Proppa is a house music producer from Chicago whose recent remixes are lighting up DJ sets across the globe—from Dom Dolla to Cloonee to John Summit and many more.

But this didn’t happen overnight...

Proppa shares the real story behind his 15-year journey in music—starting out as a drummer, battling perfectionism, finding his sound through consistent remixing and figuring out his brand and identity as an artist.

In this episode we talk about:

• What it really takes to get noticed in today’s music industry
• The mindset shift that helped him finally let go of perfection
• Why knowing who you are is the key to building your brand
• How he turned his Patreon into a sustainable income stream

If you're trying to hit that next level in your artist career, this one will give you some great tips and guidance.

Follow Proppa here:
https://www.instagram.com/itsproppa
https://www.patreon.com/proppa

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com

Join the next round of the Headliner Mindset coaching program, starting 4/7:
 https://www.nikcherwink.com/headlinermindset

Feeling stuck in your music career—even though you're doing all the things?

In this special episode, Nik shares the full recording of his recent live masterclass, UNSTUCK: The Mindset Masterclass for Artists Who Are Ready to Finally Break Through.

You’ll learn the 4 mindset and energy shifts that help artists move from burnout and self-doubt to clarity, momentum, and creative flow. If you’ve been grinding, posting, and still feel like nothing’s clicking—this one’s for you.

Inside this episode:

• Why most artists stay stuck (and how to shift out of it)
• The hidden mindset blocks behind burnout
• How to build consistent energy and creative momentum
• The real key to growing your career from the inside out

Sign up for the free Headliner Mindset Masterclass on 3/31 here:
https://www.nikcherwink.com/masterclass

And check out 6am Group's free ArtistMap training here:
https://artistmapby6am.teachable.com/p/artistmapby6am-phase1

JIA is a DJ, promoter, educator, and founder of the 6AM Group and ArtistMap. In this episode, we explore what it really means to be a successful artist in today’s music industry—and it goes way beyond just making tracks and playing shows.

JIA shares the full story behind building his promotion company and brand from the ground up, the hard lessons he learned about burnout, ego, and leadership, and why mindset is the foundation of everything. We talk about redefining success, building a career with purpose, and the importance of personal growth in the artist journey.

This episode is for any artist who’s feeling stuck, burned out, or limited by the industry’s rules. If you’ve ever questioned your path or felt like there must be more to it all, this conversation will reignite your fire and remind you why you started in the first place.

Aren Goldberg is a tour manager for some of the biggest artists in the dance music industry including NGHTMRE, Peekaboo, Dimension and more. In this episode we dive into the realities of life on the road, the biggest mistakes artists make when booking their first tours, and how to actually make money while touring—without blowing your budget on things you don’t need.

If you’re an artist, DJ, or producer who wants to tour one day—or if you’re already playing shows and want to level up—this episode is packed with insights that will save you time, money, and stress.

Follow Aren here:
https://www.instagram.com/arengoldd

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com

Nick Ruffalo is a music marketing expert who helps artists cut through the noise and build real, engaged audiences with his agency, Unleashd Creative Solutions. In this episode, we break down the biggest mistakes artists make when promoting their music, why simply posting content isn’t enough, and how to actually connect with fans in a way that drives long-term success.

We also talk about the platforms that matter most in 2024, the strategies that actually move the needle, and how to market your music without feeling like you’re selling out. If you want to grow your brand, increase your reach, and make a lasting impact, this episode is packed with game-changing insights.

Follow Nick and apply to work with Unleashd Creative here:
https://www.instagram.com/ruffmusicofficial
https://www.unleashdcreative.com

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com

Arta Majd is an entertainment attorney who has worked with labels, independent artists and industry professionals to protect their rights, negotiate better deals, and avoid the common pitfalls that ruin careers. In this episode, he breaks down the biggest mistakes artists make when signing contracts, why legal knowledge is just as important as branding and marketing, and when you should bring a lawyer onto your team.

We also dive into the realities of the music business—how deals are structured, the hidden clauses that can lock you in for years, and how to navigate negotiations like a pro. Whether you’re an up-and-coming artist or already deep in the industry, this episode is a must-listen if you want to protect your future and take full control of your career.

Follow and connect with Arta here:
https://www.artamajd.com
https://www.instagram.com/artamajdesq

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com

Are you creating from the heart or just chasing the algorithm? In this solo episode of The Headliner Mindset Podcast, I reflect on what it means to reconnect with the soul of creativity. Inspired by Julia Cameron’s The Artist’s Way and my experiences teaching The Art of Flow at ICON Collective, we’ll explore how to break free from overthinking and rediscover the joy of creating from a place of intuition and authenticity.

This episode is for anyone feeling stuck, uninspired, or disconnected from their art. I also introduce my new 12-week coaching program based on The Artist’s Way, designed to help you overcome creative blocks, tap into your flow, and create art that truly resonates. If you’re ready to embrace a more soulful approach to your art, this conversation will inspire and guide you.

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com

Dan Sugarman is the lead guitarist of Ice Nine Kills and has played on some of the world’s biggest stages. But his path has been anything but ordinary...

In this episode, he opens up about his early obsession with music, the challenges of balancing ambition with health, and how he turned setbacks—like a life-changing cancer diagnosis—into fuel for reinvention. We also dive into his passion for mentoring musicians, the power of authenticity in branding, and his personal growth journey with coaching and plant medicine.

Whether you're an artist or someone chasing big dreams, Dan’s insights on resilience and purpose will leave you inspired.

Follow Dan and Ice Nine Kills here:
https://www.instagram.com/dansugarman
https://www.dansugarman.com
https://www.instagram.com/iceninekills

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com

NITTI is a genre-bending force in the electronic music world, also known for being one half of the Grammy-nominated duo SIDEPIECE, and is now making waves with his bold new project Alt Rave. After years of grinding in the studio and locking into his craft, he’s found his stride by merging his love for rock, metal, and electronic music into something entirely his own.

In this episode, Nitti shares how he went from church bands to headlining stages, the mindset that keeps him pushing boundaries, and why building the right team has been key to his success. We also dive into the creative freedom he’s found with Alt Rave and his vision for building a community that’s all about passion, quality, and authenticity. If you’re an artist or a fan of next-level music, you won’t want to miss this one.


Follow NITTI here:
https://www.instagram.com/nittimusic
https://www.tiktok.com/@nittimusicoff...

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com

In this special solo episode of The Headliner Mindset Podcast, I reflect on the top five lessons I’ve learned from hosting over 70 inspiring conversations with artists, DJs, and industry leaders. These takeaways are packed with actionable insights to help you thrive in your career and life. Whether you’re an artist, entrepreneur, or dreamer, this episode will resonate with anyone striving for growth and success.

Here are the five lessons we dive into:

• Cultivate resilience and embrace the journey.
• Stay authentic to yourself and your unique voice.
• Treat your career like a business with focus and strategy.
• Prioritize mental and emotional health for long-term success.
• Build strong relationships and foster community connections.

Tune in to discover how these lessons can elevate your mindset and help you unlock your full potential.

Follow Nik Cherwink here:
https://www.instagram.com/nikcherwink

And visit my site to join the mailing list or book a free coaching call:
https://www.nikcherwink.com