What happens when your passion becomes your paycheck?

In this episode, San Holo and I unpack the real journey of turning your art into a business — and how to stay grounded when success starts pulling you in every direction. From his first viral remix on SoundCloud to headlining global festivals, San shares the mindset that’s kept him authentic through it all.

We talk about the creative struggle, the pressure to keep up with trends, and why staying different is both a blessing and a curse.

🔥 Topics we cover:
– The art vs. the algorithm
– Turning writer’s block into creative fuel
– Making peace with the business side of music
– How to protect your relationship with your art

This episode will remind you why you started — and why you’ll never be able to stop.

Book a free coaching call here: https://www.nikcherwink.com/apply

In this episode, Big Gigantic’s Dominic Lalli shares how he went from broke jazz gigs in New York to headlining festivals around the world. We talk about building Big Gigantic from the ground up, the mindset behind 15+ years of success, and how to stay creative, relevant, and inspired in an industry that’s always changing.

Whether you’re a DJ, producer, or artist chasing long-term growth, this conversation is packed with lessons on teamwork, consistency, and trusting the process.

🎧 Listen now and learn how to build a music career that actually lasts.

Follow Big Gigantic here:
https://www.instagram.com/biggigantic

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

100 episodes. What a milestone!

In this solo episode, I open up about the highs and lows of reaching this point with the Headliner Mindset Podcast. I share honestly about the self-doubt that crept in, the voice that told me to quit, and the support that reminded me why I started. From stepping on stage recently with Bella Renee to hearing encouragement from past clients, this episode is about the importance of having people in your corner.

We dive into:

• Why consistency is everything (and what happens when you lose it)
• How to navigate the “inner gremlin” of self-doubt
• The role of community and accountability in staying inspired
• A special announcement about the new Headliner Mastermind launching October 6

If you’re an artist who’s ready to stop spinning your wheels and lock in for the rest of 2025, this episode is for you.

Apply for coaching here: https://www.nikcherwink.com/apply

RIOT just dropped their new album The Machine on Slander and NGHTMRE’s label, Gud Vibrations, and are hitting the road for their first-ever national headlining tour.

In this episode, we talk about what it takes to build a sustainable career in bass music—while staying true to your vision and leveling up every step of the way.

We dive into:

• The grind of moving from support slots to headlining shows
• How they balanced singles, a full album, and tour prep all at once
• The investment behind their visuals, branding, and comic book universe
• The realities of touring life, burnout, and building healthy routines
• Why up-and-coming artists need to slow down, stop chasing trends, and focus on quality music

If you’re serious about building a real career as an artist, this one’s packed with lessons on patience, strategy, and doing things the right way.

Follow RIOT here:
https://www.instagram.com/riotmusic
https://www.tiktok.com/@itsriotmusic

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

Apply for coaching here: https://www.nikcherwink.com/apply

What happens when the dream you’ve been chasing no longer feels like yours?

In this powerful and deeply personal episode, Fredy Lane returns to the podcast to share why she’s walking away from her artist project at the height of her momentum — and what it really means to let go, evolve, and trust your intuition.

We get into:

• Why she decided to retire the Fredy Lane project and leave the touring DJ lifestyle behind
• The pressure to stay in the game vs. the peace of choosing yourself
• What alignment actually feels like — and how to know when something’s no longer right for you
• Letting go of ego, comparison, and “success” to find real happiness
• Her next chapter: moving to Paris, reclaiming her creativity, and starting fresh on her own terms

This is a conversation about courage, clarity, and what it means to pivot with grace — not because you failed, but because you grew.

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

Apply for coaching here: https://www.nikcherwink.com/apply

Steller just wrapped her first headlining tour — and she’s doing things differently. In this episode, we talk about what it really takes to build a career with intention, from learning to trust your gut to putting your mental health first in an industry that often glorifies the grind.

We get into:

• How Steller partnered with To Write Love On Her Arms to bring mental health resources to her shows
• Why she waited a full year before going on tour — and how she knew the timing was right
• The emotional and somatic signals she listens to when making big career decisions
• How to avoid burnout and comparison while still building a successful brand
• Why putting yourself out there on socials is a non-negotiable — even if it feels scary

If you’re building something meaningful and want to do it on your own terms, this one’s for you.

Follow Steller here:
https://www.instagram.com/stellersounds

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

Apply for coaching here: https://www.nikcherwink.com/apply

Nostalgix is the definition of a multi-talented artist—producer, rapper, singer, songwriter, and performer—and she’s here to share the REAL story behind her rise.

We dive deep into:

• How she went from bedroom DJ to touring globally (without even planning on becoming an artist)
• The mindset shifts that took her from just having fun to fully committing to her craft
• Why burning out every week was part of the process—and how she finally learned to manage it
• Her journey to finding community, mentorship and her team
• The truth about building your own universe as an artist
• How her fans helped support through her darkest times

Whether you’re just starting out or already on tour, this one is packed with gems about grinding, leveling up, and staying connected to your WHY.

Tune in for a powerful reminder: You can do anything you set your mind to—but you can’t skip the steps.

Follow Nostalgix here:
https://www.instagram.com/nostalgixmusic

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

Apply for coaching here: https://www.nikcherwink.com/apply

In a music industry that never stops moving, how do you stay grounded, intentional, and actually enjoy the journey?

This week I’m joined by Dr. Sunni, a licensed psychologist and coach for DJs and creatives, whose work sits at the intersection of mental health and the electronic music industry. We dive into the deep end of artist mindset — from burnout and comparison to self-worth, imposter syndrome, and the hustle culture that keeps so many artists stuck.

We get into:

• How to stay connected to your purpose when social media takes over
• The trap of chasing external validation (and how to break free from it)
• The common challenge of imposter syndrome
• Simple tools to rewire your brain and create lasting mindset shifts
• Why mindfulness is the antidote to burnout — and how to actually practice it

Whether you’re trying to grow your brand, build momentum, or just keep your sanity intact, this one’s full of grounded wisdom and real talk.

🎧 Tune in, take notes, and share it with a friend who needs it.

Follow Dr. Sunni here:
https://www.instagram.com/shaping_success

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