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Artist-Driven Collective Is Giving the Music Industry Back to Creators

In partnership with PennyFly Entertainment

By Chris Gallagher

Jett Prescott
Jett Prescott (Image: Provided)

Are “Label Services” Models Fixing a Broken Industry?

It is no secret that artists and the music industry haven’t always seen eye to eye despite relying heavily on each other to thrive. Even though it has been nearly a decade since renowned artists from Prince to Michael Jackson encouraged young artists to take their careers into their own hands, major labels continue to dominate the landscape of mainstream music. Yet, while it may not be obvious to the public, a very real and measurable shift has continued to show that independent artists are making up more and more of the industry’s global revenue.

There are now tens of thousands of independent artists who may not be recognised as household names, but they are generating steady upper-class incomes from their respective fanbases.

The Traditional Path to Success: Labels

When artists reach the point where they consider giving everything up to pursue their dreams, they are confronted with the same universal pathway to success through record labels.

When dissecting the major label business model, the value they provide artists comes down to three things: management, marketing, and production. Anyone who has found success in the music industry will tell you that having the right team around you is paramount. Like any other business, an artist’s career involves so many moving parts it isn’t realistic or sustainable to do everything on your own. Even if an artist has above-average business acumen and an eye for marketing, they can understandably feel like there isn’t enough time in the day for one individual to accomplish everything required to properly scale their career (on top of creating and performing the actual music).

The Alternative: Build Rome Yourself

As an artist, how do you find an experienced team you can trust to handle the business and marketing aspects of your career? Signing with a major, traditional label isn’t the only route. Independent labels, distribution deals, and fan engagement platforms are all options for independent artists. Even though labels have the success they do—they have spent decades and many millions of dollars cultivating the right team chemistry across various departments, experimenting with cutting-edge marketing techniques, and cultivating industry relationships that can move mountains when tapped on—there are still ways of doing it solo.

Independent artists usually have two main paths: building their own team or signing with a record label. Building a team requires finding and managing individual professionals across various areas like digital marketing, PR, promotion, advertising, graphic design, tour support, and business management. While this approach offers more control, it also presents challenges in terms of coordination and communication between independent contractors. Record labels on the other hand often provide a cohesive team environment with established connections, streamlining these processes. However, these label structures typically require artists to relinquish creative control and share significant profits with the label.

PennyFly Entertainment’s Approach Breaks New Ground

Enter the “label services” model: a growing niche of companies supporting independent artists without requiring the all-encompassing standard contract structures. This is where PennyFly Entertainment shines. As boldly stated on the front page of their website, PennyFly is a “by-artists-for-artists collective bringing rights, revenues, and freedoms back to creators.”

Launched in 2017, PennyFly curates major label-caliber teams for independent artists without the usual strings attached. It strives to improve artists’ access to critical industry support by providing top-tier services tailored specifically to their exact career stage, personal goals, and development needs.

Regarded as one of the top business schools in the world, Pepperdine University has twice recognised PennyFly Entertainment as one of the most fundable companies in the United States and remains the only label services entity to receive this acknowledgment. Most recently, HackerNoon crowned PennyFly among the top startups of 2023, citing their innovative industry solutions and creative use of AI.

From Artist to Label Exec: Solutions Driven by Experience

A singer/songwriter himself, PennyFly’s founder, Jett Prescott, started this movement after receiving his own label offers and has since been featured in a handful of Rolling Stone expert panels. Past interviews reveal that Prescott formed the company while mentoring under some of the industry’s best, with the single goal of learning the major label playbook and offering it back to artists.

Pennyfly logo
(Image: Provided)

Jett has gone on to executive produce over 100 singles with collaborations spanning a wide range of artists, including Kodie Shane, Gabbie Hanna, Ricky Rebel, Minzy, Ruggero, and Rebecca Black. After a nearly seven-year hiatus on his own project, Jett is expected to begin releasing his own music again before the end of 2024. Having brought charting success to relatively unknown artists still building their brands, PennyFly is poised to continue its upward trajectory as new artists seek out their support.

When it comes to discovering the right sound for developing artists, PennyFly has had long-standing partnerships with multi-platinum producers, including PJ Bianco (Jonas Brothers, LP, Kygo, ARIZONA) and Emile Ghantous (Pitbull, Snoop Dogg, Chris Brown).

Artists to keep an eye on include Junior Eurovision Song Contest finalist Tanya Mezh, Phantom of the Opera’s own Amelia Milo, viral America’s Got Talent contestant Summer Rios, and rising hip-hop artist Kiraly Payne. Timbaland recently praised one of PennyFly’s recent signings, Izzy Arden, after playing her music live on stream. PennyFly is supporting these artists through various label services while allowing them to retain their full rights and creative freedoms.

Embracing Decentralisation and Quality Relationships in Today’s Music Industry

According to those who work closely with PennyFly, the company is known for cultivating a casual work environment driven by results and real friendships with a passion for the industry—PennyFly’s CMO Skye Ruedas was brought on by his close friend and CTO Dr. Harry Malinski, who both worked to solidify mutual friend Carter Perran’s role as director of project management. Additionally, Jett’s wife Raye serves as PennyFly’s creative director, while Harry’s wife Melody assists with web development and administrative responsibilities. Though artists have long referred to those on the business side of the industry as “suits,” PennyFly seeks to reframe this mentality by supporting artists with a less corporate approach.

Today’s industry landscape is evolving rapidly. Those who embrace the decentralisation of label services are likely to find success among an ever-expanding pool of artist talent. PennyFly is truly changing the industry spectrum by granting independents the access and support they’ve always needed.


Rolling Stone UK newsroom and editorial staff were not involved in the creation of this featured content