Tom Windish likens a career as a booking agent to that of a juggler.
“It's like juggling 20 balls, and you could still only have three left, but you're still juggling them trying to figure the whole thing out,” he chuckles.
Shepherding an artist’s journey is no easier.
“A career is sort of like putting together a puzzle with your eyes closed,” he offers. “You just don't know how it's gonna look. You have no idea when you're starting. You can't just sit there and say, ‘Here's how I'm going to take this artist from playing to 100 people to an arena.’ Just doesn't work like that.”
Windish has, however, had plenty of success at doing just that, guiding artists such as Lorde and Billie Eilish from clubs to festival headliners. Having spent the past three-plus decades working across companies such as Billions, The Windish Agency and Paradigm, he now occupies the role of Head of A&R and Business Development at Wasserman Music, his roster including artists such as M83, The xx, Rina Sawayama and Vulfpeck.
Here, Windish discusses his booking strategies, how the most successful agents are operating in 2023, booking Billie Eilish at Coachella, and more…
Are you seeing any trends in terms of which channels are having the most impact on marketing and selling tickets?
Unfortunately, there's not one way that's the best way – like, just having an email address doesn't mean that the person necessarily reads it, it might get caught in a filter. If they're like a lot of my friends, they have 1000 emails in their inbox or 10,000. You know, they're not looking at everything.
And then there's text messaging, I think that's interesting. I can't remember what the stat is, but people look at their texts way more than emails. And then there's Bandsintown, and there's Seated, a platform here, where you can see some of that stuff.
DICE is interesting. That's a ticketing company, and you can see that you have 1000 people on the waitlist. So then, we could have sold 1000 more tickets, maybe we should put up another night right now.
But unfortunately, that information to me is just not transparent enough. And, you know, there's all these industries and companies built on the backs of these artists that have the fans, but the artists don't actually know who the fans are without using the platforms.
"There's all these industries and companies built on the backs of these artists that have the fans, but the artists don't actually know who the fans are without using the platforms."
That puts a lot of importance on the artists actually gathering and owning their own data…
Yeah. But it's hard. It's very hard being an artist and manager, you have so many things that you're expected to do – way more than 15 years ago, because the labels used to do a lot more than they do now. No disrespect for them, but it's just changed.
So now an artist has to make great music, they have to figure out how to go on tour for months on end and stay healthy and happy. They need to figure out how to play great live. But they also have to be masters of many social media platforms. And masters at collecting email addresses and knowing how to message their fans, collect cell phone numbers and message their fans, all this stuff. It adds up.
And each of these platforms is something you need to learn. And you don't just start using it day one and you're a master of it.
Shopify is another platform, you need to learn how to use that. And I just feel there's so much inefficiency in maximizing revenue and the power of the fans that [the artists] have, because they have to become a master of all these things, which they're not, because it's hard enough to be a master of some of those things.
And then there's always things that there isn't time to figure out how to do. You can be great at TikTok, but not great at all at direct to fan, or not good at playing a show, not good at touring.
There’s been a lot of talk post-COVID about the congestion in venues. Have you developed any techniques to combat that congestion?
Something I've been doing for a really long time is booking far in advance. I think I'm booking seven or eight tours for 2024 right now.
And I guess my attitude is, if these artists know when they're going to be releasing music or when they plan to release it, you can figure out a global plan. So I'll encourage and push that along with whatever other partners are involved in touring around the world.
Ten years ago I would book 10 months in advance, and everyone thought I was crazy for booking so far in advance. Now I book 14 months in advance if I can. If you want to get the venues you want to play on the nights you want to play them, the one way to have the highest chances of that happening is to book before anybody else gets there.
Here's another strategy that is a really good one. There are some months that people just don't like to tour, like January, for instance, February. I was going to a lot of venues for the last couple months, and I'm looking at the calendars of these great venues, and they're kind of light.
And then I was looking at March, April, May, and it's crazy. You know, it's like the longest list I've ever seen in a venue like that. I've booked some of my artists in times of the year when not as many people tour, and it can work out well.
