Fn 18: Purple Reign: What it Was Like to Work with Prince

"I think he had every brilliant idea executed in Silicon Valley years before..." — Phaedra Ellis-Lamkins

How do you go from fan to colleague to friend with an icon?

Prince’s manager, Phaedra Ellis-Lamkins, and Sam Jennings, one of Prince’s webmasters, take us on a journey of growth and evolution of an artist realizing his worth and his power. As part of a team of trusted friends and confidants, they helped “The Artist” realize tech dreams that would serve us all. We also learn that the vision of freedom we often associate with Prince isn’t what we thought.

Big thanks to LinkedIn for supporting the second season of Function.

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Anil Dash: Welcome to Function, I'm Anil Dash. So last time around, we talked about how Prince used technology to make amazing music and to talk to his fans. It was an interesting theme that emerged, which was, whether we were talking about the way Prince used drum machines on albums like 1999 and Purple Rain, or the way that Prince connected with his fans online. The common thread here was that Prince was extremely savvy when it came to technology, but he always engaged with technology strictly on his own terms. That really sets up where we're going on this episode.

Anil Dash: You might know just recently Prince's memoir was released. This is a posthumous memoir, but it was something he was working on before he passed. Dan Piepenbring who edited it does a really good job of capturing stories about Prince's early life and it's very moving and very touching as a glimpse at that. But interestingly, Dan also captured notes from his conversations with Prince around the time. And those are very focused on a very straightforward message, which is that Prince wanted everyone to create, especially black creators, and he wanted everyone to own what they create. So that idea of artistic control was probably the most key message Prince wanted to get out in the world other than his music.

Anil Dash: He fought for 20 years to get ownership of his music, his master recordings, the original work of art, and at the end of that 20 year battle, he won. Looking at it through that lens and from my seat where I sit as the CEO of a tech company, he really was a technological pioneer. We don't think of Prince as a guy sitting in basically an office park, in a suburb, in Minnesota, at his computer reflecting on how a multi-billion dollar industry would evolve, but that is absolutely one of the aspects of his career in his life. He had a vision 20 years ago that ended up being dead on.

Anil Dash: So this time around on Function, we're going to get deep with two of the people who did the most to help Prince achieve that vision. First up, we're going to talk to somebody who helped make possible Prince's recent memoir. But she had been working on a much larger, much more important project with Prince for years earlier and that was him getting back ownership of his music. And for the very first time, Phaedra Ellis-Lamkins, who was Prince's Business Manager at the time when he got back ownership of his master recordings, has agreed to talk publicly about the work she did with Prince. Phaedra, thank you for joining us.

Phaedra Ellis-Lamkins: I'm happy to be here.

Anil Dash: Tell me, how do you end up working with Prince?

Phaedra Ellis-Lamkins: So we both had a friend in common, Van Jones, and Prince had long been in a battle with his masters, and I'd met Prince a couple of times through Van and Van had kind of said, "If you want to get something done, you should work with Phaedra." At the time I was pregnant, so I was on maternity leave. Van said, "I think Phaedra should go to these meetings," and Prince's lawyer had been negotiating with Warner Brothers and so that's like I'd met him a couple of times and then I just ended up at a meeting with Warner Brothers, with his lawyer and Van.

Anil Dash: That seems like a pretty extraordinary start.

Phaedra Ellis-Lamkins: It was extraordinary. It's like be at a meeting and learn what the difference between a master recording is and a publishing, and the meeting you're negotiating is hysterical.

Anil Dash: And for people who don't know, the master recordings are the sort of definitive recordings of a record and they are the fundamental intellectual property that a lot of, at least old style recording contracts were about. And you hadn't been in the music industry in that way before?

Phaedra Ellis-Lamkins: Never. Prince and I connected because I had a strong sense of social justice. I'd spent a lot of my life focused on changing the world in a positive way for people of color and low income people. And I think he felt like the things he was in the middle of a battle for were about those principles of justice, of dignity, of respect. And so he felt like we got it at that level and he was able to explain to me how these issues were basic dignity and human rights issues, and how artists of color especially were being exploited.

Anil Dash: So I want to share a little bit of the perspective of what we saw as fans, because I was deep in that community, especially the online community. You know back in the 90s, Prince had changed his name to a symbol and really embraced the internet, and we talk about a lot of that. And had very, put it in very stark terms, that his battle with his record label was about ownership of his masters and ultimately control of his career. And his framing was, if you don't own your masters then your masters own you. And at the time when he does this, he writes 'slave' on the side of his face, which is a not very subtle statement of his feelings about the relationship with the label. And begins this battle that by the time you connected with him had been going on for almost 20 years.

Phaedra Ellis-Lamkins: Sometimes when you're in a fight, your in a principal place and I think it's important that he was at a principal place, which I think very few people sometimes have the luxury of getting to, but he was in a place where more than in some ways money, more than other things mattered, he principally wanted to win because it was a fight for justice he'd been in and he understood the implications not just for him but for other artists and artists of color. So when he was fighting, it wasn't just, I mean, he fighting for himself, he felt like he was fighting for George Clinton. He felt like he was fighting for other artists, that he was very clear that his liberation would be liberation for others.

Anil Dash: And the thing is, I think he thought a lot about that sort of historical context. This was in a tradition of hundreds of years of black artists being exploited, and in a tradition of the people he'd grown up listening to. George Clinton absolutely being one of them and George had for awhile been signed to Prince's label, Paisley Park and obviously was a huge influence on Prince's career. But you also had, Aretha Franklin had her own record label back in the 60s and 70s, and James Brown had experimented with how to release his records, or certainly Berry Gordy, whose son would end up running Paisley Park on the business side for awhile had all been sorted these huge influences on Prince's thinking about ownership, particularly in the context of being a black artist.

Phaedra Ellis-Lamkins: Absolutely. The thing I think about him that must be a challenge to be is, he was so brilliant as a musician at the same time as a business person and sometime those forces are opposed. And so as you think about making a smart decision for your music, it's very different than the smart business decision sometimes. And it was always interesting to see, to be so smart at both things and sometimes the decisions, it was clear he sometimes made a decision as a musician, he sometimes made a decision as a business person and sometimes he made it at the cross of both.

Anil Dash: So I want to get into one of those decisions that from the outside I think I got, because I had been in business and certainly been in... Like in software you think about intellectual property all the time, but that fans were mystified by, and it was his adamant, like stubborn, bullheaded views on taking down his content on YouTube and on other services online. And I want to be fair to sort of representing both sides. I think a lot of fans were like, you're hurting your legacy and you're hurting new audience, new listeners, especially younger listeners' ability to discover your work because it's not on YouTube, it's not in the places they'd expect to find you.

Anil Dash: And my understanding was, if he looked at something like YouTube, which Google owns, you have Google is this huge company, one of the biggest companies in the world. So if one of the biggest companies in the world saying, we're going to put your work that you created, wrote, performed, own, we're going to put it up on our site and we will pay you for it, but exactly what we're going to pay you, we're going to just make up. You have no way to negotiate it and you'll find out after the fact that your work is on our platform, and he's like, no thank you. Does that match what your impression was?

Phaedra Ellis-Lamkins: Yeah, a little bit. I think also what was hard is like he thought of it is a very purposeful strategy for record labels and technology to devalue content. It wasn't like it just was a business decision. So like if you looked at the statutory rates or the rates that people were being paid on radio versus the rates that they were being paid on something like streaming or YouTube, it was so much lower. So one is the way they presented the content, because someone could manipulate it and he was an artist who wanted his music presented in a very specific way. So you might have someone, I remember like dancing nude or disrespecting a woman and that was not how he wanted his music to be heard or those images to be connected.

Phaedra Ellis-Lamkins: So one is the way it was presented was different than it was intended and different than the intention of his art. Second, as a business person, it was now something that you already had a split because he owned his publishing. So he had 50% of it and then he had a percentage off of the master recording. But now you had, in places like streaming and YouTube, you now had record companies who'd re-negotiated different rates. So a record company might get more, or a music label might get more money than they would have gotten off a radio performance, or they had different incentive basis. And so it was the presentation of the content, it was the fact that they'd structured a deal around the artists and that he actually felt like, when we talked with YouTube or others, it was like he could negotiate a deal and then they went from like, it's just content then YouTube is going to do radio. And he could negotiate specific deals, but he was clear that it was only him that could negotiate those deals.

Anil Dash: You know, he's talking about his ability to understand the terms of the contract, and how he's being paid, and what the royalty rates are, and how they differ, that there was this huge evolution music went through in a very short period of time between recorded music on vinyl, and then cassettes, and then CDs into digital. But then there's different areas there between digital downloads versus streaming, and digital radio and all these kinds of different evolutions. Did he have that level of fluency where he knew all the different terms and how all the different streaming services worked, and what the different rates were, and what his different legal relationship was to all of them?

Phaedra Ellis-Lamkins: I think yes and no. Yes in that sometimes he understood the most minor detail and no, in that sometimes he didn't have as much information about the way that some of the relationships were working. One thing that struck me when I started working with him is I said, okay, we'd been in this meeting and they were going over a contract and I went through like each piece of the contract with him, and he found it really frustrating and he would get irritated with me. But it was really his property and the thing of most value to him personally and professionally. He'd been obviously an artist for so long, had so many resources and been famous that I don't think he'd been engaged in the transactional level of some decisions that had great impact for him. And he was clear on this, I think he's publicly talked about this, that he felt like he'd been mistreated or misrepresented because he didn't know the details of some of those things.

Anil Dash: There's a letter that he wrote right after he changed his name to a symbol and he put it up on the website, his first website, which was called thedawn.com. And it was briefly up there and he took it down, it's sort of classic Prince, right? It's like, I'm going to put this elliptical message up there for a short while and then disappear it. But it was the most direct thing he'd ever written to that point. This is in 1995 or so, and he sort of said this, I signed this contract when I was 17 and I didn't know what it meant.

Anil Dash: And it's the first time I'd ever seen him say anything that was short of being sort of the all knowing eye, you know what I mean? It was this thing where he's like this very human, very vulnerable, very understandable but flawed thing. Which is like, yeah, when I was 17 I was a dumb ass. And that was really striking because it was a sense of like he did get exploited and it makes perfect sense that if you have a kid who grew up where he did, how he did and you have somebody saying, I'm here from Warner Brothers, you're like, yeah, hell yeah. I want to take that deal.

Phaedra Ellis-Lamkins: I think, and you think about that at 17 and I think as you get older, you think the victory is in money, right? So I think a lot of musicians would say, or artists that I met working with him, is that people would take cash, big cash payments, because they thought that's what was critical. Right? Like now as you evolve, now I should be getting more of the money. And it's only way later when you realize, well, I just took all this cash and now I don't actually own what the cash is being made off of. And so I think that became much more clear. And I think when I worked with him, he obviously let go of a lot of people. And part of why he let go of people is because he no longer didn't want to know the details of what was going on.

Phaedra Ellis-Lamkins: And I remember him calling, like he and I had had a conversation, so then he called the President of ASCAP. And I think for him it was very empowering to be in control of himself and his career. And I think he'd always, obviously musically, and I think he'd made these amazing decisions, but like I don't know that I ever saw him more powerful or in his own power than when he was calling the owner of Warner Brother Records, not the President, but the owner or calling the head of ASCAP. And he found incredible personal power in advocating for himself. And the thing that I always helped people know is that getting his masters was about him. He did things that every person that I watched that he had hired in the beginning, he fired them because they would say to him, don't do that.

