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Women in Reggae: Amy Sheehan of Ineffable & Cali Roots

As the US reggae scene evolves over time, there are some major forces at play, shaping the scene and helping get this music in front of more people who will love it.

Two of those forces are the annual California Roots Music & Arts Festival in Monterey, CA, and Ineffable Music Group. Cali Roots, which has arguably become one of the most important yearly reggae events in the world, partnered with Ineffable a few years ago, and Ineffable manages bands like Stick Figure and Collie Buddz. Together they own and operate multiple music venues on the west coast, and they are also the parent company of Rootfire.

It’s important to understand the underlying structure in the music scene—because it’s not just the musicians making moves. There are booking agents, managers, and companies that work to support these bands and make big impactful decisions that affect the entire music ecosystem. Ineffable touches a great amount of the reggae scene through their work, and they couldn’t do it without their rockstar team.

Amy Sheehan is a person whose work has a huge impact on the reggae scene in the US. As part of the Operations team at Ineffable and Cali Roots, she has played an important role in making Cali Roots a success year after year. She is fiercely passionate about her work, and we wanted to put a spotlight on her for that reason. As a parent, she is constantly working to find a good balance between raising her daughter and growing her career—a topic worth acknowledging, not just for women but men as well.

Amy was born in Madison, Wisconsin. Her family moved to the East Coast when she was young and then eventually moved to the Bay Area. Now Amy lives in Monterey, conveniently near the Monterey County Fairgrounds where she works her magic at Cali Roots Fest every year. She joined me for a conversation over the phone recently to help me learn about her background, her career, and her thoughts on women in reggae. I was so happy to have this insightful discussion, so if you’re a Cali Roots fan, then please read on to learn about the woman who helps to make it all happen.

Note: This interview has been edited for clarity.
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KK: I’m curious about your career. What brought you to Ineffable, and what were you doing before that?

AS: It was total fate, destiny, whatever you want to call it. I was living up in Tahoe. I was probably 20 years old. I went to a reggae show that was put on by Renegade Productions. It was in the middle of the winter and the show was canceled because the tour bus couldn’t get over the hill. And I started talking to Kaati who worked for Renegade productions. She does Reggae Festival Guide, which at the time was a print magazine, but now is an online publication. And she and I just, we hit it off. We started talking and she asked, “Do you want to start putting up posters to get in free to shows?” I was a broke college student and I liked music, so I started doing that and they were a small company. I started working in their office doing press releases, and at that point we were faxing press releases, you know, it was a long time ago. Then I started working on site at their shows. They had lots of different venues, they had a couple of clubs that they had shows at, and they did music festivals in various locations. So, in the year that I lived in Tahoe, I learned a ton about music production, festival production, and promotion. Then I moved down to Santa Cruz and I worked for Gary Tighe at the Catalyst, doing publicity. At some point when I was in Santa Cruz, when I was going to school and finishing up my degree in modern literature just because I knew how to read and write well, I decided to start a company called So You Can, and the whole premise of it was that I was gonna take care of all the details, the administrative stuff, the promo, and all of that for bands that weren’t that good at it. In my experience, a lot of artists have a great part of their brain that makes them super creative and amazing and talented, but they don’t know how to write a press release and get it out to the media. I, on the other hand—I’m not a super creative, talented musician, but I’m very good at spreadsheets and databases, sending stuff out, and figuring out how to get from A to B. So for a number of years I did that for tons of bands. I did publicity all the way from from Seattle to San Diego, all along the West Coast. Whenever a band was coming out here, I’d get hired and I had little street teams that I’d work with. That’s how I started.

AS: Then at some point, I was also working for Reggae Festival Guide, selling ads every year for the magazine and doing production stuff. I always helped lay out the magazine every year and it was super fun. Kaati would always send me leads and say, “Hey, you should sell this person an ad.” So at one point she said, “Hey, you should sell this guy an ad, he’s doing shows in Santa Cruz”—and it was Dan [Sheehan]. So we met, and I went to one of his shows, and I’m like, “This guy needs help.” His front door was a mess, the hospitality was a case of water sitting on a table, and that was it. So he and I started working together, and we worked together for probably about a year in Santa Cruz. We did shows at The Civic, the Vet’s Hall, and Moe’s Alley. Then after about a year, we were like, “Huh, we kinda like each other.” We enjoyed spending time together. We were a powerhouse team. Dan had been doing shows and working with Natural Vibrations, so he had his background as well, and when we came together it just was a really good fit. We did stuff in Santa Cruz for a long time. Then probably eight years ago, I was kind of tired of the music industry for a minute, so I got a job at Stanford, at the business school. I wanted more stability, I wanted good health insurance, you know, I wanted all that stuff that you can’t really get by patching together a thousand shows. I sent out my resume to three places and that was it. I loved working in the music industry, but it wasn’t the stability that I needed. So I applied to an event coordinator position at the business school at Stanford and they hired me, which was a huge surprise to me. I probably spent the first month or two thinking that I was going to get called into my boss’s office and have them say, “Yeah, we made a mistake and hired a reggae festival person.” I mean, the business school is certainly a lot different than reggae festivals. Lots of money, lots of prestige. Then as I settled into that position, I realized that I actually had a lot to offer, and I was good at what I did no matter where I was—whether I was at a reggae festival where a bunch of people are smoking weed, or at an event where Joe Biden is speaking and we’re working with secret service. I could do both. So I worked at Stanford for three years, and then Cali Roots started to take off. Up until that point, I had been working at Stanford, but then also working with Dan to do all the Cali Roots stuff and the other shows that we were doing. Then Cali Roots got to the point where they could offer me a full time job. So I quit Stanford and we moved back down to Monterey. And here we are.

KK: Wow. That’s incredible. How amazing that in the beginning those things happened to start you off on this journey. So Dan, just so that I’m clear, is also with Ineffable?

AS: Yeah. Dan Sheehan, producer of Cali Roots, also my husband.

KK: I didn’t know that it was by working together that you guys had come together as partners, like in life! So now what does your role at Ineffable entail?

AS: It’s kind of evolved over the last couple of years. So when I first came back to Cali Roots, I was working full time as Operations Manager. I touched everything, from staffing to hospitality and just overseeing the whole shebang with Dan. Then four and a half years ago I had Makena, our daughter. And that changed everything. For about six months, I didn’t work at all. I was nine months pregnant with her at Cali Roots four years ago, and that was the year that I really had to learn how to delegate things off of my plate, which looking back on it was a really good thing. I was touching too much. Too much had to get filtered through me or Dan. So it was a really good opportunity for me to learn how to delegate more, how to trust the amazing team that we had built, and know that everything was gonna be okay, even if people weren’t doing things exactly the way that I would have done them—if they got done, it was all good. So a month after Cali Roots in 2015, Makena was born. I took six months off or so, and then I came back part time. I’m sure you’ve talked to other women in the music industry about how it’s super challenging to find the balance between being a mom and having a career. I had a career that I loved that I really wanted to get back to, but I also knew that we were only gonna have one kid and I wanted to really soak up every moment that I had. There was only one time she was going to be three months old, or six months old, or two years old, or any of that. I really wanted to be present in all of that as well. It’s certainly been challenging over the last four years as I figure out how to do both and find a good balance, and feel like I’m bringing what I can to the table with my work and feel satisfied, like I’m getting something out of that. I would say that I feel like I’m a better mom when I’m also working. I can’t just be a stay at home mom. I have to work also, but I can’t just work either, I have to be with my kid. And so, you know, luckily I’m married to the boss and so I have a flexible schedule. I’m able to find a balance, and our awesome daughter is being raised amongst our crazy festival world, which is really amazing to see.

