The Leff Exchange podcast: A conversation with artist manager Howard Greynolds

Think about one of the favorite concerts you’ve seen. You may need to reach back a little further than you’d like. For those two hours, chances are you were transfixed by the artist. And it wasn’t an accident. Behind that artist was a whole crew—lights, sound, staging, and roadies. And behind all of them was the artist’s manager, who had worked for months with the artist to shape their vision and bring that experience to life.

Howard Greynolds is intimately familiar with just about every aspect of the music industry. As the founder of Overcoat Management, for the past 25 years, he has managed such acts as Glen Hansard, Iron and Wine, and the Frames. As the enduring success of his artists demonstrates, he excels at that collaborative process of nurturing creativity at a high level.

In the following conversation, Howard discusses the many hats he wears as a manager, the importance of relationships and teamwork in the music business, and the parts of the job that still make it all worthwhile.

Scott: One of the things I like about the music industry is that it seems people who come from nontraditional backgrounds can find their way and actually be really, really successful. I’m curious how you got your start.

Howard: I fumbled my way into it as a fan. As somebody who didn’t play music, I was trying to find a way into music, and for me, it was just a bit of trial and error—of going to shows, meeting people, asking questions, trying to piece together how I might get a job in the industry.

I was going to a traditional school and thinking I was gonna get a normal job, and then somewhere along the way, I thought, “You know what? Screw it. Let’s try to make this happen. If it doesn’t, there’s always time to go to that other normal job.”

I put bands up on tour at the house I always had with a handful of roommates. We’d talk to them; we’d stay up all night; I became pen pals with them. I was trying to decide between New York, Chicago, and DC at the time because there were record labels I really liked.

I thought, “I’m gonna have to move there, get a job at Kinko’s, and figure out something.” For me, the break was moving to Chicago and catching on with a record company called Touch and Go Records.

Scott: What types of things did you do for the record company, and how did that set you up to transition into managing artists?

Howard: At the time, you did a little bit of everything. Bands didn’t even really have managers. When I showed up, I got offered the mail room. A band had turned in a record and had an opportunity for what everybody in the building thought was gonna be a song that would get played on the radio.

That was in the days when you sent out cassettes, then you sent a CD, then you followed it up with more CDs. And you were just constantly doing mailings. I mean—it was insane.

They needed someone in the mail room, and they hired me. That song was never a hit, but I got my foot in the door. I held on with everything I had to try to make people dependent upon me. When that tenure ended, they were like, “Well, that song’s not a hit, but that guy—he seems like he knows he wants to be here. Let’s find a reason to keep him here.”

I was eventually then making phone calls to record stores. Then, I was doing publicity for college radio. You kind of just worked your way through. It seemed like every year and a half to two years, somebody would leave, and a new job would open up, and you had this opportunity. They wanted to hire from within because you knew the building, you knew the bands.

All of that prepared me. In the mid ’90s, a lot of bands on that level I’m speaking about with labels like Touch and Go, Matador, Thrill Jockey, and Drag City didn’t have managers because the labels did so much for the bands that bands didn’t almost need somebody taking 10 or 15 percent.

When it came time to become a manager, I was trying to get my head around, “Is this okay to do?” And then qualification-wise, I even remember being like, “Do I know how to do this?”

In talking to other people who had done the job, I realized, “Oh, all those things you do in a day are all the things I’ve been doing for the last seven, eight years at record labels anyway. I get this. I know how to do this. I believe in this band enough. Fu** it, let’s try and do this.”

Scott: How did you view your role when you stepped in as a manager?

Howard: What I figured out early on is bands are going to choose a manager for one of two reasons. One is the artist wants to be insanely popular and successful. And they find who the biggest manager is, and they say, “This person is almost like a kingmaker. If I’m with them, everything lines up.” And then there’s the person who knows the band, and they grow with the band, so that every decision, every achievement, every success, every failure is shared.

I definitely wasn’t the former, obviously, as a guy who was figuring out how to do this. When I was working at record labels, like everybody in any industry, you’re collecting contacts, you’re collecting relationships, you’re nurturing, you’re tending garden to these things. And if you’re not, you’re not doing the job right.

