Orlando Baxter, Positive Pushups

Orlando Baxter

Interview: How to Be Funny with Orlando Baxter

Orlando Baxter is the man trying to produce comedy in his show, Positive Pushups. He’s almost the “Seinfeld” of comedy, but when people listen to his stories, they laugh. Proof positive that Orlando is funny. It’s a challenge for Orlando to get on and build a fan base, but then when everyone knows him, they come to the show to see him, that’s what makes him happy.

Below is a summary of our interview:


A quote that Orlando says he lives by is “You don’t start nothin’, you won’t be nothin’.”

His Journey

Orlando grew up in Worcester, Massaschussetts, as one of 4 boys, the oldest son. He played a little sports in high school. When he graduated, he went to college in Worcester, Massachusetts. There, he made a ton of friends, and knew he had always wanted to be a comedian. But he became a basketball coach and taught high school kids. Feeling like a hypocrite that he’s telling these kids they have to go after their dreams,  he finally went to an open Mic and did a show in Los Angeles when on vacation. When he came back he started comedy in Boston. At this time, Orlando’s very happy he overcame his fear of becoming a comedian.

A Low Point

As Orlando pointed out, we all go through a lot more failures than success. For him, in 2007, about to have his big break, he went to New York City and was flown out to Los Angeles and competed with comedians who had been in the business for over 10 years.  It didn’t happen for him and not getting it was a crushing loss. However, Orlando realized he was very lucky.

Aha Moment

Orlando won a couple of competitions early on like the South Shore Comedy Riot and the Boston Comedy Festival. But the biggest thing was linking up with Jo Koy, an American stand-up comic, who called Orlando in 2009 to invite him to Miami for New Year’s weekend, and take him on the road. That was big considering Miami is a tough comedy room. And another moment was when he opened for Jo Koy in a Comedy Central special. That made Orlando realize he has some skills.

Orlando’s work now  

He is not really the Seinfeld of comedy, but he says things and people laugh. He just tells story about life and being an  In-school suspension teacher. He stands in front of a microphone and tells him about his life and his day and the craziness about school suspensions. Orlando says it himself that he is “funny!”

What’s exciting Orlando now

He’s doing some new material as he’s not only talking about teaching, but venturing into other personal areas of his life. Also, Orlando is doing a lot more podcasts with comedians and individuals in Boston.

Lightning Round

Book Orlando Recommends:

When Things Fall Apart: Heart Advice for Difficult Times

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Helpful Habit :

He’s an active person and he frequently keeps on doing push-ups. And he always tries to look on the positive side.

Helpful Person:

Jo Koy has been such a big brother to Orlando. So he shouts out to him. Also, Cory and Sean, who have been helpful with his career.

Internet Resource:

An app called Waze, a Social GPS for Maps & Traffic

What’s Your Purpose:

“be the best Orlando” that he can be is his purpose. He’s funny and talented, so Orlando wants to maximize his abilities.

Where to follow Orlando



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Parting Words

“Keep grinding.” Do a couple of positive pushups and Orlando guarantees you’ll be back on your feet.

An awesome way to spread the word

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Jackie Abrams

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