S3 | E3 - Joel Little (Grammy-winning producer) on making Royals with Lorde, creative collaboration, and why startups are like hit songs

0:00 David Booth: You're listening to a Day One FM show. The first idea that I had when I read the lyrics was, oh, it should go, "And we'll never be royals," and then have a choir of you going, "Royals," afterwards, and she was like, "Oh yeah, that sounds okay." And then we just recorded it, and over the course of 2 days, mapped that song out.

0:20 Joel Little: 2 days, yeah, wow. Number 1 in the US for 9 weeks.

0:22 David Booth: Yeah.

0:23 Joel Little: It was only number 1 in New Zealand for 3 weeks, so don't get too full of yourself.

0:27 David Booth: Classic Kiwis, yeah.

0:28 Joel Little: Number 1 in Canada, UK, Spain, Sweden, Belgium, Belgium, Ireland, like, it just is ridiculous.

0:34 David Booth: Yeah.

0:35 Joel Little: What's the role of a producer? Like, what do you actually do?

0:39 David Booth: That's the million-dollar question, yeah. Sometimes I don't really know.

0:45 Speaker C: Welcome back to Diaspora.nz, where we're on a mission to seek out and profile the hidden gems, the best founders, operators, researchers, and emerging leaders of the great Kiwi expat community. And today is something a little bit different. I've been excited to release this episode for some time. And it's gonna require a little bit of backstory, so bear with me. In mid-2024, we sat down with Rowan Simpson, early Trade Me engineer, founding employee turned top startup investor, to get his advice on planning the Blackbird Sunrise Festival for the end of 2024. He had this incredible idea to profile one of the quiet ones, this idea that the founders of startups rightly in most cases get a lot of the credit for a given success, but behind the scenes, a lot of the impact is actually folks who are, you know, the early employees, the pivotal advisors, the early supporters who are that are so critical to building the machine, yet often get overlooked or underappreciated. Secondly, we had this idea that, you know, we wanted to explore the extended metaphor of building startups becoming this creative act. You know, it's not dissimilar to the journey of an artist or a musician, for example, who emerges from obscurity to make it on the world stage. Now, if you drew a Venn diagram, at the intersection of those two worlds would be Joel Little, at the very, very top of our list. He's one of the quiet ones. He's a producer and songwriter on Lorde's hit "Royals," scaling his Grammy Award-winning career to working with Taylor Swift, Imagine Dragons, so many more. You wouldn't believe it. Because Joel is a definition of quietly shaping the global hits from behind the scenes. Today, I'm excited to bring the live recording of Rowan sitting down to interview Joel in Wellington, though to be honest, Joel flips the script and interviews Rowan half the time as well, which is really part of what makes it so magic. They break down the striking parallels between music and startups, discovering raw talent, helping develop that early identity, the product, into something that the market resonates with. To navigating the early chaos as you start to catch on, to see product-market fit, to scale and stay true to your vision, your culture while scaling. We really double-click down into the how the Kiwi culture scales and sometimes limits us around the world. Joel shares his journey from musician to producer to selling his catalogue, an exit event in, you know, the local lingo, and to launch what has now become a foundation for emerging Kiwi artists with Big Fan. Whether you're building a startup, whether you're making music, or just interested in Kiwi culture on a world stage, this is one for you. I won't waste any more time. Here is Rowan Simpson in conversation with Joel Little.

3:11 Joel Little: I've got a million questions, a million things I wanna ask you, but let's start with the myth of the lone genius.

3:17 David Booth: Okay.

3:17 Joel Little: I think in startups, the spotlights often shine on the founders, and I think that's true of a lot of the artists that George just listed off. Then two, but it always takes a team to create something great, even if one name is always attached to the work. So maybe you can start with that question, like, what's the role of a producer? Like, what do you actually do?

3:41 David Booth: That's the million-dollar question, yeah. Sometimes I don't really know. I mean, the producer's role is basically that they're in charge of the overall sound and feel of the song. So the way that they might, like for example, I Will Always Love You by Whitney Houston was originally a Dolly Parton song. Two very different versions of the same song. Two different producers have made it sound the way that they—

4:07 Joel Little: Right, the same core underlying material.

4:10 David Booth: Same song but very different sonics. So there's that, that's probably the main role of a producer. But then there's also the psychological side, which is being encouraging, Hopefully helping them figure out what it is that they wanna say and how they wanna say it. And often with some of the younger artists that I work with or artists at the beginning of their career, it was helping them figure out what they wanted to sound like in the first place.

4:32 Joel Little: So you're a therapist.

4:35 David Booth: Honestly, some writing sessions do feel like that. Yeah, you're just like going in, you kind of have to get to the core of what the person needs to write about that day rather than just, you know, let's write a song about a breakup. It has to actually come from a genuine place ideally if it's gonna be something Yeah, yeah, yeah.

4:52 Joel Little: I mean, we're gonna get to all of the stories of the great things that you've worked on, but maybe you can just drill in a little bit on that collaboration, like in the studio, like what exactly does that look like? You're in a pretty confined space with someone pretty famous.

5:08 David Booth: Yeah.

5:08 Joel Little: And working on things that are half formed.

5:11 David Booth: Yeah, I mean, often it's working on, like it's starting completely from scratch too. So everybody's just showing up and there's, there isn't, sometimes someone will come in with the start of an idea like a melody or a few chords or something. But often it's like, what are we gonna, what should we make today? And it usually just starts with a conversation. And often there's like an hour at the start of a songwriting session where everyone's just chatting about what's been going on.

5:35 Joel Little: You haven't even picked up the instruments.

5:37 David Booth: Mm-mm, no, no, just kind of trying to, especially when it's someone that you haven't worked a lot with, you have to, get to know them a bit because there's a lot of trust involved with songwriting and any creative endeavor. So, um, yeah, it's trying to kind of get to the heart of how they're feeling and, um, and maybe get past the initial thing that they're like, oh, I feel like I should write this type of song. And then like, yeah, but what type of song do you really need to write today? And let's do that.

6:04 Joel Little: And so, um, yeah, we'll come to that role of collaboration, how you pick. I mean, I'm honestly quite envious that you get to call yourself a producer. I feel like we haven't, in startups, found the equivalent sort of language.

6:19 David Booth: Cool words like that.

