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Billie Eilish Booking Agent Tom Windish on Touring, Opening Slots and Artist Development

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The New Music Business Podcast with Ari Herstand - Billie Eilish Booking Agent Tom Windish on Touring, Opening Slots and Artist Development

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Ari Herstand
Ari Herstand is a Los Angeles based musician, the founder and CEO of Ari’s Take and the author of How to Make It in the New Music Business.
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Billie Eilish Booking Agent Tom Windish on Touring, Opening Slots and Artist Development

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This week on the New Music Business podcast, we are joined by Veteran booking agent Tom Windish. As Head of A&R and Business Development at Wasserman Music, Windish has developed the touring careers of some of the hottest names in music, including Billie Eilish, Lorde, alt-J and The xx. In this episode, Ari and Tom discuss the state of the live music industry, how booking agents operate, why tour buy-ins are unethical, the process of signing new artists, running a record label, and much more!

03:58 The State of the Live Music Industry
08:19 Advice for Emerging Artists Eager and Ready to Tour
13:14 How Booking Agents Operate
17:07 Communicating with Promoters, Talent Buyers and Collecting Money
21:04 Opening Tours and Slots
26:08 Unethical Tour Buy-Ins
30:03 Working with Billie Eilish and the Process of Signing New Artists
37:47 Artist Development, Management and Running an Indie Label
46:45 Why Tom Started a Record Label
54:33 Final Question

Edited and mixed by Maxton Hunter
Music by Brassroots District
Produced by the team at Ari’s Take

. . . . . . . . . .

The State of the Live Music Industry

Ari: Welcome to the show! How’s it going? Yes, . Good. Um, so, uh, you are, uh, You’re a, I, I’m safe to say a legendary, uh, booking agent at this, uh, stage of the game. I know that you started as totally scrappy, diy, uh, Mr. Hu Indy, all of that. But, um, I wanna, I wanna start at present day, and I wanna, I wanna talk about, we’re at the end of 2022 right now. Um, and I know you wear a lot of hats, and we’re gonna, we’re gonna uncover all those hats throughout the hour. Um, but first off, the, the hat that most people know you for as the booking. Um, I wanna hear from your perspective, what is the state of the live touring industry? Here we are end of 2022. How is it going? How is, how are we doing as an industry?

Tom: It’s been an interesting year. Um, I, and I think how we’re doing depends on who, who you are. Um, for the biggest artists, . Um, I think it’s been an amazing year. Mm-hmm. . Um, I think for medium sized and smaller artists, it’s been hard. Um, I think there’s, uh, I mean there’s a lot of different reasons that, that contribute to that. Um, there’s a lot of things that are competing for everyone’s attention these days. Um, in the pen. Um, a lot of people’s habits. And people realize they like some things, um, that they didn’t know they liked before or they liked certain things more than others. And I feel like, you know, people’s attention got taken away from maybe listening to music or going to see bands, especially, um, maybe, maybe some people spent more time listening to music cuz they were at home and had, you know, nothing else to do or whatever. Um, but going out to shows, , you know, people found ways to spend that time doing other things. Mm-hmm. . Um, and then when everything came back, um, and live, live shows were allowed again, um, everybody went on tour. , uh, or you know, if not everybody, uh, a lot of, a lot more people than usual went on tour. Yeah. Um, so. Every artist is competing against every other artist who’s out there performing, but they’re also competing against all these other things that people do with their time. Like watch a movie at home on their, you know, 10 different streaming services. Right. Um, or, you know, just go to all the other things that they, they could do. Yeah. Um, and I think that’s been really challenging. I found, uh, you know, I mean like, one of the things I love the most, Finding a new artist who sounds amazing and, and helping them. Mm-hmm. . Um, and in the old days, meaning pre covid, um, , a lot of them would like develop relatively quickly. You know, they’d, they’d go and play little clubs and people say, oh, that’s, that band’s great. And then more people would, would, uh, you know, the word would spread. More people would go to the shows. They’d get a support tour, they’d get some festivals, pitchfork, New York Times write about them, Ks u w would play them. Mm-hmm. , and before you know it, they’re selling 2, 3, 4, 500 tickets, um, in a lot of different cities. And they’d start touring internationally and like it all kind of moved like at a pretty good pace and. Now I have a bunch of artists that are, are just as interesting and good and have just as much stuff going on as those artists did back then now. Mm-hmm. . Mm-hmm. and there’s a lot of them I think are sort of staying, finding a lot harder to get the same type of gains from the audience. Um, so maybe it used to go up like this and now it’s going up like this. And I think it’s because of competition for, for people’s attention. Um, and it makes it really hard.

Advice for Emerging Artists Eager and Ready to Tour

Ari: Yeah, I mean, it makes a lot of sense. Uh, you know, the Pole star numbers would have you, uh, believe that as an entire industry, everything is doing well. I’m glad you made that distinction between the top tours are doing just fine, but those mid, you know, the emerging artists. So what is your recommendation to those emerging artists who feel like maybe they’re ready for the. Tour or, or they really wanna play shows, but you are seeing that the audience reaction just overall at that level might not be way able to meet them at the place where they think they’re at.