KK: I really respect how you want to be present for that. I also know some new moms who just completely ditch their creative endeavors, but then feel sort of stifled. So tell me about your history as a music fan. Has music always been a big part of your life, and have you always been into reggae?

AS: Growing up, I know we listened to music, but it wasn’t necessarily a focal point in our family’s house or anything. In high school I started really being into my own music. I think that was part of how you start kind of stepping away from your parents and wanting your own identity, and finding music that I love that maybe my parents didn’t love was certainly part of that process. Then I started going to shows—I mean we were in the Bay area, so I went to Grateful Dead shows at Shoreline, I saw a lot of shows at the Fillmore, I followed Phish around for a little while. I mean, I always enjoyed reggae music, but I don’t think I was exposed to very much of it until I started working for Renegade up in Tahoe. And I mean, they had everyone—Anthony B, Black Uhuru, the gamut. Let’s see, it was ’97, ’98, something like that—and they just had so much reggae coming through there. Robbie, who was the producer at Renegade, would get all these promo CDs from all the bands and one of my jobs was to go through them and give them out to radio stations, and if there were extras, I could take them home. And so that’s when I discovered Burning Spear and I Vibes and Congos and like all these great foundational roots reggae artists that I didn’t know had existed until then. So that was certainly where I was exposed to all of that. And then, I met Dan, and he grew up in Hawaii on Oahu. So he had grown up around reggae music and we started actually doing shows out in Hawaii for a couple of years. I got to be exposed to more current reggae, but the Island reggae, which was really fun too. And so, I’m a big fan of Natural Vibrations and Anuhea and all the reggae that comes out of Hawaii as well.

KK: So Cali Roots Fest is your jam, but Ineffable plans several music festivals now, including Arizona Roots which is coming up in February. Did you get to take what you learned from Cali Roots and then help with those other festivals as well?

AS: Arizona is certainly one that I got to be a part of from the beginning. Now that I’m not working full time, I get to kind of cherry pick what I like doing and what I don’t want to do, which is a luxury. One of my favorite things to do is figure out how to get a project up off the ground and what structural foundation we need to create to make that successful. I’m kind of a cautious person that probably moves too slow sometimes, but I like making sure that we’ve got all of our ducks in a row before we make a move. So I was super excited when about a year and a half ago we started working on Arizona Roots. We have some great partners out there that made it easy to come into a new market. Last year, we had kind of made a list of what’s essential, what makes Cali Roots Cali Roots that we want to continue in Arizona Roots and make sure that our culture translates to a new market. This year we’re kind of adding to that, and it’s a building block. This year a lot of what I’m doing, which I do at Cali Roots as well, is working on the nonprofit aspect, the greening aspect, which is really important to us. And I think it’s part of what makes Cali Roots so multi-dimensional. We’re not just a music festival. There’s a lot more to us than that. And so with Arizona Roots, it’s important to us to make sure that we build those in as well.

KK: As you’ve been getting all this experience doing festivals year after year, are there any surprising things that you’ve learned about making a music festival better every year, whether that’s things you learned about the fans, or musicians, or vendors?

AS: One thing that continues to surprise me is how the fans take ownership of our event, good or bad. Sometimes it’s a little challenging to have them take such ownership of our events, but it’s become something that we all own in some way or like we all hold close to our heart, without us ever setting that intention when we started this. You know, everybody says like, “Oh, the Cali Roots family.” It feels like a family reunion for the bands, for the fans, for the staff, for the volunteers, for the vendors. That’s something that has happened completely organically. It’s not like one day we sat down and said, “Okay, so how do we make this feel like a family?” It just happened. That’s one of my more proud parts of being a part of Cali Roots is having the honor of hand selecting our staff that bring their amazing A-game every single year. I always say, the vibe starts with me and Dan and then it goes to our staff and then to the volunteers and out to the artists and then to the fans. And if we don’t have good energy sending out, then we’re all screwed. I work really hard to build an amazing staff every year that really upholds all of the important elements that make Cali Roots what it is.