6:20 Joel Little: Yeah, I mean, it's like you can say that and sort of people will nod and go, "Oh yeah, that's cool." I mean, I hate it when people ask me what I do.

6:28 David Booth: Yeah, well, I do wanna know. Because we've had a few conversations now and I know that you've obviously been a part of some incredibly successful things. But what do you actually do?

6:42 Joel Little: It's a little awkward because there's some people I suspect in the crowd who I've worked with, so I can't kind of blag an answer. But yeah, I mean, I've had a lot of different roles in these companies. Like I started at Trade Me as the engineer, I was writing software code, right through to, you know, in the case of Endon Timely, I guess I was much closer to the therapist role that you were talking about at some points in those companies. So it's hard to pin it down, you know? I think if you ask my mom, I think she still thinks I just fix hard drives on computers or something like that.

7:18 David Booth: So you have the technical skill to do a lot of that stuff?

7:20 Joel Little: That was my background, yeah. And I think that was my gateway into this. I mean, not dissimilar to you, right? You're a musician first before you were a producer.

7:28 David Booth: Oh yeah, for sure, yeah.

7:29 Joel Little: And yeah, I think that's an important foundation. I think that gives you something to build on.

7:35 David Booth: So how did you discover the skill to like be on the technical side to kind of become more the— the Yoda in the room, helping people like figure out where they wanted to go with things.

7:45 Joel Little: Yeah, I mean that transition from being an operator, from being a doer to being an investor or advisor or what I'm from now on gonna call producer for companies was a whole new skill. Like I don't think I was especially good at it to start with and I sort of had to learn what worked and what didn't work. I'm sure that's true for you too. Like, not every great musician would be a great producer, and not every great producer was a great musician.

8:14 David Booth: No.

8:14 Joel Little: Which is no slight on your guitar.

8:16 David Booth: No, I'm not. So it's very true when it comes to me. But I, yeah, I didn't, um, I definitely didn't set out to be a producer. That was just something that, yeah, I guess I kind of evolved into. And I started recording my own songs just out of necessity because I was writing so many and I didn't have anyone to record them for me.

8:34 Joel Little: Yeah.

8:34 David Booth: And then figured out over time that there was a skill in there when it came to working with other people that I kind of had, and I just had to figure out how to, yeah, how to develop it and get good at it.

8:45 Joel Little: That's cool. I mean, the last role I had at Trade Me was head of product, I suppose. I'm not even sure if we would've used those words way back then. And I think now I think of the companies that I work with as a product rather than the software that we're building. Like we're building up these companies, you know, but it's a lot of the same thinking that can apply to those situations. You sort of, you know, even just that mentality of thinking about the end user and working backwards from there to the technology, for example, applies just as much when the product is the company that you're trying to build up and maybe ultimately sell.

9:23 David Booth: Yeah. So in your world, like often in the songwriting world, Sometimes you don't know what, you might start out with something and be like, let's kind of do something in this sort of world. But by the end of the day, you've gone off on a tangent. You've just kind of followed where the inspiration took you.

9:38 Joel Little: Yeah, so we do have a word for this in science. We call it pivoting.

9:41 David Booth: Okay.

9:42 Joel Little: Which is a word we shamelessly stolen from basketball.

9:45 David Booth: Yeah, yeah, yeah. I've heard a lot of words today that I, like a completely different language than the one that I normally speak. But okay, pivoting, yeah.

9:53 Joel Little: There you go. So I mean, the idea is you keep one foot planted like in basketball, netball, right? But yeah, you can go off in a new direction after that.

10:00 David Booth: Yeah.

10:00 Joel Little: And if you're gonna do that, probably better to do that sooner rather than later.

10:04 David Booth: Yeah.

10:05 Joel Little: Before you spend too much VC money.

10:06 David Booth: Right.

10:07 Joel Little: So maybe let's rewind to July 2012.

10:11 David Booth: Okay.

10:13 Joel Little: Turn your mind back when you worked on something pretty remarkable that became quite well known. I think there's actually a little, sample maybe we can listen to?

10:22 David Booth: I've never seen a diamond. Ah, yes.

10:25 Joel Little: Yeah, you recognize it?

10:28 David Booth: I do, yeah. Cheap on wedding rings. Yeah, I know this one.

10:33 Joel Little: And I'm not proud of my— So you're credited as the producer but also joint songwriter actually for that, songwriting credits with a then 15-year-old called Ella. That people may have gotten to know a little since then.

10:48 David Booth: Yeah.

10:49 Joel Little: Um, talk to us about how you met her. Like, how did you start working together with a 15-year-old?

10:54 David Booth: I know, it does seem a little sketchy. Um, I, uh, so my, my now manager, um, his name's Ashley Page. He signed my band Goodnight Nurse back in the day. He was working at Warner Records at the time, and, uh, He'd gone into management and independent label work and he had seen her— somehow all the record labels had seen Ella perform at some school talent show when she was like 12. I don't know how they've— I don't know how that happened. But anyway, he had been saying for a couple of years, there's this girl, she signed this development deal with Universal. She's really good. She's 14. And I was just like, this seems so weird to me that—

11:38 Speaker C: Yeah.

11:38 David Booth: I was like 28 at the time. And I was also kind of new to the whole collaborating thing as well. Like I'd only ever really written songs with close friends, like other members of my band. I'd done some of the Kids of '88 stuff at that point, but that was with like Sam, the singer from Kids of '88 was also in Goodnight Nurse. He was a close friend. People you knew. Yeah, people I knew. And so I was just like, seemed like the whole collaborating thing is kind of scary, let alone with a 14, I think she was 15 by the time she came in, but when they were talking about it, she was 14 anyway. Yeah, it just seemed weird. But then he was like, you really should, like, I'd just done a song for the band that won the Rock Quest that year who ended up becoming Broods. They were early incarnations of Broods. Nelson Richards, I think. Nelson, yeah, yep. And so I think there was a little bit of, they'd noticed that I could work with younger artists and had a bit of a knack for that. I had a little sister that was Ella's age, same age as her. And so I think, yeah, she came in and kind of instantly I was just like, oh, this kid is not, I mean, she already seems way more mature and smarter than I ever will be. She just had a way about her. And so that kind of put my mind at ease in that regard. And then, yeah, and then we just started like playing around with ideas. It was like, we kind of had the luxury of being like, she would come in during the school holidays or if it was like sports day at school, she'd take the day off and come to the studio. Yeah. So we kind of, over a period of months, she'd come into the studio and she was like, she would play me cool like remixes of things that she'd found on Hype Machine, which was a big website at the time. And I was playing her like old Snoop Dogg and just, we were kind of like, you know, trying to find our—

13:26 Joel Little: Trying to find our way, basically.

