84 - The Ins and Outs of Running a Creative Management Agency with Alternate Side's Zack Zarrillo

Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Zach Zerillo, welcome to Listening with Leaders. You are the co-founder of Alternate Side, which is a creative management agency, and it can be found at alternateside.co. Welcome to the show.

Thank you for having me. Happy to be here.

So let's start off with Alternate Side. Tell us about the company.

Yeah, so I co-own Alternate Side with my partner Avanj. This is actually our 10th year of working together, which is hard to believe. Um, I started working for Avanj at a previous iteration of this company, uh, when I was 19 or 20 in college when I first started managing bands. Avant had a lot more history than me. She was about 10 years older than me, so Avant had been managing for a long time. She had a little black book of relationships that I didn't have, and she needed help on some of her artists. So it was a very, you know, helpful relationship on both sides. And eventually, you know, over the years I did quite well, and we ended up making a new company together where we're partners. So Right now we're a company of 9 people. We have 7 employees that are mixes of managers and support staff, and they're situated all, you know, anywhere between LA and London. We're a fully remote company with a really excellent team.

Wow. So what kind of, what kind of artists does Alternate Side represent?

You know, there's a, it's a really wide mix. Avantia and I historically started in kind of the punk rock alternative world. And since then, over the last 10 years, we've branched out in a lot of different directions. So we still manage a lot of rock and alternative punk bands, but I manage some pop artists. Avant manages kind of like a hip-hop, R&B artist and so on. And so we're between rock, metal, pop, and indie music all over. We like to say or believe that like the artists that we work with all have some pretty common threads despite their genre. We tend to work with artists that are very independently minded, meaning they want to have as much ownership, sometimes literally, of their music, meaning they don't sell to labels or how they do things as possible. And we like to consider ourselves what managers should be, is really the CEO of the artist company. So in some ways, you know, we're managing— we have CEO of multiple companies, which in the plain business world is of course not typical, but in a management world, it is pretty typical for one manager to manage multiple artists.

And what are some of the kind of the functions that you perform when you're working with these artists as clients?

Sure. Yeah. The manager is really like the central nervous system of an artist, right? Or the heart. So everything needs to kind of run in and out of it. So the artist makes the art, right? But an artist team is pretty wide. You can have a lawyer, a publisher, a record label, a business manager, a booking agent, a publicist, and so on. It's a touring team. And so on and so on, right? All of those things really get coordinated through the manager to make sure that everyone is running at the right speed. People are picking up the baton where the other one drops it, and so on. So it's our job to coordinate all that, but also to make sure the artist is healthy, to make sure music is coming correctly. There's a, you know, we sometimes I say we're glorified babysitters, and then other, on the other side of things, we're you know, making sure the, the business actually runs too.

So give us a little bit about your backstory. How you— I mean, you, you talked a little bit in the beginning how you started getting into this in college. Tell us more about that.

Yeah, so I actually started working in music when I was 16. Um, I started a blog, uh, to talk about artists I loved when I was 16. Actually got quite popular. I sold it actually when I was 18. I kept running it through the end of college. So I ran it from when I was 16 to 22. It ended up, you know, by at its peak, there was about a million page views, unique visitors a month at points. Through that success, work, whatever you want to call it, I started managing bands and having a record label, just kind of accidentally. I didn't want to go down this career path. Uh, I, I thought I would just be a blogger all my life until I realized that you can't make money in media, which is sadly only more true than it was then, right? Of course. So just, it very naturally happened that I started managing bands and running labels. It wasn't like a plan of mine. So, um, I started managing a band that I still am lucky enough to manage today called Knucklepuck when I was when I was 20, I think, and it kind of went well right away. And so that's what got me to join Ivan's previous company, because I thought I needed help and I didn't want to lose my artist. I wanted to learn. So it's actually been a really straight path forward for me in my life from 16 to 30. Everything— there's no pivots, it's just continual. I can kind of see where everything happened, which is, I think, a little unique. And pretty cool for me. You know, everything builds for me on top of the other thing. And I don't know if it will always go that way. I think that's rare, but it's been a very enjoyable career path for me with, of course, ups and downs, but way more ups than downs at this point, which is, you know, a real pleasure, especially in the entertainment industry of all industries.

So, so what gets you excited in the morning to get out of bed? And jump, jump to work.