Phaedra Ellis-Lamkins: Part of how he built power is he had to be able to make decisions around his publishing and everyone said you have to be represented. The time he was represented by Universal, and he said, "No, I'm going to do it myself." And no one understood. Now we understood because it was out of power. If he didn't have Universal representing him, then he controlled it and he could do whatever he wanted. His business folks said, "Oh, you're going to lose resources." But practically, it was about ownership and it was about control and the fact that he then could self determine, he could make decision and he felt like if I make a bad decision, I want it now to be my bad decisions. I live with the consequences. No one else lives with the consequences.

Anil Dash: So it's so extraordinary because I think there are a couple of places where he had that power and really deployed it. And as you talk about ASCAP, obviously the biggest publishers in the world, Warner Brothers, one of the biggest record labels in the world. But he would do a tour and he would talk to the CEO of Ticketmaster or he would talk to the CEO of AEG as a tour promoter. The thing it calls to mind being in tech, is a Steve Jobs, is someone like that where you know what he did over many, many years at Apple, in addition to you invent the iPhone or whatever is we're going to make the chips, and we're going to own the factory, we're going to go all the way down to the metal. You know what I mean? Like we're going to own every single part of this.

Anil Dash: And it was sort of the same thing, which is this, if we control this, we control our destiny. Our computer's not going to be slow because some other company makes a slow chip, you know? And I think it's sort of the same thing, which is like all of a sudden he could look at other things to do in the ecosystem. I'm curious if this is something that ever intersected with you or does somebody sort of side project or ideas that he would explore? Like funk band, sort of similar to rock band, the video game where he was going to license his music to be able to play it on the instruments and of course that didn't ever come together. But that kind of thing or the eventual deal that he did with Tidal for putting a pretty large number of his albums from his catalog on their service. These were all things that he had a lot more flexibility to do because he had fought for that ownership.

Phaedra Ellis-Lamkins: Yeah. I think you're right in that he had so many brilliant ideas. I used to always try to convince him to hire professionals to execute on each one of them and often he would not want to do that, but I think he had every brilliant idea I've seen executed in Silicon Valley years before. And I remember thinking we were smart, like I think all these things you think let's try selling it direct. And he's like NPG Music Club. And I was like, what's that? And he was like, I did that 20 years ago. We did- [crosstalk 00:16:43].

Anil Dash: Yeah. He had receipts from 20 years ago, yeah.

Phaedra Ellis-Lamkins: Right. He was like, there's nothing that, we were like, oh you could do this. And he wasn't like, ah, this is how I did it. And to me the hard part is because he was so brilliant, he wanted to do all of the pieces of it and and so it's hard though, like you have to hire some folks to do some of those things. There were so many incredible ideas that he had I think far before anyone else had thought about them.

Anil Dash: That's something that I think comes up a lot, which is he had these ideas early and there was an interesting sort of thing where like his level of professionalism and discipline on music was just off the charts. So like in terms of you practice everyday, you rehearse, you master your instrument, you know your shit, right? You know your stuff. And then when it came to, here's how we're going to do something on the internet. And in fairness, I've talked to many of the people who did this work and they are brilliant technologists and have become very talented, but at the time he would take people who had come in as a photographer and say, we want you to design album covers. Or somebody would come in to be an engineer and say, I want you to get me onto the internet.

Phaedra Ellis-Lamkins: Or me, sound checking. He had me soundcheck in Baltimore. He fired the whole crew. He's like, they're not doing a good job, Phaedra go soundcheck. I was like, I don't know how to soundcheck. He's like, just do it, you'll be fine. And I was like, no, no, I really don't know how to soundcheck. And then afterwards he said, you did not do a good job on soundcheck. And I was like, shocking. I did not sound check well.

Anil Dash: I want to touch on a couple of points real quick. One of which is that sort of idea of what I've described as his battle with the record label is actually a battle for really just self-respect and a equitable relationship. And I think about one of the earliest songs he recorded, he'd come to New York as a teenager when he was in the midst of sort of figuring out his first record label contract was called, We Can Work It Out.

Anil Dash: And in it he says, WB and me naturally, he's singing about his record label and it's kind of the sweetest thing ever. It's this teenage kid and I think what might've been his first trip to New York, but certainly one of his earliest trips in New York, and it honestly sounds like he's daydreaming. Like, I'm going to be on the label that Chaka Khan is on. Like I'm going to be famous, I'm going to be a star, I'm going to be this thing and then it happens, of course. Like he becomes basically the biggest star in the label by less than a decade later. And then you get to the early 90s and he's having this reckoning of like, am I going to stay a star, basically. And he signs a big contract. And this was an era of big contracts. So Whitney had a record breaking contract, and then Michael Jackson got like a $60 million contract, and Janet gets a $70 million contract with Virgin and it's clear there's an arms race going on.

Anil Dash: And he does this deal that the headlines, and I remember reading it at the time, Rolling Stone was like $100 million deal. And the wildest part about it was, his press release said, "And Prince will become the Vice President at Warner Brothers."

Phaedra Ellis-Lamkins: I think about this a lot in some ways, the way that the tech companies have created stock options, right? It's like you think like I'm an early person in this company, I own 1% of the company, I own 2%. Imagine if you feel like you're the greatest artist that's ever been on that label and you've sold more than anyone else and they continue to make money off of you, you feel like that's partly your company too. I remember he once sent me a list of their roster and then he told me, who should be kept and who should go?

Anil Dash: Wow!

Phaedra Ellis-Lamkins: And he wanted me to have-

Anil Dash: So he was [crosstalk] for the label too?

Phaedra Ellis-Lamkins: Right. He wanted me to have a conversation with the man who runs Warner Brothers and to tell him two to let go. And I think he also-

Anil Dash: Did he make some good calls though?

Phaedra Ellis-Lamkins: I think he made some good calls. I think he sometimes made calls that weren't about selling music, but were about authenticity of experience. And so I don't know that from a business perspective they were always great calls, but he wanted to be at that level of engagement of defining who was on the label. Because he felt like he built it, like what should it become, what should it look like? And so that was really important for him. I thought he wanted to get his masters so that he could not have a relationship with Warner Brothers, the most surprising thing to meet was he didn't want to be disconnected from Warner Brothers, he wanted to have power in the relationship and to like-

Phaedra Ellis-Lamkins: ... from Warner Brothers, he wanted to have power in the relationship. And so in the beginning, I thought the goal was like get all your masters and run away from Warner and then have power that way. What was really interesting to me is I remember him saying he wanted an office at Warner Brothers. His vision for freedom, which is his journey, so it's always his vision that wins was about respect. It wasn't about separation. That was probably the most interesting thing to me, because he felt like they were only successful because of him. So his goal wasn't to leave it, it was to shepherd it to greater success.

Anil Dash: Well, I want to leave with one last question here, which is obviously it's fairly tragic and painful to have lost him unexpectedly. But what happened in 2014 was that he did get ownership of those master recordings, and it was a full 20 year battle for ownership of that work, since he had first written Slave on his face and basically burned down his career 10 years after being one of the biggest stars in the world. I'm curious if you feel like was that almost a valedictory moment for him? Do you think Prince got what he wanted for his work? For his career? Did he win?

Phaedra Ellis-Lamkins: Yeah. I mean he called someone, a friend we have in common and said, "What's something Phaedra always wanted for the rest of her life? I want to give that to her since I've gotten what I wanted." And so it was clear to me that watching him, that in some ways it's like it's something that he had always wanted. The thing that became more clear is I think as he had some of the things he'd always wanted, you start to realize, "What would I have done with it sooner? Should I have gotten the way we got it differently? What should our relationship had been with Warner?" And so I think in that moment, what he describe to me as a happiness he hadn't had in a long, long time or experienced before. And so I think for him it was that in that moment. I think as time goes on, you start to think, "Oh, what could I have done differently? Or what does it look like?"

Phaedra Ellis-Lamkins: I mean, he and a couple other folks were sitting in a room and he, which is when you know he's happy, is he calls you in the middle of the night and wants you to come hang out. He rented the club in the Beverly Hills Hotel and he wanted to... I don't remember if was an eclipse or something was happening, but he was like, "Let's just sit here and talk about it." And so he was liberated and happy and was very clear and felt like it was a victory for everyone. I'm a normally pretty private person. I think this is only the second thing that I've done to ever talk about him. I remember the thing that describes who he is best, is he was saying privately like reparations and like this is... But publicly, right?

Anil Dash: That was the context of it for him [crosstalk 00:23:55]-

Phaedra Ellis-Lamkins: It's like he felt like it was reparations but publicly he wanted to be graceful. He wanted to make a deal with them. He wanted to do another album with them. And that's what I think the spirit is he, he was complex and hard sometimes, but always amazing. And I always think about the fact that in his heart, he felt like he got reparations, but he didn't want to be seen as like running around with a victory, claiming reparations. He wanted to also give them a win. And I just think that's who he was.

Anil Dash: There's a bit of a graciousness and an artistry to even how he basically accomplished the greatest professional achievement of his career.

Phaedra Ellis-Lamkins: Definitely. And for him it was like, the part that you all don't see is like, you know, he was like, the ability to audit or figure out what he was owed. He wanted to know how many albums actually sold of Purple Rain. Like I didn't get that information and it was like we did an audit and there's just all this stuff, some of which was under a confidentiality agreement, but there was incredible victories, some of which you can't even see.

Anil Dash: Phaedra thank you for sharing this story with us.

Phaedra Ellis-Lamkins: Absolutely.

Anil Dash: Last time around on Function, we talked about all the ways that Prince used technology and the internet to connect to his fans, but one of the most amazing was he built an online music club called the NPG Music Club, and it was a subscription service. We got music and all of the stuff you'd expect, but at its height it actually did things like getting us into soundchecks. One time I got to sit a couple of rows in front of Prince at his own show, thanks to being a member of this club. After the break we'll talk to the designer and creator who helped Prince build that online community, Sam Jennings.

Anil Dash: I'm going to real quick take you back to 2002. And now, I was already a Prince fan of course, but he had started to launch a series of websites in the '90s and I'd become a member of this online music club. Now the thing to keep in mind is these had started before there was any iTunes, way before there's any Spotify. There's certainly no Patreon or anything like that. So we weren't used to even the idea of just downloading music or watching videos online, but it was exciting to get access to that.

Anil Dash: And then in 2002 there was something new that had happened, that nobody had ever seen before. We are able to buy tickets through Prince's fan club website. It was called the NPG Music Club. And what they site said was if you bought your ticket to the concert this way, you would also get access to the soundcheck. That's the rehearsal before the show, where a band would tuneup or try out new songs or in Prince's case, sometimes even a write new songs. (singing).

Anil Dash: It was pretty amazing access. The soundcheck was so intimate that Prince actually sat down with us as fans. There was only a couple dozen of us. He had a wireless microphone. So even though his band was on stage, he was sitting with us and he was talking to people, greeting them, just like a regular person, not like a global superstar. And the most amazing thing about this was that he told us in that moment the reason that he gave us access, only and exclusively to the people who are the members of this online music club, was he because he saw the members of that club as his family.

Anil Dash: It was exciting to see Prince be so groundbreaking in technology just as you've been in music. And part of what was so exciting for me as an internet geek and somebody who built websites and all that, was that I knew one of the people who'd made this possible for Prince had been a fellow fan. You see, Sam Jennings had started out as just another one of us in the online community. But over the course of nearly a decade, Sam worked with Prince to create more and more elaborate and innovative websites, culminating with that Webby award winning site that had let us get access to that soundcheck and to that special moment with Prince.

Anil Dash: Sam, thank you for joining us.

Sam Jennings: Absolutely. Glad to be here.

Anil Dash: So put us in the room. Tell us about the creative process of working with Prince on creating a project.

