Andrew McCluskey, founder of musicto, shares how he left a successful career to become a musician and eventually build a global community around collaboration. We discuss why creativity requires time, how values guide difficult pivots, and how music can help strangers form real human connections.

Monique Sar, founder of marketing agency De Vitesse, shares how she moved from becoming one of her firm’s top female financial advisors to helping creators, speakers, and brands communicate their value. We discuss why creators should charge more and how clear positioning can matter more than follower count.

Music executive and Not Dead Yet Media founder Russ Rieger has worked with artists including The Replacements, Cyndi Lauper, Prong, Modern English, and The Prodigy. We discuss building diehard local fan bases, finding creative ways to break through, and creating sustainable careers without chasing short-term attention.

Kenny Feinstein from the punk rock bluegrass band Water Tower shares how busking, livestreams, and a unique creative identity helped him rebuild his band into a movement. We also talk about learning every part of the music business, building a recognizable brand, and his latest book, More Than Talent: 7 Steps To Attain the Brand, Acquire The Gigs, and Amass Lifetime Fans.

Larry Cummings of Off The Map Games joins the show to talk about system design, small teams, Dungeons & Dragons, and why games can teach us so much about collaboration, creativity, and how people work together.

Joey Vesely of post hardcore band Trace Remains talks about growing up in the Pittsburgh DIY scene and the challenge of getting people’s attention without losing what makes the band authentic. We also discuss their new single and music video “Breathing Air”.

Post-hardcore artist MADiSON ViOLETT discusses how she was able to drop seven singles in a year without burning out. We also talk about her latest release, “Bleed for Me,” and how she landed Kellin Quinn from Sleeping with Sirens as a featured artist.

Rivkah Reyes, known for playing Katie in the film School of Rock, shares how she’s built her own creative identity across music, acting, writing, and filmmaking. We also discuss her award-winning short film "Gianna” and her latest single and music video “Miss Congeniality”.

Eric Colville of The Low Stakes Band talks about writing songs that feel true instead of chasing what sounds commercial. We also discuss their single “Upon the Wall”, revisiting old ideas, and building a regional following.

Musician and artist Jaclyn Dima talks about growing up in a musical family, finding her way through open mics and teaching, and returning to music with her latest single “I Won’t Dance For You.” We also get into genre hopping, perfectionism, and why she refuses to pick just one lane.

Dallas Jackson, Founder of TipSee Music and The Hondo Rodeo Fest, shares how he went from finance to building music tech and event startups. We talk about making song requests and tipping easier for musicians, learning by doing, using AI to stay lean, and why integrity matters when you’re building something from scratch.

Publicist and artist Dani Felt shares her journey from a successful music blog to building her own company, writing a book, and navigating both sides of the industry with a heavy focus on relationships, risk, and self-belief.

Founder of GigSalad, Mark Steiner, shares how he went from being a talent agent to building one of the first online marketplaces for entertainers long before Uber and Airbnb existed. We also talk about being the top platform for mariachi bands and Santa Claus bookings as well as an honest chat about burnout, creativity, and what keeps him inspired.

Ian and Danielle of Orphan Prodigy dive into building a band from the ground up, from overcoming burnout and mental health struggles to creating a full scale project through production, live streaming, and touring.

Chris Laxamana shares his journey from the early days of podcasting to becoming the showrunner and co-host of The Adam Carolla Show and host of the hit podcast Resume. We discuss what truly makes great content and what keeps people coming back.

Randy Nichols shares his journey through artist management representing bands like Underoath, The Starting Line, and Say Anything. We also discuss his work consulting tech companies and helping shape the future of music through National Independent Talent Organization (NITO).

Basti from Melonball shares how the band went from friends making music together to touring internationally, all while staying true to the DIY punk scene. We also talk about recording their latest album, the reality of rising touring costs, working with indie labels, and why getting out on the road still matters.

Jess Bumsted shares her journey from booking agencies and major festivals to launching growth consulting firm Root & Trellis, along with her work advocating for diversity in live music through Book More Women.

Indie Pop artist Leah Nawy shares her journey from studying songwriting and production to releasing music independently as well as breaking down how storytelling, consistency, and self-belief shape her creative process. We also discuss release strategy including her latest single “Quicksand”.

Host of Imagination Skyway podcast Matthew Krul and myself discuss our experience filming an interview on-site on the Walt Disney Studios Lot with director of Disneyland Handcrafted, Leslie Iwerks. We also talk about touring Walt’s office.