13:27 David Booth: Yeah, and then every now and then we would kind of toy with an idea of a song. And then one week we just were like, let's just make a song. Let's make a different song every day and let's just make it sound like some of our favorite artists. Like each one, we'll like, today we'll do one that sounds like Lana Del Rey. Tomorrow we'll do one that sounds like Grimes. We'll do one that sounds like James Blake. And we were just like, just to try stuff because she didn't really know what she wanted to sound like. I don't even think she knew if she really wanted to be a musician. She was like, I'm just giving it a try to see if it's gonna— if it feels right. And that week we wrote a song. The last day I was like, why don't we just make a song that's just only your voice? Like, we'll make all the instrumentation out of your voice. And it was a song that was called Million Dollar Bills that, um— Mm-hmm. That was on her first EP and I ended up putting a beat into the song later on but on the day we were like, oh, there's something about this one that's really interesting. It's kind of got this kind of pop hip-hop thing but it's also all about her voice and that was when I was like, this is where the magic is because her voice is so unique. And then the next time that she came into the studio after that she'd sent me most of the lyrics to what became Royals and My only line, my only lyric in that song that I came up with is "Tigers on a gold leash." She did all the rest of the lyrics, but she—

14:44 Joel Little: Thank you.

14:46 David Booth: It's a good line. It's all right.

14:48 Joel Little: The others are all right too.

14:50 David Booth: And yeah, so she came in and we talked a bit about kind of what we wanted to sound like. I'd made, I think just on the spot, made like basically the beat that you hear now 'cause it's so minimal. And then one of the things I always used to have to say to her is, this is going to sound crap when I sing it, but when you sing it, it's going to be good. And the first idea that I had when I read her lyrics was, oh, I should go, and we'll never be royals, and then have a choir of you going royals afterwards. And she was like, oh yeah, that sounds okay. And then we just recorded it, and over the course of 2 days, mapped that song out. 2 days, yeah, wow. And then it was done.

15:25 Joel Little: Amazing. So fast forward now a year, 12th of October 2013, Royals is number 1 in the US Billboard charts.

15:34 David Booth: Yeah.

15:36 Joel Little: Fun fact for the people as old as me in the room, Lorde was the youngest artist to have a US number 1 since 1987. Tiffany, you remember that?

15:46 Speaker C: Vaguely.

15:46 Joel Little: You're a bit young. I remember it well. What had you been doing for a year? Like, what do you do between those 2 days while you record this amazing piece of art and then a year before the rest of us realize that it's great.

16:01 David Booth: I mean, I was just still being like a broke musician.

16:06 Joel Little: Yeah.

16:06 David Booth: Just like hustling and I'd set up a studio prior to meeting Ella. So I'd set up this little studio, I started doing music for TV commercials and so that, before that I had been in the band for years but never made any money with that. Then I had a kid, I was like, holy shit, how do you like— Time to grow up. Yeah, exactly. I was fine on 2-minute noodles when it was just me, but then I had a family to support. So I kind of figured out that I had a knack for this ad writing thing. And so I'd set up the studio, but it was basically like anything that came in the door I kind of had to do. So the song started to take off, Raw started to take off, and then we quickly got in for 3 months and made Pure Heroin, the whole—

16:47 Joel Little: The album.

16:47 David Booth: The whole album, yeah. So that whole thing was made the start of 2013, like as the song was showing signs of maybe blowing up, but well before we knew like Yeah. It was actually gonna be as big as it was.

16:59 Joel Little: I mean, I sometimes blush when people talk about the companies I've worked on, but honestly, like the accolades for this are almost unbelievable. Like number 1 in the US for 9 weeks.

17:06 David Booth: Yeah.

17:07 Joel Little: It was only number 1 in New Zealand for 3 weeks. Don't get too full of yourself.

17:11 David Booth: Classic Kiwis, yeah.

17:12 Joel Little: Number 1 in Canada, UK, Spain, Sweden, Belgium, Ireland. Like just is ridiculous.

17:18 David Booth: Yeah.

17:19 Joel Little: 14 times platinum, which means 22 million copies.

17:24 Speaker C: Sold?

17:24 Joel Little: I don't know how the sales and streaming work now, but 2018 Rolling Stone magazine ranked at number 9 in the greatest songs of the 21st century. Yeah, that's crazy. Um, and it won Song of the Year at the Grammys.

17:37 David Booth: Song of the Year at the Grammys, yeah. Thank you.

17:40 Joel Little: Yeah, so talk a little bit about what it's like to have that kind of global success, because, um, I imagine you meet a bunch of interesting people. And that there are some experiences which are kind of pretty confronting at the time. Or maybe like, is your job done as a producer by then? Are you just kind of watching?

18:00 David Booth: Yeah, initially nothing really changes because there's such a massive gap between the song being successful, earning a bunch of royalties, and then it's like a year before you actually see any of those royalties. So I was still like— You were still a producer. I remember at one point I was in the studio in my little studio and I was recording some kid even younger than Ella, I think, who'd won some competition and she was singing opera and it was the day— and while I was sitting there, "Tennis Court," another one of our songs, went number one in New Zealand. Like the charts came out and I was like, "Oh cool, my song's gone number one." And then they were like, "Oh cool." Back to work. And then just back to like recording this little opera singer. So yeah, I was just, yeah, it wasn't until Maybe, yeah, like once it kind of— once it went number one, that was when a lot of the doors opened in the States. And Ashley, my manager, was like, we need to get over there and meet some people. Because I had the— it was very—

18:56 Joel Little: You'd had the flying all of a sudden.

18:57 David Booth: Yeah, yeah, I had the good fortune of suddenly every single door over there was open to me, and everybody was like, who the hell is this kid and who the hell made this song?

19:04 Joel Little: Yeah.

19:05 David Booth: Um, and we want to work with him. So yeah, I was like, time to try and take advantage of that.

19:09 Joel Little: And yeah, I mean, you made some good choices. We've got a couple of other samples, I think, if we want to cue those up, some other things that people might recognize.

19:16 David Booth: A couple of other songs?

19:18 Joel Little: Yeah.

19:19 David Booth: Okay. <LYRICS>I'll do what it takes, whatever it takes, 'cause I love the adrenaline in my veins.

19:30 Joel Little: I'll do whatever it takes.</LYRICS> I had no idea you were behind that. I've literally used that before I've gone on to speak and get into things before.

19:37 David Booth: It's a big one for, yeah, for sports highlight reels. Yeah, right.

19:41 Joel Little: That's good for the royalties.

19:43 David Booth: Yeah, yeah, yeah. And that same year, that same year I did this other song, quite different from that one. <LYRICS>I'm so high at the moment. I'm so caught up in this. Yeah, we're just young, dumb, and broke, but we still got love to give.</LYRICS> Did you write the lyrics to that one? I didn't write the lyrics to that one, no. That was all Khalid. Um, yeah, so that song now I think is the big— my biggest streaming song. That song's Diamond in America. Right.

20:16 Joel Little: Amazing.

20:16 David Booth: Yeah, but that was 2017, so there was a 5-year period from when we'd written Royals.

20:22 Joel Little: Yeah.

20:23 David Booth: To when I had the next kind of—

20:25 Joel Little: Yeah.

20:26 David Booth: Majorly successful thing happen.

20:27 Joel Little: Yeah, it was a long time between drinks.

20:30 Speaker C: Yeah.

20:30 Joel Little: Amazing. I think the most interesting thing about you is I've gotten to know you a little bit is that you seem completely unchanged by that success. I suspect that if I'd met you beforehand, you would've been probably just as recognizable, which seems really inconsistent with what we all think we know of rock stars. So, like— Or the mythology of rock stars, right?

20:53 David Booth: Yeah, yeah.

20:54 Joel Little: So like, how did you avoid all of that? Like, how, you know, why are you not like kind of washed out on cocaine somewhere?

20:59 David Booth: Mm, well, I think when I was at that age where I could have potentially, got into that world, I was still a super broke musician, didn't have, couldn't afford it.

21:12 Speaker C: Yeah.

21:13 David Booth: And that's the main reason.

21:16 Joel Little: That's a good reason.

21:17 David Booth: Yeah, no, I don't know. I think, yeah, I mean, I had, we had, when we had our first daughter, Lila, it was, yeah, it was just like, it was a struggle and I was like, okay, I need to like get my, I'd been fine kind of floating around in the band, but I was like, I need to like, I've got to get my shit together and figure out how I can do this thing properly and at a high level. And so I think my motivation just like, I'd always been motivated, but the motivation really kicked in at that point. And it was, yeah, just probably being a dad helped, but.

21:50 Joel Little: Yeah.

21:51 David Booth: Most of the really successful artists that I work with are not like crazy, they don't live the crazy rockstar lifestyle. That's how they've managed to like, to keep level-headed and keep as successful as they have for a long period of time. 'Cause you just can't live like that and actually be productive.

22:09 Joel Little: Yeah. How much, well, talk to us a bit about the pros and cons of being a Kiwi in that world maybe. 'Cause it feels like you're quite canonically Kiwi in your approach to that world as well.

22:20 David Booth: Yeah.

22:20 Joel Little: It seems like you'd be unfazed by a rock star when you met them.

22:24 David Booth: I think, yeah, I think so. I think New Zealanders are good at just treating everybody kind of equally. And I think that is actually a really beneficial thing.

22:31 Joel Little: It's a superpower.

22:32 David Booth: Yeah, because in my world especially as well, it's like trying to get people to relax and be themselves. That's when they are their best creative selves too, when they feel like they can trust you and they don't feel like they have to put on an act. They're just more likely to do something that's a bit more honest maybe.

22:51 Joel Little: Yeah.

22:52 David Booth: So I think that's helped me. I think there's definitely been like, There's a little bit of the Kiwiness that we could probably do without sometimes, but like we're not good at talking ourselves up and—

23:05 Joel Little: Yeah, so talk a bit about that. Like when, like, do you consider yourself ambitious? Like I assume you don't kind of buy into that kind of chest-thumping American version of ambition, but—

23:13 David Booth: No. No, I am. Yes, I mean, I am. I just, I'm still, I love the thrill of the chase of trying to, I love the whole— I've always been— I've always just wanted to do the best that I could possibly do with whatever was in front of me at the time. And so whether that was playing in Goodnight Nurse and touring New Zealand, it was just anytime there was a new opportunity, I was trying to take advantage of it, whatever that was. And that's kind of led me down this path to being a producer, even though that wasn't necessarily— I mean, I didn't even know that it was a viable career option when I started out in a band. I was just like, it's fun making songs and going on tour with my friends.

23:51 Joel Little: Yeah. Plus I think, I don't know, for me at least, I spent a bit of time in the States with Vaughan during VN trying to raise money from American investors and we sort of discovered that our Kiwiness wasn't really helping us.

24:05 David Booth: Right.

24:06 Joel Little: It was starting to hurt us. Like we would, I remember one meeting where the investor said, you know, how's it going? And Vaughan said, it's going pretty good. And you could sort of see his face slump because like to an American—

24:15 David Booth: He said pretty good.

24:16 Joel Little: Pretty good means, bloody terrible, right?

24:19 David Booth: Yeah, yeah.

24:20 Joel Little: Whereas to us, pretty good means pretty good. Yeah, yeah, yeah.

24:24 David Booth: That's like, that's high praise.

24:26 Joel Little: That's pretty good, yeah. But yeah, so I mean, we went through a phase where we were kind of like trying to convince each other to be more American. Like, be more American in the meetings. And it totally doesn't work because it's not authentic. And yeah, I think we eventually worked out that we need to be more Kiwi.

24:41 David Booth: Yeah, I think so.

24:43 Joel Little: And lean into that.

24:44 David Booth: I think it's just authenticity is so important. I feel like, Sometimes there's people that I work with that I can tell want me to be like that. And I'm just, I can't.

24:57 Joel Little: You kind of push back against it?

24:57 David Booth: Yeah, I just am myself. And I am enthusiastic about things when they are pretty good. So I can do that, but I'm bad at pretending to be enthusiastic about things that aren't good. And I think that's good.

25:13 Joel Little: Yeah, I couldn't agree more.

25:19 David Booth: Yeah, I mean, who wants— it's just, I don't know, it feels fake and it's just kind of time-wasting. You can't fake something actually being good. You can be enthusiastic in the room at the time.

25:31 Joel Little: Yeah.

25:32 David Booth: But then as soon as you play a song to anybody else, they're going to know straight away if it was good or not.

25:39 Joel Little: Yeah.

25:39 David Booth: Yeah, I always liked, especially in LA, we would have these nights where people would come around to the studio in my house over there and everyone would come over and have some drinks and it would always end up, you know, 2 AM in the studio and everyone would play each other the songs that they had been working on recently. And I loved it because it was such a good— it was like a good testing ground because I would— as to which songs I would actually play them. All of a sudden I would be like, "Oh, this one and this— I want to play these ones." But that one which I have been telling myself is really good, I don't want to play them because I'm now— It's not good. Being honest with myself.

26:12 Joel Little: Yeah, right.

26:13 David Booth: It's not actually good.

26:14 Joel Little: —so it flushes it out.

26:16 David Booth: Yeah, yeah, it's good. I love doing that, yeah.

26:19 Joel Little: Huh, yeah, there's probably a lesson for many of us in that in terms of the companies that we talk about too, those of us who work with a few.

26:25 David Booth: Yeah, I mean, surely in your world you have to be passionate about the things that you're going to get involved in.

26:31 Joel Little: Yeah, but I mean, I think that's another myth, the idea that they're like amazing and obviously great when you go into them. Right, right, I see. Like, you know, I think like the process of making them great is actually what makes them interesting companies to work on.

26:45 David Booth: Yeah.

26:46 Joel Little: And so that necessarily means they're often not great at the beginning. And yeah, I mean, it's a repeated experience I have where that process of kind of telling other people about the companies that I'm working on and effectively pitching that to them kind of guides you to what it is that's exciting about it. It might be hard to articulate that, straight away. And often it's the people rather than the idea or the product in the beginning that is exciting.

27:17 David Booth: That's the part that has the potential.

27:18 Joel Little: But then you work it out. And as you kind of sharpen that story about it, you actually build your own enthusiasm. Does that make sense? So then you can start to really authentically say, this is amazing and you should invest in it when you're talking to an investor.

27:33 David Booth: So through having the discussions, it becomes clear what the actual valuable parts of it are?

27:37 Joel Little: Yeah, or not. The opposite is also true. I think, the more you work on it, sometimes it reveals itself to actually be not as great as you might have hoped. Yeah. That's when you need to pivot.

27:52 David Booth: Yeah. Yeah. So I wanna see, I know that you said that you had an example of early Trademe.

27:59 Joel Little: Oh yeah.

28:00 David Booth: Situation. Speaking of some sort of development or something, right?

28:04 Joel Little: I think I do. Yeah. Can we pull that up?

28:11 David Booth: It's a little bit different.

28:12 Joel Little: It looks great to me. It's pretty good, yeah.

28:18 David Booth: Pretty good.

28:18 Joel Little: The most amazing thing about this, actually, this was Trade Me in 1999. There's a lot of nostalgia here, actually. Netscape Navigator, for those of you who are old enough in the room, as well. But this is what Trade Me looked like when I started working on it. And we thought it was great. I would've said that was great. Especially the logo, pre-Kiwi logo. Like, can we just zoom in on that? Yeah. I think if you click to the next, there you go.

28:44 David Booth: Oh yeah, beautiful. So when did you, how far along before you changed the logo?

28:50 Joel Little: I mean, pretty quickly. Pretty quickly. I think Sam gets all the credit for that original logo. I think that's—

28:57 David Booth: So good.

28:58 Joel Little: Is from the Microsoft Wingdings font.

29:02 David Booth: Yeah. It's like emojis before there were emojis. Yeah, yeah.

29:06 Joel Little: And yeah, he just colored them in.

29:09 Speaker C: Yeah.

29:10 Joel Little: That was the logo.

29:11 David Booth: Oh, good.

29:12 Joel Little: So yeah, I mean, you know, like, let's not pretend that these companies that became great companies were great, obviously great at the beginning. They were, you know, pretty ordinary.

29:22 David Booth: Yeah.

29:23 Speaker C: But—

29:23 David Booth: But there was something, there was a little something in there.

29:25 Joel Little: There was enough there to get started.

29:26 Speaker C: Yeah.

29:27 David Booth: It's the same with, I love working with newer artists for that same reason. Like, it's fun working with the big stars, but I've had a lot of, of success working with people who weren't big when I first started working with them and I've helped them figure out how to—

29:40 Joel Little: How to be big.

29:41 David Booth: Yeah, well, yeah, well just how to, like I've just helped them figure out what they wanted to sound like if they were like, I just don't really know just yet. Like this is the kind of music that I like and I wanna make, but I don't know what my version of that is. And so—

29:54 Joel Little: Yeah, let's find it together.

29:55 David Booth: Yeah, that's what I get in there and do.

29:57 Joel Little: Yeah, I'm definitely gonna call myself a producer from now on. Okay, so that was 10 years ago.

30:04 David Booth: Yeah.

30:04 Joel Little: Sorry to make you feel a little old, but if we bring this into the present day, like Georgia, as we were walking on, listed off some of the artists that you've worked with since. Taylor Swift, Broods, Sam Smith, Imagine Dragons, Ellie Goulding, Khalid, Shawn Mendes, like it's a long list. I'm interested to know how you choose. Like you can presumably choose to work with pretty much anybody now because of what you've done. Like how do you choose who to collaborate work with? What are the traits?

30:33 David Booth: Um, there's a couple things. Uh, the first thing for me that I, that I learned, especially after working with Ella, was I just— it's the— the person has a unique voice, just literally the way that they sing. Like, they don't have to be a great singer, but if they have a unique voice, I feel like that is already a great step towards setting themselves apart. Like, I'd much rather work with someone who sounded unique than saying all the notes perfectly.

30:57 Joel Little: Perfectly. We'll talk about how technology can fix that.