Tom: I think my main takeaway is to develop, develop a market or our territory before you start trying to conquer, uh, I don’t know. More than you can chew or, I mean, like I would, I would encourage a band to develop, let’s say they’re from the us, like go develop the United States or a region of the United States before you try and also conquer Europe. Um, yeah. In Australia and Asia, even though you might have data saying like, well, we have a lot of listeners in London, we have a lot of listeners in Sydney. Um, I mean often like you find artists have a lot of listeners in certain markets, you know? Right. Just so happens a lot of people usually live in those markets. la, New York, London, Sydney, Paris, um, Mexico City. Um, and I would, I would encourage an artist to like get to a place where maybe they’re breaking even or making a little bit of money in a certain place, maybe a country or a section of a country before they. And investing in another place. Um, cuz when, like, an investment is a bunch of different things. It’s financial, um, it’s also time and resources and like time and resources, you know, and money is, uh, it feels like, it seems like there’s a lot less of it to go around, uh, right now. Mm. So use it like very frugally and wise.

Ari: How much do you look at data, um, when setting up tours, especially for your more emerging artists?

Tom: Not as much as you’d think. Um, I mean, I look at it, I guess I, I always look at it, but it’s very rare that, um, the data tells me. There’s a really big fan base, fan base in a place that I didn’t realize there was a fan base. Um, and it, it’s because like the market does a really good job of, uh, of sort of showcasing what data showcases um, what do you mean? If there’s a lot of fans in Portland, Oregon, there’s a really good chance that the person who, the people who put on shows in Portland. We’ll reach out and say, I want to do a show with this artist. Okay. I’m hearing about this artist, you know, from the street, you know, from my friends, from my colleagues, from, you know, people that come to the club all the time. Um, we wanna see this band. Mm-hmm. , um, people are talking about it and often data correlates with what people are actually saying to each other. Like in person. Yeah. And then they’ll reach out. a lot of times, like a lot of people live in those cities too. And, and those are markets that a lot of artists are going to. Mm. Um, who, I mean, and another thing is that artists don’t want to go on tour forever. Um, and they, you know, let’s say they want the tour to be a month long, it’s pretty long these days. Mm-hmm. . Mm-hmm. and I could probably name. 25 of those cities because they’re the biggest cities in the country and also geographically like it makes sense to go to those places. Hmm. Um, and it’s, it would be rare that the data would say, oh man, you made a big mistake when you went to Dallas instead of Oklahoma. Cuz there was a lot more listeners in Oklahoma. Sure. If, if there were like, chances are the person in Oklahoma would would’ve said, Which isn’t to say, I don’t look at it, but I look at it more at an international level. Um, I think it’s easier there to lose, to not realize like, oh, there’s a lot of people listening in this place in Asia. You know, we should reach out to the people that put on shows in Asia or in that country and see what they’re thinking, you know, or see if they wanna book the.

How Booking Agents Operate

Ari: So you mentioned, uh, you know, someone might reach out to you, uh, if something’s happening in Portland and their fans and they wanna make a show happen. Can you, I want to zoom out a little bit and just for the people listening who might not quite grasp or have an understanding of how, uh, booking agents operate, um, can you just break down the business of booking agents and what you do and how the business works and how you make money and who makes money, and how all that works just for people that just have no idea.

Tom: Yeah. Cause I, I mean, I feel like every day a whole bunch of people reach out to me about things that I have nothing to do with . Yeah. And I’m just like the, the, the email address that they find. Um, sure. So, you know, the main thing that booking agents do is, uh, set up live performances where the artist gets paid to perform really mostly in front of like a, the public. Mm-hmm. . Um, so like we don’t book television appearance. Very often. That’s generally the, the, the publicist or mm-hmm. , the record company. Um, there might be a handful that, like an agent might have a relationship or be involved mm-hmm. . Um, but that’s not the main thing. The main thing we do is book ’em at, um, a venue where people are paying to get in. Mm-hmm. . There’s always exceptions, you know, like, we’ll book ’em in a college, maybe you don’t have to pay to get in, but the artist gets paid to perform for an audience, you know, and then sometimes we book them for corporate events, private events. Um, depends on the artists, you know, we have a few that do a lot of that. Um, but by and large, you know, they’re playing these, uh, the other places where the public’s going to see ’em, like festivals. Mm. Um, What else do we do? Um, we’re really involved in the marketing of the concert appearances where people are buying tickets. Okay. We’re not like the exclusive people that are doing that, you know? Mm-hmm. , like, we don’t really log into the artist socials and do it for them, but we’re kind of making sure everyone’s talking to each other. Timing is coordinating coordinated art work is coordinating and coordinated in that. The artist is announcing things, the venue’s announcing things, everything’s working. Um, cuz we’re in a position where we’re kind of at the center of this, the tour. Sure. Um, and, you know, it’s part of our responsibility is to make sure it goes right. Mm-hmm. , um, something we don’t do is like, we, we figure out how much the artist is gonna get paid to do that show by the club, and usually there’s like a guarantee and then, A certain number of people go, you can make more money. Mm-hmm. , um, if you play a festival, usually you can’t make more money. You just get like a flat amount. Um, um, we, so we make sure the artist gets that money at the people who make that offer, like honor it. Mm-hmm. , uh, and we’ll do some calculations afterwards to make sure everything goes according to what everyone said it was gonna happen. Mm-hmm. . But something we don’t do is tell the artists. How to spend the money that they get paid. So we don’t go out and like rent the bus for them. Find the tour manager for them best manager, guitar player, manager’s job. Yeah, sure. Uh, or someone else’s. Yeah. Um, so yeah, like often I don’t really know how much the, the artist is making on the tour, how they spend it, you know, is some, you know, other people’s, uh, Sure. And uh, you know, they can spend a lot of different ways. They can fly. First class, they could fly. On the budget airline.