KK: I do love the family vibe that you’re talking about. I’m a five time attendee of Cali Roots. Everything really changed for me when I first attended in 2014—up until then I was sort of feeling like I’m doing my own thing in Madison in a lot of ways. And then seeing Cali Roots Fest on social media, I was like, “Oh my God, three days of reggae? How do I get to Monterey? How can I make that happen?” I contacted a girl who I met in California after seeing that she was going, and said, “If I buy a plane ticket out there, can I come to this festival with you?” She said, “Buy the ticket, we’ll make it work.” And I just, yeah, I absolutely love the family vibe and going back every year. It’s really made me feel like I have found my people, people who all love this same thing. So I just want to put that out there. I’m also, you know, a big advocate for women in reggae and giving them exposure. I did see and hear some comments about a lack of women as performers at Cali Roots and basically a lot of music festivals. It’s just starting to be talked about more. So in your experience, why is there such a disproportionate amount of women compared to men playing at music festivals in general? Like what are some challenges that are making that happen?

AS: I mean that’s a really good question. I was actually thinking about that in preparing to talk to you. I don’t know if I have the right answer because I’m like, “Well, where are they?” There’s just a disproportionate amount of guy bands to girl bands. Just recently a friend of mine—there’s this up and coming woman in reggae that is looking for a new band. And she’s like, “It’d be really cool if I could get a couple of females in my band, so let me know if you know of any bass players that are women.” And I can’t even think of one. I don’t know what that is. I mean, I know in junior high when I was in the band playing tenor saxophone and having so much fun, there were girls and boys all playing instruments, and I’m not sure why at some point the girls stop and the guys keep going. I don’t know. I don’t have a good answer to that. I dunno. But I mean, we just had a meeting today with Trish from HIRIE, and I am all for figuring out how to get the women that we do have into those headlining positions and like, just keep pushing it. Ultimately, really what I would love to see is that, when that happens, they’re not called out as like, “Oh, we’re going to have a female headliner.” No, we’re just going to have a really freaking good band and they’re going to headline. It’s not like we say like, “Oh, you know Eric, male performer from Rebelution is the headliner,” you know? No, we just say Reb is playing, and when HIRIE gets to that top position I would love to just see HIRIE stand in that position without having to call out that she’s a female versus a male.

KK: Right. Oh, so many things you touched on here. It’s interesting you said that there’s an equal amount of women in those musical roles in the school band—it sorta reminds me of the field I work in, which is helping biotech entrepreneurs, and a lot of them start out as scientists in academia where there are lots of women. And then basically there’s a “leaky pipe” that people have begun to identify. If there’s so many women in academia, then why don’t they go on to be the CEOs of these companies? Where, when, and why doesn’t that happen as often compared to men? So there might be a leaky pipe in music as well. If there’s just as many women as men in academia for music, when, where does that start to drop off and for what reasons? Probably, you know, having kids could be a factor there. As a result, there’s the fact that there’s just not many other chicks to jam with in bands as much. Starting a band, I think it’s a lot easier for five guys or something who are friends to start jamming together and accepting each other as a group. I’m thinking out loud right now after you mentioned seeing the same amount of women doing music in school.

AS: Absolutely. I think, when women become moms—I mean, I know I’m not a performer, but I’m married to the boss—and I still struggled on like, “Well where is my position now that I’m a mom and I’ve been out of the game for, not even a year?” But like, shit moves on with or without you, you know? So it’s like I had to find my new footing, and I can only imagine as a musician who is always trying to make sure that they stay relevant and stay current and stay connected and all of that stuff, and they’re like, “Well, wait a second, I’m going to go have a baby, but don’t forget about me cause I’m coming back. I don’t know, maybe in six months to a year or maybe longer because I loved being a mom and I don’t want to like miss any of this shit,” you know? I’m sure we lose a bunch of women to that. I don’t have the answer. I wish that I did because then we could like jam up that leaky pipe and have more women rise up to the top. I think it’s good that we’re having these conversations.

