How to Successfully Book a Cross-Country Tour, DIY Style: Advice From Lindsay Kupser

Posted by Sam Friedman on Mar 4, 2016 06:00 AM
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LKimage1.5Photo by J. Shia

Just about every musician who wants a full-time career performing original songs and making a living off of it will have to spend some time on the road. For smaller, independent bands, this usually means doing it all yourself. While it seems like an impossible task at a far glance, there are several steps that you can take to get across the country in front of new fans.

After Canadian singer-songwriter Lindsay Kupser released her promising EP Quiet Songs, she wanted to bring the music to life on tour and promote the music she worked so hard to write and release. Email after email, she spent every day working on booking and promoting her tour and ended up with some incredible insights you can only get on the road. We caught up with Kupser to learn how the she successfully traveled cross-country with her best friend, playing night after night in front of strong audiences.

In support of your recent EP, Quiet Songs, you completed an extensive cross-country tour. How far in advance did you plan that tour, and how did you begin the task of getting the gigs booked?

I started the tour the last week of March, and I believe I started the booking process sometime around the beginning of December. I actually could have started earlier; now I'd say six months is a good place to start. The majority of the booking was finalized by the end of January or early February.

It's really just emailing... so much emailing. I felt like it was all I did for about a month, but that's the way it works! The first step for me was figuring out some kind of a route, knowing I would start east and end west, and not only trying to get shows booked in big cities, but in smaller towns along the way, too. The next step was finding venues that fit with my sound and my draw (how many people would show up), and for me, the best way to find those venues was to look at the tours of other singer-songwriters around the same level as I'm at career-wise, and start emailing the venues they've played at. I also reached out to a ton of local independent radio stations all along the route for interviews and in-studio performances.

[How to Book a DIY Tour Like a Pro]

When trying to play new places for the first time, what angle did you use to get gigs? Were you specifically looking to tag along with local bands in the area?

I actually didn't really take the angle of reaching out to local bands too much, which is something I will make more of an effort to do next time. My approach was to play as many house concerts as I could, and to play as many live in-studio radio sessions as I could. House concerts are incredibly appealing to me because I play such quiet, intimate music, and people really come to listen at house concerts. You also have a built-in audience in cities that you've maybe never been to or performed in, because the people who run the house concert are more or less in charge of inviting their friends and neighbors. You also end up making way more money than you would at a bar or other venue, because everyone there feels really connected to this special, intimate experience we all shared, and they want to take home a keepsake, aka a CD or merch!

I'm also a big fan of playing as much radio as I can. You never know who has their car radio tuned in to the local college station, and I've had a few people come up to me at gigs and say, "Hey! I heard you on the college station this morning and loved your songs, so I thought I'd come check out your gig." Even if you gain one fan in that way, it's totally worth it. It also gets your foot in the door with the station and you can leave a CD, and more than likely it will get some spins after you've made a connection with the DJs or the music director. I get pretty consistent airplay on several of the stations I've performed at live on my tour.

[How to Get Your Music Played on College Radio (And Why It’s So Important for Indie Artists)]

Self-booked tours are an impressive feat as is, but most people don’t get to see what happens behind the scenes. We’re curious: for every "yes" you got for a gig, how many "nos" did you get?

Well, as I'm sure you know, being an independent artist is general is a lot of nos, or more often just no replies. Booking tours is exactly the same. I would guess that I probably got 10-15 yeses after sending 200-250 emails. That includes follow-up emails  – bugging venues and radio stations three or four times, trying to be persistent and get a response. Many times, your email slips through the cracks and they'll get back to you after you email them a second time.

[Derek Sivers: Why Persistence is Actually Polite in the Music Business]

I actually did try to contact several artists who didn't have openers listed on their shows at bigger venues along my route and see if they'd like an opener, but sadly, I had no luck with that. I had much more luck just contacting the venues directly, but only the ones that were realistic for me to play. All of the larger venues that I had no hope filling didn't respond, and I understand why.

Playing shows is always great exposure to potential new fans, but you were also promoting your EP. How did you handle your merch and promotion of Quiet Songs?

This was my first tour, and all I brought merch-wise were CDs. I think that was probably smart for where I was at a year ago – I didn't really have much press or buzz happening, and I think if I had spent the money making T-shirts or posters or anything other than just physical music, I wouldn't have sold anything. In my opinion, you have to be at a certain level for people want to buy merch, and I definitely wasn't there yet. That being said, I did sell a fair amount of CDs to people who had never heard my music before, and that felt like a real triumph. Just knowing that my songs might be playing in people's cars in Indianapolis or Denver is exciting to me.

On the next tour, I will definitely have more merch available. It would be great to get a bit of vinyl made, and I'll try to get creative and think up some other fun ideas.

How did you finance the tour? Did you have a budget set before booking the gigs? What lessons did you learn about budgeting for a tour?