Communicating with Promoters, Talent Buyers and Collecting Money

Ari: So let’s talk about kind of who you’re setting these shows up with. Are they promoters primarily? Um, are they talent buyers at the venues? I guess it depends on the level of the tour, I suppose. And then when you say you’re making sure that the artist gets paid, How are you making sure they get paid and, and are, is it direct deposits? Are they getting paid before they play this show? Is it after? It’s probably no longer handing them a check at the venue. Auto Imagine. Or maybe it is.

Tom: It might be like that a little bit. I mean, usually, um, Yeah, we get some of the money upfront. It depends like, okay, we generally have really long standing relationships with the people that are paying artists to go perform. Mm-hmm. , I don’t know what the percentage of shows we do with those kind of people is, but it’s a lot like 80%. Um, and you know, we’ve got strong relationships, so like we will collect some of the money, um, a bunch of the time, but even if we didn’t, like they’re gonna pay. Okay. Um, because they do a lot of business with us, and if they don’t, sure. You know, it’s gonna mean they’re not gonna get to book all these other people. And the way they make money is by putting on shows. Mm-hmm. , um, generally we don’t like advance, um, the money that we collect before the show to the artists. Okay. Um, you know, there’s some rare circumstances where things are dinner different, but usually they get paid after they, after they. .

Ari: Gotcha. And they, so the promoter or the, the club or whomever, uh, they send a check. Now are they always sending the check directly to the agency or do they give it to the artist and then the artist is required to then pay you their, your commission or your cut from that? If that’s how that works.

Tom: Part of the reason we get paid up front is, uh, so that we get the money that the artist. . Hmm. Um, so that they don’t have to pay us at the end of the tour. Um, you know, I mean, just like our relationships with people who put on shows. We work with our artists for a long period of time too, so, yeah. You know, if they do end up owing us money after the tour, cause maybe it went really, really well, uh, and we collected less than we anticipate they’re gonna make or something, or I don’t know, a certain checked income or something, the artist will pay. Um, but yeah, usually some of the money comes to the agency, um, not a hundred percent of all the money, uh, a much smaller percentage than that, and then the rest is paid to the artist. And it could be through a wire, it could be through cash or check. Sure. It depends. Uh, as things get bigger and bigger, it becomes more and more official. And less. And there’s less and less like checks or cash flying around and it’s more and more wire transfer.

Ari: And just to be clear, um, you only get paid when the artist gets paid, right? Uh, booking agents model, uh, is a commission of what they make exactly.

Tom: Okay. Agents, agents generally get paid 15% of what the artist gets paid at this show, meaning like the gross fee that they. Mm gotcha. Um, so if they get paid $10,000, we get a thousand dollars. If they spend eight, eight of that $10,000 to get there, to stay in a fancy hotel, to, you know, all whatever you can spend money on. We don’t collect 10% of 2000. We get 10% of 10,000. Uh,

Ari: You make 10% or 15% you said. 10% and that’s of the gross.

Tom: Yeah. And for the larger agencies? Mm-hmm. , most of the more established smaller agencies, 10% is the industry standard.

Opening Tours and Slots

Ari: Gotcha. Cool. Um, so I wanna talk about, um, opening tours and opening slots for a minute. Um, you know, how does that operation work in terms of, uh, let’s say there’s a, a, a tour that’s completely set up for the headliner. They’re playing maybe, let’s say mid-level clubs, uh, 1500 capm, something like that. Um, For, I guess on your end, when, if you’ve set the tour up, how do you find appropriate openers? And then on the other side, if there are acts out there that wanna open these tours, what are good expectations for them and how should they approach it?

Tom: Often the, the artist headlining has a point of view about who they would like to open their fans of a bunch of different band. , they follow them on social media. They may have worked on music, played shows with them before, whatever. Mm-hmm. , they’re friends and they want them to go on tour very often. That’s what happens. Okay. Um, sometimes they don’t have an idea or the ideas they have aren’t gonna work out for whatever reason. And in that case, we’ll go and ask every agent in the business for ideas, um, and then we’ll present. A list of like, we call them submissions. Mm-hmm. to the management, presents them to the artist. Um, we usually give them some information about each of the submissions, you know, like when they’re releasing music. Um, maybe a little bit of tour history, um, that type of thing. Um, a link to listen to music, uh, maybe like some information about socials or Instagram or whatever. Mm-hmm. . Um, and we send that over. They make a decision or they ask some questions and we start, we get into conversations with the people who submitted those, those artists. Mm-hmm. . Um, sometimes an artist, like maybe they wanna play that room that fits 1500 people, but they can only sell a thousand tickets and then they’re looking for an artist who’s gonna sell 500 tickets. Um, that’s a little bit. . Um, so then we’ll go out to all the other agents in the business and ask for, you know, more specific things. We’re looking for someone who can sell about 500 tickets or maybe it’s not exactly that, but you know mm-hmm. , whatever, between two and 500 tickets and mm-hmm. , the amount of money that we’ll pay them varies. Um mm-hmm. . Yeah. The budget for openers is kind of all over the place too. Depends, a lot of it depends on how. But that artist is worth, like how much they’ve been paid to play those cities before. How many tickets they can sell on their own. Mm-hmm. , um, Yeah, it’s not always based on that, but that’s a big factor. Well, so

