Grand Slam Journey
Grand Slam Journey explores how lessons from competitive sports shape life, career, and business transitions. I host conversations with athletes, business leaders, and tech innovators, uncovering purposeful mindsets and tangible strategies — from leadership and trust to decision-making frameworks and emerging technologies, such as AI. Each episode offers actionable insights for thriving physically, mentally, and professionally, helping you navigate transitions and unlock your full human potential. Available in audio and video on YouTube.
Grand Slam Journey
90. Josh Simons | From Musician to CEO: Building a Career Beyond the Stage
Klara Jagosova speaks with Josh Simons — musician, songwriter, entrepreneur, and CEO of Vinyl Group — about his journey from touring internationally with indie band Buchanan to leading Australia’s only ASX-listed music company. Josh shares lessons on creativity, performance, and building sustainable careers beyond the stage.
Drawing parallels between music and sport, the conversation explores:
- Growing up in a music-driven family
- Transitioning from artist to entrepreneur
- Performance, discipline, and career longevity
- The creative process behind songwriting
- AI, leadership, and the future of music
Whether you’re a creative, founder, or leader, this episode offers practical insights on reinvention, mindset, and long-term success at the intersection of music, business, and technology.
🔗 Connect with Josh: 🌐 Website ︱ 🔗 LinkedIn ︱ 🎤 TEDx ︱ 🎥 Final Investor Video of the Year (LinkedIn)
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Vinyl Group is a portfolio business that has two main arms. It's got a media arm or a publishing arm called Vinyl Media. And then we've got our sort of platform side, which is our music technology companies, that all have in common this mission to connect people in the creator economy. So my real passion and zest in life is to help folks that make things and fans that consume things find easier ways to come together, extract value from that relationship. And then my job as a business person is to extract value out of that union for the business itself. And if I'm creating value for the entire sort of music ecosystem, we should be rewarded for that. And so that's sort of why we exist is to go and do that, because it is a very fragmented market, and there's plenty of interesting tools and products out there that do connect fans with um with creators, but there can always be better ones, and we're always in pursuit of a better consumption ecosystem, for lack of a better word. So it's a kind of very hyper-specific mission statement on the one hand. On the other hand, it is a portfolio company, so we have room to experiment. And you see that with delving into media and connecting these sort of legacy brands that have real value but in new modern ways. And so you see that in some of our titles on the publishing side, like Rolling Stone and Variety and things like that. So it's not a company that you would start up in your bedroom and go, I want to start a portfolio business. That's not how startups typically happen. But I suppose the history of it's probably important. I founded one of our companies called Vampa, and Vampa is like a social professional network for musicians. So you're Clara, you're a singer and you're looking for your hands.
Klara Jagosova:Hello, ladies and gentlemen, and welcome to the Grand Slam Journey podcast, where we explore the intersection of sports, business, technology, and leadership. My today's guest is Josh Simons, musician, songwriter, entrepreneur, and CEO of Vinyl Group. Josh's Journey spans from touring internationally as the frontman of Indie band Buchanan to building and leading music tech companies shaping the future of the creative industry. In this conversation, we explore Josh's transition from artist to CEO, the discipline behind performance and longevity, lessons from touring with major bands and artists, such as Coldplay, Keith Urban, and Curry Underwood, and all that it takes to build sustainable careers in music and beyond, which is what Josh is focusing on currently. We also discuss creativity, leadership, the role of AI in music and business, and how to reinvent yourself while staying true to your craft. If you enjoyed this episode, please consider subscribing, leaving a review, or sharing it with someone who would love it as well. This is your host, Klara Jagosova. Thank you for tuning in and enjoy the listen. Hello, Josh. Happy Thursday for you, Wednesday here in the US. Welcome to the Grand Slam Journey podcast.
Josh Simons:Thank you for having me. And uh yeah, Thursday morning, which means we're on the uh the tail end of the week, which is always a good place to be.
Klara Jagosova:Yes, and I'm so excited to have you. I know we only have about 55 minutes for this conversation. I want to give you all the space there is because I've been diving into your background uh as a musician, transitioned into entrepreneur and Oreo building, and your journey is so fascinating. So I'm curious where this conversation takes us. But if I could maybe do a quick intro for you, and then you can add whatever you want listeners uh to know about you. So you're a musician and the chief executive officer of Vinyl Group. I've seen some of the numbers and some really cool videos you've presented at the end of the year. So we'd love to dive into that and the creativity and uh all that you're building. You've historically raised uh over 35 million from various sources for your technology startup, which I know actually had now also become part of the vinyl group. Have toured around the world with your band Buchanan, and have lived in various places and cities like LA, London, Sydney, and Melbourne. I've also heard you have multi-citizenship, is that correct?
Josh Simons:Yeah, you got a few different passports, yeah.
Klara Jagosova:That's always helpful for traveling around the world.
Josh Simons:Yes. Makes it easier.
Klara Jagosova:And so overall, we'd love to learn just about your background, music, and even your upbringing. So before we go there, I want to give you an opportunity to introduce yourself, anything else you want to add and you want listeners to know about you.
Josh Simons:No, I think that's a pretty good summary. Yes, started in music. I mean, I'm still in music. I just I sit on the other side of the table now. So started as an artist and now I'm work on the the business of it all, which happens to a lot of artists that that don't make it. So had a decent music career, but it it had a shelf life, and then I moved into the the business side of things, which is where I am today. But I think that sums it up pretty good. It's um been an interesting career. It's taken me around the world. I've um done a lot of cool things on paper that certainly sound exciting. So hopefully I can share some of those stories today.
Klara Jagosova:Yeah, super cool things on paper and in real life. I look forward to diving into that. You toured for 10 years?
Josh Simons:Yeah, yeah. On and off. Much to my various managers' dismay. We we weren't very consistent with touring. I did have a thing towards the end where I always wanted the next um tour circuit to be bigger than the previous one. And so if there wasn't an audience for it or there wasn't an appetite for that, then we would go on hiatus until something happened that justified a a bigger run, if that makes sense. So we we didn't tour consistently, we kind of did it in in sprints. But most bands do it like that. Most bands will spend some time recording a body of work, like an album or an EP, and go into the studio for a period of time, maybe six months a year, and then they'll tour it for a year or two, and that's the cycle. And we kind of adhered to that, sort of.
Klara Jagosova:I'm actually curious because your background is just a little bit different than my typical guest because of the music. I typically interview guests at the intersection of sports business and technology, but I actually find there is a lot in common or my hypothesis about it. Being a professional musician, obviously not just the touring. If you're an athlete, you travel around the world, you live out of your tennis bag almost 200 days a year. So I imagine that's quite a bit of what music is about, and just that passion that you have to be committed and train and practice every day your craft with obviously your band. So maybe just go to the beginning. I've listened to a few of your other episodes and podcasts you were on, and I've heard there was influence of your family, your dad and grandfather were in the music industry. So perhaps that came naturally. But I'm always curious about my guests. Was there upbringing like? And how did you actually uncover the first passion for music? How did the journey start it?
Josh Simons:Yeah, it's interesting. I mean, a few things you said there, I'd separate them apart. Like, for example, the discipline of being a touring musician, being on the road, training for that, that really has nothing to do with my upbringing at all. That was a skill you learn. And music, unlike sport, typically starts as a little bit more destructive to the body. So when people first start touring, you know, they probably drink a little bit too much and they and they probably stay up a little bit too late and all that stuff. But to be fair, I know plenty of tennis stars that also do that. But then what you learn relatively quickly, certainly in your 20s, is that um if you want to do this professionally and be in the top tier, then you you've got to add a little bit of discipline and structure to that. And and so that just came from being on the road. That didn't really come from background or nothing really prepares you for that except your drive and your motivation to succeed. The music industry connection and more broadly the interest in the music, that definitely came from family. I mean, I my earliest memories of being in this world were sitting in rooms with various family members working on music projects, consuming music, just listening to stuff around a record player or cassettes, even. And that was that was our life for the first ten years of being alive. There's always a link back to the that world. For better or worse. Sometimes I I wonder if maybe it would have been simpler to just go into finance. It would have been more straightforward. Music's a hard space to make it work in because um there's a lot of people who want to make it in music, and there's it's not a huge industry. There's not a lot of money to go around. It's a it's such an interesting art form because it's something that everyone in the world consumes. You know, you'd be hard pressed to find someone who says I hate music. I'm yet to meet someone who says I'm not a music man. But as an industry it's it's not that big. So that it's a really hard space to crack. But certainly having a family that worked in it for generations, it sort of Yeah, it was probably a given. I don't know.
Klara Jagosova:Well, yes and no. I want to comment on a few things. Certainly, as I've been thinking about this interview and the importance of music, I think it's the one fabric that unites the whole civilization. I mean, it's it's part of our history ever since we remember and books write about. I actually come from a tiny area of Czech Republic, very traditional. Everybody sings, even though poorly. So it's like I've been around music, but um people pay me to shut up. Let's just leave it there. But music is part of just every single get together, whether it's family or holiday. I mean, I've used music for my tennis performance. So I always had a playlist. Yeah, there's just something that happens to our minds when we hear the right songs that we resonate with, whether it's, you know, you can call it meditation, people can call it trance, people can call it celebration. There's just so much that connection. And to your point, I love watching AGT because you just see such an amazing amount of talent that come on the stage and are just so inspirational sometimes to see these people that can barely sometimes talk, and then they start singing and it completely transformed to something else.
Josh Simons:It's that universal language, isn't it? Sport's the same.
Klara Jagosova:Yes.
Josh Simons:Sport's amazing like that too, because you watch a soccer match between two countries that speak different languages, and you look at the stadium and all the people and all the fans, politics and and language barriers, they all go out the window, and people are just there rooting for their team. It's so exhilarating. Tennis is the same. Music plays a similar, similar role in uniting folks, and and that's why there are you know some musical artists that are able to tour the world and play in every continent, and the music just resonates, even if it's not the official language. It's it's a beautiful thing. It's contagious.
Klara Jagosova:Yes. And it actually makes me ponder. I I want to dive into this because you have seen the top. I mean, you've toured with people like Cold Blay, Kerry Underwood, you've written songs for Kanye West as some of the best. And still I ponder, there's so many talented people to your point. How do you see who reaches the top and gets that shine of a light versus those who sometimes don't? What do you see the difference is?
Josh Simons:Well, obviously talent goes without saying, but there's plenty of talented people in the world who don't never make it. So there's a few other factors at play, right? And in fact, one of the reasons why I got into the business side of it was to fix some of these problems. But part of it's geography. So you you've you've got to be in the right place at the right time. Now, people sometimes put that down to luck. That's not really luck. You can pay to be in the right city and and and live in the right neighborhood and hang out in the right bars and and that certainly kind of is a pathway. It's not a guaranteed pathway, but it works. So you can if you're not born into the like sometimes where luck plays a role is you can be born into the right place. But if you're not born into it, you can certainly get on a plane or a train or you know, you can find a way to get into the to the place you need to be. So so geography plays a a massive role. Just to be more specific, you mentioned you know, writing stuff for Kanye West. Like that that was just a product of me moving to LA and and in the first few weeks, reaching out to, you know, whoever I I knew that was out there and and happened to be connected with one of his producers. It it just it it wouldn't have happened if I wasn't in town. So that that's an example of just being in the right place at the right time. Um but also putting yourself there. So there's talent, there's geography, and then I think like the third ingredient is just stubbornness. So it's interesting actually the parallel to sport because if you want to be the front man in music, you really need to do everything I just said before the age of 20 for all kinds of reasons, but mainly for mass appeal, to appeal from everyone, kids to adults. So you kind of need to do you need to have honed your craft, be living in the right place, and been at it for a while and stubborn since you were probably like 10 in order to to get there by 20, right? Which is crazy because most people don't even know what they want to do as adults, let alone as kids. So that there's that. But if you're not interested so much as being the front person and you're you're content being a songwriter or a manager or someone that's just a little one step more behind the scenes than the front person, then you've actually got time up your seats. And the the comparison to to sport is that obviously to be an elite uh tennis player or footballer or whatever, you're getting recruited at sometime in your sort of teen years probably. Um and you'll come into your peak in your twenties. And so it's the s it's very same similar in music. But again, behind the scenes people, coaches, what have you, they've actually got a lifetime to hone their craft, refine their contribution to the space. And this is where I say that third ingredient, I think, is stubbornness, because if you stick around long enough and you don't piss people off and and you work on building relationships and what have you, I think typically things will fall into place for for folks.
Klara Jagosova:The longevity and there's also something about performance, if I just stay on that. Curious how you think about it. In tennis, there's a physical performance, let's say I take the sport I have played. So you can see Novak Djokovic, for example, now is an incredible athlete, and I still ponder how we can outrun the 20-year-olds because there's like a real difference between our body regenerating in like 30s or late 30s versus like early 20s. I've lived through it, so I can feel personally the difference. I also know there's something about preserving your voice and how you're singing. Singers talk about it because that's important as you age and you're obviously performing on the big stages. How much of that do you think about or have you thought about, or is it natural progression as you continue touring that longevity and preserving your voice and refining that style, obviously, presence and everything on the stage?
Josh Simons:Yeah, it's a fascinating topic. The the voice one in particular, like a lot of singers who start touring frequently. So, you know, you sort of come out, you you release your first few songs, and all of a sudden you've got a few fans and there's demand to see you. What happens in that sort of first couple of tours, at least with me and and many others, is you get these nodules which are like calluses inside of your your vocal cords or pre-nudules. It can be a bit scary at first. And then in my case, I had to go and train like an athlete, and I had to learn something called um speech-level singing. So it's where you relearn how to sing. And instead of singing entirely from your diaphragm, you're singing mainly using the muscles in well, your power's coming from here rather than right down there. And it means that the volume is a little bit more controlled. You're not going to be quite as loud. You're also not going to be as soft, but you'll have more control over your pitch, and you can do it more sustainably. Uh, and that's the key thing, is like being able to do it every single night. Then the other key is is warm-ups. So I had to do 30 minutes of warm-ups every single night. And there's no cheats for that. Like there's some sprays that people have that's a combination of, you know, sugar water, anti-inflammatory stuff, but they are all just band-aids to get you maybe through a difficult moment. And some people do destructive things like take steroids, but it doesn't help in the long term. It just it's again, they're just dangerous band-aids. So really the only way around it is to learn to sing in a a safe way. And I chose that method, but I'm sure other people have different views on on how to do that. And then, yeah, ha have some little things that help you get through a show. Because there'll be nights where it's not working. I had I remember we've got a live album on Apple Music called Alive, and the night we recorded that I lost my voice. Not not just a little bit. I couldn't speak. I I I had nothing was coming out. And we nearly cancelled the show, but because we were recording it, we couldn't. And I was like, this is the live album for the whole tour. I was so upset. And I warmed up for like two or three hours. Just we we went back to one of the band members' homes because I didn't want to be at the venue. And we just sat there and just did it on loop, on loop, and then a bit of noise started to come out, and eventually a lot of steaming as well. So putting my head on a steamer and just breathing in steam water. And with the voice came back, and we were able to do a show. But that was only possible because there was the vocal hygiene and and the tools uh that were, you know, pretty well understood there available to to do. Um and watching artists like Coldplay and and Chris Martin as the front man, and how they're able to do ten shows in a row in a city. And and and you know, they're they're in their for late forties. And you know, to your the second half of your question, I would suggest that the the only way that they're able to do that is is conditioning. I was talking specifically about vocal conditioning, but then there's there's body conditioning and front men need that because they're running on, you know, in Coldplay's case, it's two hours of running around a stage. That's really hard to do while you're while you're singing at the same time. I know Beyonce famously runs on a treadmill and sings at the same time. I I think most people do that. Now I did that. Um it's really the only way to practice that. But it's yeah, it's just conditioning, and that's probably the same with with Novat, right? Is when you do it consistently for that many years, your body just gets used to it, and that's probably why. But it is crazy that someone in their forties is still uh to your point able to outrun someone in their twenties when as we all know, I'm in my the second half of my thirties now, things take longer to heal.