I, I wanna make my artists have a good living. Um, some people, I think over time, you know, especially historically, of course, like money and art or business and art is, is an oxymoron, right? And, and it used to be very faux pas-ish to talk about stuff like that, but it's really important to me that my artists who make amazing music that I care about are able to survive from that music, are able to make a career and a living from that music. So what gets me up is, is finding success for my artists and making sure they're getting treated the most fair way and have the most control over the current and future of their music as possible. I, I always, I say to artists, usually when I start managing them, for example, I've worked with a lot of artists. Most artists, when I start working with them, are quite young, anywhere from 15 to 22. So They might not have a bank account, right? They might not have— like, think about it, they definitely don't have a credit card, right? Or lots of stuff like that. So, you know, just as an aside, financial literacy, teaching my artists is really important to me because it's so easy to just push that off on your manager or your accountant or your tax person. But I set up Roth IRAs for an artist, for a band of mine that was doing quite well. And they were like, we have no idea what this is. And what I said to them was, look, I hope we don't know each other when we're 55, but I hope that when you pull your retirement money, you think of me in that moment. So I want to— management is interesting because you're really so focused on the literal, like, what is happening today. But it's also quite important to me that in the time where things are a little bit more quiet, I can do a lot of work to think about the artist tomorrow and many tomorrows.

Wow. So what is it that, what is it that, uh, that's unique about you that you bring to the table that makes you successful?

That's a good question. Um, I, I think this is probably a really boring answer, but I have found that especially in music where there's no rules in the music industry, mostly for, in a lot of ways, bad and good, right? Like you can, I, I started as a 19-year-old kid managing bands. Like what, what did I know? Right. But I had good instincts or was able to learn good skills and evolve over time. A lot of people don't like— what I'm trying to say is I'm very organized, very project-focused. I'm very straight line. I can delegate. I get things done. I don't lose emails. I find, and this is boring, I find organization is where most managers mess up. And go with SKU and where we never do, right? Like, I'm not saying we're the best management company in the world. I'm not saying I'm the most, like, cool at parties with artists or other, like, industry people, but we get our job done right. And yes, being cool or, you know, being chummy with all these industry people is also important. It's not that we have good relationships with folks, of course, but that stuff doesn't matter if you can't get the daily grind of this job done. That non-glamorous stuff, making sure your artist has a passport or visa or so on. Um, and that we get that done.

Hmm. Wow. So that, that requires a, a lot of eye for detail.

And yeah, I mean, detail is key. Um, detail is key. Like, uh, there's so much information, right? Like getting a passport number wrong for the visa application can mean your band does not get into the UK, right? Like And there's a thousand examples of that.

So, so you're training your people all the time to pay attention to the details, get it right the first time.

Exactly. Exactly. And yeah, our staff, it's like we only hire people that are very attention-minded and need to be really competent in their own workspace, not just ours. Right. Especially like when we hire a junior manager, what we call a day-to-day manager, a lot of that is to take logistical focus off of us so we can think more big picture, right? As like the CEO of the company. But that only works if those people are as good or hopefully better than me or my partner at those things. And it's really hard finding those people.

I bet. I mean, there are not a lot of people that want to do that hard work. And, and yeah, a lot of people who want to do it well.

And the music industry is a very glam— it can be glamorous, right? You can— I was just, I, you know, I had the good fortune of being able to be in Europe for a couple weeks around festivals that my artists were playing and included some vacation time with my wife and so on. Like, that's amazing, right? Like that, that this job career can afford you like the ability to go see your artist in Spain and Germany and so on. I think a lot of people get caught up in the glamour of, I'm just gonna go out and be on all these fancy places, right? Me being able to go there only works for the rest of the year. I am locked in here, right? And I live in Philadelphia. A lot of the music industry, of course, lives in LA or New York. And I've lived— I'm from New York, so I understand that. But I, I want to be working for my artists. I am interested in the work. I love the work much more than I love being at a show at 10 PM at night, if that makes sense. I'm there for the work, not the glamour. I wanna, I wanna, uh, appreciate my successes and my artist successes, of course, but I, I like to do the show cuz I like the work.

How do you, how do you identify an artist that you're willing to work with? What are the, some of the traits that you're looking for?