Ari: Gimme an example of, uh, maybe let’s say you’re, you have a mid-level, 1500 cap style level, uh, tour and headliners are doing just fine. Uh, you know, they’re gonna sell out the whole tour with, without needing any, any help. Um, Could an opener expect, uh, to open that tour? And how does that work? Uh, is the headliner providing, uh, are they paying them? Are there expenses covered? Are they hopping in the bus? Is there food lodging? Like, how, how does all that work?

Tom: So I’d say, uh, paying 2 50, 250 to $500 a show Okay. Would be pretty standard. Mm-hmm. , um, sometimes it’s more. I think that would be pretty generous if it was an artist that didn’t have a history of selling tickets anywhere. Sometimes the number fluctuates depending on the size of the market, cuz you know, artists get paid different amounts in a larger market than a smaller one. Um, Cuz more people buy tickets, um, people pay more for a ticket in a big, you know, whatever it is. Sure. Um, and you know, in terms of like what else is supplied to the opener? It depends. Um, there are cases where there’s space on the bus or the artist will carry some of the equipment for them so that they can travel in a smaller vehicle, carry some of the merch for ’em. Um, Sometimes they’ll let them use their front of house sound person or, um, whatever the case, they don’t really provide hotel rooms. Mm-hmm. . Um, but even then, like, it’s more often than not, like it’s the artist’s responsibility to show up at the venue at a certain time with all your stuff, get on stage, sound check and play. Mm-hmm. . Mm-hmm. . Um, and it’s just all on you to figure out how you’re gonna do it with the budget. That is, uh, supplied there. There’s always like an exception. And with that, there’s a lot of exceptions, but most of the time that’s how it works.

Unethical Tour Buy-Ins

Ari: So, um, what is your opinion of tour buy-ins where, uh, the headliner is requiring their openers to actually the money flowing the other way where the openers are, they’re asking for the openers to pay them for the opportunity. To open their tour.

Tom: I’ve been doing this for around 28 years and I’ve never done that. I’ve heard about it. Yeah. Um, haven’t really, God

Ari: Bless you Tom Windish!

Tom: I’d say probably most of my peers don’t really operate with that either. Um. Like, I’ve never, I’ve never had a band like get offered to go on a tour where they had to pay to be on it. I’ve had people offer to pay our, some of my clients to be on the tour. Yeah. Yeah. Um, but that’s kind of a red flag, big red flag in, in my book. Um mm-hmm. the most, I mean, the most important thing to me is the musical combination. And for the headliner to feel like the music of the opener is something that they want their fans to hear. Mm-hmm. , you know, I want the fans who are buying these tickets to feel like they’ve gotten value out of the money they spend and the time they spend to show up. Mm-hmm. , um, , um, I feel like the best opening slots are ones, you know, where the, the headline. Is really involved and is really passionate about the opener. Mm-hmm. , uh, really likes the music. You know, like you’ll go to shows and you’ll see like the headline, the singer or something will come out during the open art artist set and sing with them or say like, we really love this act, really hope you pay attention. And then sometimes that band will go and like sing a song with them and the headliner set, like those are the best and where it makes the biggest impact on the opener’s career.

Ari: Hmm. . I’m glad you said that. It’s a red flag. And I’m, and I hope that everybody listening to this right now, uh, heeds that advice because, you know, we hear, um, we’ve heard the horror stories like years, a few years back it came out that, that mo this is well documented, that Motley crew, uh, charged their openers, uh, like a million dollars to open their tour and then their, uh, stage hands. Come out during their sets and, and shoot them with super sos full of urine. And they were like forced to open and like play before the doors opened and shit. And it’s just like, you know, no respect whatsoever. Um, and I’ve, I’ve also heard of tour buys where. The headliners just couldn’t draw and weren’t selling tickets, even though maybe their Spotify numbers were doing really well. And so to kind of help break even, they charge their openers a lot of money for that. Where for the openers, they would. Play by the time they were playing, there’s five people in the room. And so it’s just like not a good deal all around. Um, you know, so I, I appreciate that that is your perspective and that’s where you stand and that’s how you operate because, uh, frankly, I think it’s, it’s flat out unethical to, uh, charge your openers to open for you. And if you can’t figure out how to make money by selling tickets and running a music career, Then maybe you should be in a different line of work. Um, and so yeah. That’s, that’s nice to hear on your end as well.

Tom: I mean, I do think, like my peers, you know, and there’s, yeah, there’s probably a few hundred agents in this country that I would consider my peers. Yeah. They all kind of operate with the same standard. Mm-hmm. , the buyon thing I think is very unusual. Mm-hmm. , um, for the types of acts that I’m working. .