Sam Jennings: Prince was one of those musicians who cared a lot about his visual presence and put a lot of thought into how he's represented. So, as a visual designer for him, I kind of got the sense sometimes that if he knew Photoshop, I'd be out of a job, because he really liked being a part of that. He really wanted to be able to get in there and mess around with things. So there were a lot of times, there are a lot of situations where I'm working on the computer and he's right there with me, kind of helping me make decisions, pointing out, "What if we tried this, what if we tried that," looking at fonts, saying, "That works, that doesn't work." And I found that he had very strong opinions. Sometimes he was a little more casual, but oftentimes he had very direct ideas. Like, "No, I like that or that definitely doesn't work."

Anil Dash: Take me to the like sort of mid, late '90s. What were you doing online?

Sam Jennings: So just like you, when I first got online, I started looking around for Prince fans too. I was in college in the '90s and the internet was just becoming a thing. Like it was just becoming this thing everyone was talking about. And being in college it was really great for me because it gave me an opportunity to really learn it, be around people who are also trying to figure it out. And coming at it from an artist perspective, like how do we use this as an art tool? How do we use this as a design tool? And I just kind of took my knowledge and took my energy and started applying it to like, "Well let's figure out where the Prince community is. Where are the, where are the Prince fans online?" And building websites and reaching out to people. I was in Chicago, so reaching out to other Chicago fans and started organizing parties and saying, "Hey, we're all meeting online, let's meet up in person and like talk about this thing that we're into together." And just kind of building community. That's really what it was about. And making those connections.

Anil Dash: And Chicago was always one of the biggest fandoms for Prince. I mean, that was a city he loved and he went to a lot, but also the fans were always kind of real hardcore. And I remember seeing sort of flyers, there'd be like Sam Nation events and people would get together at a club and listen to the music or just hang out.

Sam Jennings: Yeah. You know, I started doing parties in my loft and just invited people over to my house, and then I got the opportunity to move it to actual nightclubs. So we started doing it in clubs and I wound up doing that for about 14 years, which is pretty amazing. But once a month we'd have these Prince parties.

Anil Dash: That's incredible. So I want to go back a little bit. So you had gotten online, like a lot of us, you were in college or whatever it was. People had their AOL account back in the day. What was the first place that you connected in and were you in chat rooms or were you on, like they had the internet news groups back then? What did you connect in and see those Prince fans on?

Sam Jennings: So the first thing I would connect with is like IRC, IRC chats, connected with people that way.

Anil Dash: And for people who don't know, that was sort of, if today you use Slack or other group chats, things like that. That was that version of that same technology but back 20 years ago.

Sam Jennings: Right, right. And also connecting with people in AOL as well. And the Prince mailing list that would go out, the email mailing list, finding people that way. But yeah, a lot of going online chatting, and just trying to search around and just find those people hiding out.

Anil Dash: Great. So you become part of the community, you're on the mailing list and in the chats. You let folks know, "Hey, I'm having these loft parties, come by." And then you start making websites online, right? Like you had made like a fan site.

Sam Jennings: Right? Yeah. Was for the Chicago group. At that time, this kind of predates like search and any kind of official sites. So people hungry for Prince content would kind of create these networks where like, "Oh, have you heard about this site or have you heard about that site?" So I wanted to make a destination point for people, at least in Chicago to kind of have a resource to share information about when concerts were coming up, when things were going to become into retail, that kind of thing.

Anil Dash: All right, so you are doing these little news updates. You're saying maybe there's a new single coming out or there's a party that's coming up. How do you go from that to getting on Prince's radar?

Sam Jennings: I would say, it was really kind of just luck that Prince was in this mode of being a do it yourself artist at that time. In the mid '90s he was still kind of reeling from his Warner Brother thing and trying to figure out a way for him as an artist to work outside of the system. He was very dedicated to that. And of course, since the internet was, you know, rising in popularity and becoming more of a thing that everyone was into, he saw that as a great opportunity. And so the people who were also seeing it as a great opportunity, we were almost in a way like in the same circles. Prince was out there in AOL Chat. He was talking to fans, he was getting excited about having this connection.

Sam Jennings: And so it wasn't that odd to find him kind of reaching out to these same online fans to do projects for him. So the first project being the Crystal Ball website, which I was not a part of, but then also Love For One Another, which came after that, which was going to be a charity site for him. And he wanted his fans to be a part of that directly and to build it and work on it and write for it and all those kinds of things. So I did get involved in that project, just from him reaching out to fans and trying to find people to be a part of it.

Anil Dash: So I'm going to go back and explain a little bit of context for people who may not be as deep into it as we are, but Crystal Ball was a collection of unreleased songs, things that had been bootlegged and that were from the vault that Prince had had. And this was a crowdfunded record in 1997. He's like, "If I get 100,000 people to say they're going to buy this record," like Kickstarter style, "Then I'm going to make this record." And then it didn't originally have liner notes. He said, "My fans are going to make a webpage for each song that has all the lyrics." And this was just regular fans, like folks like us that were just around, who they're like, "Hey would you go and I've got a remix I've never released, I'm going to put it out there and you're going to put together a lyric page for it."

Sam Jennings: Yeah, exactly.

Anil Dash: So that's, I mean that alone sounds wild, right? Because he's still, he changed his name to a symbol and things, but he was still a huge star.

Sam Jennings: Yeah. We are only, we're talking about like '96, '97. So this is not that far away from his '80s heyday.

Anil Dash: And also he'd had some hits, like he'd had The Most Beautiful Girl In The World not that long before, a year or two before. So this is something that is kind of wild, to see somebody this big a deal reaching out in this way. And then you move on into, he's got a charity website called Love For One Another, which is a charity he actually ran until the end of his life. And he is like, "This has got to have a website. What I'm going to do is get the fans to all build it with me together." And in our minds we imagine the tap on the shoulder, right? When you get called in. How did you get the call? Like what was the mechanism by which you were summoned by Prince?