Um, so one is that Ideally, they have some control over their catalog, meaning their music. We want our artists to be able to control their narrative. So much of what we do is leverage. Like, what I tell artists is, I want the ability to say no for you. Because that means we've succeeded, right? It's tough to work with an artist where they have to say yes to everything. Maybe that's because of their financial situation. That's because of, they've made bad deals in the past or so on. We typically work with artists that have never had a manager before, which means they're very early in their career. It's rare that we start working with an artist that has severed ties with their previous management. We do it, we've done it, but it is like 1 out of 10 of the artists we work with, probably. So we spend a lot of time investing, growing artists from 0 to hopefully 100. And we're really looking for people that, again, follow the same kind of streak of independence, of collaboration that all of our artists hopefully have, so we can work together. This is a real partnership. Ultimately, we do work for the artist, right? But this is a true partnership. We need to be able to trust each other. We need to be able to do things without them knowing, them do things without us knowing, and make sure it's all going to be cool in the end.

How do, how do people find you, artists?

I've never actually had an artist come to us that we then manage. Typically it's we go to the artist, or someone else that we work with in the music industry, like a lawyer or a booking agent or another manager, even a record label, suggests us to an artist, or we find something on the internet. It's rare that an artist comes to us. It's not impossible by any means, but that's just, again, we're typically finding things really early. So a lot of artists that are that early don't even know what a manager is or what they do, right? So a lot of our job is discovery, frankly. And, and that's the only way to have this company cuz we've, we have found, picked, worked with. Amazing artists.

So most of the artists are based in what, LA and New York, you would say?

No, um, I manage one artist that lives in Brooklyn. Looking at my list here, zero artists— oh, two artists that live in Brooklyn and zero artists that live in LA. They live in the UK, they live in Chicago, Detroit, San Diego, Brooklyn, Salt Lake City, uh, Western Massachusetts.

They're all over the place.

All over the place. I, I, yeah, I've actually never— I've lived in Philadelphia on and off for 12 years. I've never managed an artist that lives here.

That's interesting.

Yeah, I know the rest of the company, it's really that scattered too. We have people in Florida, we have people in Georgia, we have a couple artists in LA that I don't personally manage but are in our company. It's really all over. Um, Yeah, I would actually be surprised if we manage as a company 3 art— more than 3 artists that live in the same city. Wow. Maybe even state.

How long, how long does a typical engagement last?

I mean, do you think, uh, like how long do we manage an artist for?

Exactly.

It, I mean, it completely varies. I, most of the artists we want to manage, you know, the goal is of course to never end the marriage, right? Like when you go into it, and it is really a marriage in a lot of ways. It's very intimate. It's very personal. I know the Social Security numbers for all my artists, right? Like it's a personal relationship. I am just looking at my roster. I've managed one of these bands for 10 years, right? I've managed a couple other for 5 to 7 years. Some are more in a 2 to 3 year range, but the ones that are in that 2 to 3 year range, I intend to go longer. Sometimes a band we manage breaks up, right? And it's not that we've stopped managing them, it's just there's nothing to manage anymore. Or sometimes you drop an artist, or you do get fired, right? Like, all these things happen. And but in 10 years of doing this, I, I would guess percentage-wise of all the artists I've ever managed, I would guess I'm still managing 70-plus percent of them in that sense. Wow.

And for these artists in the genres that they're in, how long does their, how long can their career last?

Really varies. For example, I manage one punk band currently and they've been doing this for 10 years. I think they can keep doing it for a lot longer, but it depends. Also, managing a band is much different than managing a person, right? And over time I start to manage more individual artists and bands because you only, one, have to feed one mouth. You don't have to make decisions to like 4 or 5 people at a time. And logistically it can be a lot easier too. So, you know, I manage some singer-songwriter types. Their career might be a lot less than the bands, but it also has a chance to be a lot more elongated too because maybe they— the one-to-one money ratio is a significant thing. I mean, money in the music industry is really hard. So, um, it depends. I mean, I think the longest artist we've managed at this company is probably 12 years, and, and they're still going strong. They actually just had their most successful month of touring ever, 12 years into being a band. Wow. So, but then we have artists that are really flash in the pan, right? It's like, oh, this thing is huge, and then a year later, 2, 3 years later, it fizzles out and we either part ways or there's just, again, not much to manage anymore. We, especially with tools or apps like TikTok, we live in a very different landscape than when we started 10 years ago. Spotify didn't even— streaming in America did not exist when I started managing my first band. So it is a really changing industry still.

