How To Pursue Your Dream & Make a Living As An Artist with Derek Hough

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Lewis and Cesar

Coffee Conversations

We've been best friends for 14 years.

I convinced my best friend Matt (known as Cesar on social media) to work with me 2 years ago.

It’s one of the best decisions I’ve ever made.

He is analytical and calm when I dream big and want to take action right away.

He runs a huge part of the business and I don’t know where I’d be without him.

Since so many people have asked me about my team and how we work together, we decided to sit down and do a twist on the solo round format.

This time, Cesar is asking me questions and we talk about how we’ve created the business as it stands today.

We also end up telling a ton of stories I don’t think I’ve ever shared on the podcast before.

"When we're afraid, we can't have fun."  

"Make your life a game you want to play everyday."  

Cesar was there for me long before I had money or was well-known.

He supported me so much in college (while I convinced him to ditch studying to come out on the town with me).

So when we sat down to talk about what we have learned on this journey, we ended up reminiscing a lot about where we came from.

We got into what playing football taught us about life and business.

How stretching out of your comfort zones is where all the growth happens.

We even got into my strategies for meeting girls when I first moved to New York City.

I loved having this conversation with Cesar, so let me know if you enjoyed it as well in Episode 508.

Some Questions I Ask:

In this episode, you will learn:

  • How I finally convinced Matt to come work with me (12:20)
  • Why it’s so important to build a team to get to the next level (15:23)
  • How playing football in college trained us for our careers and success (18:02)
  • How we’ve built a team that works so well together remotely (18:30)
  • How Matt and I shake up our routines to get new ideas (21:50)
  • Why we are still committed to hard workouts 10 years after football (23:15)
  • The story behind my “Red Rose Challenge” when I moved to NYC (25:45)
  • The quickest way to connect with an audience when you are starting out (35:35)
  • Why it’s so important to do the things that bring you joy on a daily basis (39:38)
  • Why stepping into leadership in high school was challenging for me (46:32)
  • The story of me trying out for the senior year musical and overcoming my fear (51:58)
  • Plus much more…
Connect with
Lewis and Cesar

Transcript of this Episode

Music Credits:

Music Credit: Next Galaxy by Extan

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