9 min 58 sec

Upstart Producer Turns Nostalgic Concerts Into Modern Money

A casting producer for NBC’s “The Voice” curates indie concerts on the side to create experiences and profits.
Events Music Service Unique Ideas

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What It's About

A casting director for The Voice drops the mic on tribute style concerts.

Business Model
Skills Required
Event Planning & Coordination
Profit Potential

Words of Wisdom

An event has at least one big difference from other business models: a fixed deadline that comes with other unchangeable variables. If no one signs up for your online course on ballroom dancing, you can try again later. But if no one shows up at a physical venue you’ve booked, you have a bigger problem.

Therefore, PR is essential. You absolutely must have a clear plan for how you will attract people to your event. This should include an easy way for them to sign up (and pay in advance whenever possible) so that you know what to count on.

Fun Fact

Turns out, whether it’s rock ‘n’ roll, jazz, hip-hop or classical, your gray matter prefers the same music you do. For a while, researchers believed that classical music increased brain activity and made its listeners smarter, a phenomenon called "the Mozart effect."

In recent studies, however, they’ve found that people with dementia respond better to the music they grew up listening to. If you play someone’s favorite music, different parts of the brain light up—that means memories associated with music are emotional memories, which never fade out—even in Alzheimer’s patients. [SOURCE]

Notes from Chris

Episode 951
Lamont Leak has always loved music—but his first musical side hustle did not love him. After saving nearly $1,000 from two summer jobs, a then-fifteen-year-old Lamont hosted his first event, a party for high schoolers in his hometown of Detroit. He rented the venue, got the DJ, promoted the event like crazy—and it was a flop.

He was devastated—all of his money and his hard work were for nothing. Fortunately, he kept the faith and the devastation wore off after about a week. Then he reassessed his plan for the next attempt.

This time, Lamont built rapport with his vendors so he didn’t have to pay anything upfront, he found a venue at half the price in a prime location, and he picked a better day to hold the event. The lessons he’d learned paid off well—his event sold out and earned him over $3,500. Not bad at all for a teenager.

Fast forward several years to 2016. After living in Atlanta for a while, Lamont was now based in Los Angeles to pursue his dreams in the entertainment business.

He got a job as a production assistant in Hollywood, which he says is just about the lowest job you can have. Basically, you do whatever the producers, crew, or artists need. It was tough work with long hours.

But, Lamont kept a good attitude! His work ethic and bright personality helped him advance. After a while, he was getting PA jobs with higher-profile events like the Oscars, and then with higher-profile TV shows.

But he was also looking for a side hustle. Not only did he need to supplement his income, he was looking for a creative outlet. While living in Atlanta, he had hosted music showcases for up and coming artists because he loved giving artists a performance platform. The showcases were also a great way for him to connect and build relationships in the city, in addition to the income they brought in.

So with those experiences in mind, Lamont decided to host showcases once again—and soon The Live Playlist was born. Lamont knew that Los Angeles was much more competitive than Atlanta. But that was okay because he had an idea. He decided that The Live Playlist would a showcase with a nostalgic twist. So how does it work?

Specifically, it’s a series of unique, immersive experiences that breed culture and creativity with Music and Art. The events are nostalgic music experiences that feature up and coming artists reimagining and performing music from well-known (often legendary) artists.

One show, I LOVE THE OLD KANYE, featured performances of Kanye West’s top hits and another recent event, the SOUL SESSIONS brunch, featured a live music tribute to R&B legends Usher and Brandy.

All of Lamont’s work has paid off well. He’s now bringing in a steady $4,000 per month in profit—a beautiful sound to anyone’s ears!

Lamont says he can’t imagine ever giving up his side hustle, even when the hours are long. He also said that while he enjoys his job, it’s his side hustle that keeps him going. The Live Playlist allows him to express his skills and creativity without limitations. And, for him, that is more valuable than money.


  • The Live Playlist: Follow the beat—head on over to Lamont's website to learn more about this nostalgic side hustle!

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"My side hustle is honestly what keeps me going. While I enjoy my day job, my side hustle allows me to express my skills and creativity without limitations.​"
—Lamont Leak #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau