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Diplo - Grammy Award Winning DJ: “Don't Be Afraid of Failing” artwork

Diplo - Grammy Award Winning DJ: “Don't Be Afraid of Failing”

Finding Mastery with Dr. Michael Gervais

April 9, 2025

How do you stay ahead in an industry that never stops evolving? Today, we are diving into the mind of one of the most prolific, boundary-pushing, and curious creators of our time—Diplo.

Speakers Wes Pentz, Michael Gervais, Emma

TopicsSelf-ImprovementEducationHealth & FitnessMental Health

Wes Pentz (0:00)

I've always found the freedom to just take a huge turn and never be afraid of it. And I think that's what always kept me interested in music. But that's me just being an artist. I can go anywhere, and I'm not afraid to fail. Some projects might work, some projects might not. But if you believe in your vision, you can make anything happen with music.

Michael Gervais (0:15)

How do you stay ahead in an industry that never stops evolving? Welcome back, or welcome to the Finding Mastery podcast. I'm your host, Dr. Michael Gervais. By trade and training a high-performance psychologist. And today we're diving into the mind of one of the most prolific, boundary-pushing, curious creators of our time, Diplo. Perhaps you know him from his music career, with chart-topping hits and game-changing collaborations, or for headlining some of the biggest festivals in the world. And just to make that point, he did a concert in Cuba where 500,000 people showed up. He built an entire creative empire as a DJ, a producer, an entrepreneur, a risk taker, and a cultural pioneer. Obviously, you're running marathons, right?

Wes Pentz (0:55)

I ran one full marathon.

Michael Gervais (0:57)

Could you imagine running one, like dosing?

Wes Pentz (0:59)

I did that. That's what I did.

Michael Gervais (1:00)

I know.

Wes Pentz (1:02)

But it made me run really fast.

Michael Gervais (1:04)

Are you hard on yourself?

Wes Pentz (1:06)

I expect more on myself. But I think that's one part of the process of being, quote, unquote, successful. You aim higher than you can reach.

Michael Gervais (1:13)

The success has catapulted him into the spotlight, and that too has had its consequences.

Wes Pentz (1:18)

When you're a musician at a high level and you're a father to a high level, and then also like a boyfriend or a husband, those three things, you can't be successful at the same time. I'm lucky to have my children because I find love with them. Like that's pure love. I will die for them, you know?

Michael Gervais (1:32)

In this conversation, we explore how Diplo stays ahead of the curve in an industry that is constantly evolving.

Wes Pentz (1:38)

I was always okay with falling back and starting over again. That was the key for me, because that gives you the freedom to not have the pressure of like success, but eventually I got it. Even today, take everything from me. I feel like I had the motivation to start over again and build something.

Michael Gervais (1:51)

So with that, let's jump right into this week's conversation with Diplo.

Wes Pentz (1:59)

All right.

Michael Gervais (2:00)

I am stoked to sit down with you. Do you want me to call you Diplo or Wes?

Wes Pentz (2:04)

You can call me Wes.

Michael Gervais (2:05)

Wes?

Wes Pentz (2:06)

Yeah.

Michael Gervais (2:06)

I know you as Diplo.

Wes Pentz (2:07)

Yeah.

Michael Gervais (2:08)

Okay. So we're getting a little more intimate now. Yeah. Okay. Good. You know what I want to talk to you about? I want to talk to you about three things. I want to talk about the early experiences in your life that shaped you, that were materially important for who you are today.

I want to explore like your creative process, which I think is a really tricky thing to talk about. And I also want to understand like, what do you hope the impact of your work and your music is? But to start with, help me understand your process to work from the inside out. Like whether that's therapy or sitting down with somebody or doing that internal work, however you might do that.

Wes Pentz (2:44)

I never really had therapy, but I have a lot of great people in my life that accept me and give me, they tell me what I'm doing and how I'm doing and...

Michael Gervais (2:54)

So you have truth tellers around you?

Wes Pentz (2:55)

Yeah, I have a lot of people that are very critical in a good way and a bad way. So I really appreciate them.

Michael Gervais (3:00)

Yeah. Are you a truth teller to yourself?

Wes Pentz (3:02)

I think so. I think I do keep a lot of lies to myself. And I kind of, I always, I think I'm better than I was, but I, you know, I have a lot of coping mechanisms that I always, at least I'm absurd of them. I'm not a drinker. I don't really do that many drugs besides psychedelics. And I don't ever find an excuse for my behavior. You know, I always find it like, I always feel like I take responsibility as much as I can for what I do and how I do it. And then as a father, you just always feel a little bit more like you have to be, you know, fully responsible for yourself because you have to, you have to show your kids that you're a good, a good man. That's kind of like my.

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