I was fortunate enough to have somebody send me some music to say, “Hey, could you help us find a record label for this? This is my buddy’s stuff. And here’s my stuff as well.” And that happened to be Iron and Wine, Sam Beam. The person who sent it to me was a guy named Ben Bridwell, who had a band called Carissa’s Weird. Ben is now lead singer of a band called Band of Horses, which went on to become really successful, and credit to him. He’s a great guy.

The Frames was a different sort of relationship. They were making a record in Chicago with Steve Albini. I had a number of Irish contacts, and they said, “There’s a great group of guys; would you mind connecting with them?” The Frames were at a point of just reinventing themselves. They’d been on a major label; they’d been through the system. It was a totally different experience in terms of what set of tools I would need to work with them and eventually manage them. But at the time, it was really about helping this record they were making find a home.

Scott: Talk about the full range of things you have to attend to as a manager.

Howard: Ultimately, you’re trying to oversee every aspect of the band’s career, which, on its surface level, just feels really large and overwhelming. What you realize is there’s just sectors of the music business. And the biggest one is the record label. Next is the booking agent. Those are two main drivers. And then the publicist and all that stuff.

The creation of the music is this other thing. And oftentimes with the bands, you might hear about new producers, new engineers, new studios. You’re putting these things on their radar.

As you get in sync with the band, you have an idea of where they want to make their record, how they want to make it, whom they might want to make it. Or maybe they say to you, “Hey, how do we get in touch with so-and-so? Can you figure that out and make that happen?”

The short answer is—if you’re doing your job right, you’re involved in almost every aspect of their career, from the creation of the record, the release of the record, the touring, the moments in between. It’s why I don’t have a lot of clients—because you find that your time is the key to all of it.

I kinda looked at what I wanted to do with these folks. And every time I’ve had an opportunity to take on more and more acts, I’d think about how it’s gonna take away from the thing that I love doing the most for these couple bands. It kinda stops me from taking on more than I can handle.

Scott: There’s also probably an advantage to having your hands in everything.

Howard: Definitely. It’s a blessing and a curse. It’s also what the artist is in search of and the relationship they wanna have with their individual manager. Sometimes you feel like you’re working for an artist, and sometimes you feel like you’re working with an artist. And those are two very different feelings. Each artist identifies success differently. I like to joke that I don’t manage bands, I manage expectations.

For Sam, the artists he admired were J.J. Cale and Bill Withers, who have these long careers, but they also weren’t selling out stadiums. You don’t think of Bruce Springsteen and J.J. Cale in the same sentence. That doesn’t mean that Sam doesn’t have a part of him that wants to play a stadium. Mind you, I’m sure he does. But he was after this sort of dignified career with longevity.

When I first met The Frames and Glen, there was a sense of, “Let’s take over the world. And what doors do we have to knock on? What rooms do we have to play? What tours do we have to do? How do we become the biggest band on the planet?”

There was just this drive that was relentless. It’s super exciting and intoxicating when you’re in that: you’re driving them, they’re driving you, and you’re all kinda going for it. Their version of success always felt a little different than maybe what Sam was in search of.

Identifying that as a manager is also very key because you wanna find those opportunities for your bands that satisfy these internal drives that they have.

Scott: I’m curious with someone like Glen: he was in The Frames; he went out on his own and has a great solo career. He starred in the movie “Once” and won an Oscar for best song. He ended up then staging a theater production on Broadway, all the time releasing music. When someone like that comes to you with a creative idea, what do you see as your role in nurturing it and sometimes pushing back, if necessary, to help guide them to the best result?

Howard: First, you’ve got to figure out if it’s possible, and how much it’s gonna cost. You gotta get through a couple of hard conversations because, at the end of the day, so many ideas that an artist might have are whittled down to money: How do we afford to do these things? How do we execute them?

Those are key, key moments in a discussion with pushing back, but also you gotta know that if they’re coming to you with this idea, your job is to help them make it a reality. So you’ve gotta find that balance. But ultimately you say to yourself, “Okay, is this possible?”

I will say with Glen, so much of the credit for his success really still lies with his just internal drive and over a 30-plus-year career of keeping himself open to opportunities. We’re just kind of hanging on, sometimes trying to figure out how to keep up with him.

When he comes to you for a tour, and he says, “I wanna take 18 people on tour. I really wanna have this.” Then the discussion becomes, “Well, are you willing to play this size room?” “Can I get the ticket price to here?” You’re trying to find a balance between what you’re comfortable charging the audience because you have a responsibility to them, but you’re also trying to figure out, “How do I afford to get 12 people over from Ireland to the States for a day of rehearsals?”

