wilker and Denver Startup Week for asking me back and everything they do to support the Denver community.

This year I custom built a storytelling session that is broken up into 5 parts:

1 – Storytelling Framework: why I don’t like Story Spine and Hero’s Journey and a simple framework that will literally never fail you. I also break down the storytelling of Fresh Prince of Bel Air’s theme song. Luckily no one complained about our use of Will Smith. If you don’t like him, I understand. Hate the artist, not the art.

2 – Conflict: why it’s the critical element to all great stories as well as the secret sauce that creates drama and raises the stakes. This section includes Sarah Blakely’s origin story and how she grew up in a house that embraced failure and first got Nordstrom to carry Spanx.

3 – Succinct: when it comes to storytelling, less is more. During this section I highlight Grandpa Simpson, the worst storyteller of all time, and then retell how Bob Iger used simplicity to get himself appointed CEO of Disney and become one of the most admired brands on the planet.

4 – Segue: powerful stories always connect to a moral, or teaching moment, that persuades your audience. Examples in this section include the Aesop’s fable about the dog and his reflection as well as a killer story about a CEO who “accidentally” left his screen share on during an all-hands meeting. Just to break the ice in the middle of quarantine.

5 – Details: concrete details are what draw your audience in and make your story memorable. During this section I told the stickiest story I know about how a frozen chicken turned an entire sales team around and then closed it out with Jeff Bezos’ “door desk” innovation during Amazon’s early years.

Have I piqued your interest? If so, check out the entire 60-minute session now by clicking here: