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This week on the New Music Business podcast, Ari sits down with Jaclyn O’Connell, a digital marketer, creative strategist, artist manager, and founder of Bittersweet Media and Good Grief Management. Jaclyn has provided creative marketing solutions and hands-on artist management for artists and labels of all scales and sizes—from emerging artists to well-established acts and both indie and major labels. They have supported gold and platinum records and worked with artists including Wild Rivers, Cavetown, Julian Baker, and Cold War Kids. Drawing on experience in both marketing and artist management, Jaclyn offers a sharp, insider perspective on what it truly takes to build a sustainable career in today’s music industry.
In this episode, Ari and Jaclyn dive deep into the realities of modern music marketing — from navigating ever-shifting social media algorithms to building effective fan funnels that turn casual listeners into ticket buyers and lifelong fans. They also unpack the current touring landscape, direct support deals, and the hot-button issue of tour buy-ons. Whether you’re an artist, manager, or just curious about how fan engagement really works, this is a conversation you won’t want to miss.
http://instagram.com/jaclyn_oconnell
Chapters
00:00 Building Direct Relationships with Fans
03:09 Navigating the Social Media Landscape
05:49 The Importance of Mental Health in Artist Management
09:05 Innovative Monetization Strategies for Artists
11:55 The Role of Community in Artist Growth
14:58 Understanding the Fan Journey
18:05 Challenges in Touring for Emerging Artists
21:03 The Evolution of the Live Music Industry
36:21 The Ethics of Tour Buy-Ons
39:09 Navigating the Challenges of Touring
43:05 Building Artist Relationships and Mental Health
46:04 Defining Success in Artist Campaigns
48:02 The Role of Social Media in Driving Streams
51:01 The Nuances of Going Viral
55:29 The Fragmentation of Viral Success
57:23 Conversations with Labels and Ownership
01:01:23 Balancing Management and Business
01:10:25 Setting Boundaries in Artist Management
Edited and mixed by Ari Davids
Music by Brassroots District
Produced by the team at Ari’s Take
Order the THIRD EDITION of How to Make It in the New Music Business: https://book.aristake.com
Transcript
Jaclyn O’Connell
Incentivization, there are a lot of like built in tools that you can use, where it’s like, you’re only releasing discount codes for merch via those links or via those profiles, where they can only get access. If they’re on the email or SMS list. They’re getting access to specific things like BTS maybe they’re getting access to new demos that aren’t on DSPs. You can only get them, so you’re really treating it. And I know that a lot of artists have started Substacks for that same reason and patrons for that same reason, but this is just a way it’s, you know, costs nothing for them to sign up and they get direct access to the artist, and they can get a lot of cool, exclusive things behind the scenes. Or it doesn’t feel like a heavy lift for either party, but there still is a building of a deeper relationship outside of social media.
Ari Herstand
What’s going on? Welcome to the New Music Business. I’m your host, Ari Herstand, author of How to Make It in the New Music Business, the book, Third Edition, out now everywhere, all formats, ebook, audiobook, hardcover, however you like books, you can find the book today. My guest is Jaclyn O’Connell. Jaclyn is a digital marketer, creative strategist, artist manager and just overall entrepreneur. And we talk about everything today. We talk about the algorithm. We talk about the state of social media, the point of social media. We also talk about the funnel, how to convert fans from a cold audience to a warm audience, going on tour, buying tickets, streams. What is driving streams these days? All of it, we go into it, and Jaclyn has an interesting perspective as both an artist manager, working directly with artists on running their own careers. So touching all aspects of it. We talk about the touring landscape, we talk about opening direct support payments. We even touch on tour buy ons. And Jaclyn has a very interesting response to that which you’re going to want to listen to. And then as a creative strategist, as a marketer, they run the marketing agency, bittersweet media. It’s a full service creative marketing company, and Jaclyn started that in 2018 and through that, they’ve worked with labels of all sizes, indie, major artists of all sizes, gold and platinum records they worked on, and artists like wild rivers, cavetown, Julian Baker, Cold War kids, the five oh twos, tall heights, they’ve worked with a bunch of artists. So we had a very wide ranging conversation. And I really enjoyed chatting with Jaclyn. And I think you’re gonna really appreciate this episode. You can find Jaclyn O’Connell on the socials, on Instagram, it’s just Jaclyn, j, A, C, l, y, N, underscore O’Connell. You can find their management company, which is called Good Grief Management. You can find that on the socials and also the website Good Grief Management. And then, of course, Bittersweet Media is Jaclyn creative agency. You can find all of us that make the show happen at Ari’s Take on the socials. Find me at Ari Herstand on Instagram right now, if you wouldn’t mind, just pause this episode. Leave us a five star review. However you’re listening to this on Spotify and Apple podcasts. Give us a thumbs up. Subscribe on YouTube, leave us a comment on YouTube or Spotify. Hit the follow button if you want this to pop in your feeds. But most importantly, and we talk about this on this episode too, the best way to stay in touch is through our newsletter. Get on our email list. You can find that at Aristake.com head over to Aristake.com sign up on that email list. That is the best way to stay in touch with us and stay up to date on all the goings on of the new music business. All right, let’s kick into the show.
Jaclyn O’Connell, welcome to the show. Hey, thanks for having me. Hey, hey.
So as many people in music tend to do you wear many hats, and I was, personally, I was a bit overwhelmed even just reviewing everything that you do, and I don’t know how you handle it as the person who does it all, but if you wouldn’t mind just breaking down what you do, I know you have a management company. I know you have a creative agency or consulting and do social media. But I also read somewhere that you said Tiktok has destroyed the music industry. So I wanna get into all of this. But just like, you know, 30,000 foot view, let’s start there. Just like, who are you? What do you do? Maybe give me a little background on how you got to where you are right now. Yeah, absolutely. 30,000 foot view. I own two companies. One company is Bittersweet Media. It’s a creative marketing agency. We do a full service creative campaigns with a focus on community growth for artist labels and also brands. And then the other company I own is Good Grief Management, solely Artist Management. It’s more like management partnerships. It’s kind of a new look at the management relationship with our.
Artists and managers. And so those are the two companies I own. I got started in music about 10 years ago, and I have been in digital marketing for 10 years, and I’ve owned Bittersweet. That was my first company. They owned for eight years. And so that’s kind of a 30,000 foot view. Got started in a really weird way. You kind of just like, make friends, and then someone opens door and then other doors open. Yeah, yeah. Well, cool. Well, so, you know, we are at an interesting time in the industry. You know, I we, I’ve really been focusing on these direct to fan platforms and super fan platforms. And, you know, we had even on, we just had band camp, and I’ve been exploring a lot of these because I feel like as an industry, we’ve been obsessed with metrics in the streaming era, and like Spotify and obviously Tiktok over the last five years has dominated the complete conversation. And you know, everyone I talked to on like, the macro side of the industry, where we’re talking like major labels and even some of the big, bigger Indies.
It still is, and like, oddly enough, and managers, all this is just like the conversation is still confined to
Jaclyn O’Connell
TikTok and Spotify, and Instagram pops in there too, but it’s like, that’s it. And it’s like, I’m curious, like, your approach as a as a manager, but also as a having a creative agency, you know how you deal with that, especially when, like, the pressures of these metrics and these numbers are shoved in everybody’s face. And like, how do you work with your artist? Artists where they’re constantly being bombarded by this comparison, these comparison metrics of like, well, so and so’s got so many more monthly listeners than me, whatever that means, you know, and so and so’s got more followers. Or, why isn’t this real performing well? Or why isn’t like my TikToks, I can’t reach my TikTok audience anymore, you know all of that, why take any of that and go wherever you want with that? I know I just put a lot there, but, but I feel like, you know, this is an interesting time in the industry right now. You’re so right. It is a it’s also like, a really, like, volatile and, like, very vulnerable state of the industry right now, just because of like you’re talking about, you know, the algorithms are choking everyone out. It’s choking reach for all of artists. And it’s, it’s not like they can’t use those platforms. If you’re an artist and you’re trying to, you know, expand your platform, expand your listeners. Why wouldn’t you use the free tools that are available to you to get to fans? The frustration that I literally just had with one of my artists right now is, you know, you have a set number of followers, but because the algorithm has choked all of that out, organically, you are being forced to pay to reach people, which is obviously their corporation. That’s what they want you to do. But the frustration is less about like the number itself, the metric we try not to get into conversations where it feels unhealthy, where we’re comparing the number to the value system of them. As an artist, I really focus heavily on the mental health aspect of that. And even at the marketing agency, we do a lot of like, I call it social media therapy, where I go, why is that number, or the metric of a video view, like, reflective of how you’re feeling about, you know, the success of this rollout. Why does that? Why does it matter so much to you? And we really try to unpack some of that. Sometimes it is, it’s just like, I just want people to see it. It’s like, that’s totally valid, right? And so for the artists that, like, I manage, or we have, like, more of a an emotional relationship, where we can have those conversations more free with freely, you know, we talk about like, it’s mainly just like, they’re just bummed, right? Like, you know, one of my artists put out a song on Tuesday, and then they just had someone comment and say, Hey, I didn’t even know you put out new music, two new songs in the last two months, and I’m seeing a post from weeks ago, and I said, reply to that comment and then get them to sign up to your lay low, because we really are focusing heavily on, how do we reach them directly? We have to get them off the platforms, because the platforms are truly choking out. Just to clarify, people that don’t know, sorry to interrupt, but lay low. I just want to clarify for people have never heard of lay low before. Yeah, this is kind of an email list provider, but I’m assuming you use it for text messaging as well, because that’s kind of how they got known, right? Yeah, well, lay low. I had been a fan of Laylo when it first, first came out many years I think it came out, like, right after the pandemic or during the pandemic. And I was like, Okay, this is kind of cool. It like, combines email and SMS, which we haven’t really seen yet in the industry so far. And then what I think that they’ve done really well is they’ve listened to the community, they listened to the entertainment industry, and said, This is what we need, and they’ve actually made so many more options for touring, VIP opportunities, merch connections, they’ve actually listened to what the artists need to grow their businesses and to deepen those relationships and deepen their revenue streams, because that’s you’re being ours as a business. But you hit on a good point with that is like whatever service.
Or, you know, you’re using, because there’s a bunch out there for SMS or email management, or, you know, it’s essentially getting that fan, if they are fan, to sign up for your newsletter so you can own that relationship and not depend on these tech platforms that will, as you call it, choke everyone out. That’s the word I’ve been using, because it just feels like they’re all being, like, choked out right now. It’s like, it’s the conversation that we’re having. Like, I’m having this conversation multiple times a week with artists, where they’re like, I don’t know what’s going on. And I’m looking at the stats. I’ve done this for 10 years. My job is to study algorithms. My job is to understand organic strategy, what’s working, what’s not. And I’m looking at these numbers, I’m like, You’re doing everything correct. You’re doing everything this platform would want you to do, and they’re still punishing you. So let’s move them off the platform. Let’s get into a deeper relationship with them. Let’s like, like you said, own the relationship with those fans. And really, you know, super serve those people who want to be super served. And how do you do that? How do you super serve to speak to that? Yeah, so most of the time it’s not just like, getting people to, like, sign up or, you know, if you have a tour announcement, getting pre sales, that’s obviously helpful. Those are kind of the low hanging fruit. But it’s incentivization. There are a lot of like, built in tools that you can use where it’s like, you’re only releasing discount codes for merch via those links, or via those profiles where they can only get access. If they’re on the email or SMS list. They’re getting access to specific things like BTS maybe they’re getting access to new demos that aren’t on DSPs. You can only get them so you’re really treating it. And I know that a lot of artists have started substacks for that same reason and Patreons for that same reason, but this is just a way it’s, you know, costs nothing for them to sign up, and they get direct access to the artist, and they can get a lot of cool exclusive things behind the scenes. Or it doesn’t feel like a heavy lift for either party, but there still is a building of a deeper relationship outside of social media.
Ari Herstand
And what is kind of how are you approaching with your management hat on, how are you approaching building an artist’s career in this day and age with the pressures of the social media, with the low paying streaming numbers or streaming revenue? I mean, you touched on a couple of these things, merch, discount codes, you know,
Jaclyn O’Connell
deep getting them on your email list and stuff like that. But yeah, is there a monetization possibility there to super serve this audience in a way that benefits the artist bottom line? Absolutely. So there are a lot of like, creative ways to do that. It could be, like I said, kind of talk a little bit about, like, exclusive merch drops, talking about exclusive content. I think diversifying, I hate to sound like a soup, but diversifying the portfolio, I tell a lot of artists, people that I market for, and people that I manage. What I mean by that is like, it’s unfortunately, because of how volatile the industry is right now, you can’t just be a musician. You have to like, show more of your personality. People want to care about something more they want to feel like they can relate to you in ways. So is it that you like weave in comedy to who like how you’re sharing? Is it that you have a hobby that you want to share with people? Is it that you stream on Twitch? Is it that you have a Discord is are these things that like you can build these relationships and also open up those revenue streams to exclusivity to those people who are being super served. It takes a it’s a longer grind. It’s not an easy it’s not an easy, like flick of the switch,
Ari Herstand
right? Are there any platforms, or just any ways that your artists
Jaclyn O’Connell
have super serve their community in ways that have increased their revenue that you’d like to speak to? Yeah, I’d say Patreon is probably pretty easy. Patreon, yeah, I have an artist that uses Patreon, one of them does, and then the other one that does, actually, two artists play Patreon, one that uses it, just like, personally, for his like music and stuff, and then I have Evan Weiss runs Storm Chasers Limited, and it’s basically a community run record label. It’s really incredible. They’ve been running it since the pandemic. They release a vinyl record every single month, and there’s a really active Discord server, and it’s all three different tiers of the record label, and it’s all through Patreon.
Ari Herstand
Interesting, yeah, I found that, you know, Patreon has been around for a long time now. It’s, you know, we started when we’re talking about kind of crowdfunding, it was like, Kickstarter was like the first and that was crowdfunding. I look at it as, like, 1.0 Patreon comes along, and it’s kind of like crowdfunding 2.0 where it’s this, like, right subscription, more or less service where it’s just ongoing support.
But I never found, I never felt that Patreon really catered to the music community, or really had like it never, to me, seemed, which ironically, because Jack Conte, the CEO and founder, yeah, is a musician, right?
Um, famously, of like, you know, he had, uh, Pomplamoose and now Scary Pockets, and he has a solo stuff. But it never, it felt like, you know, because he was more of a YouTuber first, than a musician. And so it was like, for creators, not musicians. And I just never felt that Patreon really penetrated the music vertical, if you want to call it in the tech speak,
and so that’s why we’re seeing all of these other super fan direct to fan platforms coming up, because it just didn’t seem like it integrated with music very well. So I’m curious, like the musician that is on Patreon, or maybe if you’ve had those conversations with your artist, maybe why you’ve guided them there or elsewhere or not there, or if there’s other ways that you have found that your artists have been able to monetize their fan base, I think you’re really the conversation where it starts about like adding a revenue stream like that outside of the standard revenue streams of being a musician. When we talk about that, it’s a really huge commitment, right? It takes a lot of energy to put into it. You for Patreon, like a lot of things in music, you get out of it what you put into it for the most part. So you have to be committed to a schedule. You have to be regularly sending updates. You have to be sharing demos. You have to be regularly, like, posting things that you’re not posting absolutely anywhere else, there has to be, like, a close knit community of people who are engaged. It has to be really exclusive, like a really exclusive club, but I’d say I agree with you 100% that, ironically, Patreon hasn’t really super served the musicians they’ve they’ve done well for like, other entertainment, like podcasters, community comedians, you know, like Caleb hearing does really well with his so true podcast, and that’s all through Patreon, and they get a lot of exclusive stuff. So there are ways to do it. You just have to be creative and you have to be committed. Yeah, right. And so, you know, I we’re kind of speaking simultaneously about both ends of the spectrum of, kind of, well, I guess the funnel, if you really look at it, like marketing terms of just like, you know, a cold audience versus a warm audience versus a hot audience. And it’s just like, if you think of that funnel as in, like somebody comes in at the very top, this is this marketing speak. But it’s essentially like, you know, someone discovering the artist, and they’re not necessarily a fan yet, and maybe they heard one song on a playlist or on a Tiktok, or a friend told them about it, or whatever. They’re not a fan. They might just be a listener, or they might have just discovered and then all the way down that funnel to the bottom, where they’re actually, like, supporting the artists, and they’re buying stuff, they’re purchasing, they’re subscribing, whatever it might be. They’re buying a ticket, buying some merch. They’re converting. They’re converting, as we Yeah, as the marketing speaker, like, speak to the journey a little bit, maybe the fan journey, and how you work that with your artists, or maybe maybe your agency clients, in terms of, like, finding this cold audience, because I guess it’s like, you know, it’s streaming right now is kind of, depending on who you speak to, can be both ends of that spectrum, both ends of the funnel. And it’s like, some people are like, Well, only look at Spotify as like the new radio. Don’t look at it to monetize, and don’t look at it for a revenue stream, because you’re going to be disappointed and if you make some money from a great but that’s how fans can discover you, or whatnot. Other people are like, I’m making a great living from Spotify and from streaming revenue, and that is the way I make money, and that’s how I’ve done it, or whatever. So, you know, I don’t know, speak to that a little bit of just like, top of funnel. Like, how do you encourage your artists to find new fans and then, like, go through that journey? Yeah, I think in order to answer that question, I kind of have to take a little bit of a step back, because this is something that I think a lot of people don’t realize, is that consumption behaviors of fans and consumers, it’s completely changed over the last five years, like the way that we read things, the way that we consume things on our, you know, our phones and on social media and elsewhere, the way that we resonate and how we make a decision has completely changed. I think that’s really been very clear on it. To use an example, right now, ticket sales across the board, are struggling. We just saw that Beyonce was having a hard time telling selling ticket sales. I mean, there’s a lot going on in the world right now, so the the amount Live Nation profits are off the charts. We won’t go, yeah, Live Nation. We’re
Jaclyn O’Connell
doing just fine. Yeah, they’re doing fantastic. But meanwhile, meanwhile, hardest can sell tickets, right? But that’s a perfect, like real world example of kind of what you’re talking about, right? Like, there’s this top level funnel of, like, discovery, you know, you have this Spotify, but the consumption and the discovery of what’s happened from 2019 to 2025, is completely different. The way that we have to, yeah, the way that we have to reach people is.
Because now I’m sure you’re seeing, for example, on because we’re constantly battling algorithms. Everything we do is controlled by algorithms. Now you’re I’m sure you’re seeing a lot of HQ accounts and a lot of archive accounts for artists like Chappell Roan, Olivia Rodrigo, they have these kind of HQ accounts that are run by the artist, but maybe they’re run by the team. Maybe you think they’re run by a fan, but it adds more to the algorithm, and it adds more into the discovery feed, because it’s not an official page, it’s not a business page, it’s just a personal profile where you can kind of skirt around the algorithm in a new way and add more fodder to the conversation, to the Explore tab, to the for you page, without it, you know, kind of clogging up the standard, you know, the main profile, but it adds more to the conversation, and it feels organic. It’s not really organic. A lot of teams are running these things. Yeah, that’s totally fine. That’s totally valid. It’s a great way to skirt around the algorithm, but that’s that consumption is different. It’s much different in how discovery happens now, and it’s about, sorry, oh no. I just wanted to clarify for people that don’t know what you’re talking about and don’t don’t know what HQ accounts mean, or anything like that. Just if I am understanding this correctly, I’ve seen it so it would be a little one may call it annoying, or an artist would think it’s annoying if they’re posting, as an extreme example, let’s say, 10 reels on their Instagram a day, and bombarding their followers of all of Just like short form video after short form video after short form video after short form video, right? Are not relevant? Yeah, any. Yeah, exactly, not relevant. You go to their Instagram profile and then it just like, it doesn’t feel like it’s, it’s from them, which is like what fans have expected is like your social media is coming directly from the artist, but what you’re saying is what is happening, which I think, I mean, you’re deeply embedded in this, but I don’t think a lot of people realize this, to be honest, is that there are these secondary accounts run by their teams. It looks like it’s run by a fan. So I’ve seen like the fan account a lot and but it’s more like mostly not a fan, and it’s their teams or whomever. But the etiquette of that is they can post as much as they want, because it’s the algorithm is not showing
Ari Herstand
the is not showing you only post that of who you follow like they used to. Like it used to, it is just showing you what they think you want to see. So if you’ve engaged with, like, use a chaperone, example, a chaperone post in the past, or like, oh, well, here’s a chaperone fan account or whatever, but here’s a video that’s doing well from three months ago. We’re gonna send it into your feed. And this chaperone HQ or fan account or whatever from their team, but you don’t know, it’s their team. They have flooded the platform with hundreds of videos, and of those hundreds, maybe seven, have done really, really well, and now those are going around. It’s this trial and error. And so I think what you were kind of getting to is that you know what is necessary now in 2025 which wasn’t true in 2019 is that how consumption has really changed? Is because you the algorithm is dominating and dictating everything you need to test so many more things out and flood the zone. Yeah, I hate to use that term with all of this content, so something breaks through. Is that, is that, is that that’s 100%
Jaclyn O’Connell
you hit the nail on the head, and it’s there, like, you know, there’s the the secondary count, there’s tertiary, there’s like, four, so four to five fan accounts, right? That they’re just like, flooding out as much like content as possible that doesn’t really fit in cycle, on the on order, that the artist doesn’t want on their main feed, which, you know, that has curated, that there’s a lot of eyes on it, but there are these tertiary accounts and these kind of auxiliary accounts that allow because of how volatile the algorithms are. I mean, it’s really incredible how just I’ll use Instagram explore chat as an example, I can go in and I can go in and start liking a bunch of chaperone stuff, and like I might like watch all two, maybe two reels in full. I refresh my page, and immediately I’m bombarded with Olivia or Chico, you know, Chappell Roan, all of that world, Taylor Swift. I’m immediately bombarded with tons of videos with it, because it’s like, oh, you watch two videos, you must really like this. And that is why the consumption levels have changed in the way the behaviors have changed, because of how volatile those those algorithms are. But people don’t really think about that. That’s not their job to think about they want to go on these platforms. They want to chill out, they want to zone out, and they want to just look at stuff. And so there’s not their job to think about this. But as an artist, part of your job is to understand how.
