Amir “Cash” Esmailian and Tony W. Sal of XO

Tony W. Sal and Amir “Cash” Esmailian of XO.

Courtesy Photos

The Weeknd's co-managers Amir "Cash" Esmailian and Tony W. Sal of XO made Billboard's "40 Under 40: Music's Young Power Players" list this year, and for good reason: The Weeknd, who just kicked off his first arena headlining tour with two sold-out concerts in his hometown of Toronto, is reaching pinnacles and holding records with his No. 1 album, Beauty Behind The Madness, and virtually sold-out The Madness Fall Tour, ending Dec. 19 in Miami.

The Weeknd, whose birth name is Abel Tesfaye, has a close-knit team around him at XO and the two main men are just as interesting as the artist himself.

Cash, 31, who was born in Tehran and raised in Ottawa, left his landlady in Miami with all his belongings after his best friend Hawk sent him MP3s of Tesfaye's music in 2011. He flew to Toronto to meet the young man who would later be known as The Weeknd and never returned to his pad. He was helping out initially and started co-managing Tesfaye with another person, long since gone, when 2011's House of Balloons just came out.  He also has a clothing company called YCFU.

Sal, 35, who was born in Lebanon and came to Canada at age 15 -- first to Montreal, then Ottawa in his late teens and finally Toronto -- came on board to help Tesfaye right before the Trilogy release in late 2012. He had started domestic hip hop label CP Records in 2002 with rapper Belly (Ahmed Balshe) and had considerable success with Belly, Massari and Mia Martina before funneling his entrepreneurial knowhow into Tesfaye's career; he now operates under XO/Sal & Co as CEO.

Billboard asked them both the same questions and got some unexpected answers.

My greatest accomplishment of the past year was…

Cash: "The greatest accomplishment for the past year was that we overcame the challenge that we had with radio, which started with the record we put out, 'Often,' and it went from 'Often' to 'Earned It' and now with 'Can't Feel My Face' and 'the Hills.'"

Sal: "That would be seeing Abel's song 'Can't Feel My Face' hit No. 1 on the Hot 100. That was truly special."

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What was your first paid job?

Cash: "My first paid job was making CFL cards in the basement. CFL is the Canadian football League. My older brother's friend, his dad owned the cards. They were called Jogo. I was in the basement putting all the sets together so I could make some money for the holidays. I was 12. It was actually really cool."

Sal: "Oh my god, that's really funny. I was about 15 and I convinced my friend's mom to give me the keys to the family restaurant.  It had been out of business and closed for years then I reopened it cheaply and operated little high school parties for our neighborhood.  And then I had my friend help me collecting door and then DJing. I was pretty successful doing it and then we got caught and we got shut down [laughs]."

What was your big break in the music business?

Cash: "Meeting Abel. I met him through my best friend. His name is Hawk. I’ve been friends with him since I was four years old. One day he sent me Abel's music and at that point I was living in Miami. I came back to Toronto and … we've been together basically every day 'til now."

Sal: "My big break happened recently when we partnered with Apple and then to see The Weeknd music and the whole recognition worldwide. That was a blessing big time."

Were you ever in a band?  

Cash: "I was never in a band, but since my early teens I've always been infatuated with the studio, so I'd be hanging out at all the local Ottawa studios and all the Ottawa basement studios. I just always had a love for that. I was just hanging with my friends that were rappers, producers, engineers, just trying to find what I like to do in music."

Sal: "No, never."

My mentor:

Cash: "My mentor was my father always because I'm originally from Iran and he left there and gave everything up, came to Canada, drove a taxi cab, so myself and my older brother could have freedom and make our own decisions on what we want to do. He is still my mentor, but he passed away two and a half years ago."

Sal:  "My mentors are Monte and Avery Lipman. Two reasons: It's great to see Republic become where it's at, but I love the fact that you still see that family vibe where you see them all fight together and push together. Because they're brothers, it's not like a huge corporation where there's so much distance between everybody. I feel like they're brothers, like the whole company are brothers, so I like how they've built their company. Solid guys too."

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If I were not in the music industry, I'd be….

Cash: "I'd be owning a bunch of lifestyle/fashion stores around Canada. Even when I was younger, I was a partner in a store before in Ottawa. I always liked clothes, getting clothes, finding clothes and sharing the clothes with other people and selling clothes so it was always a passion of mine. When I was a kid, I went to New York just to buy different colored New York hats because they didn't sell them in Canada."

Sal: "A NASCAR driver. I swear, anyone that knows me knows I love speed, so I would definitely be in car racing. Last year I got three different birthday gifts to go do that type of drive fast [courses] and choose the car and do laps."