Klara Jagosova:Yes. I've censored myself the older I grew, the more admiration I continue to have, obviously, for him, and then You have to fine-tune. I'm guessing it's the same with music, what you had mentioned. Actually, as you continue to grow, there's different things that you have to add or remove that will make you better and more successful. So in ma in many ways, the things that brought you success in your 20s are not necessarily, in fact, sometimes completely opposite to what you may need to do and start adding in your 30s, and how much time you start focusing on the rehab and order additional things to support your performance. So the hours and where you spend your hours in a day are distributed somewhat in different activities. Is that similar?
Josh Simons:I think just because anyone who's sort of still actively touring into their 30s and 40s, you'd have to assume they might not be the biggest band in the world, but they've turned it into a career at that point. Just by virtue of that switch from uh flash in the pan to career, I think almost um certainly your priority it's not so much that they shift, but there's just some things you need to do less of for it, for example, practicing early on is really important as a band. Like you certainly we would do like three or four nights a week. When you're actively touring, you might do that in the lead up to a tour, but once you're on it's like being on the circuit, once you're on the circuit, practice stops because your practice is the performance. Now you might do soundcheck, which would be like warming up, but your your need to sort of do extracurricular hours of that, it sort of it diminishes. And so you you're probably focusing more on your general health than the actual craft itself. And in some ways, I think as you get older with everything, when you give space to your primary focus or area of expertise, it actually gives it room to improve rather than what you do when you're in your 20s, which is sort of hyper focus on something to build to build the muscle. That's probably that shift that happens. I see it in business too. When you start a company, you're over every single little detail. And then there's a point in time where it actually becomes important that you can step back a little bit so that you can take an objective view of of how things are going and that that makes you a better operator. And I imagine that's the same in sport, and it's yeah it's the same in music.
Klara Jagosova:Mm-hmm. I love that. Um, taking a note because I want to come back to it. But before we transition, I'm curious. I've been listening as a preparation for the podcast to your uh songs and uh some of your albums. Do you have a favorite one, Josh, that you and the band played or that you wrote? I don't know if there's different ways of favorite ones, the one you performed versus what's your secretly favorite?
Josh Simons:Yeah, that's a good question. I mean, there was um a song I'm very proud of called Run Faster. It came at a tricky time for the band when we were one group of four men, and then we were offered a record deal, and that deal fractured the band in many ways. And and so that was the first song I wrote after the band was a bit fractured, and I had to kind of rebuild some of the people. And the way I write music is kind of the way I I approach business, is I do I love collaboratively working. So I might have 10 people in a room and go, you try this, you do this, you do this. And and just having all those people around makes me more productive. Um, but it also brings something unique to each song, each album, each tour. So I love assembling people as a general rule. Every venture I've ever done in life is just literally assembling people and and creating stuff. I love that. Run Faster is a bit of an exception because it's probably the only song I ever wrote, like end-to-end, I'd say 99% without input. It was almost all me. And it also happened to be probably one of our bigger songs. So I love that song. I don't ever listen to it. I don't think I've listened to it in a probably five years, but I'm proud of it. I know how it goes. Um and then we only did two proper albums, but the second um second album had a song called Um Coming Down, which is like a dance song that that did okay in um in Europe, but more so than Australia, where everything else kind of happened. That song was just written during a period of change for me. You know, I'd I'd tried living in another country for a while. I got quite sick, my first ever kind of serious health scare, and I didn't really know I didn't really know how to handle myself, I didn't really know how to handle people. When I reflect on it, it wasn't the nicest years of my life. Like I wasn't very kind to myself or to others, and and I was a bit probably a bit resentful and angry as a young as as plenty of young men go through a stage like that.
Klara Jagosova:But I wrote And women, I'm pretty sure. Yeah. I'm sure.
Josh Simons:Yeah, I'm sure I just don't have that I just don't have that perspective. But I wrote that song in the middle of it, and it's it's a dance song, and it's a very personal song, and but it's also gentle and and kind of lovely. So there's something about that that it wasn't our biggest hit by and like it didn't really do all that well. It again, it sort of did okay in I think in Ibiza. But aside from that, I'm really proud of it. I'm proud that I was able to make something beautiful in a period of chaos.
Klara Jagosova:On that note, um, always curious about real creators. People say podcasters are creators. I was like, sure, yes. And I I I don't consider as real creators.
Josh Simons:I mean, I'm it's a different art form.
Klara Jagosova:Yeah. I'm just curious how you come up with everything from scratch. Like how do you come up with the song, the melody, the lyrics? What does that process look like for you?