Far your discoverability is going and so using Spotify, for example, as a marketing platform, as opposed to just calling it a digital service provider, a DSP, it’s like, okay, Spotify, editorial, playlisting, it’s nice when it happens, but it’s not moving the needle for artists these days. It’s not the thing that’s actually helping growing sustainable careers. But the two pillars, the two things that I have been saying over and over again to teams, to my artists, the things that are actually moving the needle for artists is consistency and community. That’s the thing that’s actually moving the needle for artists these days, and it can come in many different ways. It’s not just about social media. It’s not just about digital advertising. It’s about are you releasing music consistently? Are you feeding your as you say? Are you feeding the zone? Are you feeding the system with enough information and are you also nurturing those relationships with those fans, or are you just putting something out and letting something happen, right? How are you really, truly engaging when something happens, not just promoting it over and over again? How are you nurturing conversations with your fans. How are you nurturing the relationships to grow and which can be very you know, honestly, time consuming and tiring for some artists, and that’s why being an artist is very hard, yeah, for sure. Well, I like that consistency and community. I think consistency is a little bit more understood by most artists, whether they like it or not, they’re like, Okay, consistency just means release songs consistently, consistent, consistently, regularly. You can’t just release an album every three years and go silent anymore. We got to release music regularly. As much as they might hate it they want to work in album cycles, okay? I got it consistency and then like, also consistency. Like, we all know, you know, posting, you gotta post a bunch and you maybe post a bunch of, okay, that’s consistency. What do you mean by community? When we speak, like, specifically, yeah, how do you engage with a community? So there are multiple levels, kind of, like, what I talked about, how you can’t just be a musician anymore. And what I mean by that is like, there has to be more of you that you kind of have to share with people, like, for instance, let’s say you’re an avid reader and your musician, but the reading part is just you as a person. It’s you as a person who just likes to read. That can become a marketing driver in some ways, which sounds really crass, but it’s the it’s the truth, but it also opens the door for more community. Do you want to start a book club? Is there a way for people to get connected through a book club and around your music? Is there a discord community that you can be talking about books as well as talking about music? Where are the common threads for people to resonate outside of just the music, where you’re just like, Listen my new song? What’s my new song? What’s my new song? People get tired of that really quickly. So we have to find other avenues for people to care about and, like, really relate to someone as a human being, outside of just being a musician. So that’s an example in terms of, like, you know, digital communities. I think we all know what that means, social media and like, Discord, and you know, if you want a Patreon or broadcast channel, you’re really trying to deepen those relationships. But in real life, you have obviously, touring in shows and being able to see people in person. But you also have these more, these artists who haven’t really gone on, like, full tours yet, but they’re doing well, and something’s happening for them on social media, and they go to a park and say, I’m going to be in this park at this time, come over and I’m going to play some songs for you that is community. That is like building community, because you’re bringing people together in a real space to have a relationship with you for an hour or so. And that is, those are memory makers for those fans.
Ari Herstand
That’s great. Thank you.
Let’s speak to touring a little bit. You know, like as an artist manager, and you’re working with these artists, and I know many of your artists tour, how do you determine for, I guess, a more emerging artist that doesn’t have much tour history, and they might have a little bit of traction on social media, a little bit on Spotify, you know, streaming services or whatever, but we all know that that doesn’t necessarily translate to ticket sales. How do you approach touring for an emerging artist?
Jaclyn O’Connell
Great question. So for an emerging for an emerging artist, I think it really depends, like, emerging is kind of an umbrella term, you know what I mean? Like, it’s, there’s different levels of what emerging means. Is it that they’re they’ve played only five shows in their regional area? Have they done have they booked like a little Weekender tour, meaning like Thursday to Sunday in their region. Are they living? This all depends on where they live, too. It’s so much easier to tour the Northeast where I live than it is to tour the West Coast. And I have artists who are on the West Coast, and it is much harder. Things are so much more spread out. You cannot get to things as easily and do a weekender so easily if you live.
In Texas, for example, right? So really, when you come to emerging artists, it’s like the different levels, like, I’d say Level One is you’re you’re reaching out to talent buyers and promoters in your area, and you’re just getting added to as many bills as possible in your city or in your surrounding cities, right? That’s level one, level two, and maybe you’re not going to pay that well for those shows. Unfortunately, level two is you get a community of people. You have some friends. Maybe you put Plan A run of shows. You’re doing it DIY. You don’t have an agent right now. You’re still maybe trying to figure out what how deal structures work. And really is still figuring it out. And that is, I think, part of being an artist is trying to figure out what those deal structures mean and how they affect you as an artist.
And then level three is maybe you have an agent, and then maybe you’re starting to, like, get pitched out for certain things. You’re going out on smaller tours, again, probably not getting paid as much. You’re probably getting paid 150 to 250 a night. And then level four, you’re moving up, you’re being more direct support. You’re getting 500 to $1,000 a night. So it really is. It’s a grind, like everything else in music, especially in the indie alternative space, that touring is a true grind, and it takes a lot of effort and a lot of work. And the live industry, I’d say, in addition to like, the like the like rights management portion of the industry are the two, in my opinion, most antiquated parts of the industry. They have not evolved at all.
Ari Herstand
Okay, so I want to, well, okay, speak to that they have not evolved. And how would you have liked to see it evolve and how it has not evolved. Well, the live industry, we need to get rid of merch cuts. Why do we have merch cuts? I don’t understand why. Yeah, that needs to go away. You should not take a percentage a cut of an artist merch Absolutely not, unless they’re going to give us a percentage of the bar exactly and so then it’ll be like a fair deal. So merch cuts need to go away, I think also the like rate in which we’re paying supporting artists on shows. So that can be, obviously a bit harder, because it becomes in the originating deal, when the headliner books the show, you have a budget for support. Yes, it’s up to the agent and probably the artist and the manager to decide how much budget they have set aside for the support artists, whether it’s one or two. I don’t know anybody who’s doing four band bills at this point, because I don’t have the stamina for that anymore, but if you have, you know, a two person Bill, you have, you set aside a certain amount of budget, and that’s in the originating deal. That number fluctuates a lot depending on what size room you’re playing. However, I don’t think that it’s actually grown to a sustainable rate for someone to go out on a six week tour. You’re asking someone to give up six weeks of their life. Gas is so expensive if they don’t own a van, renting a van is expensive. Insurance for your instruments is really expensive. You have to eat on the road and all of that. You’re not working at that time. If you have a part time job, you know it’s it really is touring is very has only gotten more unsustainable, and the evolution of the live industry has not balanced for that. So the way that people are paid now, they’re still being paid as if, like, gas prices are fine. It’s not, you know, 1000s of dollars to rent a van for a few weeks. It’s still, it hasn’t balanced out to meet that kind of inflation that the artist is having to deal with. Is that on the headliner, or is that on the promoter? Or how does that change? I mean, like, let’s, let’s take, like, a small club, club tour. For instance, they’re playing, you know, maybe, you know, a small to mid level artist is playing 250 to 500 cap rooms all over the country. You know, maybe they’re getting a guarantee of $2,000 a night, or something like that. Versus, you know, if it’s a sell out, they get a bonus or versus, whatever, a cut of the door or something like that. But let’s say they’re averaging two grand a night, or something like that. You know that’s going to be, one would argue, maybe barely enough for them to break even. How are it? But they need direct support, because they’re going to need a little bit of that support in filling the rooms. So what are you suggesting, if they’re not, because what I’ve seen in these levels is like they’re going to give their direct support, 250 bucks a night, which is going to be a losing tour for that direct support. I don’t care if you’re touring solo or with the band or whatever, that’s just not, that’s not going to be sustainable. Maybe you’re going to make it up in March, maybe, but probably not so. So I’m not, I’m not saying that you have the answers, but do you know, I have some suggestions, please. One, it would be so great if lightning she would stop buying up all the small clubs and then charging crazy rates and service fees on ticket sales, because that’s actually the number one reason why now people are not buying tickets to shows because they’re $25 plus service.
