Ryan Kairalla on Being Different, Bringing Innovation, and Breaking The Business

Entertainment lawyer. Podcast host. Education Advocate. These are just a few hats worn on the daily by Miami-based Ryan Kairalla. Perhaps best known in the music industry for Break The Business, his book and podcast, Ryan’s outspoken support for creators of art (as opposed to record labels) has him alternating between being the most hated man in a room full of suits, or crowd-surfed to the front of an independent music revolution. 

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Somehow, Ryan Kairalla found time to sit down for a Skype interview despite his busy schedule – and let me just say, he is the real deal. Wanting to work in the music business since Junior High, Ryan would frequently try to sneak copies of Billboard Magazine into class behind textbooks. After graduating from New York University School of Law, his first entertainment clients were artists being offered their first record deal, and the conversations went something like this…


Artist: “Hey, could you look over this record deal for me? Just let me know what minor fixes I should ask for.”

Ryan: “I can’t in good consciousness let you sign this contract. It’s a horrible deal.”

Artist: “But it’s my shot, man! This is my big break! I’ve honed my craft my whole life for this opportunity.”

Ryan: “Please don’t sign.”

Artist: *signs anyways* *career and life gets destroyed*

Ryan: *feels like crap*

Picture this very situation taking place again and again. Ryan Kairalla, distraught that his attempts to help weren’t making a difference, began searching for another way. So, he went out and interviewed independent music business professionals and his findings were eventually compiled into a book: Break the Business: Declaring Your Independence and Achieving True Success in the Music Industry

“My record label friends hate me now, but I made new artist friends who are much cooler,” Ryan smiles over Skype. He’s sitting in his podcast studio, with framed degrees and a ukulele collection on the wall, earphones and a serious radio-style mic setup. After the release of his book, he started the podcast as a way to continue the conversation. “I want my podcast to be what my listeners want it to be.” 

Conversations are a big part of Ryan’s daily life, from well-known members of the independent music business coming in as guests, to his most common legal work, helping musicians get their releases out. Not only does he help with trademarks, copyrights, and such, but he also shows them how to use digital distribution platforms, and introduces them to others who they would get along with, empowering them for when Album #2 comes along.

For a music lawyer who practically shouts from the rooftops “I want to artists to win!” Ryan has been asked more than once if the lack of record label negotiating means less work for him. His answer? “In the record label world, all I get to be is the guy who reviews your shitty record deal. It’s better, more interesting work for me if the independent artists were kings and queens, and I would be their legal counsel! Labels need artists more than artists need the labels, and indie artists are the coolest. The little guys tend to be the ones that change things.”

As well as practicing entertainment law in the States of California, Florida, and New York, Ryan Kairalla is a strong advocate for innovation in education. In fact, he currently does work with a small college in Florida that offers post-secondary level classes to low-income high school students, many of whom are children of immigrants, helping reduce their tuition fees by graduating sooner. “A lot of lawyers do the same thing every day, it’s so repetitive. That’s not for me.” A “normal” day for Ryan could include “lunch with someone in the industry, doing stuff for the show, reading and researching industry news.”

One of the biggest values that point Ryan’s compass through life is fairness. He is a firm believer in the idea that the creators of the art should be the ones who get paid the most. “The money is all out of balance.” Very choosy about who he takes on as a legal client, Ryan Kairalla often asks himself “does this person represent my ideals?” (for example, he point blank refuses to work on any mom-ager deals). However, he believes “it’s never too early to have a lawyer, especially where intellectual property and exclusivity is involved.” 

PRO TIP: LOOK INTO PRO BONO LEGAL AID FOR THE ARTS WHEN FIRST STARTING OUT AND BROKE. 

Going forward with his podcast (which has 128 episodes as of writing this!), Ryan wants to do more regular segments and have music live in studio. For those of you who have ever listened to an episode, you know that Ryan asks every one of his show’s guests this question at the very end: for this interview, I flipped the script and surprised him by asking it first.

Clarence: “Do you have any last tips to share with the indie artist listeners out there, to help them move their careers forward?”

Ryan: “Embrace something new. Don’t feel like you have to do it the same way as everyone else (for example: 12 song albums every 2-3 years). If you’re good at music, and also good at other stuff, use it… I tell artists all the time to start a blog or a podcast… You’re an entertainer, a content entity. All these tools are accessible to you, absolutely free. It’s critical to be distinctive, to stand out. Oh, and how do you negotiate a record deal? Don’t.”

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