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A conversation with the unifying architect, A&R Executive and Creative Manager 

September 2019

Words + Photography by Michelle Sullivan

A game I like to play with executives and creatives is -  who would you get on the field for? It’s inspired by Fantasy Football, although it’s a question that we can apply to most areas of life - for today I’m drilling down on the music business. 

Ponder it - who would you get on the field for? ‘Any Given Sunday’ style. It’s a fun game, a flex for the mind, while also inviting you to explore the personification of your values. We ask - in a reality of opportunity cost and a world of infinite possibilities - which of these do you hold most dear? 

For me and within a professional context - I would think about the qualities that I personally attribute to great leadership. Does the person making the call embody these attributes for my trust? 

1. Do they possess Emotional Intelligence?

2. Can they adapt proactively?

3. Do they deliver reliably? 

4. Do I understand the vision?

5. Do I connect with them in spirit? (the quality that we can’t measure but we feel it)

In getting to know Steven Carless through August - I can confirm with confidence that if he was making the call, I would be taking to the field! There is a leadership quality in Steven that is incandescent -  and he’s got the stats to back it up: 

Executive Producer for Nipsey Hussle “Victory Lap”, Artist Manager and Partner with Nipsey Hussle for The Marathon Agency.

A&R Executive for Beyonce The Lion King: The Gift.

A&R YG, Big Bank - Triple Platinum.

A&R Executive Dave East - Paranoia 1 & 2

Steven ticks boxes for radio promotion, street team activation, artist marketing, A&R (gold records, platinum records, records that shifted culture) and creator advocacy. But none of this is why I would ultimately answer the call. I would be won over by who Steven is as a human being - with a leadership twist. He’s like a good Paul Smith shirt or a Zadie Smith novel. He’s approachable and he helps me understand things without making my questions seem stupid - it’s a quality that reminds me of another ‘who would you get on the field for?’ favourite -  Jennifer Justice. 

After a career that spans 17-years of working with people across cultures, continents, industries and scenarios - when I know, I just know. Steven Carless is present in the moment, he can explain the vision and then the steps we need to take us there. He talks often about purpose and asks seriously about intentions. I believe that he will get us across the line … and if somehow we lose the play - I would be delighted to stand tall on his team, and then get back to practice. Enough said really. 

I’ve taken a different structural approach with this feature. I know he’s got the goods and so I’ve attached his resume and A&R credits at the end of the interview - read them at your leisure. My focus is to drop you right into the middle of a delicious conversation.

Today my memory is taken back to 2016 and a phone conversation with Jac Holzman (Founder of Elektra Records and Nonesuch Records) where he asked me - “Michelle, how will you move the needle in this work that you are doing?”

Jac - say hello to Steven Carless!

MICHELLE : Talk to me about your ideas of leadership. What does it mean to you?

STEVEN: One facet is about availability, because people want to know that there's someone they can trust for an answer, clarity, direction for solutions and problem solving. At the most basic level, it's about availability for those in your care. Leadership is guidance. People want to learn from teachers - I know I do. It’s a two way street.  So if you're a teacher, you're leading and guiding over whatever challenge it is. I think these are the basic principles that anybody, anywhere in the world can tap into. I think about my children and I know that's what they look to get from me.

M : Tell me about mornings at the Carless home? 

S: I get up at about 6:00 AM every day and my two kids are up between 7am and 7:45am. When my son gets up, he wants to play with things. I'm like - no, you gotta get dressed, wash your face … he's always wrangling - I gotta wrangle him. The guidance is like practice - get up, go to the bathroom, clean yourself up and then you can go out and frolic throughout the house …  It’s the same with my daughter. In my practice with them, I wake them up to music every morning. 

M: Which songs?

S: There's nothing specific. It can be anything that I'm working on at that time. Could be upbeat songs, or soul.  This morning I was listening to some mixes from an artist that I'm working with. My daughter's always asking questions - What's that? It's fun to watch because I can see her immediate responses to the music. To me, it's all vibrations. My kids don't always understand what they're listening to, but they understand the vibration. The music gets them upbeat, bouncing around and gets them into flight. Their blood is pumping and the wires are connecting. As their Dad, that's my practice and my morning regimen, and overall, that's how I want them to experience life. I try to practice energies and great vibrations - burning scented candles for them and creating a whole aura for our home.  It's smiling. Smile! Say good morning. Did you drink water? How are we taking care of your health? These are the things I view as healthy - happiness and water ...

M: Fantastic. Are they now accustomed to these daily things?