31:01 David Booth: Right, yeah, well, yeah, that can be fixed, yeah, easily enough. But, um, but so there's that. That just makes my job a lot easier because I feel like if you're not trying to disguise a crappy voice with a bunch of music, you kind of like, you can just get to the heart of the song and keep it quite simple. I do like to, when I can, just production-wise, keep things pretty simple to stay out of the way of a great voice and of what the song's trying to be and say. So yeah, so a great voice and then also something to say, something unique to say or a unique way of saying the same thing that everybody else says.

31:34 Joel Little: Yeah.

31:35 David Booth: You know, like writing a— there's a million love songs, but people are still writing new love songs that connect with people in a different way.

31:43 Joel Little: So the fact that Ella was a poet first before she was an artist.

31:47 David Booth: Yeah, I mean, she would like bring in words on a page and be like, I don't know what the chorus is or what the— like, and we would— I'd be like, well, this part feels kind of like a chorus. And I'd never really written songs. When I first started writing songs, I would sit with a guitar and hum a melody and then try and find a lyric that fit the melody. Whereas with her, she had all these amazing lyrics, and I was like, okay, well, how do we sonically and with the chords and with the melodies tell the story that this lyric is— that these words are telling?

32:16 Speaker C: Yeah.

32:17 Joel Little: And How do they sound?

32:19 David Booth: Yeah, and do them justice. And that was really fun. Like, I wish that more people would write like that, actually. I'm always encouraging artists to bring— I mean, some people are just, yeah, you know, you just, you have to work however works best for you, but—

32:32 Joel Little: Sure, yeah.

32:33 David Booth: Yeah, and she quickly learned as well how to still write great lyrics to a melody. Like, I would hum a melody again doing my— this is going to sound crap when I do it, but— Yeah. And then she would go away and write a lyric and come back and sing it and I'd be like, damn.

32:50 Joel Little: So you, I mean, the traits you've described so far are still kind of how they sound or what the words are, but like talk about the personality traits maybe that you look for. Like how do you choose, how do you decide that someone is someone that you're going to enjoy working with? Or maybe enjoy is not the right term to optimise for.

33:08 David Booth: I mean, I guess those first couple of things are before I even get in the room with them. Those are the things that I like, if I get sent a bunch of music a bunch of different new artists, or even with bigger artists. I've definitely said no to big artists, much to my manager's disappointment, just because I actually thought that I couldn't. I was like, they're better off with someone that is enthusiastic about their music.

33:30 Joel Little: Yeah.

33:31 David Booth: And that does that kind of thing really well. The other thing is when I hear it, I have to feel like there's something that I can add to the equation, which It's probably similar for you with your line of work.

33:44 Joel Little: Yeah, I mean, that's definitely true. Yeah, if I don't see a role for myself, it's kind of, you know, it's just money then that you're investing. And there's lots of people who can invest money. Yeah, I mean, one of the things I kind of try and find pretty quickly when I'm deciding whether someone's someone I wanna work with is just listening to the questions that they ask. Right. I get a lot of people who reach out and say, you know, can I have coffee? I'd like to pick your brain.

34:12 David Booth: Yeah.

34:12 Joel Little: It's like, that doesn't sound like fun, having your brain picked.

34:15 David Booth: Yeah.

34:17 Joel Little: But like when they come with a specific question and they say, you know, I'm wrestling with this gnarly thing.

34:24 David Booth: Yeah.

34:24 Joel Little: And it seems like you might be someone who could help me with that. Like all of a sudden that's a much more interesting conversation.

34:29 David Booth: So what kind of thing would that be? Is there an example of that?

34:33 Joel Little: Yeah, I mean, if I think back to some of the original conversations with Ryan and Scoff, who are the founders of Timely, for example, like they had a pretty good product sense. Like, you know, my background was in product and in building things, but that was also their background. They could do that pretty well. And they were thinking a lot about the shape of their venture. Like they were trying to decide if they wanted to go down the more aggressive venture route or more bootstrappy kind of approach.

35:00 David Booth: Yeah.

35:01 Joel Little: They were trying to think about they had a little bit of money from their previous exit and so they were trying to think about how aggressively they should scale. And so they were really just wanting advice around that kind of the shape of the company and how to think about building that company product that I was talking about before.

35:18 David Booth: Yeah.

35:19 Joel Little: And those were fun conversations. I was way more interested in talking to them about that stuff. And we actually, it took about a year of those conversations back and forth. Before we all kind of sheepishly broached the subject of, you know, maybe I should invest in this rather than just have lots of coffees with you.

35:37 David Booth: Yeah.

35:39 Joel Little: But you know, so that long incubation period I think is one of the other things that made that a great venture. It was like there was a pretty solid foundation of working together.

35:47 David Booth: You built trust and—

35:49 Joel Little: Yeah, I had very high confidence that they were going to be great founders and that I'd be able to contribute to it by the time that, that investment happened.

35:56 David Booth: So is it generally you'll take that amount of time before you really dive into something?

36:01 Joel Little: No, sometimes I've been much faster than that. But I think if you plot the ones that have been great, they're all the ones that—

36:08 David Booth: They're those ones, right?

36:09 Joel Little: They're all the ones that were longer. Yeah, like the ones, someone else said this actually earlier today, the fast decisions weren't always the best decisions.

36:17 David Booth: Yeah.

36:17 Joel Little: I mean, the other, I guess it sort of ties into that as well is I really, I try and find coachability. I don't know if this is relevant to you, I suspect maybe, but like someone who can listen, take on that feedback, put their own stamp on it and then do something with it. Like not just kind of ask for advice for shits and giggles, you know, but to actually make the thing better.

36:40 David Booth: Yeah, yeah, I mean, yeah, I guess as a producer, my role in that situation would be like if somebody's singing a song And it could be as small as like, I can't understand those two words in that line. Can you say them a bit? Or like, oh, this needs to feel a bit, like I'm not really believing what you're saying. Like those kinds of things. And being able to do that with someone.

37:04 Joel Little: You have to kind of know them to be able to say that.

37:05 David Booth: You have to kind of know them. And yeah, and there are still some people who are like, I think it's fine the way it is.

37:09 Joel Little: Yeah, right.

37:09 David Booth: And you're kind of like, well, it's not, but it does get to a point. And that's generally, I guess, I guess another thing like that, once you get in the room with someone, you find out if they are willing, if they're wanting it to be a collaboration or partnership like that.

