This Is What Touring as an Indie Artist Really Looks Like

Four insiders share invaluable information about touring successfully as an independent artist.
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The first time I met Pure Powers, the man had a fire in his eyes. It was getting late in the day on a hot LA afternoon, at the tail end of TeamBackPack’s annual underground MC competition, and Pure was one of only a handful of rappers who were networking just as hard when the final curtain fell as he was when the weekend’s first cypher got cracking.  

I wouldn’t have imagined that by the end of 2016, Pure would accomplish with several successful touring runs what most upcoming rappers only dream about, but in just two years, he has shared a bill with some of the most legendary names in underground hip-hop. That success started with a strong will set singularly on one goal: understand everything it takes to build and execute a successful hip-hop tour from the ground up.  

There’s a whole lot to learn, and if you’re staring down the barrel of your first stretch on the road, even thinking about where to get started can be overwhelming and discouraging.  

Of course, if you’re a casual rap fan, this might already sound all backward. Popular narratives, often fabricated by successful artists themselves, portray touring life as one big party and a handful of big paydays. According to old MTV shows, Russ’s Instagram feed, and at least twenty to thirty Tech N9ne songs, if you rap well and drive around the country rapping at people, success is waiting to be devoured by those who are hungry enough to work for it.

In the real world, though, touring as an independent artist can be a nightmare, financially and otherwise. For underground rappers hoping to make a career out of their music, touring is an essential element of generating revenue and connecting with fans, but it’s also so daunting that independent artists often don’t know where to begin.  

Fear no more, indies. DJBooth always has your back.  

In the conversation that follows, synthesized for clarity from four separate interviews, we’ve assembled the combined experience of industry professionals who represent four different perspectives on the music business and booking an independent tour.  

Meet our Panel: Damien Ritter is the former CEO of Funk Volume, the business mind and co-founder of Still Movin and a longtime indie hip-hop insider. le'Roy Benros is an A&R with First Access Entertainment, music business entrepreneur, and the Director of Booking at Sounds of Brazil (SOB's) in New York City. Reid Clow is a former artist manager, self-taught booker, and promoter, and is currently booking tours for The Palmer Squares. And finally, Pure Powers is a Sonoma County, California-based MC who has toured with Del the Funky Homosapien, various other members of the Hieroglyphics, Zion-I, Gift of Gab and tons of other underground staples.  

While I encourage artists to dive into these answers and insights in order to gain a deeper understanding of what building a successfully monetized tour really entails, hip-hop heads without artistic aspirations of their own should follow along, too. Your mind will be blown by all of the challenges that await independent rappers with dreams of hitting the road.

Thanks to social media, many independent artists who are just starting out in the industry don’t fully understand what planning and executing a tour actually entails. What would you say is the biggest misconception about hitting the road?

Damien Ritter: “I think most artists think they’re ready to tour before they’re really ready, from a demand perspective. It’s hard to get to the point where you can tour. Even just to bring 50 people out to a show is pretty impressive, and to be able to do that across the country—very few artists are actually able to do that. Even to get 50 or 100 fans to consistently come out is a hard thing to do.

“The other big one is being able to perform back-to-back shows, keeping your voice strong, just having the stamina. Especially in the early days. If you’re touring and you don’t have the biggest budget, you might be wearing multiple hats, in addition, to actually performing. It should be fun at the end of the day but it also can be pretty damn stressful.”

Pure Powers: “People think that they’re gonna go out there, and every night is gonna be crackin, and they’re gonna come home with a ton of money and a bunch of fans, and it’s gonna be career-changing and life-changing. Like when they’ve hit their first tour they're bona fide. Artists really think that once they tour once, they’ll have a career. And it’s a huge milestone, but in a lot of ways it’s just a first step.”

le’Roy Benros: “These young managers and artists with one hit, maybe a song on the radio—okay, I understand you are getting $20K or whatever at these nightclubs—but in order to have a real career, going on tour, you gotta build your hard ticket values, because that’s where your value really stands. These are fans that are paying specifically to come and see you.  

