The recipe for a good singer/songwriter is as follows: some strong finger-picking skills, a voice that could either melt butter or crumble a mountain (whatever the mood calls for), and a ton of heart. Ryan Montbleau brings all of this to the table along with a sharp wit and a great attitude. Even after nearly 20 years in the music business, he’s still just as easy to talk to as an old friend that you haven’t seen in a while.

Montbleau’s first introduction to playing music came when he was given a guitar for Christmas at eight-years old. He came from a some-what musical family, with a brother who played bass. Yet, singing and songwriting was a passion that developed following his graduation from college. After four long years of studying, he eventually realized that music was what he wanted to dedicate his life to.

“[Music] was totally a passion… I couldn’t put that genie back in the bottle.”

“I went in as a chemical engineering major, and left as an English major. But I was studying poetry and writing, so it was a lot about the writing. And then I was as passionate about music as anyone…I just kept playing, I became really obsessed with playing guitar. Then I didn’t start singing in front of myself even, until I was 21.”

However, like most musicians at the beginning of their path, Montbleau wasn’t immediately playing stadiums packed with adoring fans. Instead, he began his music career paying his dues on staff at the original House of Blues (HOB) in Boston. Working for the HOB is where he began to understand and appreciate the industry side of the business.

“I would answer the phones and sell the tickets in the box office, I kinda did everything. It was my restaurant experience, I barbacked, scrubbed the bars, I sold t-shirts,  I was a host, but mostly I worked in the box office. So it taught me about tickets and about guest lists and about bands and all of this stuff. It was pretty sweet.”

He continued, “It was a house in Harbor Square that they had converted into a venue upstairs, a restaurant on the middle floor, and I worked in kind of a little dungeon of a box office under the stairs. But the venue only held 230 people standing, so it was small. There was live music 7 nights a week, so it was bands from all over the world coming in every single night and just playing this small club. So just to see the reality of that…of seeing bands loading in and loading out, their setlists, the reality of a band on the road playing small clubs.”

After a little while being behind the scenes, Montbleau eventually gained the courage to step in front of an audience, bringing his signature sound and passion for live music along with him. This is when his music career really began to take off.

“Eventually I got the guts to go up to this guy, Tayo who did the booking and give him my demo tape, which was a tape at the time. I started getting these Saturday matinee gigs, and then once in a while, I would get a night towards the end. I basically just played any gig I could possibly get for a few years. I just wanted to get out there and play.”

Watch his full band perform at the House of Blues in Boston on 12/5/14 below:

From there, Montbleau entered into a relentless touring schedule, one that he still keeps up to this day. Eventually, he had made enough money to quit his job at the House of Blues, and make music his full-time career, one which has evolved significantly over the years. With thousands of tours under his belt, his career has been as much about growth, as it has been about his love for crafting music, much of which feels like a real conversation with the man behind the music.

When it comes to Montbleau’s personal sound, there is no better display of his craft than on his records, many of which are stripped-down, raw and emotionally-driven. One of the most impressive was his last album, Woodstock Sessions. The album was performed and recorded in front of an audience, giving it a special kind of love and energy that is hard to find anywhere else. Though Montbleau does perform the album with Boston natives Tall Heights, it really feels like a musician baring his soul with just a guitar, some friends and a whole lot to say.

Here is “All or Nothing” (featuring Tall Trees) off the ‘Woodstock Sessions’ album:

“Each record is so different. I’ve spent my 10,000 hours just touring, building and creating this career around playing live shows forever now. The amount of time I’ve actually spent making records – since a lot of those are live records – but the amount of time I spend doing that compared to the amount of time I spend performing is really small essentially, so now I really want to get better at making records. My last couple of records were very raw and stripped down and kind of sad, but I stand by it. My heart is on there.”

Montbleau is currently back home in Vermont writing and recording what will become his lucky 13th full release.  He expects the album to be much more upbeat and happy, just in time for the long winter.

“This one is getting a little more fleshed out, there’s a lot more of full band kind of stuff and we’re building these tracks and really getting in there…I’m pretty proud of it so far, it’s forcing me to really get my hands dirty with the recording progress.

Some of the songs are really well done, I think they’re some of the best songs I’ve ever written. Then others I’m kind of building as I go…. This one has a little more hope, more fun, I just felt the need for things to flesh out.

“For me, exploring how to make tracks sound and feel good, how to be viscerally moved by music… I haven’t explored that as much as baring my feelings into a raw songs, raw words, so the goal for me is to do both.”

In addition to Montbleu’s full band set on Saturday on the Meadow Stage, he will also perform with Hayley Jane as one half of the beloved duo, Yes Darling. The duo create songs about the massive ups and downs of being in a relationship in a (nearly?) satirical way. The songs are entertaining, and often way too relatable.

“It sort of very quickly had this thing, we just quickly figured out. We became this duo, these quintessential male-female archetype kinda characters and then we wrote off of that, and we were able to draw from real experiences and make stuff up. I don’t know why, but we have the chemistry to do that. We sort of blur the lines between reality and fantasy, there’s something special about that.”

The duo’s Shakori Hills performance, taking place Sunday, October 6 at 5:00 p.m. on the Meadow Stage, will be one of their only performances for the rest of the year. They are currently in the middle of writing songs, producing videos, and most importantly, putting together a stage production of their act. Though the full stage production will not be put on at Shakori, much of the humor and performance of the production will be on full display on Sunday night of the festival.

“It’s gonna be very stripped down, we’re trying to turn the whole thing into a play. We have people building sets, we have light designers, we’re trying to flesh it out into this big thing. But we can also do it just totally stripped down, just the two of us. So that’s what we’re doing on tour.”

As for the full band set, Ryan and his band are hoping to bring a good time and good energy to the festival.

“This time we’re coming back with the whole band thing and coming in hot. So what I’m going for is trying to move your body viscerally with the music and the band, but also tug at your heartstrings and your mind. I just want to rope you in with the lyrics and kind of get us feeling like we’re all together and not alone.”

You can find all of Ryan Montbleau’s music on all major streaming services. Also make sure to be on the lookout for his new album this winter. More information can be found on his website www.ryanmontbleau.com.

Ryan Montbleau Band, Meadow Stage, Saturday, Oct. 5, 8:00 p.m.

Yes, Darling, Meadow Stage, Sunday, Oct. 6, 5:00 p.m.