S: Oh yeah! My son, he's younger so he needs a little bit more guidance. But as soon as I turn on the music ... he's up! I have a Bluetooth system throughout our home. I'll turn it on from downstairs, and that first song goes through every room. So wherever they're at, they know it's time to get up!

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I am feeling this responsibility to be a teacher for everyone around me. Asking - what do I know and how can I pass that information on?


S: I grew up a certain way. I didn't grow up like my kids. My Dad's a music person, he's a DJ, and my uncles are singers. I didn't get this type of parent.

M: We remember these things! I can recall key moments from my childhood that influenced my life. The smallest thing can have the most weighted impact.

S: Exactly. To me, the basis of any practice is learning. Every morning with those children - I want to teach them something. I want to teach them about the love of music, how good it can make you feel and how motivating it can be … I don't have a scientific background, but I do know that it does something for them neurologically - it must because it does for me. It pinches on the emotions. Pinches on the adrenaline. You can always link your favorite songs to certain moments in your life. 

M: Definitely. We carry our practices out the door each day - good and bad. 

S: I believe in sending my kids off into the world with good energy and I'm predicating it with values and principles. They know … be polite, have structure, take care of yourself. That's really what I'm trying to teach them: take care and here's some new information - take it out into the world with you.


M: What do your kids think you do for work?

S: I don't know. My daughter just knows I work. I left this morning and she said, “Are you going to work?” I'm like, yeah! I'm going to work. It's something that she can't articulate yet and so I help guide her to always be asking me questions. My daughter is very thoughtful. 

… And then when it comes to work, I try to have it the same way. I try to work towards a rhythm for whatever I'm doing, especially with artists and our conversations - we must always be asking questions. Isn’t that what we get from our parents? They are our leaders. Whoever they are rubs off on you, depending on how much exposure you have to them. You know what I mean?


M: I completely understand - I feel all those things from my parents.  Tell me about some of those anchor values that you got from your mom?

S: My mom … my parents had me young, so my parents were like teenagers with children.

M: How old were they?

S: My mom was about 18 or 19. My mum was so young and all they focused on is work. My mom’s practice is to cover the bases first. I need to make sure I work so I can put food on the table. That's a whole program. Dad's a little bit different. He's a little bit more nifty. I feel like he's a lot more adventurous, so I quantify it as his ability to explore, and then dissect things. He'll try anything … He'll go out - be this and do that. He's like, I'm not worried about it, because I understand how to beat it … he blurs the boundaries of rules. My parents are the ultimate dichotomy. I feel those things in me, both of them … but when I think about morals, values and principles that are within me - they are from my grandmother. She's a nurturer, caretaker, caregiver - she grew up as a nanny at other people's houses. Her nature is - you come down, you need something to eat? Make sure you say please and thank you. Say - May I?

M: How much time would you be with her? 

S: I would go to her house every Thursday to Sunday, that was the program. Sit at the table. Legs straight. Sitting forward. My dad would leave early in the morning and come home late at night. It's the same thing I do now. My mom taught us to be independent. My Dad taught us how to not be afraid of anything. 

M: Is your sense of being polite from your mom?

S: Yeah, I think so. My mom is an amazing woman. She doesn't hold back or bite her tongue. She's dry, flat, poignant and bright.


M: How would you explain to me what it is that you do in your professional life?

S: I’m definitely feeling in this new transition. I am feeling this responsibility to be a teacher for everyone around me. Asking - what do I know and how can I pass that information on? Maybe before I was practicing in the shadows. Now I feel the responsibility of coming forward and working from a coaching mindset.  Maybe someone needs help, for me to be the air for them or help them problem solve. Whether It's business partners, colleagues or peers - I am here to be sharing information and hoping that they can take something useful from it. 

M: I understand what you mean. 

S: It's almost like Alison Wonderland, I fell down the rabbit hole and now it's this whole new thing. 

M: In your work with all these incredible artists, I can imagine that the conversations you have are both transformational and rather delicate. 

S: Because I'm not an artist, the one thing that I try to do is draw a very bold line through it - I have an opinion and taste. I know the difference between someone's artistic expression versus an opinion, and so I want my approach to be one of always learning. Finding out the information and helping the artist make informed decisions. We won’t always agree with the artist, but let’s approach those conversations with substance. Then we can say "we think this might be a bad decision for you, but here is all the information you need. If you still want to go ahead then that’s okay. We are here to support you." 

M: That’s definitely a coaching mindset. 

