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Earlier this summer we put together a guide on how to hit the summer music festivals with the whole family. Life is good Festival, the most kid-friendly fest around, is rapidly approaching and we’re getting pumped to share in the positivity. To help get you as excited as we are, we caught up with the exceptionally talented recording artist and curator of the Life is good Festival Coffee House, Ryan Montbleau, to talk about how he got his start, how he got where he is today, life on the road, and much more. Oh, and did we mention we’re giving away a trip for 4 to the fest? If you haven’t already, enter here. Enjoy!

GGS: First off, can you tell us a bit about yourself and how you got your started in the music scene?
Ryan: Yeah, well, I’m 36 years old, I’ve been playing music – doing ONLY music for the last ten years… My father gave me a guitar when I was like eight or nine, and I didn’t really play very much until I was in college. I mean, I played but I didn’t really start playing a lot until I was in college. Then I started writing poetry, and then my senior year of college I started singing. So I was 21 and I was getting out of college and kind of singing and writing and playing all came together and I figured I think I wanna make music. So, I’ve just been trying to figure out how to make a living out of it ever since, and I’ve been doing that for the last ten years… I started out by just taking anything I could get years ago around Boston, and now I’ve been touring the last ten years solid, all over the United States… And, yeah, I’ve played a lot of shows.

GGS: Today you’re touring all over the place and playing alongside some of the all-time greats… what do you think it was that got you to this point?
Ryan: What is the quote? “Persistence and determination alone are omnipotent.” Persistence, you know? I mean, I’ve persevered the whole time and not only to get out there and to build a career but to get better. I’d like to think I’ve gotten a lot better over the years and that never goes away. I think just having the persistence to improve at what you do. Hopefully, I do that. [laughs]

GGS: Can you describe for me a real “wow” moment? Where you kind of stepped back and thought “hey, I’ve really made it”?
Ryan: Yeah, I mean there have been some great moments. I think for so many years I just wanted to be able to make a living at just music and not working another job. And it took me some years to do that then eventually it was sort of a gradual path. Martin Sexton was always kind of a big hero of mine when I was starting out, then in 2010 we were touring with him. We were his back up band, you know what I mean? I was his guitar player. Opening for Dave Matthews, and playing Jazz Fest, and playing at the Fillmore, that was… Crazy. I was like “how did this happen?” And then Last summer I got to be part of this tribute to Curtis Mayfield at Lincoln Center in New York and that was amazing, I was doing the encore with Sinead O’Connor, the original Impressions, and the Roots were playing, ?uestlove was playing drums. There are just those crazy moments where I kind of look around and I’m like “Man, I don’t know how I got here but I’ll take it.”

GGS: Have you had any embarrassing moments along the way?
Ryan: [laughs] Oh, I’m sure. Man, I’ve probably blocked them out of my memory.

GGS: That’s not healthy, you’ve gotta talk about it! 
Ryan: I know! I’ve gotta get it out. [laughs] That’s funny. I mean I know there have been many. You just kind of throw yourself out there, and if you do that 200 nights a year for ten years, stuff happens. It’s a minor one, but I remember we were in Kansas City, and our percussionist, Yahuba, at that time – this was years ago – at that time he hadn’t been any farther west than, like… Buffalo. So all these cities we were going to on that tour I would introduce him and I would say “Hey this is Yahuba’s first time in-“ wherever we were, Chicago, Wisconsin… So I was doing that every night and we were in Kansas City, we were on the road and I was kind of out of my mind tired, and I said, “Ladies and gentlemen, for his first time in Iowa, on the percussion…” Everyone laughed and kind of called me out on it… I tried to recover saying, “Well, it’s his first time in Kansas, too.”

GGS: You’ve been playing the festival circuit this summer; any recommendations for can’t miss festivals?
Ryan: Over the years, High Sierra out in California was one of my favorites, getting to play Jazz Fest in New Orleans was just an honor, and then for us, we do Gathering of the Vibes every year in Connecticut. That’s kind of our home, big Northeast festival we do. Life is good is really a special one though, Life is good is really different, it’s so pristine and so overwhelmingly positive… the fact that they raise all of this money for children… I love it because it’s like this pristine fest, it’s great for kids, the best fest for kids that I’ve ever been to, but it’s also great for adults, you know? If you want you can just hang out and drink beer and go see great music, it’s just great for everyone… I love that.

GGS: Tell us about how you got involved in curating the Coffee House for the Life is good Festival.
Ryan: They asked me to do it. I’ve built a good relationship with those guys in the last couple years, they’ve become good friends of mine. Bert and John who run the company, these guys are amazing. This is totally positive, these people really believe in what they’re doing. They’re just really inspiring people. So, we’ve played the festival the last couple years with our band and this year they wanted to change it up – they always want to change the lineup – so they just asked me to do this solo thing and curate this coffee house space and I’m loving it. I’m so glad they let me do it.

GGS: What advice would you give to musicians that are where you were some years back, just starting out?
Ryan: I would say you have to be in it for the long haul. If you really wanna do it for a living, for me, it’s a long road and it doesn’t really stop. It’s not like you’re going to make it to some point quickly, and you’ll have just “made it” and everything’s all set. I don’t really believe in that. It’s a journey. And, I would say you really need to appreciate the people who allow you to do this. You know what I mean? If you play some show and there are only three people there, you better really appreciate the three people that came out to see you. [laughs] Because, well, they’re all ya got. And you can sort of build a relationship with your fans. It doesn’t have to be really close or personal, and in some ways it shouldn’t be. But, you really need to appreciate them and sort of take care of the people who help take care of you, even by just replying back to them on an email, or saying hello to them, or whatever, buying them a beer… And not as some kind of ploy to make it or something, just you should genuinely appreciate the things that allow you to do this.

GGS: What’s the best prank you have ever pulled off or seen pulled off?
Ryan: [laughs] I’m not much of a prankster myself, but there have definitely been some. You have to have some laughs on the road. Somebody else said, “The good times are fun, the bad times are funny.” That’s kind of the way you have to approach it. One time, years ago, we all got into the van and Yahuba, our percussionist, he had an air horn. Like one of those horns in a can, and we waited for poor Matty, our bass player, we waited for him to get in the van and then we all blocked our ears and just let it rip right in his ear. It was really a cruel joke, it was really bad actually. He’s still mad about that one… The tough part about stories from the road is that I could sit here – once I got going – I could sit here for days on end telling you story after story after story…

GGS: Well, we’re glad we got to hear a few! Excited to see you at Life is good!