Josh Simons:Well, every song's different. But as I got better as a writer, and I've written far more songs than so there was my band that for people listening, which is called Buchanan, and that was it was a fun project, but it was quite a short project. It didn't last that long. And there was only two albums and a few EPs. But I've written many more albums than that for other people. And so my writing career is longer than my artist's career, just for context. As I got further and further into my writing career, I started writing lyrics earlier in the process. This is different for everyone, by the way. But earlier on, I would write all the music first. And there's merit in that too. So I'd write really interesting music and I'd I'd sess over instrumentation and string parts, oboe parts, and all this. I wanted to make it as big as possible. I just kind of, when I first started, I just wanted to throw the kitchen sink at everything. I just loved maximalist stuff. And then lyrics were kind of an afterthought. Thank God every album I ever did, I would have a theme. So that helped censor the lyrics and it kind of acted as a quality control. But if I didn't have that, they probably wouldn't have been very good. Later on, because I was working more with other people and you'd go in and you'd go, What's your project about? How are you feeling? What's going on in your life? I would prioritize writing lyrics earlier. And it changes how you write songs. It makes it more about the story and less about the sound. Um, although good songs are a product of the two in equal parts. So yeah, that's a that's a very long way of saying it it sort of changed over time. But in terms of how do you do it, I don't know. How do how do you play tennis? Yeah. How does anyone do anything? Like it's it's something that you like doing, you put the time in and you realize at some point I'm okay at this and you get better at it. But yeah, I don't know.
Klara Jagosova:But I would have thought it requires probably a lot of reflection, a lot of observation, because you always have to put in some sort of emotions or unique perspective into that story. One thing I I'm in Austin now actually admire comedians as well. I've been watching a lot of the comedy shows, Kiltawney, et cetera. Comedy is really big here. I was like, oh my god, that would be so cool to get on a stage. And then you realize how hard it is to write a one minute of a really funny, you know, story or something that trails from A to Z and has a narrative because the vast majority of people who are on the stage fail, right? So I'm I'm kind of putting that perspective. Yeah.
Josh Simons:Yeah. Comedy is different altogether because most professional people in the arts will probably agree that comedy is the hardest art form. The reason being is that every 15 to 30 seconds you're pushing for a laugh, which means you're constantly setting up for your next act, right? Where with with tennis, we break it down obviously into sort of game, set, match. Music, we break it down into tracks on an album, but we're talking about 12 tracks, one album, four points, you know, six games, three sets, two sets. You know, so that there's sort of we break it down. Comedy's hard because you've just got to go hit, hit, hit, hit, hit, hit, hit. So I think most most artists would agree that the comedy is probably the hardest art form. I was actually in Austin about a year ago at the mothership. I also love comedy. It's it's my as a fan, it's my that's my release. It's I spent a lot of time attending a lot of shows and and listening to a lot of things. And so and I love Austin. It's such a great city for that. But yeah, I I just I think that one's a little bit different. It's just harder. I wouldn't want to try it, to be honest.
Klara Jagosova:One more question before we dive into vinyl group. Yeah. I feel like we already have too little time to talk about all your amazing business endeavors that you have, but also curious how it happens you've toured with the big names like Coldplay, Kerry Underwood. I'm actually curious how that match happens. You obviously describe the talent, geography, and then kind of perseverance, just being stubborn and reaching out, not being shy. But how how does it happen? Oh, yeah, let's go do a tour together. This is a perfect match. How do you create that?
Josh Simons:Yeah, well, by doing those things. So in the case of Keith Urban, I I got a call from my agent during a period where actually everything was going a bit quiet. And I I'd put in the effort, I'd been in the right place, I'd I'd been stubborn, I'd made the album, I had the talent, I'd put the effort into the universe, and I hadn't quite gotten anything back yet. And the lesson in that was, you know, that it was the right thing to have put the effort in because then I I got a phone call. I think I was in Meetham in Cannes. Um, and we were there for Vampa, which is one of the vinyl group products, and I was there with my business partner. And it was day one. I sort of thought the band project was on one of these hiatuses again, like, you know, things have gone quiet again. I'm sure at some point I'll come back to it. And then I got a phone call saying, Do you want to go and do this tour? And I was like, uh-huh. It's sort of a validation moment, right? It was and then the tour was only four or five months later. And then when we got on the tour and I I met Keith and I spoke to him, he just said he'd watched one of the I did like a TED talk where we played some of the new album, and he just watched somehow that came up on his algorithm and or someone sent it to him maybe. But he'd seen that and he he said we could have hired much more famous people, but I really liked your energy. And so that's how that one happened. And so that that that is uh just literally a result of putting putting stuff into the world and and getting something back. With the Coldplay one, that was funny because I was in Perth, which is in Western Australia, and um we were actually at a Coldplay show and I got a call from an artist who I would later sign to to vinyl's portfolio of companies. And he called me after the show and I hadn't spoken to this guy in a few years. I knew him because we're in the music world and people have people's numbers. And he said, What do you what are you doing? I said, I'm at a Coldplay show. And he goes, I'm supporting Coldplay in a year. They haven't announced the dates, they're announcing it today or something. Can you help me get that show together? And I said, What do you what what help do you need? And he I need to do get an album together, and I need to do promotion and I need to do some production and some, you know, writing and blah blah blah, all these things that need to happen. And I just said, How can I help? And that's how that happened. So that was a weird one in a good way.