The hardest business lesson I ever had to learn was…

Cash: "The hardest business lesson was following that voice inside you and believing in yourself and going with your own instincts. Sometimes you want to go with your instincts and other people might not think it's the right decision, but you know that it's right inside of you. Just follow that."

Sal: "For me, it's focus on your craft, not on numbers. Some people think I'm crazy, but I think that's what made us who we are. Definitely I try to apply it always in my business."

My most treasured music-related possession or collection. 

Cash: "It was the first plaque I ever received for music. It was a gold plaque for Belly's first album called The Revolution. At that point, I was the head of his promotion and his marketing and we really worked everything hands-on and hand-to-hand. Just getting acknowledged with a plaque from the music business was a huge accomplishment for me. I still cherish that plaque. It's on my wall in my living room at my house in Toronto."

Sal:  "All the plaques on the wall in my office. I walk past each one of them, I'm proud. You've seen me come up; you've seen all of us work hard. You see where we are now. All the plaques that are No. 1s and that are certain certifications mean a lot to us.  My U.S. platinum plaque for the Weeknd's album, Trilogy, is definitely one that meant the world to me because it defines the success to the foundation of Abel's career. The Trilogy is a classic album that will live on forever. Also Belly's Juno award that he won in 2008 [for Rap Recording] is also very special to me. It was the first Juno Award we won and the first big award we received in our home country."

The one style item I can't live without is…

Cash: "Anybody that knows me since I was a kid, it's baseball hats. I love baseball hats since I was a little kid. Now that I'm an adult, I still love my baseball hats. Believe it or not, I'm like a hoarder. I have all the ones I've had since I was a kid at my mom's basement still in Ottawa. I probably have in the thousands. My favorite ones today, I obviously wear my XO ones; I love to death; I cherish; and a brand called Just Don, which is a high-end baseball hat. If I'm working, I have certain hats that I'll wear if I know I'm gonna be with Abel or in an environment where it will be really hot, I'll work with that. I collect hats and sneakers. I have more sneakers than I do hats. The most valuable oldest ones I store them at my mom's because I don't want to be tempted to wear them."

Sal:  "My Mophie battery pack, my phone charger for iPhone. I have like four of them and when I leave home or the office, I have one on my phone and two in my back pocket."

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The person I call when I'm looking for advice or guidance is…

Cash: "I don't just call one person. I call our team. I call Lamar [Taylor]. I call Abel. I call Sal. I call Belly. I call Drop [Martin Wong]. Those are my team. Those are the people I always look to for advice. I also call [agent] Joel Zimmerman and [lawyer] Kenny Meiselas."

Sal: "There is a lot of people I take advice from but I would say Kenny Meiselas, who would be the person if I had to make that call and it's serious, he'd probably be the person I would call and get advice."

The song/concert/experience that made me want to be in the music industry was:

Cash: "The one that really sticks out for me is when I was a kid I went to the Up In Smoke Tour [at SkyDome in Toronto]. It was Dr. Dre, Eminem, Snoop Dogg, Ice Cube. I had never seen nothing like that before with my own eyes and I'm like, 'Wow. I want to do something like that one day.'"

Sal: "I heard a song called 'Bohemian Rhapsody' by the band Queen; they were my favorite growing up. Their music always inspired me growing up, through rough times in Lebanon during the war. I definitely connected with the music and it was very inspiring. To this day, I hear that song and I'm zoning [laughs]."

My most memorable encounter with a music artist was…  

Cash: "I'd have to say when I first met Puff (Puff Daddy/Sean Combs) because I was grew up looking up to him, everything that he did. It was our first show in New York and I got a phone call from someone in his office, saying, Mr. Combs is coming to the show today. I'm like, 'Who? Puffy Daddy?' and I went outside got him in and got him settled in and just meeting him. The great moment was when Abel was onstage performing his record -- it was a small venue in Brooklyn, like 500 people in there -- and I looked up and there was a railing on the top section and Puff was right at the railing and he was singing every song word by word, passionately. He was a part of the show almost. That was an incredible moment for me, seeing that."

Sal: "It would have to be Belly, the day I met him [in Ottawa] and he convinced me to get into the music business. I didn't know anything about the music business at that the time, but the fact that he trusted me so much and I was willing to take that chance and now he's my best friend, almost 20 years, and we believe in each other."

My top-five desert-island records are:

Cash:

The Weeknd: Trilogy

Kanye West: My Beautiful Dark Twisted Fantasy

Dr Dre: Chronic 2001

Belly: Up For Days

Michael Jackson: Bad

Sal: 

Queen: A Night at the Opera

The Weeknd: Trilogy

Belly: Up For Days

Snoop Dogg: Doggystyle

The Weeknd: Beauty Behind The Madness