Sam Jennings: Right. So being a part of the online community, you get to know people like you were mentioning earlier, and when it came time for this project, he kind of tasked a couple of people to kind of piece it together. One of them being Kathy Adams. And I knew her and I was familiar with her and since I always building websites, I was one of the people that they approached, "Hey, would you like to participate in this?" So I think there was a little trial and error at first, but eventually we kind of narrowed it down to a solid group of people. And there wasn't any direct contact with Prince per se. I mean these were entirely done online. So we were literally going into message rooms and having private message chat conversations with-

Anil Dash: Like an AOL chat room?

Sam Jennings: Exactly.

Anil Dash: And so it's project managing you making a website for Prince through an AOL chat room?

Sam Jennings: Completely. Yes. And so there were representatives from Paisley Park who it was understood that they had authority to make decisions, but it was never explicitly said like, "Oh that's Prince talking to you right now." But you didn't know who it was. It was sort of just a name on the screen.

Anil Dash: Right.

Sam Jennings: And I think from Prince's perspective, he loved that anonymity. It could have been him, could have been somebody else, but he just loved the fact that he could potentially talk to somebody and not have it be like, "Oh it's Prince," or be held responsible if he said something strange and people would run off and be like, "Oh, Prince said this." And I think he really liked having that kind of freedom and relaxed atmosphere to just have conversations with us and not have it be like an interview or something like that.

Anil Dash: Okay. So, you're in there. The fans have come together and I remember built out sort of a first version of the site. And by modern standards, it's not the current aesthetics that the web has, but it was cool. It was like this thing exists. And then it starts to sort of mutate and iterate from here is a page describing my charity work into something that starts to be about the music and about his career. How did that evolution happen?

Sam Jennings: You know, again, kind of going back to his fascination with the internet and that connection with his audience that was direct. In a way, he started to use it in a way like how people use Twitter now. So there wasn't a Twitter, but there was a news section and so he could send a message out to his fans directly from him, commenting on a TV show or a concert he saw or something political or the record industry, and he could just put it out in this news section and have his views out there. And again, it wasn't something like a Prince quote, it wasn't like a Prince interview, but it was a message he could get out there through the website and connect to his fans and connect to his audience.

Sam Jennings: And over time I think that appeal, he kind of warmed up to it and warmed up to it, and he said, "Well, I can release more music this way, and I can do other things directly. I can actually interview other artists through this website and just kind of use it as my playground." I think that having that conduit, initially starting out as a charity site, but then realizing, "Oh, I've got this way to communicate directly that I don't have to go through anybody else." And of course, he really loved that.

Sam Jennings: There weren't really artists using the internet as a playground. There was still that sort of fear and that sort of animosity towards the internet of like, "Oh this is going to destroy the music industry. This is going to ruin artist's livelihood."

Anil Dash: And they had one janky official site made by their record label.

Sam Jennings: Yeah. Yeah. Something pretty terrible that was basically just an online press kit.

Anil Dash: So I want to go into one of the specific things. So you start to build these sites and there were sort of a lot of iterations. There's lots of different versions of it, and you're polishing up the graphics and you're making it a little more professional. And also, the internet itself, the web itself was changing a lot. So new web browsers would come out and you could do new tricks and things. But one of the things, one of the names you mentioned in the mix there was Napster, right? And so Napster comes out around '99, 2000. And I should give some history because there are people listening who won't remember it, because they weren't allowed to use it yet or they weren't old enough.

Anil Dash: But this was revolutionary, and it was just really the ability to transfer MP3s and you could search and say, "Show me When Doves Cry," and here's 10 different versions of it that you can go and download. But it was the first time people had seen, one really just listening to music on the computer. Right? So not just like on your disc man or whatever you had back then. But two, that you were going to get this music transferred instantly, that there might be obscurities, rarities, unreleased things, things that weren't legally officially out there in the record store. And so it's almost impossible to overstate what a revolution it was.

Anil Dash: And this happens at the same moment as Prince is sort of saying like, "How can I use the internet?" Had you come into the fold enough at that point that you ever had an interaction or a conversation with Prince about like what does this new distribution and technology mean?

Sam Jennings: Definitely. I mean, like I said before, it was pretty tough of mind at that time. We're talking like late '90s, early 2000s. The record industry was definitely reeling from this idea that they didn't control the channels anymore, and that people were going to get this music whether the record labels wanted them to or not. And so you could approach it with like, "Oh, that's terrible and we should stop Napster," which is what the record labels did at first. Or you could approach it like, "Well, the genie's out of the bottle. How can we use this to our advantage? Like what are the benefits for me as an independent artist?" And I think the obvious one is like, well...

Sam Jennings: ... the artists. And I think the obvious one is like, well people are going to Napster because they want music. So if they want music from me, why don't they just come to me and I'll create my own essential Napster, a download service? That makes more sense to me than trying to sue people or whatever. Because, as we saw Napster goes down and something else just takes its place, and then eventually the record labels just have to give in and start their own digital services at some point down the road. But this predates iTunes. This predates all that stuff. So he's saying like, "People want to download my music, there's a demand. They're going to get it from somewhere. Why don't they get it directly from me? Why don't we give them a way to support me directly as an artist?"

Anil Dash: So that's amazing, because I found this quote from August of 2000, which is very ... I mean, Napster had barely been out a couple months at that point. And there was a statement that had been up on Prince's website at the time, "From the point of view of the music lover, what's going on can only be viewed as an exciting new development in the history of music." This is Prince talking about Napster in 2000. And then you fast forward maybe six months later, and not even much later than that in Prince releases a single. This is a song called The Work, which I love. It's a James Brown kind of pastiche. (singing). And he puts out the work on Napster, which I don't think any major artist had done at that point.

Sam Jennings: Right. Yeah, definitely.

Anil Dash: Were you involved in that?