Klara Jagosova:I love that. So it seems like there are some nuances and variances, and sometimes obviously people need to know about you, but also add it perhaps serendipity, like the right video needs to get to the right person. And I I did watch the TEDx doggy performance last night, that 10 minutes or whatever. I'll edit it in show notes. I I agree the energy that super stood out. So transitioning from the music to business, I actually ponder a few things. One, usually it happens when you're a personal athlete, you're transitioning to the next period of your life. There's quite a bit of identity wrapped up in like, okay, what do I do? I'm I'm an athlete, but I'm not anymore now. Whatever you choose to decide for yourself, there's this crisis that you go through. I wonder if it's the same kind of for you or musicians overall.
Josh Simons:It's identical. It's i it's identical. It's the same. And I'm watching a lot of my colleagues who were maybe a little bit more successful than me as artists, who are now well into their 30s and their stuff, it's not hitting, the fans aren't coming back. I think I was so lucky. I went through this like seven years ago. And when I went through it, I was still at the peak of my career. So I was still doing these big shows. I had already started because uh because of what I said, I sort of went on hiatus and I when things were quiet, I'd go and do other things. I'd already started getting into the business side. So then I sort of had this like beautiful crossover where I was able to sort of sculpt how I wanted to enter the business world. Like everyone who goes into business and starts up an idea, there's risk and it costs money, and someone's got to fund it, and you've got to put your time at risk and all that, you know, fun stuff. But I got to do that while still having this music project that was like kind of healthy. And so I had this two-year crossover where music was winding down, but business was sort of ramping up. And I appreciate that most people don't get that. For most folks, I think there's kind of a bit of a probably an abrupt stop to the phase one, and then there's that crisis, and then you ri reinvent yourself and you go and you have your second phase. And I I still went through the crisis, like I still had the emotional sort of thing of what am I, who am I? Um, but I was able to do it um without worrying about money so much, like it still had a bit of a buffer. So that was a really big help. And it was a in hindsight, a fairly graceful transition.
Klara Jagosova:If somebody woke you up at midnight, Josh, would you call yourself still musician or would you call yourself executive officer? Or what's your title? I wake you up at midnight, you have to the first thing that comes to your mind.
Josh Simons:Yeah. Literally, my social team and people who do our marketing and IR and PR, they argue over this. I don't know. Online, they call it a disambiguator. So you are Josh Simon's ex. You are Clara X, and you need what is X? And I'm not comfortable answering the question. I don't know. I wouldn't call myself a musician. I don't want to call myself a business exec. I like the word entrepreneur because it's I think it's all-encompassing. It sort of reflects your ability to do multiple things. But entrepreneur also can be quite a flaky word as well. So I don't know. And also, no one will care once I'm gone. So I don't think it's that important question in the grand scheme of things.
Klara Jagosova:So transitioning to the vinyl group, I've been reading through your website. You're building a technology that connects culture and commerce. What is the big mission and what would you want listeners to know about it? Because there's a lot of different brands. I wrote some of them down, but would love to hear your perspective and view because it seems to be a full, complete umbrella of ideas and projects. It seems like living that musician life actually really allowed you to see some of potential the gaps in the market that seems like you're now actively looking to fill.
Josh Simons:Yeah, that's right. And that's exactly what we're doing. Vinyl Group is a portfolio business that has two main arms. It's got a media arm or a publishing arm called vinyl media, and then we've got our our sort of platform side, which is our music technology companies that all have in common this mission to connect people in the creator economy. So my real passion and zest in life is to help folks that make things and fans that consume things find easier ways to come together, extract value from that relationship. And then my job as a business person is to extract value out of that union for the business itself. And if I'm creating value for the entire sort of music ecosystem, we should be rewarded for that. And so that that's sort of why we exist is to to go and do that, because it is a very fragmented market, and there's plenty of interesting tools and products out there that do connect fans with um with creators, but there can always be better ones, and we're always in pursuit of a of a better consumption ecosystem for lack of a better word. So it's a kind of very hyper-specific mission statement on the one hand. On the other hand, it is a portfolio company, so we have room to experiment and um and you see that with delving into media and and connecting these sort of legacy brands that that have real value but in in new modern ways. And so you see that in some of our titles on the publishing side, like Rolling Stone and Variety and things like that. So it's not a company that you would start up in your bedroom and go, I want to start a portfolio business. It just doesn't sort of that's not how startups simply happen. But I suppose the the history of it's probably important. So I I founded one of our companies called Vampa, and Vampa's like a social professional network for musicians. So you're Clara, you're a singer and you're looking for your first ever producer, you go on Vampa and and you can do that in minutes. And that is actually kind of a microcosm of what we're trying to do more broadly with the group. But I grew that business as a standalone venture for eight years, then I sold it to an Australian public company that I subsequently sort of took over and reframed and re-reshaped as vinyl. And that's how it comes to be a portfolio business because you've got multiple things and assets that you own, and they all do similar complementary things, and then you start working on a portfolio strategy that sort of hopefully helps all of the assets rise and you start bringing products together. And so that's how you find yourself at 35 running a portfolio business. It sort of looks a bit probably funny on the surface. But hopefully when I talk through it like that, it actually makes a little bit of sense of of how something like that comes together over time.