KK: Yes. When we think about what can we do to help overcome these challenges, I think talking about it is the first thing. And especially having people like you who are even saying that they care about this and would like to see women like HIRIE as a headliner. Eventually when things are equal, we won’t need a “Women in Reggae” series on Rootfire. But, but in the meantime, that’s sort of something that we have to do, which I know can be kind of annoying at times to say like, “Oh, this ‘Woman in Reggae’ or this “Female CEO'”. You know what I mean? But it’s coming from a good place.

AS: This is happening now because it’s not the norm. It’s just not equal, we don’t have the equal footing.

KK: Right. And then eventually when there’s a new article in Billboard Magazine about HIRIE, they won’t have to put the headline as HIRIE, female-fronted reggae band.” It’s just gonna be HIRIE, the same as how it’s just Eric from Rebelution. Well I love talking about this. Thank you. Those were great answers. So Rootfire is Ineffable’s charity arm and we give interest-free loans to bands to release albums, and produce blog content as well. I’m curious about your thoughts on the impact that Rootfire has made so far, and the impact that Rootfire could make in the future for the reggae scene.

AS: I love the system Rootfire has created to allow bands that would not normally be able to produce the music that they do, to continue moving upward. And HIRIE was a recipient for one of those loans in the past. I mean, anything that we can do to support these bands to continue to climb and keep our small niche of reggae relevant and current and feeling like it’s continuing to progress is incredible. And I love that you guys have come up with such a creative way of doing that. I don’t know anyone else that is right now.

KK: I agree with you, that being able to help bands that may not have otherwise been able to put out an album is really exciting. So my last question for you is about the future. What are the future plans for Cali Roots, or anything new that you can tell us that you’re working on?

AS: Are you asking for insider details? Haha!

KK: Oh yeah!

AS: Yeah. Without saying too much, we are always looking for ways that we can continue to bring this reggae rock music to more people. And we’ve been involved in summer series in Avila Beach and up at Somo which is north of San Francisco. Ultimately Dan and I love doing festivals, and our dream is to produce incredible, amazing festivals with lots of integrity and fun. We would love to do more than just Cali Roots in Arizona, and have these music festivals go to other cities, and continue to create a platform for all of these amazing artists that we work with to continue to do what they do, and keep growing and progressing in what they’re doing as well.

KK: Thank you so much Amy. Is there anything else we should touch on in this interview?

AS: I’m stoked that we’re having this conversation, and I think that the more that men and women can continue to make sure that women are getting their due credit and getting the space to be just as creative as the guys to bring their best game as well is incredible. I feel so fortunate that my daughter gets to grow up in this industry seeing women like Trish, Kimie, Eli Mac, Anuhea and like all these super strong, amazing women doing their thing. ‘Cause I know that she’s super inspired by all of that and it’s really cool to be in this industry with all these amazing people. We have amazing women staff, you know, onsite as well. I looked to find out how many women to men we had like on staff last year, and it’s over half. And you know, Dan always says he loves working with all these women because we know what we’re doing. And like, it’s amazing. We have all these total type A personalities that would maybe not necessarily get along in other parts of what they do, but onsite at Cali Roots, there’s just this incredible powerful force that we all feel, whether we’re a fan, or a musician, or staff, or volunteer. It’s so awesome that I get to do what I do, that our daughter gets to see her mom do the stuff that she loves doing. I just feel really fortunate.


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Kayla joined Rootfire after following this music around the country for years. She has been hosting reggae radio shows in Madison since 2010. Her newest installment is '2 DUB', Saturday nights at 10pm on 89.9 WORT FM. She is the 4x winner of 'DJ of the Year' at the Madison Area Music Awards. You can follow her on social media at: @djkaylakush

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