Everybody wants to be a rapper, and every rapper wants to rap for a crowd. You often hear artists talk about the high they receive from performing, and that incomparable rush they will constantly chase. Once an artist realizes this, they learn that one show could never be enough. There’s now this hole in their hearts that can seemingly only be filled by the sound of a crowd before them. The thought of going on tour comes to mind, with dreams of being able to perform every night floating in their heads. While every artist likely wants this for themselves, how do you know when you’re actually ready? Do you have the fan base that you think you do? Do you have the mental fortitude to take on this journey? Have you considered the often forgotten physical requirements and vocal stress it would take to perform nearly every night? For Nick Oliver, the genius machine behind Oliver Booking Company, this is all second nature. Helping artists tackle these issues is his bread and butter, and that’s why nobody books tours like him.

When I talked with rapper turned booker Nick Oliver, who knows this business all too well, we discussed the actual logistics of a tour, and what would be required to make said tour a success. Using himself (or perhaps his former self, when he was best known throughout New England as rapper Ordeal) as an example, Nick Oliver eloquently explains the cold hard truth: not every good rapper is ready for a tour. Before he was booking some of the best concerts and tours for your favorite artists like R.A.P Ferreria, Psalm One, Ceschi, BrainOrchestra, Sadistik, and a hundred others, he spent more than a decade, performing and touring himself. After spending most of his younger years writing and gearing himself up to be an artist, Nick became Ordeal and started performing throughout his home area of New England. Opening up for larger acts coming through his town, and putting on some local shows of his own, Nick began to soak his feet in the world of performing. The hunger to do more drove Nick out of his comfort zone as a rapper, and forced him to learn how to do more- specifically, how to tour. A new opportunity presented to him would put the ball in his court, and force him to make it or break it. Knowing that Nick had only performed locally as Ordeal, his friend and frequent collaborator Abbadon presented him with the chance to go on his first tour. The only catch was that he would have to get ten shows booked and added to the tour if he wanted to be welcomed along. Not wanting to let this opportunity pass him by, Nick had no choice but to learn how to book.

“He (Abbadon) hits me up like, ‘Yo, have you ever been on tour?’ And I’m like ‘I’ve never even performed outside of New England.’ But he basically tells me like, ‘I’m going on tour, it’s me, Kristoff Krane and Sadistik, and we’re trying to do a big national tour. Everyone’s booking shows, if you can book 10 shows you can come on tour and you’ll get paid a percentage from every night we perform.’ So I start talking around, learning what I can, and I end up booking 13 shows, a third of the tour. That was my first experience REALLY booking things. I had booked local shows for myself and friends, but that was my first taste of booking a tour.”

Let’s fast forward some years to when Nick Oliver realized he could book tours for others and turn this into a serious business. After doing a few of his own tours and helping in the booking process, Nick says he “didn't even realize how many different people I made connections with. Like, my mental rolodex was fucking SWOLLEN with contacts.” He began to notice that friends and collaborators would essentially ask him to middle man a connection with other artists he knew. The gears began to spin in his mind. “Instead of telling these people my contacts, and giving them everyone’s numbers, I could just book tours for them. Why would I line everything up for them to do themselves when I could actually just take charge and start doing the booking? That’s when I realized I could book my own tours for other people and help them out while making some money. Like, if I have this skill and this ability to kind of facilitate and link people with shows, and then I can like charge a fee for every show that I book, I can make a little bit of money, and help these artists that are putting in a big investment to become ‘real rappers.’”

When we discussed the commitment required from an artist to make a tour successful, Nick Oliver used underground legend Jonwayne as an example. For his “Rap Album Two” tour, booked and run by Nick Oliver through Oliver Booking Co, Jonwayne performed 46 shows in 55 days, doing stints of 6 days in a row in 6 separate cities with only one day of rest before the next 6 days begin. Referring to a tour like this as a pseudo “Oliver Booking Company - Tour Bootcamp,” Nick Oliver explained how it preps greener or less toured rappers for the “anything can happen” crazy life of performing.

One of the biggest problems I notice in the music industry these days is how transactional things can feel. With the digital world making it normal to expect minimal to no contact or communication between the producers you get beats from, the artists who do your covers, the publishers printing your albums, and nearly every other aspect of the industry, it may seem expected that your booker would view you as a client rather than a person. It can almost make us forget how communal and collaborative music should be. Artists whose careers exist almost exclusively online can find it difficult to translate their work into a physical presence. The idea of performing for a crowd or going on tour can seem so unfamiliar and daunting to these artists, and not knowing how to navigate that foreign territory can make them miss out on one of the most important, and, not to mention, FUN parts of being an artist. While he’s not here to hold hands, Nick Oliver would never shy away from business with an artist who is ready to WORK and prove they want to take things further every day. He isn’t a magician, and he can’t perform miracles, but if a rapper is truly ready to tour, there’s perhaps nobody better than Nick Oliver to guide them, and show them what to expect from this life.

“I'm not a magic wand, okay? I’m a facilitator. If you have a fan base, and you have people that want to see you and give you money, I can find those people and bring you to them so that they can give you that money. Okay? I can do that. But if nobody knows who you are or you're just getting started out and you’re like working your way up, just kind of like playing some shows and putting out a record… like, I know people will hit me up like ‘Hey man, I’m putting out my first album on bandcamp, can you book for me?’ I’m just like, ‘Bro, come on dude. You gotta give yourself a chance to develop.’ With the Jonwayne tour for the example, he fucking kills it and up to that point had already been killing it. But he had never toured like that, I mean like 45 dates in like 60 days? Do you wanna eat sleep or shower at all? But you know what, he did it. There were stumbling blocks, and problems like every tour, you know? Like, you miss your girl, you miss your home, you miss your relaxation. But sometimes that’s what it takes. My job is to set up the route that these artists need to take to accomplish their goal of touring.”

Around 10 years deep into his career as a booker, Nick Oliver has fostered real life connections with his clients that reach far beyond the realm of business. He wants to help people succeed, and he wants to make people’s dreams come true, but he won’t overextend himself for someone who isn’t ready. If you’re a young rapper who is starting to make a name for yourself, you should look towards Nick Oliver as a beacon of light in the nuanced world of performing. When you find yourself in a position where you’re ready to take on a challenge in touring, Nick Oliver will push you every step of the way. As him and his friend R.A.P. Ferreira say to each other, he’s in this “until the wheels fall off.” Look for Oliver Booking Company’s upcoming tours this summer with amazing artists like R.A.P Ferreira, CoDefendants. Shrapknel, Phiik and Lungs, and many more.

Making me incredibly excited with his amazing choices, I am thrilled to say, here are twelve movie recommendations from Nick Oliver:

• Dream With The Fishes, 1997
• Altered States, 1980
• Magnolia, 1999
• Julien Donkey-Boy, 1999
• Welcome to the Dollhouse, 1995
• Palindromes, 2004
• Goodfellas, 1990
• No Country for Old Men, 2007
• Requiem for a Dream, 2000
• Drugstore Cowboy, 1989
• My Own Private Idaho, 1990
• Midnight Cowboy, 1969