Jaclyn O’Connell
Fees. But meanwhile, Beyonce and Tayler swift and Sabrina Carpenter, Billie Ellish are all on these stadium tours, and people want to spend $1,000 going to those shows, right? They’re spending $1,000 because they’re buying the ticket. They’re buying parking. They’re maybe getting babysitting. They’re getting drinks that whole night. Cost of unload then they don’t have $25 plus service fees to go see another indie developing artist. And that’s where we’re seeing a huge discrepancy in the industry of like, where you know where the money is going and where the consumer can and not can and can’t spend money. So there’s not a lot of like, balance in that department. So one, balance. Two, I’d say, Live Nation, stop buying all the small clubs. Three, I would say it has to be an agreement, right? I had this discussion with a lot of artists. One of the artists that we manage, great grandpa, they are so, so thoughtful always about how much the supporting act is getting. And it’s a direct conversation from the jump with the agent of say that we have one support artist, and this is what they need to make. And if that comes out of their guarantee, they understand, because they’ve been in that position before. There is a direct conversation about that that happens at the front when we’re booking the show and starting to, like, go through the deals with the
Ari Herstand
agent, interesting. And what’s your opinion on tour, buy ons. I don’t
Jaclyn O’Connell
think I’ve experienced those
Ari Herstand
where, where, like, the headliner charges an opener to buy on the tour. You haven’t Okay, so that’s why I haven’t experienced like, because that’s stupid, I agree. But unfortunately, we’re seeing it happen still, it’s a practice crazy. No, I’ve never heard of my desk, try to email me and say, like, do you want to buy me on a tour? Be like, I have somewhere where you can stick your thumb. Yeah, no, for real. And I’m glad you say that, because unfortunately, it is still fairly common. I’m hearing about
it very frequently where, where artists are asked to buy on and it’s usually like, you know, the artists that like are not like are maybe breaking even on because No, no. Artists that are playing like big theaters or arenas are asking their openers to buy in. It’s the ones that are playing clubs that are barely scraping by, and they’re looking at their numbers as in, like, well, you know, maybe I can make double my guarantees if I charge a super, you know, well, to do artist that comes from a wealth of, you know, family money, and they’re just getting started. They don’t know any better, so maybe they’re gonna pay me 1000 bucks a night to play to 200 people a night, and they’ll look at it as an investment, instead of running ads or something. They can, you know, use that money to get in front of my fans. I’m not defending the practice by any means. I think it’s completely unethical, but I do see the argument for the headliner, who’s like, how do I get make this tour sustainable?
Jaclyn O’Connell
If, if you’re a manager and you’re looking at a tour and the headline tour, and depending on how comfortable you are in the red, you know, as a managing company and with your with your artist, that discussion has to happen before you get to that point, right? Like, can you actually bring out the tickets? And if you can’t, don’t do the tour. Don’t tour. And do more. Do more, more development work. Do other things. Do some underplays. If you’re like, if this is a tour right where it’s like you’re trying to do three house and cap rooms, and it’s like you’re not really sure, and you’re a little apprehensive about it, and you’re you’re starting to go down this thought path, don’t do that tour. Do some cool underplay is play in the subway station like Green Day did, like, do some weird stuff that people are going to talk about on the internet for you and help you do the marketing for you and continue to develop you. Play the 150 cap room and sell it out in three minutes. That’s a talking point. That’s a marketing driver. Those are press points. Don’t try to put yourself in a situation where you’re going to look like an a hole and be like, you want to pay to be on my tour? Because that’s that’s crazy,
Ari Herstand
yeah, yeah, no, I agree. But the reason I bring it up is because I know this is happening frequently, and I’m seeing this happen, and I’m talking to artists that are getting these offers and, and also, you know, talking to managers that are, like, having this dilemma, you know, as it’s just like, you know, it’s like their artist is like, well, you know, maybe they can bring 100 to 200 people a night. And that’s also at a very challenging, like, booking standpoint, of just like, What books do we what rooms do we book them in? If they can only draw 100 people for per show. It’s like, you play the 250 cap room and it’s going to be half empty. Some rooms only have the 500 available, but they’re probably that’s way too big for them at this point. They’re not going to make enough money. The guarantees are not going to work out. And it’s like, it’s such a, it’s such a that’s such a weird and challenging position to be in.
Jaclyn O’Connell
And you’re like, Okay, you know. And those artists might have 200,000 monthly listeners, and you’re like, wow, that looks like they’re doing pretty well. They might have 50,000 Instagram followers or something like that. And you think, okay, you can bring out 100 to 200 people in every city you go to doing okay, but then it’s not really sustainable. And that that’s the level that I’m seeing this happen at that is, I mean, that makes sense, but it’s crazy. I think that, like me as a manager, like the way that I think about it is like we have really, like, serious conversations about if the room is half empty, or if it feels like it was a small show, or a lightly attended show, or there’s a high drop count, you know, people who bought tickets and didn’t show up. You know, when we have those conversations, it really is like, that’s when the therapy starts to come out in their management partnerships. Part of this is because it’s not fun to play to, you know, 50 people in a 200 cap room, right, right? But it unfortunately, is part of the grind that happens, and you and your artists have to decide that that’s what’s right to develop and continue going because whether, whether or not there are people in that room, you know you have you sell 50 tickets out of the 250 and then. But it’s about having the tour date, it’s about having the marketing driver. It’s about being able to go to the distributor. It’s about being able to go to DSPS and say that they’re going on tour. It’s not just about what’s happening in the room, because obviously, like, if it’s a door deal, sometimes you got to take the L and that sucks. And but that’s a decision you’re making with the artist. And you’re making a decision like, okay, you know, we have a couple of door deals on this tour. They might not be outstanding shows, but here are the guarantees, and here’s what your potential walkout is. And so you’ll probably go home with X amount, but I think that that becomes part of like not wanting to have that real conversation. It’s like almost avoiding that conversation, which can be uncomfortable, but we have to have these real conversations with these artists. Be like, this is a business. You need to understand how to grow and develop this business, and this is a part of that, definitely. So let’s talk about that grow and development of the business. And, you know, putting, I guess, your kind of creative agency hat on with bittersweet media, how do you approach growing and building?
Ari Herstand
Let’s, I mean, keeping it kind of in the music realm, and like, with an artist, or maybe a label hires you, or a management company hires you, an artist hires or something like that. What is your approach to,
Speaker 1
I guess, just grow and develop and build that that either that artist or the song. Or what happens when you bring on a new client and tell me about that relationship and approach? Yeah, I’d say it starts on a very transparent conversation. I kind of tell them all about the company and like our philosophy at bittersweet, we’re really heavily focused on the mental health of the artist, because content is and community is such a big portion of their
Jaclyn O’Connell
of their business and of their development. And we have a long conversation about what they’re willing to do, what they’re not willing to do, and have a little bit more deeper conversation about, you know, in terms of, like, what are things that they think are like cringe, or things that they like, they like or they don’t like, getting to know them as a really big part of that process, and also, trust building is a really big part of that process, especially if we’re being taken on to do social media, which we do, that’s Probably primarily what we’re hired for, is to help with community growth and social media. And so it becomes a bonding experience. And I speak very transparently, as you can tell, and the cornerstone of bittersweet is collaboration. We’re not just there to, like, give you a schedule and say, Here’s your schedule, buddy. Go ahead. It really is like, how can we help you get this done? How can we support you to make sure that this gets done? Lot of artists go through ebbs and flows. Some of them have good weeks. Some of them have bad weeks. We’re really, like, knowledgeable and thoughtful about when an artist is having a bad week. We can see it 10 miles away coming up, and we’re like, Ooh, they’re kind of wavering a little bit. Let’s go into our reservoir of the content that we do have. Let’s build out a week for them and go in do all the posts for them, so that way they can take a little bit of a break and they’re not having to feel like they’re constantly creating content all the time. That mental health creative workflow is a lot of what we do to ensure that we don’t hit that burnout level with artists. So trust, trust building, is a really big part of it. Collaboration is a really big part of it in terms of development. So getting into the nitty gritty, the first thing we do with a social client, for example, is we get the access to everything, and we’re not even touching anything. We are just looking at everything. We’re pulling all the numbers, and we do a full analysis of all digital assets and social media, and so a full audit of everything, and then we do a platform strategy based on that information. Why are people there? What are they reacting to? Well, how can we get them to stay and what are some interesting ways that we can spin this? What are some experiments that we can try? And I think sometimes ours are open to that.