S: You can't force people. You’ve got to let them discover, even when it breaks your heart. I look at my children. I want them to behave and do right, but they're not always going to - because they're growing, they're learning, they're understanding themselves, their environment and social circles. Because they don't react the way I want them to react, that doesn't mean it's the wrong reaction. I parallel that to the work I do with artists - I have to give them responsibility to make decisions and understand why? There is no right or wrong. My job is to help steer them, with all of the layers. For example - there's an artist who I might be working with and we were on a call recently and it came down to these things … tell me - do I believe you? Do you have the experience? Can you lead me? Can you guide me? Can you give me good advice? 

M: How did you break it down? 

S: I said, it's just advice, but I can’t give you strong advice unless you tell me what you want to achieve. What I think you should achieve and what you want to achieve are two different things. We have to ask why? Why are you looking to do this deal? Who is the right partner for you? On one hand - you can wait it out and make the commitment to yourself so you can have more control over the things that you create. Or if you trade those rights now, they go into the hands of others and then you really have to trust that label. Maybe that’s what you need? If the label are willing to take a shot on you, invest in a monetary way and with resources - that’s also trust in a future return. You know? So there's a balance, but what do you want? With the artist I am always here to help them get clarity and for us to learn the information so they can make the right decision for themselves. 

M: Why do you think you see things this way?

S: Because I have to sleep at night. Because it’s not just about us - it’s about our kids kids kids kids. That’s the moral of the story.


M: From all the conversations you have, what do you feel is timely? 

S: Everyone's saying they just want a fair exchange, but it all depends on what the scenario is. What is the context? It can’t be generalised. If I'm a record company and I'm trying to sign an artist - I want that artist. But the artist might not be educated on what the best deal is for them. Everyone needs to be educated. I believe in the responsibility that is on both sides. How do we help the artist? What do we need so it works for the record company? It's the label’s gamble and they're putting up all the assets, bandwidth … and all the money. The artist is bringing all their years of time, heart, hope and their own investment - all that energy. We need to be looking for the balance between the two … If we seem to be having the same repeat problems with certain artists - let’s take time to figure out how we can reassess? Can we put a new arrangement into place? What can we do to set new habits? The chronic patterns are generally the ones that we have already witnessed. So in answer to your earlier question - that’s where I want to be. At the intersection of those things. Right there - coaching and leading us together. 

M: We are in a creative-heart industry. It’s important to be on the field with emotional intelligence.

S: Yeah, it’s difficult. It’s a balance. I totally agree. It’s delicate.


M: Talk to me about trust. 

S: Trust is a big word because it's cliche, but it also has a lot of depth in it - think about someone you trust or something you trust. Trust is like the opposite of fear. If you have trust in something or someone, you'll do anything. There are no limits. 

We can’t allow trust to get lost in the ideology of managing people, workplace environment or even the creative process. It’s not as much about what we know or what we believe - but it’s about trust. Do you trust me? Do I trust you? 

M: Can you give me an example?

S: The army or the marines are a great example. They're taught in the alignment of the infrastructure. Stand in this line. Seven inches from this one, seven inches from that one, and we're going to practice and practice and practice - until it's precision. What you can trust is that you are responsible for yourself first. Then thy brother, thy sister - get your stuff right because then the person next to you can trust you. Everyone believes - we are going in and we know we're all going to get out. That's what we believe and if something happens with our brother or sister, we're going to pick that person up and take them with us … We are all getting out of here, and we're leaving with the baggage.

M: It's complete psychological safety.

S: Even if someone was going to get hurt - we would not leave that person. Those men and women of service aren’t fighting because of their paycheck - they are fighting for Country. That's big. To me, that ideology is missing in our music business and we have a responsibility to it - how can we learn? This music business can teach you to be all about yourself and cover yourself. Look out for yourself, and that's not wrong, but to me that doesn't serve. I'm here at this level. 

M: The effects of that way of leadership are - 

S: Limitless. I always tell people, man, if you think about Martin Luther King, everywhere I go in the United States, every city has at least one Martin Luther King Boulevard - the man died at 38. When you dial that back -  it's amazing. I can't minimize that, but what type of individual has dedicated themselves to the empowerment, education and lifting up others - roads and statues exist because of his seismic dent in the world. 

As a principle for myself, I think of Maslow's hierarchy of needs: The highest human act is to inspire. It ripples through generations. When I dial it back to this small thing, that's where the seed is. That's where I’m at. Tupac said, I may not be the one that makes change, but I might inspire someone else that will.