37:22 Joel Little: Yeah, exactly, make it better.

37:23 David Booth: 'Cause I don't have the type of personality where I'm like, no, this is the way that it has to be. 'Cause they're also the one that has to go out and sing it and perform it every day. And so if they're not happy with it, then that's not a good way to end the day. But at the same time, if I think that—

37:42 Joel Little: Yeah, and sing it thousands of times.

37:44 David Booth: Yeah, forever. It's a massive song. It's his whole career. Yeah, yeah. When I was with Khalid, he has a song called 18, and the chorus lyric is, because I'm 18 and I still live with my parents. And then, but he was about to turn 19, and I was like, you're gonna have to sing this song. You'll be like, we should change the story. The story of the song needs to be like, looking back on it after the first chorus, it needs to be because I was 18, and that'll make a bit more sense. Like, uh, when you're— It makes more effort later on. Yeah, yeah, yeah. I love it. Just little things like that. So it's funny, yeah, finding people that are willing to to just genuinely collaborate and it's not like a power-tripping competition.

38:22 Joel Little: And do you think you can, like, what's your success rate of being able to tell in advance if someone's gonna be good to work with like that? Is it better than a coin flip?

38:31 David Booth: Yeah, probably, yeah. It's not a huge amount that aren't willing to collaborate generally, it just happens every now and then. And sometimes there are artists who I'm like, I love their music, I feel like I could really bring something and add something to this. Um, they seem cool, and then we get in the studio and there's just no creative connection whatsoever, and we're both like, damn, that sucks. Like, I wanted it to work and it just doesn't. You can't force it. Like, it's a, it's a thing that can— I guess you can— it can develop over, over time, like you say. But sometimes, especially in the songwriting world, sadly, you only have like a day or two, a few days, yeah, with them because they're you know, you're both in LA, they're from the UK or whatever, or they're off on tour and going back to New Zealand. And if it doesn't work that first day or two, then that's kind of your shot.

39:20 Joel Little: Yeah, yeah. Since you mentioned LA, let's go down that road. Like, can you just quickly compare what it's like doing the work you did in New Zealand with the time you spend in LA?

39:29 David Booth: I love going to LA. It's super intense. I lived there for 4 years and was definitely ready to be back in New Zealand more when we moved back. But I do love the hustle of it. I especially, I think as a Kiwi and being quite laid back, it's good to be around that energy. It kind of like lights a fire under you a little bit as well. But I always joke and just say I love going to LA and then I love leaving after a couple of weeks. Yeah. Because it's good to—

39:59 Joel Little: That's exactly how I feel about San Francisco. Like for, But for tech companies, that's kind of the center of the universe. And it's an amazing place to visit. It's like an injection of optimism and energy. And it wears you down after about 48 hours.

40:12 David Booth: Yeah.

40:12 Joel Little: It does for me anyway. So it's kind of fun to go there. It would be harder to be there, I think.

40:18 David Booth: Yeah. Yeah, and I kind of figured out how to have my version of LA, like which areas to hang out and which to avoid. I have the studio at my house, which always helps. But I do, Yeah, I do love going over there, and, and, but then being able to come back to New Zealand and be away from it and be away from all of the, you know, the, the fake enthusiasm.

40:38 Joel Little: Yeah.

40:39 David Booth: You actually— I feel like I hear songs differently in New Zealand than I do when I'm there.

40:42 Joel Little: You hear them differently?

40:43 David Booth: Yeah, like a demo that I've made there, I'll come back here and be like, oh, that's not good, that part needs to change. Like, um, yeah, it just gives me a good perspective on it, and I can listen to it in less of a Yeah, without buying into all the typical like bravado nonsense talk over there of everything being amazing.

41:02 Joel Little: Yeah, so you need a bit of it, but not too much of it.

41:06 David Booth: Yeah, it's a balancing act.

41:07 Joel Little: Yeah, like I think one of the interesting things I reckon is when you go to Silicon Valley, an American startup doesn't call themselves a US startup, but like a New Zealand or an Australian startup goes there and they call themselves a New Zealand startup. Up.

41:22 David Booth: Why is that?

41:23 Joel Little: I think it's a crutch.

41:24 David Booth: Right.

41:25 Joel Little: I think it would be much smarter for them to just acknowledge that they're just a startup like everybody else. And I suspect that that's true for artists in LA. Like, you can, you know, by the time you get there, you're one of.

41:38 David Booth: Yeah, yeah, you're there for that reason. And generally everyone that's there has kind of reached a certain point. I mean, there's a lot of people out there just slogging away and trying to get their chance. Yeah, but everyone's acting like they're already a star, that's for sure. Yeah. Yeah.

41:54 Joel Little: They're actually a barista. Yeah. Okay, so we'll keep the timeline rolling. 2021, you sold your catalog.

42:03 David Booth: Yes.

42:04 Joel Little: So this is, I mean, another piece of jargon for you, what we would call an exit.

42:08 David Booth: Okay.

42:11 Joel Little: How did you decide to do that? Was it hard to sell your babies?

42:17 David Booth: Yeah, it definitely was. It was, yeah, it was the reason that I decided to do it was, I mean, it made financial sense.

42:29 Joel Little: Yeah, someone offered you more than—

42:30 David Booth: Yeah, exactly, it was enough, they made me an offer I couldn't refuse. But I kind of felt like at that point, like when I had, after the whole, Lord thing happened and our lives got completely upended and, you know, changed and it was an incredible ride to go on but we weren't trying to make a big successful song, we were just trying to make something that we liked.

42:53 Joel Little: Sure.

42:54 David Booth: And so I really had, I felt like I wanted to prove to myself that I could do it again and I kind of set a few goals and did that a few times over and then that kind of I would say that the pinnacle of that was the Taylor Swift.

43:09 Joel Little: Yeah.

43:09 David Booth: Working with her, which was an amazing experience. But then after that, I was kind of like, man, I've just, I've been doing it at this level now for 10 years, like 20 years total from when I started Goodnight Nurse when I was 18 or whatever. And I feel weird. Like I feel like, now what? Like it was like a kind of a weird, um, and so, um, then the catalog sale thing came up and it just kind of felt like it was closing a chapter, closing one chapter, and made me actually feel more motivated about, okay, well now I'm kind of like royalties-wise I'm not getting any because when I sold the catalog now this other company collects all those royalties and—

43:52 Joel Little: Yeah, of course.