Sam Jennings: Yeah, we were in talks with people over at Napster. He would say things like, "Hey, can you get in contact with so-and-so?" And we would organize these AOL chats, which is kind of funny, but through assistance or whomever, we would get these people in a chat room, and he would ask questions and talk about the record industry. And again, he could kind of skirt around with like, this may or may not be Prince, but it was him, and he had some genuine curiosity. He wanted to know what, what they thought about this. Were they just tech guys who were just kind of messing around, or did they actually have kind of loftier visions of what the music industry was about?

Anil Dash: So I want to go forward from there. So he starts to iterate. he starts to experiment and Prince's record label and band were called the New Power Generation. And so, he called everything NPG. And he launches a thing called the NPG Music Club. Where did that come from? What do you know about how that concept arrived?

Sam Jennings: So we did Love For One Another, and that lasted about a year. And then at the end of that he said, "Well we're going in this direction. I want to shut down Love For One Another, the website, and I want to create something that's specifically focused to music." We had this interim site, NPG Online LTD, and that went for about a year. And that was sort of our sandbox to kind of kick around ideas to lead to the NPG Music Club.

Sam Jennings: And during that time we had a lot of meetings. We had a lot of discussions. "How is this going to shake out? What's it going to look like? What can we count on from him as far as what he wants to give out? What can we count on from our partner as far as the technology? How can we create a service that people are going to be into, but doesn't totally just give away the whole, everything in the vault." These were a lot of questions we had, and when we met with a lot of different people to try and figure it out, it took about a year to get something going, which led to the NPG Music Club.

Anil Dash: And part of this to give context, the technology is evolving at this point. Most people ... there were people who had a computer that didn't even have speakers on them, right? There's no smart phones yet. There's no ... well, Apple doesn't even release a iTunes until 2001, and and the store doesn't come until later after that, right? So, this stuff is very, very new. You're extremely cutting edge in being able to even capture a song and putting it in a form that people could download.

Sam Jennings: Yeah. And I think that was the big challenge is that we were doing something that there really wasn't a blueprint for. And another thing we had to consider, too, is we had an international audience. So we might have a great internet connection in Chicago and Minneapolis, but we were trying to reach people who were also in Poland, or some other countries that may not have been up to par yet as far as the internet speeds. So for them to download a three and a half meg song could have been a big ordeal for them. So we had to take that into consideration, too. We don't want to just make it a completely high-res experience that is going to block out a whole audience that hasn't quite got the internet connection yet.

Anil Dash: So you were sort of commandeered into, "Now we're going to build basically Prince's bootleg version of iTunes on your own website from scratch with ..." and how big is the team working on this?

Sam Jennings: Pretty much me and whoever our partner was going to be.

Anil Dash: Okay. So you a partner and the ghost of Prince in a chat room decide to build iTunes on your own, at a time when he's can't stop giving the middle finger to the entire record industry.

Sam Jennings: Right.

Anil Dash: And so tell me about the launch of the first version. Does Prince come out and play your guitar solo, and there you go, you're up on that? How does that moment happen when the switch gets flipped?

Sam Jennings: I would say we had a little bit of a rocky start, because our first partner was a company called [Techadence 00:47:54], and their idea was to do a downloaded piece, essentially a player, which was popular at the time. You had Real Player and things that. So the idea was to download a player that would be your conduit, and download music and videos, and you would access everything through this player. Just unfortunately though, it just wasn't dialed in enough, and people were having-

Anil Dash: It was janky.

Sam Jennings: Yeah, it was janky.

Anil Dash: I used it. It was janky. And they were like ... and what was obvious to me being in tech was they were like ... they wanted to get Prince so they can be like, "Look, Prince uses our thing and you should too. And now we're going to be the new iTunes. We're going to be the hot software." So, they're trying to get over, but it didn't work and it was frustrating to use. So you all are sort of stuck with that for a little bit.

Sam Jennings: And they had some really cool ideas and some really kind of big visions of what could happen. But ultimately people were just frustrated. So we just said, "You know what guys? We just got to pull the plug, and we're just going to go really simple. We're just going to make it a subscription. We're going to make an MP3 downloads, and we're just going to do it that way. And we're going to do monthly additions," which was very successful. That first year, it was all monthly additions where we're giving out a very specific amount of music every month, and people could count on it. And if you signed up for a whole year, you got more music, and plus you got these ... essentially we'd call them podcasts now, but essentially these audio shows that Prince was producing at Paisley Park.

Phaedra Ellis-Lamkins: Again and again, they placed the car before the horse, offering us crumbs from the table. When in fact, with no music there will be no table at all. You are listening to NPG Audio, owned and operated by Creatives of Music. Get a dictionary on some scuba gear, because we've got to get deep.

Sam Jennings: I mean it was pretty amazing the amount of content that he gave out that first year.

Anil Dash: And the wild thing about this is today, you know a lot of us have Patreons that we support online, or we go to Band Camp and we buy somebody's record, and we listen to it, or you check out somebody's SoundCloud, and they might have a membership thing if you want to download a special track. But it's pretty common infrastructure, right? Millions of us, we get music this way. We connect with artists this way. We certainly are like, "I paid for the Patreon, and got the exclusive to listen to the podcast. That's a mix tape for my favorite artists." That's the thing that exists.

Sam Jennings: Right.

Anil Dash: 20 years ago, this is mind-bending, and especially because it's like ... Prince who again, big deal artist. This isn't, I'm somebody that's just breaking into the industry, and I hope that somebody is going to support my Patreon for 20 bucks. But those monthly audio shows, the podcasts were, he's mixing songs together. He's narrating the thing himself. There were unreleased songs that were in the mix on these things (singing). And they were going out every month. And I mean that was ... and then nobody did it again for 15 years, until just now we've got all this stuff back.

Sam Jennings: Right. I think also too, broadband caught up with the rest of the world, so those kinds of things ...

Anil Dash: Yeah, we're all still on dial up then, too.

Sam Jennings: Yeah. So obviously podcasts work a lot better when you're in a streaming universe than they do with a download universe.