Huh. So it strikes me that, I mean, if you're talking about TikTok and Spotify, that the internet drives so much of a musician's success. And is that, that's something that you guys manage?

Oh yeah, we manage all of it. Yes. Uh, we, we're not posting hopefully on TikTok for our artists, for example, but we're engaging in all those conversations. Absolutely. I mean, social media is the least favorite part of my job that I have to deal with, and it's probably my weakest. Point, often we'll hire a marketing team to work with our artists. Some of our artists are amazing at the internet, right? Which is why they're successful in the first place. But often those same artists will get burnt out by it because it's so grueling. People can be so mean, even if you're only hearing one voice to the 99 that are complimenting you. Mental health in the music industry is an incredibly challenging, you know, Yosemite to climb, right? Like, right. Yeah.

So are artists making most of their money off of touring these days or off of their recordings?

It really changes per artist. A lot of what we've done at the management company over the last 5 years is have our artists own more of their digital, more of their music, which in past gets them paid monthly. So, you know, we manage some artists that make 5 and 6 figures a month and a year by owning their music, which is very rare. That's one of the most beautiful things about how the music industry has changed. That was impossible even 10 years ago, definitely more than that, because of streaming. Streaming has enabled that. I'm sure you often see that people complain that streaming doesn't pay enough, and that's true. Certainly I'd love it to get paid more. But we work with a lot of artists that do incredibly well on their recorded income. And some of those artists can't sell 300 tickets anywhere in America. Really? And we work with some artists that can sell 50,000 tickets across America and the money they make from their music is a drop in the bucket. So it really depends. It is what we want, you know, in a lot of ways, like the digital income is more secure. So that is when we're talking about new artists, those are maybe more of the artists we're looking at first. Because it's kind of puts them on a steady salary if, you know, hey, I can make $10,000 every month for my music for at least the time being. Wow.

Huh. Fascinating. I mean, I, I, I know very little about the business, so it was just listening to you. It's a, it's really interesting.

It's a very interesting field. And I, you know, one of the things I've really enjoyed over the last few years has been growing that business for our artists and really managing it.

How do you deal with the drama? Which I'm sure there's a lot.

I'm not, it's not like I am super, I'm 30, right? So it's not like I've been doing this for 20 years. It's not like I'm in my 40s or my 50s, but I'm a pretty mild-mannered person. I'm very rational. I'm not gonna raise my voice about anything. People get upset about stuff all the time. I try to be the most fair to my artists, especially with outside parties, right? There's a difference between drama external to your artists and internal, right? External, I'm always going to be trying to get the best deal within reason for my artists, right? So I might fight and fight. For my artist to get an extra penny. Internally, if there's drama or there's issues within the band, it's just really about talking things through and hoping you can come out the other side. And again, that goes back to the mental health point. There's drama when maybe someone's just annoyed with people, and then there's drama if someone's having, you know, should be seeing a therapist or should maybe be on medicine or whatever. And sometimes I have to go find my artist therapists and make sure they're taking their medicine and stuff like that. And that's not a the most thrilling part of my job, obviously, but it's, it's, it is part of my job.

Yeah, interesting. Well, we're just about the end here. One more question for you, Zach. What's one thing about, one, what's one thing about yourself that we would never know about unless you revealed it to us?

Oh, you're gonna like this. I own a donut and coffee shop.

You're what?

I own a donut and coffee shop. Here in Philadelphia.

You own a coffee shop?

Yeah, it's a donut shop. Donut shop?

I do like that. That's unexpected. Uh, there's a whole story behind that, I'm sure. So you manage musicians and cook donuts?

Um, thankfully for everyone, I'm not cooking the donuts, but yes.

Oh, good for you. Well, this has been a lot of fun. Thank you so much for your time.

Yeah. Thank you so much for having me.

Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you please share this episode on social media? Just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes. Go ahead and subscribe. Your thumbs up ratings and reviews go a long way to help promote the show and mean a lot to me and my team. Want to know more? Go to my website, DougNoll.com, or follow me on LinkedIn, Facebook, and Instagram. That's @DouglasEnoll. Thanks for listening, and we'll see you on the next show.