Logistics is such a huge thing. The amount of “good cop, bad cop” that gets played between you and an artist—or you and your team with anyone in your office—is so valuable because you’re basically just trying to figure out how to afford to do these things.

It’s exciting, but it’s not creative; it’s just this mundane exercise: Is it going to involve us driving from New York to Kansas City to the first show? Who’s willing to do that? How much does it cost? How do we make this happen?

At the same time, when you finally get there to the first show and you’re standing in that room and the doors open and the lights go down and the house music comes down—the rush of it all, it just makes it feel so worth it. Whatever you spent the last month or two arguing about, going back and forth, trying to help them with their vision—it’s just like, if you’re in it for the right thing, man, that moment is just like, “Okay, here we go. Here’s the next 30 days. It’s not gonna be easy, but it’s gonna be awesome. Each night for these three and a half hours from doors to the end of the show.”

And it’s super exciting. That’s the reward when you’re looking at your artists, and at the end of a night, they’re like, “Yeah, man, that was great!”

The show is never really just done. Each night, each room brings its own new set of hurdles and limitations. How you’re going to dial that in. Is it a Tuesday night versus a Friday night? Is it 75 percent sold versus 100 percent sold? How can you create an experience?

Scott: How do you manage that responsibility for almost everything that happens on the tour? I’d imagine you must feel a huge obligation to get everything right.

Howard: You find the right people to help you: tour managers, production people, lighting person, front-of-house monitors—everybody that’s outside of the band that goes into a key moment. As you build into doing a tour, yeah, the pressure mounts. You wake up in the middle of the night. But really, it’s about finding the right team. This is a place where I really like the word team because, especially in the live music sector, the shows are so much about teamwork.

It goes back to relationships and everything you do as a manager. This is true in any business, you know—treating people with respect so that they wanna come back and work with you.

But ultimately, you’re looking to create a network of like-minded people who are hardworking and have the same goals for you and your artists when you head out. My stress goes down when I know we’ve built the right team to go out on the road, and that’s when I don’t have as much of it just crashing down on us.

Scott: Talk a little bit about how much the music industry has changed over a couple of decades. What have been the biggest challenges and how have you addressed them?

Howard: Well, I’ve been at it long enough to see a number of changes, which scares me at times. It used to be a tour advertises the record. And now, the record is really the advertisement for going out on the road. “Oh, they got a new record. Cool. They’re playing shows.” That shift probably was drastic for bands who didn’t like to tour.

Primarily coming out of the Touch and Go–Thrill Jockey system, those bands liked to tour—they play clubs; they then play bigger venues as they grew. They were always willing to go on tour.

That shift then led into festivals: We’re gonna get a festival; we’re gonna release our record in March. Our record will feel fresh when we hit that first festival in Coachella. Because we got Coachella, let’s build our record release around that. Then, festivals popped up everywhere. I don’t think it’s a secret that bands are overpaid for festivals as it is right now. I mean—they’ve kinda ruined it. I have no idea what will happen now post-COVID.

So you’ve got the festival circuit that created its own monstrosity of how people might release records to capitalize on the press tent. And then touring in the summer, which you didn’t used to do many, many years ago, and now you tour a bunch in the summer.

When I first started at a record label, the CD was king. The CD was great to everybody. You made it for practically nothing, you sold it to a distributor, distributor sold it to a store. And the markup was enough that even if you didn’t sell a lot of CDs, you could make a little bit of money. There were plenty of bands who weren’t quitting their day jobs back in the day, but they were still able to make some money on CDs.

Then Napster comes along; it feels like it kinda just decimated everything. And that was the first time record labels had to reinvent themselves after losing this cash cow of a CD. You know, technology has always led the industry, no matter what we wanna believe. That’s where it begins.

All of a sudden, the internet creates a playing field that’s so level—in a good way and a bad way. And everybody’s got to reinvent themselves overnight. Some were better at it than others. A major record label sees the world in one way; an independent label sees the world in another way. Occasionally they’ll overlap, but they definitely are different beasts. The independent labels were quicker to embrace streaming because I think they felt like it gave them a certain ability to manage distribution, which was always one of the enemies of a smaller label.