Working with Billie Eilish and the Process of Signing New Artists

Ari: Yeah, that’s great. When you are looking, um, or I guess, what does it take for you to kind of start working with a new act? And maybe you can kind of give us some examples of artists that you started working with. I mean, most famously, uh, Billy Eilish, of course, you know, you started with her very early on in her career. I believe I heard somewhere, read somewhere that you signed her before she’d even played a single show. Is that. .

Tom: Yeah. Yeah. Um, yeah, I started working with her young. I mean the, I need to love the music. Okay. Um, and, you know, I meet, I meet the artists and the people that work with them. Um, when we start talking about working together, and I mean, I want them, I want to get along with them too, and have like, you know, I mean curious, like where they see their career going sometimes. It’s hard to say, you know, if you’re young or just at the, or at the beginning of your career, like, um, you don’t just sit there and say, I wanna play stadiums. Um, that’d be kind of unusual before you’d play a show. Um, sometimes you might say that. Um, and I wouldn’t really balk if someone did say that. Mm-hmm. . Um, but I mean, I need to love the music. Um, and I mean, I work with a bunch of artists. Don’t sell 1500 tickets a night, but I love their music and, uh, I’m very proud to work with them. Um, and, you know, I listen to their music in my spare time. Um, I listen to all my clients’ music in my spare time, . That’s, that’s nice to hear. I mean, I, I love all the, the artists I work with. Um, there, I feel like my wife has asked me this the other day, like, if I’d ever booked anyone. because of the money and not because of the music. And, and, uh, there was, I, I can’t remember which band it was, but a long time ago I did that, um, one, like once, one or two times. And I sort of convinced myself that wasn’t the case, that I loved the music, but I could tell when I made like my first phone call that my. , um, and passion, uh, was not in it the same way it was for everybody else. You know, it’s very easy for me to do my job. I call it people who put on shows and I tell them, you know, you should book this artist. They’re amazing. Yeah. You know? Yeah. I’m not making it up. Like, I believe they’re amazing . Yeah. Um, and I want them to listen to them and I hope they enjoy them. And if they. It’s fine. I don’t take it personally. Sure. Um, I’ve been told no, you know, way more times than I’ve been told Yes. In my, in my career. It just kind of comes with the territory. It’s fine. But yeah, I, I love the artists I work with. Maybe to a fault, . That’s great. I sometimes take on artists that are very, very early in their career. Cause I just think they’re fantastic and. , um, it takes more than just a, a passionate booking agent or even a connected booking agent to become successful. Mm. Even if I got a band, a bunch of tours. Yeah. Um, if they didn’t have other key members of the team. Um, like it, it’s hard to connect all the dots. It’s an incredibly complex business. with a very unclear roadmap of how to develop . Um, yeah, there aren’t many books to tell you how to do it.

Ari: I know one, ha! That makes sense. Um, So, but, but when it comes to working with new artists, it’s great to hear that. I mean, you have to love the music, but I’m assuming there’s other factors that typically go into that because at the end of the day, it is a business too. And if they’re not making much money, I mean, I guess your, you have the luxury. Of having enough artists that are paying the bills where you could probably take more risks on emerging artists that maybe it takes a little bit more time before you start earning from them, uh, versus some other agents which, you know, need every dollar to kind of keep the lights on. Um, what does it come, I guess, in, when it comes to you, when, when do artists typically. Come to you where you’re considering them and who and how are they coming to you?

Tom: I have artists email me every day. A bunch of artists. Yeah. Um, and not just artists, but you know, people from labels, lawyers, managers, publicists. Sure. Um, agents in other parts of the world, promoters. Yeah. Um, and you know, the artists are at all different stages of their career. Um, it’s really nice when there’s a label involved, uh, or people to help release the music that have a track record of releasing music and being successful at that. Mm-hmm. it’s nice when they have publicists, some board, radio, promot, you know? Mm-hmm. , the more established the team, the better chances of success, you know? Mm-hmm. , um, but. I mean, I still take things on relatively early when a lot of those pieces are not in place. Um, sometimes I help get them in place. Mm-hmm. . Um, I do feel like there’s been, we’re in the midst of kind of a seismic shift in the music business where there’s more artists than ever. You know, we. All the time about how more and more tracks are being uploaded every day. Mm-hmm. . Um, and I think a lot of people that provided a lot of different services in the music business are less willing to take things on until it has a certain amount of momentum, you know, either on its own or with. Other people doing the work. Right. Um, I mean, I, you hear about labels that are like, well, we don’t want to talk to you until you have whatever, you know, a million Instagram followers or this amount of engagement or Right. That can sell this many tickets or, um, and, and then I feel that too, you know, because I think it takes longer for an artist to develop. Yeah. Um, and if they can’t get to a certain place on their own, Maybe it’s a sign that they’re not gonna get to the next level or several levels higher. Mm. Um, yeah, I, I think I’m quite a bit more flexible with that type, with those types of things. And I take things on sometimes very early. Yeah. Um, but, you know, in my position, I need to be careful of having too many artists that can’t sell tickets. Yeah, yeah. Or can’t sell many tickets because, you know, It’s always on me to like, get another support tour, get another festival, and then I need to go out to people who are headlining and who book festivals and say, book this artist that can’t really sell tickets. Uh, right. And then they’ll go do those things and they still can’t sell tickets, so I need to go do it again. You know? Yeah. And if it, and it’s hard. I can’t always just deliver either, you know? Sure. I mean, I have acts that, yeah. I submit them for a lot of tours. They don’t get any of them. Mm-hmm. . Um, and then at a certain point the artist is looking at me saying, what are you doing? You know, like, isn’t your job to get me on tours and festivals? And, and I’m like, isn’t your job to have people listen to your music and, you know, wanna buy a ticket? Um, um, but yeah, I think I’m, I’m more flexible than, than a lot of people that do what I.