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M: Talk to me more about this … 

S: It’s a principal that is at the centre of everything. I might not be the person who makes monumental change, but it might be my kids. My little girl might grow up to be President of the United States. How can she get there if I don't sow the seeds for her? I need to do the work so she has that opportunity. When I came into the music business, when I got in, I just wanted to be in it. You know, you look at it one side and there is the promise of these lavish and materialistic things, but for people like me who come from low income families, even poverty, those things become the crown jewel of the heist. You know? Now it’s about - how am I going to make a meaningful impact?

It's very important for me that there is a function, because I know what it can lead to and I've experienced it. There was a time, together with some of the artists that I’ve worked with, we changed our mindset : We said - let's stop doing it to be about us. We decided to be forward focused - how can we bring up our brothers and sisters?


M: Let's talk about developing trust with the artists that you work with. Developing trust as practice and process. Trust is not something that can be faked. I love a story that Anthony Bourdain tells, where he says that you can't lie in the kitchen and that's why he loved it so much. There is no room for bullshit. You can either make the omelette or you can't.

When you are working with creators, what's your process in helping everybody come together towards that collective goal? 

S: It starts with respect. I respect you and your process. My opinions are only here to help because once you have identified that you respect someone - you get some flow.  When they know you respect them, they feel less stress. Respect is mutual and it's a doing word. It's like - we can learn a lot from how respect is in the animal kingdom. 

M: At heart, how do you want your artists to think of you? 

S: That we respect each other’s mind. 

If they are on their game, i’m here to help them realize that and I'll take them through. Hopefully they’ll say - this guy is a good guy. Then our relationship grows and the connection is deeper. Even if it’s a challenging situation. Maybe the honor is in the difficulty. 

M: As humans, perhaps all we are seeking is that mutual respect?

S: Respect becomes respecting and then it turns into trust.

S: It's a beautiful day, isn't it?

M: Glorious. We have the most magnificent view in the city.

S: Yeah ...

M: ... and so you were saying...


S: In my journey now, I'm very clear about it. I've forged lifelong relationships with the people that I’ve worked with. I don’t take it lightly.

M: When you think of the context of the artists you work with. Do you think of them as clients or customers?

S: The label is really the customer. 

M: The label is also selling executive talent. The artists come to the label and they want to be part of it because they want to do business with great executive talent. 

What makes a happy customer?

S: Getting what they want … and what do they want? Whatever they sought you out for. 

That's it. We are selling experiences within a business context.  People listen to music alongside experience and that's what streaming and playlisting allow you to do. They allow you to ask - do you want to be in a good mood? Do you want to be in an upbeat mood? Do you want to be in an adrenaline mood. Do new songs make you excited? We just put a price tag on it. All those things occur on a neurological level - you want something that just speaks to your emotions or to your experiences. When you really break it down, we are all customers and asking the same questions - does this song speak to me? Does the artist look like me? Does that person endure the same things that I've been enduring? Does it line up? That's really what it is. The music business simply puts price tags in different places.


M: As we move into what will be a monumental year - what do you feel a responsibility for?

S: I feel a responsibility for the people and the artists. To the art creators and the people that work for the art creators. I want to play the infinite game. Keep the ball in play. At the point of sale, It's done. You got what you wanted - now are you going to repeat? Can I super-serve your repetition? If we do that, then there is a business. In this music business, we are selling something a lot more intellectual because we moving through how people live. The way people live here in New York is not how they live in Kansas or in Seattle. So our work has to have respect for those nuances. I'm not doing this for the transaction. I'm doing it to put forward ideas, empower the creatives and executives around me, and to create opportunities. I'm here for that.

M: To me, the mind is such a significant part of your personal style. These ideas you work through are just as important as the uniform that you wear. So, if we're suspending our imagination right now, taking us to the end of life and then looking back - how do you want your place in history to be seen?

S: I'm gonna need some time on that. That's a big question! 

M: I think you are on your way.

S: I'm not there yet, but I know that ideas become life. Every day we come outside and we try to be better, for each other … I was in school and my friend was like - oh man you are doing so well! I said - It's not that I'm doing so well. This is the standard of what I should be doing. Other folks - they had more opportunity. To get financial information, economics, elevated education. I didn't get that before I was 26. Yet other folks were getting that information that since they were out of the womb. That’s why I’m taking all that I’ve learned (and still learning) and I feel a responsibility to lead through teaching. Coaching. Whether it’s my kids, my peers or my artists. Let's understand the power of information and what we can do with it. It's powerful. Come play. Have you seen the movie "The Matrix?"

M: Yes! 

S: It's my favorite movie of all time. That's how I feel.