Upstart Producer Turns Nostalgic Concerts Into Modern Money

This transcript was generated from the episode audio and may contain minor errors.

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What's up, my friends? I was in Atlanta recently, where today's story begins, and I wanna give a shout out to Atlanta Food Walks. If you are ever in the ATL, also known as the A, the Big Peach, check them out at atlantafoodwalks.com. I have no affiliation, I was just a happy customer. I really enjoyed what they're doing there.

And I also think it's great to go on walking tours in lots of cities. You can learn a lot, even if you're from that city, and you get to experience spots you'd otherwise probably miss. Today's story is not actually about food tours. I just thought I'd throw that in because I was thinking about it as I worked on this story. And in this story, a casting producer for ABC's "The Voice" curates indie concerts on the side to create experiences and profits.

He spends just $1,000 to get started, draws on a sense of nostalgia, and is now earning $4,000 a month through his after hours project. He's thinking about what comes next, considering expansion, and also just sees it as a wonderful creative outlet. So I'll tell you all about that. Upstart producer turns nostalgic concerts into modern money. The story is coming up in just 30 seconds.

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Lamont Leake has always loved music, but his first musical side hustle did not love him back. After saving nearly $1,000 from two summer jobs, a then 15-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 hard work were for nothing, at least at first.

Unfortunately, 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 up front. 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 events 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 in the industry.

Basically, you do whatever the producers, crew, or artists need. It was tough work with long hours. But still, 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 as well.

But he was also looking for a side hustle. Not only did he need to supplement his income, he was also in search of 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. Those 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 this time he would call it the live playlist. 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 be a showcase with a nostalgic twist. So how does it work? Well, 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. For example, one show, "I Love the Old Kanye," featured performances of Kanye West's top hits. Another recent hit, "The Soul Sessions Brunch," featured a live music tribute to R&B legends Usher and Brandy. Lamont estimates that his startup cost was once again just about $1,000. He negotiated partnerships with venues and deals with vendors, just like he did in high school, which he says reduces his costs.

For each show, the process begins with designing a theme and then scouting out venues before negotiating the final deal and date. Then he reaches out to potential performers. While he has built up a solid network of relationships, Lamont says that this part of the work still involves lots of emails, calls, and direct messages to pitch artists on the event. Negotiations with each artist come next, a process that is sometimes easier than others. While his events may not offer a global platform, he says that the live playlist's reputation and buzz, especially among local artists, has helped secure deals.

To promote those events, Lamont relies heavily on strategic media buys that reach his target market. This is largely on Facebook and Instagram. He also regularly updates his community through organic social media. And lastly, the artists from each show promote their performances as well. All of Lamont's work has paid off.

He's now bringing in a steady $4,000 per month in profit, a beautiful sound to anyone's ears. Of course, challenges are constant. While promoting his events, no longer requires him and his friends to pass out 10,000 flyers by hand, like he once did in high school, he now faces other obstacles. With each event he hosts having its own theme, it's like starting from scratch each time. Creatively, he is constantly working to curate the right blend of artists and songs to be performed.

This is key because one bad performance or song could throw off the entire night. Lamont says he respects each artist's ideas while also keeping his vision in mind. This can sometimes make for intense rehearsals with the house band and artists, but they're usually able to work through it. And for him, his vision continues. He's working to grow as a producer and an entrepreneur.

After graduating from the entry-level production assistant jobs, he now works with talent and casting for NBC's hit music show, "The Voice." He travels all over the country in search of artists, a task that requires lots of hours and miles on the road. Lamont says he can't imagine ever giving up his side hustle, even with those hours being long. While he enjoys his job, it's the hustle that keeps him going. The live playlist allows him to express his skills and creativity without limits. For him, that is even more valuable than money.

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All right, if you're gonna put together events, keep a few things in mind. They can definitely be successful, but good to have the lay of the land. An event has at least one big difference from other business models, and that is a fixed deadline that comes with other unchangeable variables. If you have an online course about ballroom dancing and it doesn't work out, well, you can try again later. But if nobody shows up at a physical venue you've booked for your ballroom dancing class, you've got a bigger problem.

Therefore, PR is essential. You absolutely must have a clear plan for how you will attract people to your event. This needs to be primary, not secondary. It should also include an easy way for them to sign up and to pay in advance wherever possible so that you know what to count on. Then, like Lamont learned, you don't always need to pay for venues and vendors.

Sometimes there's another way to partner. Now, of course, those venues and vendors may be small businesses or side hustlers of their own, so I'm not saying you should go around expecting everything to be free. I'm just suggesting that you look for win-win situations where people or companies are happy to partner with you because it's good for them too. And that can save you a lot of costs, especially in the beginning, when you're trying to learn how this crazy world of live events works. So I will leave you with that today.

Inspiration is good, but inspiration with action is so much better. If you wanna check out the show notes for today's episode, learn more about the live playlist. Just come to sidehustleschool.com/951. That is episode 951. Thank you so much for listening, my friends.

I'll be back again tomorrow. My name is Chris Guillebeau. This is "Side Hustle School." [Music]

From the "Onward Project."