Klara Jagosova:Yeah, I love it. And it connects probably a lot if I go back to some of the experience you described being on a stage and performing and building this tenure and longevity as a musician in the energy. I've seen some of your LinkedIn posts, even last year stating, you know, the cold plunges and sleeping eight hours. Yeah, that's really nice, but the real life doesn't really work that way. So that grid and perseverance that you have been putting into this last year. And I know you had four acquisitions, and anybody who knows MA knows how hard MA, let alone one is, not even four. So just kind of reflecting it can look like all that big mess, but the effort and energy that it takes to put it together in the right way. How do you reflect on just that last year or any parallels you want to draw? How you your musician life being on a tour, I can imagine playing music with those big names and till who knows when in the morning prepared you for that and being able to put in the right hours and effort?
Josh Simons:Well, I think you the answers in the question. So I think doing those big tours, they certainly prepare you for what's required in business. There are times, even the Coldplay thing, whenever that was a year or two ago, they're doing like 360 shows or something. We only did 10 or 11. But by the end, I was like pretty burning out. And that's because I was also running the business at the same time. But those sorts of events, they condition you, coming back to something we talked about earlier, they certainly condition you to understand what's required to make things work. When we're looking at a year that has four MA transactions, first of all, you can't look at it as the whole because you'd be overwhelmed and you wouldn't get anything done. So you get very good at compartmentalizing the whole thing and and breaking it down into chunks and and treating those chunks in sprints and going, okay, we've got to get this done in the next four to eight weeks. So you get very good, I think, as a leader in breaking those down into manageable bits that you can assign to various team members and take on yourself. That's number one. And then the reality is it it's quite lonely during the process, and it it is hard work because there are plenty of points, especially during MA, where it would be easier to just go throw up your hands, walk away. It's all too hard. Anyone who's ever bought a house probably has a an idea of just that, which is something that's been very standardized, and plenty of people go through that. And they're it's still stressful. It's stressful even for someone who's bought many places. And so MA is just like that, but times a hundred. And where there's less structure and where there's more room for parties to, you know, get creative, both good and bad, and and and then experience plays a huge role too, because when you've done enough of them, you can typically have a pretty good um radar or alert of what to look out for and what to solve up front. A lot of it's like what can you solve up front so that it's e it it gets easier as the process goes on instead of skipping skimping on things up front and then having to solve really complex things further in the process. It's hard to speak about um examples of all that without breaking confidentiality rules. M ⁇ A is is tricky business. And I would argue that the transaction is one art form, and then integrating businesses that you've bought into your broader company is a completely unrelated art form. And the the simile to music there is being able to write really good songs has nothing to do with being able to perform them really well on stage. And yet to be a successful artist, you have to be able to be good at both. And it's the same in business. So you've got to conquer the art of buying and negotiating, getting a good deal and not getting screwed over. Then you've got to win at at integrating and not screwing up the culture and not losing the revenue. And so it's not for the faint of heart. But again, you if you looked at it like that, you'd probably go, no, no, I'm not gonna even try it. That sounds too scary. But you don't look at that. As a business person, you you just see it as another exciting challenge, and you you go in and and hopefully, because of experience, you you don't stuff it up.
Klara Jagosova:It seems like you're doing fantastic because there's looking at the number, you've grown 190%, 14.4 million is it as of end of last year, and four acquisitions. And then I've been reading actually, this is something that I'm also curious how you, as a musician and creator, look at it. You're positioning yourself or a profitability and also boosting the profitability with AI and some of the focused cost control strategy. So, how do you look at maybe there's two areas obviously AI within your business, and that could be quite a bit from operational perspective. How do you automate things, maybe add agents to where there's silos or where there's things that are just repetitive and mundane, but also how do you see the AI in the music industry? Because there is a lot of talks about AI now being able to create music and songs and lyrics. I actually have a bunch of apps on my phone that are able to do that. Curious about your perspective.