Where do underplays fit into your strategy?
They're a good thing. An underplay is to build buzz. It's nice to have a line down the street, turn people away. I feel like it could make people in the room feel like it's more important that they got in there, than if there were people selling tickets for $5 outside and it was half full.
It’s a strategy of like, we're gonna go sell all this stuff out, get people real excited, and then come back.
Another strategy I have is multiple nights. I book multiple nights with a bunch of my artists because even though there's a ton of data out there, it's hard to tell what it means.
I have acts that have 10 million fans on Spotify or monthly listeners that sell no tickets. And I have artists that have 500,000 fans on Spotify that sell a ton of tickets. Same with Instagram, same with TikTok, same with all these platforms. And the data point that's really important to me is how many tickets they sold last time.
That's what I use the most.
I like that there's data and you can see people are listening. And I look at the comments and people seem excited. But I've had so many cases where it just hasn't worked out the way we thought.
How important is TikTok for you?
I think a lot of people in the music industry are critical of TikTok and maybe Instagram. I've started finding artists that some of them have millions and millions of followers. And a lot of people in the music industry will say like, ‘Well, they can't sell any tickets.’ And that might be true.
But I'm finding more artists are utilizing that platform to build a fan base. I work with this guy named Cian Ducrot that I found several years ago, and he's really worked TikTok really hard. And it's really working for him, and everything we're doing is selling out and he's touring with Charlie Puth, he's touring with Ed Sheeran.
And it's because of TikTok that people are hearing about him. It's because he goes on to the platform himself and is making videos and communicating with whoever wants to watch, he does it every day, and more and more people like it and watch it, share it.
He's creating content videos that he believes in, that are very authentic to him. And it's been working
"I think a lot of people in the music industry are critical of TikTok and maybe Instagram. I've started finding artists that some of them have millions and millions of followers."
What's the most important period between tour announce and opening night in terms of selling tickets?
It's right at the beginning. We try to put as much of the resources into the very beginning.
You want to have a big announce and a big onsale. And then if you're spending money on advertising, you save the rest for the very end. So you do some at the beginning, or a bunch of it at the beginning, and then save a little bit for the end if you need to close it out, or if you need help.
Are there particular techniques to really turbocharge that onsale or that presale?
I try to do it around some other moment that the artist is going to have, like we're announcing an album, or we're announcing our first single in a long time or new video. Hopefully the biggest moment they're going to have.
And then I would try and tag team a tour announce and onsale with that, because when you put out songs, when you put out videos, that's the kind of call to action to your fans to go and listen, to do something, and that's when you're going to have the most number of fans paying attention. And maybe money being spent for that call to action, too.
So I want to roll that attention into this second call to action.
When you get presale data, how do you use it?
It depends. There are a bunch of tours where we'll hold a second night in case things go really well. It's tricky, though. We book these things really far in advance, we don't always announce them right after we book them, especially if they're over a year away.
And you can't just hold a venue for six months, eight, nine months because maybe you're gonna sell a lot of tickets.
There's another sort of a misconception in America, I think it might be more common in America, [about] upgrading venues. So that's moving from a small one to a big one. A lot of my clients from Europe ask about it a lot. And we do it sometimes – say you sell out the 300 cap right away, we're gonna move it to the 900 cap. I wish it was that simple.
But because venues are so booked, generally that 900 cap is already booked. But also, [in America] venues are often booked by one company, they have an exclusive on it. And if you move it, you can only move it to another one that they operate.
Part of the reason is they need the tickets to stay within that promoter’s system. And if they were to move to a different system, you'd have to refund all the tickets and then move it, and no one ever does that. The person who sold the tickets originally, the promoter, they would not want to do that. They'd refuse. You just don't go and play your competitor’s venue and cancel a sold out show on them.
So you’ve got to get real creative when that happens. And sometimes it works out. Sometimes it doesn't. It has an odd way of working out a lot.