But sometimes artists are not because they are like they have a very specific esthetic, or they have a very specific way of writing their captions. So we try to acquiesce to a lot of those that uniqueness. Every campaign that we do and every social media account that we work on, they get fully unique support. No one gets the same ideas, no one gets the same plan. It takes a lot of work and a lot of trust building and a lot of time, but to us, we see that pay in dividends when an artist, you know, hits a follower goal that’s really important to them. Why it’s important? I don’t know, but it’s important to them, and hey, we can help you achieve that. And through that, it’s through the two pillars, community and consistency. How are we building a plan and a strategy and a long and a content calendar that goes back to those two pillars? And then, how are we again? How are we super serving the people who are like in the WhatsApp groups or the Discords or in the Laylos? How are we super serving the people who have taken that extra step to deepen the relationship so that all goes into how we approach a digital campaign, and what are the goals of these campaigns, and especially for artists. I mean, you mentioned like a follower goal, but that’s so nebulous. I mean, what are the actual goals and how do you determine if a campaign is successful or not? It really depends on the team. I think everyone has their own like idea of what success is. And I always ask people like the artist and the management team and the label, all three of them have different ideas of what success is. So based on those conversations, based on that kind of like intake process, we have our own numerical goals, like, hey, we want to grow your followers and your Gatorade by 15% right? We have those standard numerical goals just because we want to make sure that we’re moving things forward and we’re moving the needle, but it optically into, like, the whole picture. What’s important to the artists sometimes is, I just want people to see more my stuff, or I want to create a visual esthetic that matches my music. And that’s why we are. We have, like, a creative director on staff, so we will do art direction, and we’ll say, Well, what have you tried this and this? What have you tried filming it with this composition? So there’s a little bit more creativity to it, and experimentation of like, this is how I want to be perceived, which is a question I ask artists a lot, like, how do you want to be perceived? What do you want people to know about you the most? And so it starts with a lot of those questions. The goals for the manager, streams, baby, they want streams. They want to grow that artist. They want numbers. They’re focused on really specific things and metrics. And so we obviously have to include those in there. We have to ensure that we are not just growing on the platforms, but we’re taking them and they’re converting to ticket sales. We’re trying, you know, if there’s a tour converting to streams, you know, with new albums where we’re converting to merch sales and that that process getting through that funnel is different for every artist. Yeah, let’s speak about streams for a minute. I mean, what are you seeing that is driving streams the most these days?
Uh, social media.
Ari Herstand
But in what way? When you say social media, because, like you mentioned earlier, that Spotify editorial playlists were not moving the needle like they used to. So what is moving the needle? And when we’re it was social media, specifically, like, you know, 2020 2021, even into 22 a bit it was like all Tik Tok. And it was like all, right, if a song goes viral on Tik Tok, you know that we see a direct train, uh, translation to streams on on Spotify and Apple Music and whatnot.
Has that approach changed at all. Is it the same as it is in 2021 in what way specifically are you seeing that streams are being driven from social media?
Jaclyn O’Connell
So yes and no, I think that it has changed. I think yes, it has changed in, I think the way that we look at a promotions timeline, schedule. So in 2019 to 2023, ish, you’re like, I’m gonna read, I’m gonna put out 15 to 20 seconds of my song on Tiktok and Instagram, and I’m gonna push that sucker for six weeks before it’s even out. And that is what happened to a lot of people. They went up viral during those moments, and then they tried to, like, immediately scramble and like, how do I get people to take action? Like, how do I, how do I maximize this moment? And so some people did it really successfully. I think someone who’s done it really successfully recently is Lola Young. She’s like, gone viral twice, and she her team has done a really beautiful job of taking her up the right steps without trying to over, blast it and, like, overcook it. And what I mean by that is there are times where someone goes viral. Maybe they’re getting, you know, millions of streams a day because the TikTok is going viral, and the streams are correlating to that. But then they’re like, oh, let’s go on a headlining tour and try to.
Sell 5000 cap rooms that does not translate. And what they did is they found the right press partner. They found the right moments. They found the right live opportunities, live session opportunities. They really, I think Lola’s team did a really good job of like, growing that organically without over cooking it too fast.
Ari Herstand
Sure, is it still about like going viral? And what is going viral mean these days?
Jaclyn O’Connell
I hate to say it, it’s, I am like, anti virality. That’s not a goal that we put down when we’re going forth, like, in terms of metrics, at bittersweet like I say in meetings to people, my goal for you is not to go viral. I actually don’t want my artist to go viral because I think that it creates an unsustainable relationship between the fan and the artist, and it creates unsustainable demand for the artist. And it’s it’s it. It it skews the system a little bit
in my opinion. However, if it does happen, because sometimes, most of the time, you literally can’t predict it when it happens. If it does happen, we have all the tools to like, help sustain it as long as possible, in an organic and consistent way. That is through, you know, new content, it’s through new opportunities. There’s press, there’s radio. You’re going outside the realms of social media, and you’re maximizing in other parts of the of the web to be able to get to new people who might come across that song. It’s not just trying to contain it to social media and get as many creates and as many Spotify streams as possible. You’re going outside and looking at the whole picture of the business of, how can I maximize this and get as much people to pay attention as possible?
Ari Herstand
Are you seeing thatvideos, individual videos from the artist that, quote, unquote, go viral? Are doing better? Is, I should say, more helpful for the artist’s career than a song that gets a bunch of creates, as you call it, a bunch of individual videos that use that song.
And I guess what’s the difference in how it translates to streams or fans? So that’s a great that’s a actually really great question. You’re it’s about the nuance of the algorithm. So a specific video that would go viral,
Jaclyn O’Connell
but maybe has low amount of like, people creating their own video with that sound on Tiktok, let’s call it. You know that that has a limitation to it. There’s a there’s a window, and it’s much, much shorter than the alternate so you have to really act so fast if that happens. And what I mean by that is, if it’s a new song, and you in the songs out in a week, you’re renaming the sound on Tiktok to say pre save the song, or song out this day. You’re being a little bit proactive about how to get people you have the pre save in your in your bio link. You’re trying to get people to to pre convert before the song comes out. That’s the goal, right? Take them off the platform and go somewhere else and convert in a new way. That’s the goal. But you have to act so much faster. When it’s just one video that’s yours and you’re getting you’re not It’s not converting to more creates. The opposite of that is, if a video does okay and it’s like, oh, it’s reaching more people than usual, that’s weird, but all of a sudden, you’re seeing your song everywhere, and everyone’s using their that your song in their videos. That relationship is what’s wrong with, you know, the music industry right now, because it creates, even though it makes, more awareness about that 15 second song, but then only people care about is that 15 second song, or 15 seconds of that song. I mean, it happened to Mitski. Happened to Lizzie McAlpine. It’s happened to a lot of artists, where people only go to the shows because they want that 15 second clip of like, I went and saw this show, and I saw this 15 seconds of this song, and then they leave, and it’s like, it doesn’t create a sustainable relationship with the fan. It’s just everyone’s living in their own world, and they want their own moment. That’s the reverse of when a video goes viral with a song in it. It’s a very different situation. And are we? Are you still seeing that these days,
Ari Herstand
in terms of our songs still going viral like that with lots of creates. Are videos going viral or has it become less frequent and more fragmented? Are you seeing you know that songs aren’t necessarily taking over the platform like they did in 2020 / 2021 where, like, everyone’s rallying around a Megan Thee Stallion song, or, you know, Old Town Road or whatever, and now it’s like fragmented by community. And is that more helpful, necessarily? Is it happening more frequently, but, but not as much at scale on a big level? Does that help artists maybe find a more niche audience that theoretically might be more engaged or not, or is it more detrimental these days?