43:53 David Booth: That's what they were with them. Um, so I was like, I'm not getting any royalties from— I kept my production royalty, so I sold my songwriting royalty up to the end of 2019.

44:02 Joel Little: Which is, I don't know, it's a bit like selling the UI and keeping the database or something like that. But yeah, right.

44:08 David Booth: Yeah, but they're two different royalty streams.

44:11 Joel Little: Yeah.

44:11 David Booth: So the producer royalties come from the recording of the song, songwriting royalties come from the actual songwriting.

44:16 Joel Little: Yeah.

44:18 David Booth: So I still was getting the producer royalties and still working as a producer, but it actually motivated me to be like, hey, why not? I gotta like try and build a second catalog and Yeah. See the chances of it being as—

44:30 Joel Little: Start again.

44:31 David Booth: Yeah, yeah. I was like, I don't know if it'll ever get to the level of that, of the first one, but it's kind of exciting to start again and just push myself and see where I can.

44:40 Joel Little: It's kind of amazing. Like, this is my experience. You have this amazing big success and the first thing everyone asks you is, what are you gonna do next?

44:47 David Booth: Yeah.

44:48 Joel Little: I'm like, geez, man, I just did something pretty good.

44:52 David Booth: Like, pretty good, you know?

44:54 Joel Little: And yeah, like it is, I totally resonate with that feeling of like proving to yourself that you can do it again.

45:00 David Booth: Yeah.

45:00 Joel Little: That was definitely the feeling that I had.

45:03 David Booth: Yeah.

45:03 Joel Little: Like working on subsequent ventures. And I think I can relate to the feeling of that kind of exit too. Like, you know, there was a moment for me in 2021 where Vind and Timely both were sold or acquired within quick succession and felt great. Like it felt really validating to know that all of that work work that we'd put in with all of those people. And it had been a rocky road for both of those companies. But to have that as kind of the thought that would stick in people's minds about those companies, that was, yeah, it was a nice feeling.

45:37 David Booth: Yeah, that's cool. So did you have like, afterwards, was it a daunting feeling, what's next? Or was it like, you're excited or?

45:45 Joel Little: Yeah, so more recently, no, I feel like I went through this, post-Trade Me where I found myself getting quite angry when people asked me what I was gonna do next 'cause that had been hard enough in my mind. And I was really lucky that the way that that fell for me, I was able to start into a new startup, which turned into Xero, which was ridiculous. But that was a young team and it was sort of, we were starting again a little bit. And so yeah, I guess I went through that then rather than more recently.

46:15 David Booth: Right. Yeah, got a bit more perspective on it now. Yeah, that's right.

46:20 Joel Little: And I mean, yeah, I'm interested to hear what you're doing now, now as well, because like you haven't just kind of— No, I'm still just doing— Taking the money. You're doing the work, but you're also doing Big Fan. So talk a bit about that because that's super interesting to me.

46:34 David Booth: Yeah, so we were— and to be fair, we were doing— we'd already bought the building before we sold the catalog.

46:41 Joel Little: Yeah, which does speak to the royalty checks you were getting, Joel, just for clarity.

46:44 David Booth: Yeah, I mean, I was just wondering I wanted to do something nice, man.

46:47 Speaker C: Yeah.

46:47 David Booth: So my wife and I bought a building in Auckland in Morningside and we've set up a charitable foundation. So we've renovated this building and turned it into a not-for-profit multi-room recording studio and live music venue, all ages live music venue.

47:06 Joel Little: Yeah.

47:06 David Booth: Thank you.

47:08 Joel Little: Yeah.

47:09 David Booth: Yeah. And it's cool too. Like it's a great space. There's a real lack of especially all-ages venues around. This is like 200 capacity. It's perfect for new bands to come and cut their teeth. And we put in state-of-the-art sound system.

47:21 Joel Little: Cut their teeth, did you say?

47:22 David Booth: Yeah, yeah, yeah, yeah. State-of-the-art sound system. And all the studios have all the same gear that I have in my studio. Like, it was— I really wanted to make a point of making sure everything—

47:32 Joel Little: Yeah.

47:32 David Booth: When people are in there, they know that they're using the same stuff that I use every day to—

47:35 Joel Little: Yeah.

47:36 David Booth: To make, you know, big songs.

47:37 Joel Little: It must be awesome.

47:38 David Booth: It's so cool. And we've just— I mean, we just, uh, have had a whole run of different programs that we've done over the last year. And one of the things that I got sent through some stats yesterday, one of the coolest things was in the, we've been, we did this thing for a year and a half and through all the programs, 205 songs were written by new, like younger writers and producers, which is super exciting to me. Thank you. Just the fact that 205 pieces of music Pieces of art that didn't exist now do.

48:10 Joel Little: Super cool. Yeah, yeah. I mean, this is how ecosystems develop, right? So well done for doing that. And the exact same thing in startups, like seeing the people who have worked on these companies that I've had the privilege of working on at the very beginning now come out of those and start to work on their next ventures or even just feeding their advice into the next generation of ventures. Like that's how success builds.

48:32 David Booth: Yeah.

48:32 Joel Little: Well done, man. Thank you. I think the screen is about to start flashing red at us, so.

48:37 David Booth: Cool.

48:38 Joel Little: Thanks so much for your time.

48:39 David Booth: No worries. It's been a privilege to chat to you. It was fun to chat. Yeah.

48:42 Joel Little: Thank you, guys.

48:45 Speaker C: And that's a wrap. Thanks for listening. As a quick reminder, make sure you hit subscribe over on your favorite podcast player so you can keep getting stories like this landing in your feed every Friday to help power you through those weekend chores. For my day job, I'm an entrepreneur in residence I'm Darryl Booth, and an investor at Blackbird Ventures. We're backing best Kiwi and Aussie founders no matter where they are in the world, back home with global ambitions or out there building generational companies. My personal sweet spot is pre-seed and seed. I like to say there's no check too early, so drop me a line anytime. That's dbooth@blackbird.vc. This episode was produced by Day One, the podcast network for founders, operators, and investors, and is part of the Day One network. Thanks again. Look forward to seeing you back next week.