Artist Development, Management and Running an Indie Label

Ari: So let’s talk artist development a little bit. Um, you know, you are now, uh, a manager. You also, uh, kind of run an ind label. And, uh, you’re co-managing this artist, uh, with Chris dos, who a previous guest on the show as well. Uh, Danielle Ponder, and, uh, I had the, uh, good fortune of catching her at school night. Uh, one of the best shows of the year, in my opinion. I mean, she’s a powerhouse performer. I, I’m curious, um, you know, and it was actually fun. Uh, Chris calls me one. Um, out of the blue. Um, he does that sometimes. It’s interesting. He’s called me a few times just randomly out of booth. It’s always a nice, it’s always a nice call. He called me one day and he is like, Hey, Ari, I’m with this artist. I just started, uh, Danielle Ponder and, um, You know, she’s a big fan of, she’s a student of yours, she’s in your courses and she’s read your book and, uh, just wanna say like, Hey, you know, we’re, we’re working on this stuff together. And, and she’s right here. And she, he hands the phone over to her and we start talking. I’m like, oh, that’s so cool. And I actually did, I wasn’t familiar, uh, very much with, uh, her music and I hadn’t seen her live or anything. And then just, I mean, it seems like she kind of came out of nowhere. Powerful talent. Um, not, you know, I, I guess we could say the opposite of like a Billy s who started when she was 13. I mean, she’s, um, I guess she’s older now. I mean, she, I know she’s had a full career as a, I know corrections officer and, and all of that stuff. Talk, talk to me about kind of how you and Chris and, and that whole development of Danielle Ponder and, and just like now. On all the TV shows and playing festivals and headlining rooms and is incredible and has absolutely exploded over the last year. But I’m curious how that all happened.

Tom: It all began because, uh, I, I’ve done a lot of shows with Chris and school night over the years. Um Sure. Book a lot of artists there for a really long time. And at the beginning of the pandemic, um, I kind of have this like business develop. Role. Um, which just means I talk to a lot of people that are building things that they think will be helpful to artists and a lot of times they’re like, talk to Tom. He loves, he loves hearing about this stuff. Um, and I’ve invested in things like that and have helped things like that and listen to a lot of different things. So in the beginning of the pandemic, there’s a lot of livestream talk. Um, and I probably listen to 50 people with different livestream platforms. Um, and I started calling up Chris, um, and saying, you know, what’s going on with school night? You guys, you know, you don’t have any shows. Um, I’m talking all these livestream platforms. I think this could be really helpful. Mm-hmm. for you. You could start doing shows again, and there’s probably people out there that would pay you to put things on, on their platform and I probably called them about it. Five or six times. Um, and then eventually helped, helped them do a deal, helped them do a deal with Twitch. Twitch. Um, so I was talking to ’em a lot. Um, then they started booking shows, you know, uh, what was it like virtually or, um, you know, like online showcases and then yeah, in person and, and because we were talking more often, um, we were talking to each other about new bands we were hearing too. That’s kind of the thing that I think both of us enjoy. A lot. Mm-hmm. , uh, finding great new artists. And he had found Danielle. She was singing on another band’s track. Hmm. And he thought, you know, that track is, you know, pretty good, but that, that singer is amazing. What’s her deal? He reached out to her, um, and eventually got in touch with her, and then he called me up later that night, or sent, or sent me, sent me a song, what do you think? And I was like, this is amazing. And he said, would you wanna manage her with me? Um, and at that time I had a lot of extra time cuz I wasn’t booking concerts. Right. Um, you know, I got the story, I got on the phone with her, um, and I was like, this is, this is great. I would love to help. And we decided to manage her together. Mm-hmm. . And that was about, about a year and a half, almost two years ago. Um, we eventually signed. A short record deal with Future Classic, um, Waserman, the agency. I work with Bookser, but I’m not her agent. Oh, wow. Um, she got a great publicist. Um, she’s got an amazing team and we’re out there, you know, doing everything you’re supposed to do when you’re trying to become a successful musician. Yeah. And it’s, it’s going really well. Um, but it’s, uh, it’s going really, really well. When people hear her and see her, they regularly say, you know, she’s amazing. I love her. You know, I see people cry at every show I go to, people who’ve never heard her before. Um, she’s really powerful. Um, and what I, one of the things I’ve learned, uh, is you just gotta keep doing it. Mm-hmm. , um, she asked me a few months ago, you know, what’s the plan for next year? And I said, we’re gonna do more of what we’ve done this year. Tour, put out songs. Do press radio, do everything, and eventually things are gonna, you know, stick in a different way. Um, but everything’s going great. Mm-hmm. , we’re like a snowball right now that’s just getting bigger and bigger, bigger. But she’s kind of like, I don’t know if she’ll reach a point where she like blows up overnight, or if it’ll just be like a steady growth. It will probably be a little bit of both, you know? Sure. Um, But if she does blow up overnight or like reach a new level, like she’s gonna have to keep doing, you know, what she’s doing now, putting out more good songs, doing more great tours. Yep. Um, and that’s what she’s doing and it’s going great. It’s really, it’s really awesome.