Jaclyn O’Connell
That’s a big question. I think it really depends on the artist. It really depends on like, what they’re willing to do to, like, push into like, lean into that moment, right? There are some artists who are like, I don’t care. I don’t care that that’s happening. I want nothing to do with it. Let it do its thing. And the manager, they were like, Please do something. And, you know, and they’re like, you know. And I work with an artist who is continuously going, you know, quote, unquote viral, or having lots of creates on his songs, but he doesn’t even have to log into his Tiktok. And so it’s like, he wants nothing to do with it, right? And so it’s like, but that is a boundary that he set, and we respect that boundary. And so, but for other artists who are like, they want that to happen. They want that moment to happen because they think it’s going to solve lots of problems and get in front of so many people. But it doesn’t it. Doesn’t it. It’s different. Like you said, the whole, the whole back in 2019, 2020, everybody’s rallying around the Beyonce and making the making the salad songs like that, the whole platform. You couldn’t get away from these songs right now. It’s not like that anymore. It’s way more fragmented. And like you said, it’s way more about getting your niche audience and really focusing on, you know, getting like, you know, getting inside jokes with your fans, and, like, being like, a little bit weird, or having, like, a weird sense of humor and like, something for people to latch on to. It’s not so much about that one viral video. It’s, it’s nice when it happens, but it really that’s not the thing that’s making a sustainable career, right? And I would imagine that a lot of artists and managers might want something like that, potentially to help grow the team. So I’m curious, like now with your management hat on, it’s kind of like when you’re looking for team members to partner with for your artists, namely record labels, you know, and it’s kind of like, what are the conversations that that you’re having with labels when it comes to that? Are they still solely and obsessively focused just on social media numbers and virality and all of that, and stream counts and all of that? Or are you having different kinds of conversations these days with labels.
Speaker 2
I’m not having conversations with labels speak to that. I’ve, you know, one of my artists has an album coming out this year. We haven’t announced it yet, so I can’t really talk about it, but we pitched her album to a number of smaller labels, thought they might like it didn’t get any bites, and we’re like, that’s okay, let’s do it ourselves. So Bittersweet, or, you know, Good Grief, I have a white label distro. So I distro all you know, if my artist is independent, which Evan Weiss, who’s in like four bands, he Intuit over it is one of his bands. He owns a majority of his catalog. And so we distro all of that. And then we also were the pipeline. The pipeline is this company called distro direct, okay, and so they only take 10% which is great. And then I’m able to take my 15% so the artists is only seeing a loss of 25% from that commission. Right? There are other companies who are taking upwards of 20 and 30% which is wild to me, just for distributing music. So I’m not really talking to labels that much. I want my artists to own their catalogs. I want them to own their careers. I want them to if a song does happen to go viral, it’s all theirs. Everything belongs to them. I’m not even if that happens, I’m not even going to be close to entertaining conversations with a major label, because I just don’t believe in that system, right, right, right? And, yeah, I was mostly speaking to independent labels because, I mean, you know, there are pros and cons, of course, like totally pro of owning everything is you make a bigger piece of the pie and you have complete creative freedom, all of that stuff. You know, the pros of working with an indie label, there’s infrastructure, and they can open doors and set you up on tours and, you know, just give you more support in that realm. You know, as a small operation, I’m curious, you know, if like, those conversations happen, or like, how you, I guess, get over those hurdles of maybe having a smaller team and trying to achieve some of those goals, you know, without the support of an indie label, it’s difficult. It’s a lot of.
Jaclyn O’Connell
Work. It’s a lot of commitment, right? Like walking into I’ll speak to my management partnerships, so I walk into those relationships and say, we are going to work together. I’m not going to do everything for you. I know I can do everything yourself, but we’re going to work together.
Our management commissions are very different. We take 15% on net and not on gross and the reason for that is because if they don’t make money, then we don’t make money. And that’s why I call it a partnership. And we also have contracts where they’re all sunset deals, because I believe in the fact that, like for a lot of these artists, I’m not really going to turn a profit or make commission or whatever you want to call it in the maybe first four to five years of working with them. And that’s okay, because I’m investing my time and my energy into them, and we’re working together towards a common goal. And again, I have a marketing agency. That’s the thing that’s keeping the lights on,
and that’s where, like I have my employees. I have salary employees there at that company, but they’re doing the marketing work, the management is a thing that I love to do. I love to work with artists. I love to connect with them. I love building relationships with them. And when I really believe in them, I want to be able to uplift them as much as I can. And that is the way they like to describe it is I’m lighting all of the paths that are available to you. I’ll tell you what I think the outcomes are, and then you decide, I’ll tell you what I recommend, but if you don’t choose that you need, this is your business, because I’m not. I might not be here tomorrow. You might decide, hey, this isn’t working out. You need to be okay with that decision, and that’s really important to us when we’re talking about like the conversations with artists and the decisions I was in great grandpa was on run for cover, and run for cover is a fantastic indie label, and they’ve done a really, really beautiful job with great grandpa and their most recent release, patience, moonbeam. So we could not have done that without them. You know, I think with how important it was for the five year, you know, post five year comeback of great grandpa, run for cover was instrumental to to that roll out. We came in after they had signed to run for cover, like, shortly thereafter. So I didn’t really have that conversation. But I’ve known Tom and Jeff for, you know, almost a decade at this point, but when I’m thinking about, like, pitching, you know, music to labels, I’m really not. I’m more interested in having the artists and that’s a licensed deal, so I’m more interested in license. Interested in license deals. If we’re talking to a label, I’m not giving those masters away, that’s for sure, right? And so, and then owning the catalog. I’m a big advocate for owning the catalog. Yeah, no, that’s great. And you know, it’s,
Ari Herstand
I think on
the
conversation is definitely shifted over the last 1015, years, where ownership has become so much more prioritized,
and because the access now has broken down, and I guess artists now have direct Access, theoretically, to their fans,
Speaker 1
there is a lot more understanding of of how to do it on your own, without the support of a label. I think, though now, we are also now getting to this point of saturation, with 100,000 songs being distributed every day to DSPs. How does the artist stand out doing it DIY, when everyone else is doing it DIY. And I think a lot of artists now are coming around and thinking, well, maybe it would be helpful to have the support of a known entity, like an indie label or something, and but yeah, and, you know, giving up a little bit more, because, sure, you’re not making as much of the pie, but the pie is a lot bigger, absolutely. And I think, like I said, I think having that infrastructure is so important, especially when there are so many moving parts. I think when you’re when an artist doesn’t have as many moving parts, it’s a little bit easier to contain, because you’re still building all of those parts together. They’re still like, I can hire a publicist by myself. I can go get the vinyl pressing by myself. I can do the label services by myself. I can do the editorial pitching. I have a distro. I have the tools that they need in the toolbox, right? But they’re not overwhelming to a point where I feel like I’m missing something. I’ve I’m turning over all the stones, because they’re still very manageable. Maybe the next thing that we’re doing, which is the hope, the next thing that we’re doing, we do need more infrastructure. We do need more, you know, team members and people to do that. Maybe it’s an artist direct deal with someone like AWAL right, where we’re able to just have a one year deal, it’s licensed, and then we can move on with our lives. And that is a stepping stone. I’m I get really itchy about, like, the long term contracts and, like, you know, three to four record deals like those things make me very itchy. I really, I think, because, I think, because of how the industry has changed, and because of how.