Josh Simons:Yeah, you can you anyone can type in a prompt and make a pretty high-quality song now. It's amazing. The chat around um AI, even around our company, has been really hard because everyone, when I talk about AI, I think people think I'm talking about generative music AI, and I'm not. We don't currently own any companies that have a horse in that race. I did a panel with the president of Warner and a couple of other labels and uh a few months ago in Sydney. We were talking about this topic and they get very fired up because for them it's you know, there's a copyright um dilemma and and they represent the interest of artists and all that. And and to an extent we do too. But again, we don't really have a horse in the race because we're not making those products. And what I've learnt from being in music, also just watching the industry forget about participation, is that every technological interruption or change inevitably has to be embraced. And the music industry usually wins the sooner they get on board and and do it legitimately and get licenses in place and commercialize these new technologies in ways that are beneficial to the maker of the technology, the maker of the music who's teaching the technology in this case. But my point is it typically gets worked out. So my position on generative AI is I think it's really cool. It's another tool. I don't think it replaces humans, not in its current state. I think it it it's an interesting ideation tool. And obviously the big caveat there is I only support it if it's properly licensed and the original rights holders that are whose music it's being trained on are getting remunerated. That should be a no-brainer position. And yet I've found that I think some people haven't been very clear on my my stance on that. So I'll be clear there. On generative AI, think it's cool. I think other people will solve it, and obviously the original creator should be remunerated. Moving that to the side, because I, again, I don't actually have a horse in that race. I'm far more bullish on the role of AI in business process automation. We've done a lot of work in that area already, and I find that endlessly fascinating. It's actually it's kind of not sexy when you get into the geeky parts of it, but it's also incredibly tantalizing to consider how it can be so transformative and accelerate things in the way that funding once upon a time might have accelerated certain things. This is available for virtually nothing from a cash perspective. And so that there's just so many ways that I'm watching other businesses use it. We've done quite a bit with it. We've spoken a little bit about how we've incorporated it. As a public company, we've always a little bit more delicate about uh exactly how and when we talk about things and and what we're doing. But we use it every day, we talk about it every day. It's a real focus at the moment uh to how do we get 10x results out of certain parts of the business that we previously weren't getting much growth in, and and AI is making all of that far easier to consider and and it gives us more options when we strategize as sort of managers of the group and we look at well, we've got limited resources to a portion to each of our companies inside of the portfolio. AI just completely upends that because now we we've actually got unlimited resources if we bring in people who can get agents that are working with each other or with a supervisor. And that's where we were just able to run and grow uh much faster than we could before with whatever cash flow we had available to us.
Klara Jagosova:Yeah. I love that you're really using it as an amplifier where it works best and how do you continue to do more. I love using it for the mundane things, but how do I use my brain energy for the things that really, really matter and where I can truly add value instead of like filling out a form that AI can do pretty easily.
Josh Simons:Yeah, well you see you there's like you read a lot about AI slop and and uncertainly when I see feedback from folks that maybe aren't technologists or entrepreneurs or in creative fields, and I see a comment on my personal Facebook feed about how AI is crap or it doesn't do this very well or that. My experiences, and this is applies to almost anything in life, it well before AI, is the quality output is usually determined by the quality of the inputs. And so if you're putting in good information, good plans, good data, good direction. Some people call that prompt engineering, but whatever. Give me good direction, good data. And I've typically found that it can be for me, things that used to take me six hours, I'm doing in six seconds and multiple times a day. I think it's objectively made me a better business person. There's no two ways about it.
Klara Jagosova:I love that. Sounds like we might do next episode how Josh is effectively applying AI into a business. That would be awesome for many to learn. I know we're right on time, Josh. I have two quick questions that are the only two questions that are consistent for my guests. Number one, 2026 is starting. What would you want to inspire people to be doing more or for lyself?
Josh Simons:I think the message I sent to my team this year is I just want to see um I want to see everyone playing to their strengths this year. This kind of is because of partly what we've just been discussing. But in a startup, everyone's wearing 30 hats, and then you hit a certain scale, and I don't think we're quite there yet, but we're approaching it, where your requirement for generalists shifts and you suddenly need specialists. And it's a pretty aggressive shift. And I'm seeing that we're living through that at the moment. And so from a culture standpoint, rather than just turning over the whole business, you instead I think start to understand what are people's strengths and and how can they play those specialist roles. It's more of a shuffling of the chairs on the deck rather than, as I say, throwing it all out and starting again. So that's my focus this year is identifying strengths and then really amplifying those in people.
Klara Jagosova:I love that. And I do see that in synonym when applied well with AI. That's pretty much kind of the path to success. And the second question, this one hopefully is super easy. I will add your LinkedIn and your website to the show notes. But is there a specific way, your favorite medium, how people may want to reach out, get in touch, or follow you?
Josh Simons:Yeah, probably LinkedIn. Who would have thought if you told me 10 years ago that's where I hung out most online, I'd say, what happened? What went wrong? But um that's how it's turned out.
Klara Jagosova:And keep doing it. I've been following you obviously now for a while and your posts as well as your creativity. One of the questions I know we we didn't have time, but I love your musician talent adding it to make your earnings reports and updates fun and entertaining. So continue with that.
Josh Simons:Yes. We're not quite sure when we're gonna restart that this year. It will happen at some point, but we're gonna take a little break for a few months.
Klara Jagosova:I'm certain it takes a lot of preparation alone, and uh it is fantastic.
Josh Simons:The last one took a bit of extra work, so we're taking a break.
Klara Jagosova:Yeah, that was great. The video that we are the world song where you guys recreated. I will add it to the show notes for anyone who wants to listen. I thought it was fabulous. Thank you. Josh, thank you. I certainly wish this conversation was one of the longer ones. I know you're tight on time, but I appreciate it. And if you're in Austin, I don't know if you're going to South by Southwest this year, but we'd love to meet up in person for dinner or maybe go to the comedy show together. Yeah, yeah, yeah.
Josh Simons:100%. Let's do that. Okay.
Klara Jagosova:Awesome. Thank you so much. Have a great day. If you enjoyed this episode, I want to ask you to please do two things that would help me greatly. One, please consider leaving a review on Apple Podcasts, Spotify, or any other podcasting platform that you use to listen to this episode. Two, please share this podcast with a friend who you believe might enjoy it as well. It is a great way to remind someone you care about them by sharing a conversation they might be interested in. Thank you for listening.
