Kosha Dillz & Flex Matthews

Episode 240


Learning To Believe In Yourself

“You never want to be the person that accepts your situation and complains when you get there.”


It was such a buzz to record this episode live at the Feast it Forward Festival. Kosha Dillz is an improv artist and freestyle rap teacher who performs in the street all over the world. He’s been rapping for over 20 years, and one of his songs, “Cellular Phone” – was featured in a Bud Light Superbowl ad. 

Kosha Dillz has a special gift for freestyle. As an artist, he can rap about anything and everything (as you’ll hear at the end of the episode). Through his artistry, he dreams of uniting various groups of people for the better. 

Kosha Dillz’s story is one of hustle, determination, humility, and inspiration. It’s a tale of NEVER giving up. 

As you’ll hear in the episode, it takes a particular sort of courage to be able to freestyle. Kosha Dillz shares with us the pressure of having to wow the crowd within 30 seconds to keep them hooked. In this episode, we talk a lot about the art of being comfortable with being uncomfortable and how the freestyle world inspires you to believe in yourself. 

Here’s a flavor of what we explore together. 

  • How Kosha Dillz got started. 
  • Learning how to create a show that grabs people in. 
  • Cultivating a relationship with fear. 
  • Embracing synchronicities. 
  • Learning to believe in yourself. 
  • Proving yourself to others. 
  • Learning to love yourself. 
  • Sticking with the dream and knowing it’s going to happen.
  • And more…

I love to talk with people who love what they do. This conversation with Kosha Dillz was so creative and so much fun. I can’t wait for you to check it out. Be sure to listen right to the end so you can hear the impromptu rap inspired by our conversation. 

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