“When you’re trying to gauge your value, you really can’t see that at a club that might already be packed and then you have one song they want to hear. That’s a huge misconception I see with even bigger artists who are touring for the first time. Whatever, that’s great, but in order to show real numbers, you have to build your hard ticket numbers. People have to be excited to pay to see you play, you have to have those kinds of fans to make money and for me to want to pay you as a booker at a venue.”

Reid Clow: “It’s not a game. Yes this should be fun, yes we all love music, but this is work. This is a job. This is something we’re doing because we have goals and we want to get to a certain place.  Sometimes you’ll have certain artists on the road and they’ll think it’s a vacation.  

“Yeah I get it, we all love weed, whatever, and it can feel like a party out there, but you gotta remember it’s your party. You’re the one putting this on. That’s my best advice and something people don’t really look at the right way when they’re just starting out.”

What can an artist really get out of touring when they're just getting started? Realistically, what are some tangible goals to set upon embarking on your first tour?

Dame: “First of all, your first goal should be that everyone is safe. Safety first and foremost. But you definitely want to put on a good show, you want to leave people satisfied to the point that when you come back, they’re gonna tell their friends and it’s gonna be bigger. Depending on where you are financially, you would hope that you would at least break even and the hope is to make money from your merch or even from shows if you can get venues to pay you. But if you go in the hole, it means that you weren’t ready or the demand wasn’t there yet.”  

Pure: “You should come home with a bunch of contacts from artists in other areas you met along the way; contacts of venues, bookers, promoters. You should come back with some fans. Which you need to stay engaged with, by the way. Hopefully, you can even turn those new fans into people who can help push a show in their area when you come back. If everything goes well, you should be learning and growing.”  

So, where the hell do you actually begin? As an indie artist staring at a map and hoping to tour in places you’ve never played, what do you have to do to make that goal a reality?

Reid: “Looking at the act and depending on the fan base, you really gotta stay flexible. If it’s your first time leaving your home market, you’re probably not gonna expect to get paid very much, if even gas money. You gotta be willing and prepared to invest time and money into early tours because a lot of the time you aren’t going to be getting paid.

“What I do when I’m looking into a city I’ve never booked an act in before is I’m literally searching Google for “Live Music” in whatever city we are trying to hit, and going from there. Digging through venues on Facebook, finding some good fits, having an email drafted. At the end of the day, it’s just a numbers game. That’s the hardest part is that kids these days don’t wanna pick up the phone; our generation is afraid to talk to people. But you just gotta do it. Cast a wide net. Don’t get overwhelmed.”

Dame: “Our first tour we had to book ourselves, we didn’t have a booking agent at first, this was like 2011. I booked the RAW Tour, and that was just us announcing on our social platforms that we wanted to do a tour, and then sorting through inquiries that came in and connecting the dots, reaching out to cities in-between and finding the right promoters in those cities to work with.

"We strung it together like that. It was tough, but I feel like we had to do it to prove to big booking agents that we had demand. And to prove it to ourselves that we had not just an online fan base, we had people that would come out and support us.”

OK, so, you’ve got your eyes on a city and you’ve got a Google doc filled with venue names. How do you approach a booker that you’ve never worked with before?

le’Roy: “I’m glad you asked that question because there have been situations that really just hurt me [laughs]. When dealing with a young artist or a new manager, what I don’t like to see is a manager coming to me and saying, 'This is how much it’s gonna cost, this is what we have to see.'  

“First off, you don’t know how much I have to offer. You don’t know if there’s a sponsor. There are details that you don’t know. So how can you come to me, telling me, this is what I get for this show?

“I’m also a manager. There have been times when I’ve reached out for a show, and in my head, I know what we should be getting. But it’s always better as an artist or a manager to let a booker make an offer. There have been times where I got an offer and it’s like, ‘Oh shit, if I’d thrown out the first number I would have gotten 50% less than what you’re trying to give me.’ But what advantages do you have by showing your hand?”