Budget-wise, I just sort of went on the road and hoped for the best. I knew I wouldn't be making much money, and I was prepared to even lose some money in the process, so I had a little saved, and I was really doing it just to get out there and get some exposure for my music. I knew I would make a set amount at maybe three of the shows, and the rest were just percentage of the door and CD sales, so you never know, really.

In the end, I basically came out even, which I think was lucky. These days it's almost impossible to find venues that will pay you a guarantee – everything is percentage of the door, and when you're playing in cities where you don't know anyone or have never played before, it's entirely possible that five people will show up, and you'll make pretty much nothing. On the other hand, the house concerts I played were very successful monetarily, and those would get me through for another several days.

The biggest expense for me was gas, and it wasn't even that bad. I tried to stop at grocery stores and stock up on cheap and healthy snacks instead of eating out. I also only paid for accommodations in one city – otherwise we either stayed with friends or people we knew in each city, or the house concerts would put us up. In Omaha, I did an interview on a great music podcast called Worlds of Wayne, and he put us up for the night as well.

I really wasn't thinking about making money too much; I was just thinking about doing things to further my career, whether they paid or not. A good example of this was playing Daytrotter, one of my absolute favorite live-session music websites. They feature huge names, and I was so thrilled to be able to go record for them. Even though it was far out of the way of my route and didn't pay anything, it was completely worth it. I will always choose to lose money and do something great like that than to skip it. But on my next tour, I will definitely be a little more conscious of a budget and will make it more of a priority to come out of it with some money.

[A DIY Guide to Booking House Concerts and Supercharging Tour Revenue]

Your touring schedule includes Canadian Music Week and Youbloom LA – two huge festivals! Tell us how those opportunities came about.

I got both of those opportunities through Sonicbids! I've been using Sonicbids for years, since I was a teenager and had my first few demo recordings up online. I think it's a really great tool for booking festivals and for companies looking for music that you wouldn't otherwise hear about or know about. It's not the only way I look for gigs, but it's definitely one of the ways. I applied for Canadian Music Week through Sonicbids for the first time this past year, and was so thrilled to have been invited to play in Toronto. I think it's going to be a great chance to share my music with other artists and industry professionals.

The Youbloom LA Festival I also got through Sonicbids, and it was really excellent. The best part of that festival were the panels they had with some of the biggest names in music business. I learned a ton and there were only a small number of musicians invited to play, so we were all able to have one-on-one time with the panelists and get advice. I don't think I would have even known about the festival without Sonicbids.

I use Sonicbids to help keep things somewhat in order and in one place, and it's been great. I've also gotten non-exclusive licensing deals for web series and small TV shows, some radio play, and I found my radio distribution company as well as my TV licensing team through Sonicbids. I'm just now in the process of signing a bunch of licensing deals for the E! Network and MTV, which I'm excited about!

If you could give advice to an independent musician looking to book a cross-country tour, what would you say were three of the biggest lessons you learned that you wish you would’ve known before you embarked on yours?

First, do not try to book venues that you know you can't fill. Of course we all want to play the Troubadour, but if you can't fill it, it's a waste of time for both you and the venue. You won't make any money, and the booker for the venue will never let you play there again! It's harsh, but true. Start out really small. It's so much better to play a house concert or a small coffee shop or bookstore that's full of people than to play to an empty room with a big stage and cool lights.

Second, perfect your emails to venues and radio stations. Make sure you keep them really concise. Think about the kind of email you would want to receive if you got 100 a day. You should include a link to your music and a quick description of your sound and instrumentation, but really the only thing the bookers care about is draw – that magic number of people you feel confident will show up to your gig. Be honest with your draw, and remember that even though you may have friends in the city, not all of them will show up. Playing in a city where you know literally no one is always the hardest. Those are the cities you want to try to do house concerts, or a venue that has a consistent audience no matter who is playing. If you do know other local bands or artists in the city, always mention that in your email. A lot of times a booker will be happy with the draw number you gave and like your music, but they still want more of a guarantee that they will make money, so they'll ask you if you know any local musicians who could join the bill.

Third, just try to stay healthy. I really made an effort to eat somewhat healthy on my tour and to get as much sleep as I could (which sometimes still wasn't much). I can't imagine getting sick on a tour you painstakingly booked for months, and then having to cancel shows. That's heartbreaking to me. Also, if you are a solo artist like me, bring someone! My best friend came with me, and not only was it way more fun, but we split the driving time. Doing all of that driving alone would have been complete hell, so if you're not in a band, make sure you think twice before going out on a 10-day or two-week tour knowing you're doing all the driving (tired) alone!

Grow your music career with Sonicbids

Topics: Musician Success Guide, Music Business 101, Booking Gigs & Touring, Sonicbids Success Stories

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