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.