Reid: “The most important thing is professionalism, reaching out to these people with a well-crafted email. Something that’s not too long, people don’t have time for your bullshit. Get your grammar and spelling on point. This all sounds like common sense, but it’s not always common in this industry. Yeah, this is the music business. If you send an email with three typos no one is gonna be trippin' but you have to think about how you are conveying yourself and your brand, or not, as a professional.”  

Now that we’ve covered the basics, how does an artist transition from being on an unpaid tour, or planning a tour that breaks even, to actually walking away with a few clams?

Pure: “People get scared about this but it’s a straightforward answer. You gotta show a promoter that you can get heads through the door. And sometimes you gotta be selective, some people won’t pay you, and some will, and you have to wait for what you’re worth sometimes.  

“Going out with a headliner, you can sometimes work in a small cut for you. Maybe you’re not getting guarantees, but you’re getting a small slice of the door. Then it’s on you to make it work, to help book stops where you can make money, where people are gonna be there. And bring people out, prove your worth."

Dame: “It takes a while to get good enough to put on a good show that people actually want to see. What showed us that we had the right demand for Funk Volume was that promoters were hitting us up from cities that we’ve never been to. When you get to the level where there’s money to be made in a city, independent promoters and bookers are going to want to work with you.

“But it’s not just understanding what you’re making, it’s also understanding what you’re spending. You have to budget your tour appropriately. If you fuck up the budget, you’re gonna fuck up your money, and you’re gonna lose heavily.  

“And you gotta prepare for all the things that are unexpected. Your van breaking down, you lose a microphone; there’s any number of things that can happen. You gotta make sure you’re appropriately accounting for the rental car cost, the hotel cost, the gas cost, any insurance you might need to buy. To have somebody who understands what you're spending, what you're making, to make sure that you can afford the tour, that’s invaluable.”

Reid: “The money isn’t going to be amazing at all in the beginning. The advice I have if you are going to be trying to break even or maybe even bring in some money is to focus on where you can draw. Hypothetical, say you know you can draw a crowd in San Francisco and San Diego. OK, maybe, you get $200 or $300 at those shows, and maybe you don’t get paid for any show in-between but it’s possible to turn that into a tour that breaks even.

“In order to transition into getting paid, it just takes time, effort and hard work. That’s always gonna translate into making money. Also, hit up towns in the middle of nowhere, small towns where there’s no competition for things to do. They are going to be more excited to have you providing entertainment, and they’re gonna be more likely to pay you even if you aren’t a huge act.”

Let’s talk numbers. Where does a booker’s offer come from?

le’Roy: “Supply and demand is my thing. We can have big acts in a 400-cap room like SOB's because that affects the ticket price. If I’m like, ‘You know what, I wanna book Jay Z,’ people might say ‘You're crazy.’ But when's the last time you could see Jay play in a 400-person venue? I might charge $3,000 a ticket. I’m not saying that’ll get Jay there, but it’s all relative to what you're making at the door and the bar, that’s where my offers come from.

“Where do I break even? What’s the worst case scenario? Say a big hail storm hits, how many people are walking through that door? If the room holds 400, can this person bring in 200 people at a minimum? If I can say yes, I’ll start my offer based on that. Now, if my expectations are exceeded, I may give you a bonus or I may structure a guarantee versus a door split and give you whichever is higher. At the end of the night, if the gross exceeded our guarantee, it’s a success; win-win.”

How can the artist gain better leverage in the negotiation process? How do artists demonstrate value to a venue?

le’Roy: “For me, a big part of it is about how often you play a market, and about putting out content to build demand. It’s not a bad thing to hold out.  

