100 Conversations on My Way to the Comedy Stage | Dear Business Coach Podcast

100 Conversations on My Way
to the Comedy Stage

A journal report on my first 100 podcast interviews
and the comedy stage that's waiting

"I think my set is no good. But I guess I'll just have to pretend like it is."

When I was in sales, I learned that more than earning a commission, I like it when people say yes to me.

That's why I started a podcast. Same drug, different delivery system.

After 100 episodes of The Dear Business Coach Podcast, I interviewed a comedian about his book. Then I hired him to speak at a workshop I produced. Then I hired him as a coach. Then he talked me into trying standup.

This is the story of what happened next.

📍 Where I Am Right Now

I have one more writing session with my comedy coach. Then we book the date. Then there's no backing out. The problem? I think my set is no good. But I'm doing it anyway.

This book is my way of figuring out how—by revisiting the 100 conversations that got me here.

Chapter 1: The Yes

"Everyone thinks I'm a business coach. I'm not. I'm just the person asking the questions. I basically have an avant-garde, unscripted podcast where I get to ask people anything I want as long as I call it a business interview."

About saying yes to things that terrify you. About the addiction of putting your work out into the world. About the difference between a podcast guest saying yes and a comedy audience laughing.

Read Chapter 1

Chapter 2: The Sales Job I Can't Quit

"Building rapport involves shutting up. I have interrupted some of my favorite guests because I let myself get too comfortable."

About the skills that transfer from sales to podcasting to comedy. About learning when to talk and when to get out of your own way. About the one thing you can't interrupt: a laugh.

Read Chapter 2

Chapter 3: The People Who Show Up

"I still get nervous before every call. Every single one. Right before I hit record, there's always that moment where I think: What if this one's awkward?"

About the guests who surprised me most. About what podcasting teaches you that only you and the guest will ever know. About earning the yes from an audience who paid money to be there.

Read Chapter 3

Want More?

I release new chapters weekly on Substack. Or listen to the conversations that started all of this on The Dear Business Coach Podcast.

Listen to the Podcast Subscribe on Substack Book Office Hours

💬 About The Dear Business Coach Podcast

100+ episodes of unscripted conversations with business coaches, comedians, entrepreneurs, and people who are figuring it out. Each guest gets a meet-and-greet first. No one pays for production. And I still get nervous before every single recording.