PEOPLE

Tell me about someone who has been critical to your career?

My grandma, Twinnie, who is the namesake of Win Music. She inspired me to do stuff that my parents didn't tell me to do, and to indulge in culture that the regular kids around me thought was weird. Twinnie is the most likeable human of all time. Even at the age of 49 (she's been 49 for about 25 years), she can still do the splits and stuff. She was a dancer back in the day.

START

How did you get started with your business?

The obvious is my family, with lots of labels. Sam Weiss, my grandfather, and Hy Weiss, my great-uncle, had Old Town, Sam, Win amongst others. Michael Weiss, my uncle, started Nervous, and Barry Weiss, my cousin, has helmed all of the majors seemingly. Daniel, my dad, is Glassnote. My mom even did promotion for CBS back in the day.

But none of that is what made me want to get into music. For me, it all comes back to DJing. The short version is that I DJ'd when I was young, but stopped in college because it was too hard logistically (crates between NY and Boston, and no room for decks in my dorm), and so I worked full time in film. I got back into DJing when I was segueing out of certain types of film gigs, it took off and I switched to DJing full time. I started curating, booking, programming, A&R and eventually decided I should do it all for myself rather than others. That became Win Music.

CULTURE

Tell me a story that demonstrates the Win culture?

One time when I was working at another label, I had the entire room agreed on signing an artist, but when I challenged the head of A&R to make a move, he replied, "Sorry Sean, we all can't live the idealistic way you do, we have to put on jeans that fit us," as a reference to my being a "hipster" and wearing skinny jeans, I guessed. I don't wear skinny jeans, just to be clear.

Around that time I was DJing and booking shows as well. I wanted to book cooler shit. That cooler shit couldn't get any traction because managers, agents and labels were not really supporting. They'd tell me artists needed more Facebook Likes. I realized that if I wanted to get these artists here, I had to do it myself. I started using my clout as a DJ to book these guys. Instead of going for the obvious rooms, I’d go for the ones that I could pack by myself. So I'd bring artists over, get them enough money to be here, and have them play the more high end rooms for 150 people. That was easy for me, because the chichi people are less discerning about talent. I'd book them for 150, then maybe next time lift that to 300, then 400, with the talent driving a small amount of the audience. Once I could do that, I was able to convince my promoters to book them in our bigger rooms.

Another artist I did this with was Flight Facilities. Win and Glassnote just released their debut LP. They headline Webster Hall on December 4th, and it will most definitely be sold out. Of all of the artists I booked in my early days, it's the Flight Facilities story that makes me the most proud. They represent everything I want for Win Music, all with their career arc, the way they communicate with their audience, and the genre of music they make.

TALENT

What does Win Music stand for?

Culture, expression and connection. I want to work on projects that are reactive to culture, and then propel that same culture forward. I want Win to translate the underground to the mainstream, and be a bridge of artist development between the DJ labels and major labels.

Is there a particular area of talent that you are seeking to add to the company?

I'm looking for operations, PR and marketing people. I want to scale the PR and marketing vertical to be something we can do as well as anyone else out there, regardless of size. And then I need more people to help me organize and operate the various verticals I'm working in. Sometimes my brain is focused on A&R, sometimes events, sometimes a startup, and I need a team to create cohesion.

Tell me about a highlight from the last year?

I started Win last year. I had some ideas that I wanted to test. They worked out, most notably validated by the Grammy nomination, which changed everything.

What challenges have you faced?

My challenges are very personalized. I come from a different background than most of the industry. A lot of it helps, but there's more in my way than people realize. I'd say team building and perception are my toughest challenges. I never learned how to build a company, and I do not have the reservoir of contacts that I need to build my team properly. So that's taken me longer than I'd have liked.

It's difficult for me to obtain help from peers, because I think most assume I don't need it given my background. But I do.

CELEBRATE

How do you celebrate?

I'm constantly traveling and throwing events, so I don't go on vacations or celebrate anything in particular. It's like that Simon Rich article in the New Yorker last year, he says that we're always celebrating and it makes no sense. I like to have quiet moments when something really great happens. The rest of my life is loud, I like the special moments to be quiet. I go to the movies by myself and eat lots of popcorn, that's my favorite thing. Long walks home late night weeknights, I get to see my city how I remember it from growing up. Raw. Sounds dramatic, sorry.

One time I bought myself white rabbit fur Margiela sneakers to celebrate. That's the only time I ever did something like that. I can't really talk about it here though. It's my greatest accomplishment. I'm happy to talk about it off the record...

If you could provoke change in any area of the music business, what would it be?

Here's where my idealistic-hipster-wearer-of-skinny-jeans persona comes out (if you don't get the reference, you didn't read this interview).

If I really had the power, I'd decimate the physical and download parts of our business right now and force streaming on audiences. Our industry would lose historically unprecedented amounts of money in the short term, but that actually already happened once and we're still here. The profits from streaming would come faster, and our business would see a faster return to health. The music industry used to be a place where people went to make money, and creative brains went to use their minds to innovate. I think that the sooner we get that investment and brainpower back into our offices, the sooner we get back the respect and clout we used to have. The music industry should be respected.

TM

* Sean was photographed in Los Angeles by George Byrne for The Manifesto.