And all of a sudden, you’re just on everybody’s phone or everybody’s computer as technology started to advance, and MP3s became the norm. As a manager, your job is to keep up on these trends and know what the heck’s going on. But the labels—if you have the right partners, oftentimes they can kinda lead you, and you can kinda see what’s working and what’s not.

Scott: How did you and your artists weather the pandemic? Is there anything that you’d see as a positive coming out the other side?

Howard: Like anything, there’s gonna be good and bad, so focus on some of the good. I feel that COVID has made everybody regroup and recalibrate. And new things like streaming shows have probably been normalized a lot more.

I was thinking about online streaming. I think clubs now are gonna offer bands the opportunity to even make more money than what they’re making at the door if they’re willing to stream the show. I don’t think a band will be able to do that every night, but this normalization of streaming shows is gonna be interesting to see how long it lasts, where it goes. It’s gonna be really nice for an artist. There are some artists just starting out, and they’re playing three shows in a weekend, and they come home, and they’ve barely broken even.

You have to go to those markets, but at some point, when you’ve done that five times in those same markets, you’re just starting to really wonder. The luxury of being able to just stream a show—make that same amount of money, not leave your house, probably be mentally in a better spot to create more—is gonna be really nice for them and the whole world.

If a band has a fan in Germany or ten fans in England, they can tune in to that because the band is not getting on a plane maybe to go over there for another year or two. It’ll be really nice for artists as a revenue generator and as an awareness thing. If you have a new record, you could easily do a record-release show in your hometown that you could also stream. So, everybody has that sense when the record drops like they’re part of that first handshake, that first introduction to a new record, which is always the most exciting as well.

The one consistent throughout COVID-19 whenever I would talk to another manager is that none of us knew what the answer was gonna be. We had a conference call with some great people who manage some really great artists. And every time, I felt like I came away from those Zoom calls more as therapy than answers. You know, we were just trying to figure out what the heck is going on.

And everybody’s well was different. Did you have money to live and get by for a year? Did you need live streams to create income? That was a really tricky thing.

I was fortunate enough that my guys, Glen and Sam, didn’t do a lot during the pandemic. They had been looking to get human from having toured so much for the five or seven years prior to that. We had gone into 2020 with this idea that it was gonna be quiet anyway. And then, of course, they got more quiet than they asked for, but it was one of those things that was a mixed blessing. They just were like, “Wow, great. This is the time off that I’ve been wanting to take.” And there would always be an opportunity that arose.

Scott: For as long as you’ve been in this business, what do you still get excited about with your job? What are the things you look forward to?

Howard: The rush that you feel when you hear new music, even if it’s not my own artists. But especially when they send you something, and they’re like, “I’m thinking about this song”—it’s super exciting. I would say that’s definitely the first and foremost: the discovery of new music.

It’s still such a fun part of the job that makes me feel like I’m a kid again. And when your artist does it, helping them create and see through a record or an EP—or just a single song in this day and age—when you can just put it out versus an album, you can just put it up on Bandcamp or share it on Spotify.

That, coupled with finding a new way to reach somebody and get some new fans and engage the old fans. What you find, especially in a long career like with the bands that I work with, is that you have people that come in and out of their lives with these artists.

Someone will write you and say, “Man, that song just crushed me. It touched me in this way, helped me through a bad time, helped me make a life decision.” Those are humbling and super rewarding as a manager to feel like you’re not the guy writing the music, but you’re helping get it out into the world. That’s still a rush.

I think one of the challenging things is figuring out where we’re all headed and how to have a career. I still try to wake up each day and find new, inventive ways to make my artists feel exciting for their fans and for themselves and try to be on the edge of whatever’s next and new, especially as our industry changes.

COVID-19 has totally made that a big-old question mark. I don’t think that’s another train coming at the end of the tunnel. I think it’s a light, and I sure hope it is because I feel like we need to get there. It’s gonna be nice. It’s gonna be nerve-wracking. There’s gonna be a new learning curve on how we view shows. I’m nervous but excited. We gotta figure it out because music and art just mean too much to us. It’s a common thread in all our lives.

Scott Leff

Scott is the founder of LEFF. He’s spent his career helping executives and subject matter experts tell their story in a compelling way. In the process, he’s had the opportunity to work with C-suite executives, politicians, academics, and Olympians, not to mention dozens of talented writers, editors, and designers in the business world. Scott developed the concept of “lean content creation” as a cost-effective way to support comprehensive, integrated communication strategies.

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