"Venues are often booked by one company, they have an exclusive on it. And if you move it, you can only move it to another one that they operate."
How do you get creative with that?
Sometimes you build in extra days just in case something happens. So if you add a second day, then you don't have to play that same venue or that promoter’s venue network, you can do whatever is available. Hopefully something's available.
Sometimes bands do two shows in one night. Not everyone wants to do that, but some do.
Some venues have two shows in one night, every night. It'll be two different bands, like two different shows. Not many do that. But some do.
What do you see the most successful booking agents doing in 2023?
You have to add value. You need to be an expert in knowing where to play, knowing how to get the most money out of these places, thinking of everything that's going to affect an artist on tour and for a period of their career.
Like, why are we playing here? What's it going to lead to?
The best agents, they've got a real vision for the artist, they can talk about it to the other team members, to the band, and those people trust them, because they see the vision coming true.
You need to put your foot down sometimes to other people – the label maybe will have opinions. And if you really don't think it's the right thing, you’ve gotta stand up to it. But I think [good] agents can verbalize why you need to do it this way.
I think one of the trickiest things is putting together a package with other artists. And great agents are good at doing that. Great agents think of everything, all the time, and they're out there constantly talking to everybody and figuring out, what's the best now. And it's always changing.
I imagine there’s also a lot to be said for developing an artist, and not pushing them into bigger rooms before they’re ready, even if they could fill them. Is that something you're conscious of?
Definitely. But there's no hard and fast rules about any of this stuff, whether it's booking or any other part of the industry.
So sometimes you want to underplay, sometimes you want to do something a little bit bigger so you can show growth, and sometimes you swing for the fences. I had Vulfpeck play Madison Square Garden, and I swear 90% of the industry thought we were crazy. And they sold it out. And then it became an amazing story. You don't want to do that too often, because it's not that easy to sell that place out.
How did they confound those expectations?
They’re so interesting. No manager, no label. Not only do they have a large email list, but they know a lot about their fans and their fans worship them. So one thing was, they didn't do any other shows around then. So people from all over the place bought plane tickets and went. It was a big moment. They made a movie of it. It was a really special thing.
Do you get nervous for your artists when they’re playing a show like that? Or Billie Eilish headlining Coachella?
Yeah. Sometimes I'm nervous for myself, because I was the one who said this is what we should do! [Laughs]
One of the things with Billie that we did…a bunch of years ago she was playing Coachella [2019]. And a lot of people thought she should be on the mainstage, one below the headliner. And we really pushed for her to be the closing act on the second biggest stage.
And there was a lot of resistance to that. And we really stood up for that and said, ‘Look, that's a really important slot. A lot of amazing artists have done it. We all believe she will be headlining the mainstage someday soon, she probably could have done it then even. But if she plays one below the headliner this year, and then she comes back and plays Coachella the next year or the year after on the mainstage again, maybe as a headliner, it's not going to feel that much different than the time before.’
And we ended up coming back [in 2022] and headlining the mainstage. And that was incredible. And also the moment she had on the second stage was insane. I've never seen more people at that stage. Everyone from the festival went there, and the people that were there will remember it forever, because it was like, you had to be there.
"I do believe the time is coming when data will really be able to help people figure a lot of things out – pricing, variable pricing of tickets, what size rooms you should play."
Have there been any innovations in the past five to 10 years that have impacted the way you do your job?
We have a lot more access to data now than we did. And I wish I could say that I do more with it than I do. And I do believe the time is coming when data will really be able to help people figure a lot of things out – pricing, variable pricing of tickets, what size rooms you should play. All of that I think is coming.
And now I have a lot of [data]. And I look at a lot of it and we make decisions based on it, like where to play. Definitely internationally. I book globally for a lot of artists now and we're looking at that data and saying like, ‘Wait a sec, there's a lot of listeners in the Philippines. What's going on? Let's call up all the people we know in the Philippines and see what they have to say, and let's send them there. See what happens.’
And in the old days, we never would have done that.
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