Jaclyn O’Connell
Know, how much can change in one year of an artist’s life in a development, development level, right? You really have to look at like, maybe I only need to be with you one year and then remove on. And that benefits everybody, because then I can grow and I can move on and do something else. And it benefits also whoever you know invested in that one year, because they can make their recoup, because I’m moving on and moving up. And I think that there is that kind of like not having to feel pressure to be in a long term contract anymore. Yeah,
Unknown Speaker
I’m curious,
Unknown Speaker
as a business owner,
Speaker 2
as you know, an artist manager, but also running Bittersweet and just, how do you manage your time? How do you approach everything, and how do you like it? You know, an artist manager is a full time job.
Ari Herstand
Being an artist manager, theoretically, for one artist could be a full time job, let alone, you know, six or seven or eight or however many you have in your roster.
How do you like be the manager where the artist feels that they are being taken care of by their most important person in their career, but also run these multiple businesses, namely, you know, bittersweet, which is keeping the lights on, like you said, which is the bread and butter and which is important to sustain everything else? And how do you prioritize, or just even keep all of that together?
Jaclyn O’Connell
You know? I asked my question every day, you know, and I think that, like, it’s so funny, because it’s like, no day. I think everyone says this in music, no day is the same. Nothing, nothing you do every day is going to replicate ever I mean, I was just literally in Atlanta yesterday for music is speaking on a panel. My flight was delayed, and I didn’t get home until 3:30 this morning, and so, and then I have a whole day of work. And so it’s like there is a level of, you know, I’ve been owned. I’ve owned Bittersweet for eight years. Being a business owner. For that time you’re just like, it is your child. It’s your everything you do everything you can to make sure that it’s like nourished and you keep growing. And for the first two or three years, I did everything myself. I learned how to do video editing, I learned how to do graphic design, I learned how to solve my clients issues so that I could be a one stop shop. And now I’ve grown it into something where we are successfully doing that, and I don’t have to do everything. I have a creative director, a social media coordinator and a senior strategist, and having them has revolutionized my ability for time management. My senior strategist, who’s out in LA, Dani, she’s been with me the longest. She’s been with me for three years, and she helps me run a lot of the business. So she has her clients. I have my clients. We share a lot of that workload. Hey, if I need to take this over, if you take this over, I’m on vacation next week. She knows she’s running the House next week, and she’s used to that because she’s been doing it for so long. And that becomes like, I think, as a business owner and as a boss, you know you have to allow the people to grow in their position and empower them to make mistakes. You have to empower them to do the things that they the way they want to do it. I’m very type A I’ve done things my own way for a really long time. The beginning of the business it was all about this is the way I want to do it. This is my vision. And then being able to give some of that over to someone and delegate is a really hard thing to do, but once I unlocked that in my brain, it opened up lots of more time for me.
And then I got to curious about I got a little curious about management. I was like, oh, maybe this is something I’m interested in, which, by the way, I did not realize this. There is no certification for being an artist manager. There’s no degree you need. You can just walk up to an artist and say, Hey, I like your music. Do you want me to manage you? Which is bananas. That doesn’t happen in any other industry that it still blows my mind to this day. So I started building relationships, and like, you know, Evan and I had worked together previously because one of my clients was Triple Crown records, so I worked with him via, like a marketing lane, to help him roll out one of his records figure and so we got along really well. I’ve always loved his music. Actually, one of his one of his word over at songs is my wedding song. And so we got to know each other and bond, and now we’re great friends. And now I manage him. I’ve managed him for almost four years now, and he’s in multiple projects, and so that’s that takes up a lot of the roster. But even though, I’d say for Evan, because he’s in four of the acts that are on the roster, they’re not all happening at the same time. And that is strategic. So like this year, it’s all about pet symmetry, and then like next year, it might all be about intuitive, right? So we’re really strategic about not overlapping the projects too much, and ensuring that like he’s also not like losing his mind.
And then for the artist to answer your question about, How do I make sure that they feel like they’re getting taken care of? How do I make sure that they feel like I’m there for them? They all get one hour with me every single week? Yeah.
I sit with them for an hour every single week, and we go through what’s happening in their lives, what’s going on, what can I do to support them? They get full access to me, which a lot of I’ve actually realized, a lot of managers don’t do that, where they’re just kind of like, you know, checking in here and there. But I like to feel like connected, and then I know what’s going on emotionally with my artists, so they understand where they are mentally and where they are, you know, productively in their in their careers. Do you have, like, a texting relationship with them too, or phone calls where it’s open ended, like that? Or is it limited? Is this, is it more? Is it more like, Okay, we’re going to speak. Do you set those boundaries of, it’s going to be an hour a week, but outside that, I’m only accessible over email or something, or, um, we have a texting relationship. I you know the email really only happens for like, business related things, but I’m so happy for them to like, text me if it’s like, after about 7pm on a weekday, and if it’s on a weekend, I’m really only going to respond with like, let’s talk about in our meeting, if it’s on, if it’s not urgent, if it’s like I can tell they’re spiraling, or I can tell something’s really wrong, or they’re on tour and something’s obviously happening, I’m going to address that immediately, because that’s a little bit more urgent. But my boundaries, one of my goals in 2025 was to have better boundaries with work, because it is my entire life. So part of that is, hey, after 6pm after 5pm Eastern, I don’t do calls. I don’t do phone calls. It’s pretty rare for me to do a phone call up after 5pm eastern now, and that’s just for my own sanity, because I am on calls all day. When it comes to the management clients, you know, they can still text me, but they know that, like, I’m not gonna do anything until, like unless we meet, if it’s something that they asked me to do, I’m going to make sure that it’s done. But most of the time those conversations of like, what they need and what we need to do in the coming week, that happens in that meeting? Cool. Well, Jaclyn, it is, it is currently past 5pm Eastern, so I want to make sure that we are respectful of your time, and that you can relax after your 3:30am landing and all of that. And I appreciate going in so many different directions with me this afternoon. It was fun, but, yeah, absolutely. And I appreciate all the insight. And you know, you’re in a very unique position based on all the different roles that you’re playing and that you’re that you’re doing in this crazy industry that we’re in. So I have one final question that I ask everyone who comes on the show, and that is, what does it mean to you to make it in the new music business? Oh, boy, it meant something so different when I started my company is and now I think to make it is, I just want to leave. And I think this goes for all types of clients and and people that I manage. I just want to
whenever I walk away from this, because it’s, in my opinion, it’s not a forever thing. Whenever I move on from this, everyone feels like we had a really good time together. We did a lot of really great work together, and that we’re, you know, a lot of a lot of what we do in music is so personal and so emotional, and so that we can continue to, you know, build and grow our relationship. But to make it, I don’t know, man, I just sent us a little emails, and then, like, if people pay their invoices, that’s good with me.
Ari Herstand
Jaclyn, thank you so much. It’s great.
Today’s episode was edited by Ari Davids with music by Brassroots District and produced by all the great people at Ari’s Take.