Ari: Yeah, she’s awesome.

Tom: She was a public defender, not a corrections officer.

Ari: Ah, excuse me. Public defender. Thank you. Yeah. Um, yeah. And uh, and, and she was doing that when. When she kind of, you started working with her, she was working her day job.

Tom: Yeah. So, um, she’d been, she, she, she grew up with, um, six brothers and sisters. Her father was a pastor and she sang in his church Uhhuh and everybody said you were put on this earth to be a singer. And that was what she, uh, planned to do. And when she was in high school, her brother was sentenced to 20 years in prison and she decided to become a public defender. Wow. And, and she then shifted gears, went to, you know, went to school for that, did that, um, did that for about 10 or so years. Um, but that whole time she was recording Vic herself, putting out records. He. Booking tours, um, herself with her, uh, with a woman she collaborates with. Um, and they had gone, you know, around the us around Europe, um, and right before the pandemic, she quit her job and she had decided like, this is what I, I wanna sing. This is what I wanted, this is what I’m happiest on stage. Um, and then the pandemic happened. So she went, got her job back. Um, and then Chris. Wow. Wow. Chris called her up, . It’s a pretty great, it’s a pretty cool story.

Ari: That’s incredible. And you know, it’s a testament to kind of, uh, taking that leap and, and knowing when it’s your time and knowing just kind of that leap of faith and, and it’s essentially like manifesting. She knew like, well, this is the time for me. This is when I need to, and, and, uh, obviously you can’t control the pandemic and, and you can’t control those things out of that. But she knew that this is it. And when she kind of quit that job that’s. The universe decided to take over. It’s like, all right, this is now going to, to start happening for you because you decided that this is, you’re ready to make it happen. And that, that’s, that’s really cool. That’s really inspiring.

And the, I mean, the reason I decided to do something I’ve never done and manage an artist, uh yeah. Is that I, I fully believe in her. And, and I I do think she was put on this earth to sing. Yeah. Uh, and, and when she’s on that stage, She makes me very happy. Yeah. Uh, and I, I really believe in her ability to make everyone very happy. Uh, it’s, she’s extremely powerful. Um, yeah, it’s been really. It’s been really cool and we’re just getting going.

Why Tom Started a Record Label

Ari: Absolutely. Yeah. Yeah, no, for sure. And it’s, uh, been really exciting to watch, uh, I mean from a distance, just as kind of seeing her trajectory grow, but more so being at the show, which, you know, even in that, that, uh, electric with small room of. School night at, at, uh, Bardo. Um, it was, you, you get it. I mean, it was, it was so powerful and, and so inspiring and uplifting and, um, yeah, it’s, it’s, uh, yeah, she’s incredible. And that’s, that’s great. So, um, but you also. Started a, a record label, um, while the records, um, talk about that. Why did you do it? What’s the experience been like that I it’s a wildly different skill set and different avenue of the industry than, than, uh, booking. So I’m curious about that. Um, ,

Tom: I started a label with Future Classic, um, Probably six months before the pandemic. Okay. And then the pandemic happened and I had a lot more time to spend on it. Sure. Um, and you know, one of the reasons I wanted to do that and to manage was that I wanted to learn about other sides of the music business that I had never had time to. Explore, um, or like actually do, and you know, honestly, like even though I’ve done this agent thing for like my whole adult life, um, those areas were kind of like, uh, like behind a curtain or something, you know? I didn’t really know what it meant to put out a record. I didn’t really know what it meant to manage. Sure. Not that I do now, um, , but I know more. And, uh, honestly, I mean, I wish I had. 20 years ago, I think it would’ve made me a much, much better agent at a much younger age and build a better agency that better served, um, you know, other people in the business. Um, I mean, I think it’s incredibly diff difficult to develop an artist these days. Um, you know, you’re dealing with a really small group of people that are on this team that are, you know, their, their task is to develop the. Um, but it’s not as coordinated as I as it should be. Hmm. Um, often the agents like over here doing this thing and they talk to the label once in a while. Manager’s kind of in the middle trying to keep everything together. Um, when the reality is, like we, there’s a handful of people here are ma, you know, in a really big case, like a dozen or, or maybe 20 or something. Uh, and we’re all like trying to accomplish the same thing. Um, and we should all be talking more together about how we can do that. You know? Yeah. What do I need that would help, you know, what do you need? Um, and often like those, those things are not communicated, um, until much later, you know, until the night of the show. You know, can I get this person on the list or something? And I, I could have taken that, I could have, you could have gotten 30 people on the list if you had asked me six months ago. no problem. You know? Now we sold all the tickets or whatever, you know? Right. Um, um, but yeah, I, I, I did it mostly to learn about what it was like to put out records. Um, and also, um, for a long period of my, my career, I would, the way I would hear about new artists was they calling up labels and managers and, and everyone else in the business and saying, what are you hearing about? Yeah. Because I wanna book ’em. Yeah. And I really didn’t go to those people with, uh, like things to bring them, you know, opportunities for them. And at a certain point I thought to myself, some of these people must think I’m kind of a jerk for asking them what’s, you know, what they’re hearing. Um, but I never bring anything to them. So then I like very intentionally. Would go to people and say like, I found a band that I think you should put out their record, or you should manage, and, you know, I’d love to book it if you’re, you know, if we, if you get involved. Yeah. Um, and that worked out really well for some bands. Um, but I also realize like most of the time they don’t put it out. They don’t, you know, they don’t release the record. They don’t, um, um, manage it. And, and I decided like instead of just telling people. In some of these cases, I’m gonna put my money where my mouth is and I’m gonna do it myself. Um, so that’s what I did. Hmm. Um, and really, I mean, it wasn’t like I thought I was gonna be incredibly successful. I really didn’t think about that at all. Um, yeah, I just found an artist that I thought were great. Um, but I do find it incredibly challenging. I had, I had some records go really, really well. Um mm-hmm. , I had others that I did pretty much the same things for, that didn’t go well at all. Hmm. And I don’t really know the different, you know, why did that work and that didn’t like, I like each of these songs the same amount. Yeah. Um, and, uh, I find like, I guess the way my brain operates, like I find that really challenging. I, I. I have no structure to, like what makes a successful record. Sure. Um, anyway, it’s been really, it’s been fun and I, I, I think I’ll put out some more records. Um, cool. At some point. Right now I don’t have any plans to, I’ve been really busy booking this year and managing.