“The example I want to give is The Weeknd. I tried to book him when House of Balloons first came out. And I was on a fuckin' manhunt to book The Weeknd. You won't believe what I was trying to offer. $60K at SOBs! But he was able to build that demand. And the way he was able to build that was because he kept turning me down, and I was so pressed to be the first one to book him in New York that I went to ridiculous extremes to try to do it.  

"It’s a classic example of what it can do if you strategically hold out. And if your product is that strong, you can hold out. Curiosity will generate, all of a sudden people are sharing the music, and you’ve skipped a few steps and you’re playing bigger venues than you would. But to build up your demand, it’s content.”

Reid: “To start, everyone’s online audience is different, so you can’t just show a venue how many likes you have on your page. Some people have online audiences that they’ve bought, that aren’t real. So, okay, you have 100k followers on Instagram, you’re verified, but can you draw?  

“And if a venue isn’t convinced that you can, that’s where you have to be flexible. Say, ‘If we get people in the door we get our cut, whatever it is.’ It’s a game, it’s politics, and it’s gonna be different for every single venue, especially with these small businesses.”

I know this is a sensitive subject for a lot of artists, but is there any value in paying to get on a tour?

Dame: “Yeah, the only way to really tour, if you don’t have the demand yourself, is to pay for it and try to buy onto a tour, which I never would really suggest unless you can afford it and you’re guaranteed a spot where people will actually be there. Artists will buy into an open tour spot and end up playing to empty rooms before the door even opens.

“You have to negotiate that, and hopefully negotiate some merch space to recoup costs. But I’m kind of against touring unless you can get guaranteed a certain level of exposure. Or prove that you’re worth some tickets. You can try to barter, offer to tour manage or sell merch in return for a spot on a tour if it doesn’t make sense to buy a spot."

Pure: “It’s tough, and you definitely don’t want to be doing it for very long. You can’t just be a dope rapper unless you have a lot of money from your parents or someone who is bankrolling you who has a lot of money. You have to wear a lot of hats, get a team together, find the people who are willing to work with you and keep it lit, keep at it.”

Any final words of wisdom to pass on to independents trying to tour?

Pure: “Del told me to keep it funky once. Just be funky. [Laughs] If you make a mistake, don’t let them know. And tough it out, go through it. Sometimes you are gonna be like, ‘Man, maybe I should just go home.’ I’ve been on tours where people go home early. And I can’t recommend that. Even the shitty experiences are golden because you are gonna learn from them. Keep your head up.”

Dame: “I’d always put more money into the music and the visuals and into content to create demand online than I’d put into touring. The game’s changed a bit, when [Tech N9ne] was coming up, you sort of had to do that, build your demand on the ground, show your face and perform for four people in the hopes that next time you play for 16. But Travis will tell you, they lost a shitload of money touring in the very beginning. We never lost a dime. That’s the difference between then and now.

“And when you do get the opportunity to tour, have a good show. There are not very many artists that put on a really good show, so I’d encourage artists, when they do get that shot, be ready.”

le’Roy: “For me, it’s about a long-term strategy. At the end of the day, it’s the manager's job to understand this information and relay it to the artist and explain why maybe an offer is low or what the big picture is. If it’s a short-term move for you, yeah, go get that money. But if it’s about a career, a big picture, you gotta build up your fan base. You have to build.”

Reid: “You gotta think about the product, about the experience you are providing. From a bar or venue’s perspective, if an act is gonna come in and turn a venue into a party for a night, and me as a booker I can guarantee that, you’re gonna have the start of a solid relationship.”

The most important takeaways from Reid, Pure, Dame, and le’Roy? For artists, start building now and get your hands dirty. Pick up the phone. Believe in your worth, demand it, and know what that worth is in a venue’s eyes. Treat this like your job, and clock into work on your tour as often as possible. Do that, and stay positive, and you’ll be headed in the right direction for a successful tour.

As for the hip-hop consumer, think about how much it really takes to get out on the road now that you know a small bit of the story. Whenever you can support independent touring acts in your city.  After all, a successful tour is impossible without a devoted audience.

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