Ari: Yeah. No, that makes sense. Uh, when it comes to, well, I’m curious, uh, what have you seen the similarities, um, and differences between when it comes to marketing and promotion? Uh, when you have your label hat on versus your manager hat on versus your agent hat on?

Tom: I mean, you’re, you’re not talking to totally different people, but I mean, agents talk to very different people. Then labels, uh, and manager kind of has to do everything. Okay. Um, yeah, I mean, I’ve learned, like I have so much respect for managers. I, I feel like it’s one of the hardest jobs in the world. I feel like running a restaurant is one of the hardest jobs in the world, but I think it’s easier than managing an artist. Yeah. At least when you, when you, uh, run a restaurant, you. Yeah. You know, you own the brands. Yeah. The brand can’t fire you. Landlord can raise the rent, but, uh, you know. Right. Your boss can’t fire you. Yeah. Um, and the manager’s gotta do everything they get, you know, you just don’t know what’s, what’s gonna come up on a daily basis that could, that could throw you off the tracks. Yeah. Um, and man, I mean, it’s just, it, things have shifted so much. To the manager in the last decade or so. Mm-hmm. , it used to be like the record company did a ton of stuff and the manager had to make sure the artist like, kind of fulfilled the obligations and, you know, promoted the record and showed up and, and everything. And man, now the manager’s gotta do everything.

Ari: Yeah. Yeah. Yeah. That’s, that’s great. And I, and, uh, I think every manager that’s listening right now is not in their head in agreement and, and so appreciative that, that, uh, you just acknowledged how, how challenging, uh, their, their jobs are.

Tom: Yeah. I’m not, I’m not knocking, you know, everyone else. I mean Right. It’s, it’s difficult to develop artists no matter what hat hat you’re wearing. Yeah. Yeah. Yeah, I wish it,

Final Question

Ari: I wish it was easier. No, that’s great. Um, well, Tom, this has been incredible. Uh, I so appreciate you taking the time and, uh, you’ve dropped so many, uh, gems and, and I know that everybody listening is, is so appreciative of everything, um, that you’ve said. I, I have, uh, one final question that I ask everybody who comes on the show, and that is, what does it mean to you to make it in the new music business? .

Tom: I’s a good question. Um, and that I think that answer has changed as I’ve gotten older. Yeah. Um, you know, right now I wanna work with artists that I really believe in and I wanna help them realize their dreams or what I think they’re put on this earth to. Um, whether they’re selling out stadiums or arenas, or selling 500 tickets a night or 200 tickets a night. Yeah. Um, you know, I, I work with, uh, I work with a band called Low. That I’ve, I’ve booked for the last 28 years, I think.

Ari: Saw them in Minnesota, I think probably 20 years ago.

Tom: They’re incredible band. I mean, sadly the drummer just passed away, um, which is really, really sad. But, uh, you know, that band is incredibly successful to me, and I think to them too, like, um, yeah. And no matter they’re the biggest they’ve ever been, uh, right now in last year. They put out their most successful records, they sold the most tickets. Um, and I mean, I love them as much last year as I did 28 years ago. , um, being able to work with them is, uh, I guess my definition of success, you know, and they’re amazing. Like I feel very, uh, very fortunate that I get to work with people like.

Ari: So cool. Tom Windish, thank you so much. That was great.

Tom: Thanks. Okay, bye.

About The Author

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Ari Herstand
Ari Herstand is a Los Angeles based musician, the founder and CEO of Ari’s Take and the author of How to Make It in the New Music Business.

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