Anil Dash: Well, I want to talk about the zenith of this, maybe the apex of this, which is you'd had a couple iterations of the site. you got it working. I don't know how much you can talk about the business aspects, but what did it look as a subscription business for people signing up? Was there a good subscriber base? Was Prince happy there's a lot of fans paying for this?

Sam Jennings: I would say that Prince is one of those guys that is never completely happy with numbers, and I think that applied to his record sales. I think that applied to everything. If he sold a million records, how come he didn't sell 2 million? And so that was sort of an ongoing thing. I think that kind of spurred his experimentation like, "Okay, well we did this and it did whatever. What if we tried it this way? And what if we tried it that way?"

Sam Jennings: The subscription sales, I think they were great. I mean, they sustained the business. They paid for my salary, which he really liked. We also did the presale tickets. So that was another thing that we were doing that hadn't really been established in artist fan clubs yet either, where we were making, especially on the Musicology tour, we were making tickets available to the fans before anybody else. So if you wanted to get tickets and get the best seats, you had to join our club.

Anil Dash: So I want to get to maybe the most princely thing about his online explorations and all this innovation, which is that you have in rapid succession two of the most surprising things that happened with all of the technology that he did, especially with the NPG Music Club, which is a one probably the pinnacle recognition that you got, which is a Webby Award. Talk about that moment, about what it meant to see that work acknowledged and what you heard from Prince about that.

Sam Jennings: Yeah, I would say that for me personally, that was definitely a big high point. Because we're doing this thing. I'm working with Prince. It's successful. People love it. There's always that feeling of like, "Well, we could do more," or, "We could have better numbers," etc. But then to have the industry come out and give us the Webby, and also to give Prince a lifetime achievement Webby, which was based on all the things that we'd done over the years, it was pretty awesome to have that, and to be a part of the ceremony, and go there, and still have my Webby all these years later that for whatever happened afterwards, I still have that. And it was pretty exciting. And I think for Prince personally, he wasn't so crazy about awards. It didn't mean a whole lot to him, but I think he sort of felt, "Well, we won this Webby Award, as far as the internet goes, maybe this is the highest the NPG Music Club is going to achieve? What if there's something else we could do?" Again, that restless, always wanting to challenge himself kind of vibe, which was just who he was as an artist.

Sam Jennings: So he even said that the night that we won the award. We were sitting at Butter, which was a club in New York City, and talking about it, and he was like, "Well, what do you think about maybe shutting the club down now that we've won this award?" And my heart kind of sank, because this was something I'd been a part of for five years, but also it paid my salary, and I was like, "As long as there's a Plan B, I'm okay with it." And we didn't make any decisions that night. But eventually over time he said, "Well, what if we try something different? What if we turned into this kind of thing?" And eventually those plans kind of got sidelined, and he got really into Vegas, and then he went to ... did the Super Bowl in London. So he got caught up in other projects. And so we never quite had that internet presence ever again, which I think is unfortunate.

Anil Dash: I think everybody's question for anybody that ever got to collaborate or work with him is like, "What was that moment of you two sitting in Paisley Park, or in some studio somewhere where you had that conversation and got a glimpse into the creative, where you were ..." You're at the table with this legend and you're doing this work together, what's the moment that stands out that's a story that you tell your family that's like, "This is what I got to do?"

Sam Jennings: Right. One that really stands out is when he was staying at the 3121 house in Los Angeles ... He had a guest house, and he'd set up one of the guest houses as a music studio, and that's where I had my computer. And one afternoon we were sitting there, and we were working on stuff, and I would kind of make playlists to play while he was in there, stuff I thought he would to hear. And he says to me like, "Hey, what if you download some music that we listen to?" We were talking about '70s music, and we were talking about Steely Dan and Fleetwood Mac, and artists you wouldn't normally expect him to cite as influences.

Sam Jennings: And so we downloaded the first Steely Dan record, Fleetwood Mac, Rumors. We downloaded Chicago, one of their first records. And we just listened to them all the way through, and just listening to them with him, and having him talk about the music, and, "Oh, listen to this part," and he'd get excited about a guitar solo or something that, and just really kind of break it down and talk about his experiences as a high school kid listening to this stuff. It was just really, really great. It was just a very kind of casual, easy moment. We're still working. We're still doing our thing, but just to have that going on simultaneously, that was a moment that really stood out.

Anil Dash: That's such a wonderful image, and I'm glad you got to have that. I think one of things I see as a fan is I was so thankful for that glimpse, us being on the outside. Just you love the music, being a fan, whatever. And for me in particular, being in tech, working on the web, knowing how hard it was to be able to download a song online and be like, "Wow, they they got it all working," I was so grateful, because it was this glimpse into one, the world of an artist we cared about, but also a glimpse into the future we all knew was coming. We knew this is how we were going to listen to music. We knew this is how we were going to be fans. We knew this is what we wanted to be part of. I think that was such a gift. Well, Sam, I'm so grateful for you joining us on Function. And as I said, I'm so grateful as a fan that you opened the doors for us to have access to the work of the genius that we might not have otherwise had. And also the inspiration for me that tech could be an enabler of people's creativity. So thank you for your work, and thank you for joining us on Function.

Sam Jennings: Absolutely. Thanks for having me.

Anil Dash: This whole season on Function, we've been talking about trust in the internet, and trust in technology. And the funny thing is, I think if you are a global superstar, like Prince was, you can't trust a lot of people. It's hard to put yourself out there, especially because he was a very private person. He liked to control his image. But what's interesting is if we look at that message Prince had about ownership, whether it's ownership of music, or ownership of your work online, he really did put that into practice for how he engaged with technology. He had all these different websites over the years where he connected with fans directly. But what was less obvious was that he used those to let people in. He used those to build trust with people. And if you look at the course of his career, whether it was a someone like Sam Jennings who built all those websites with Prince over the years, or even Prince's, his second wife, Manuela Testolini. These are people that Prince first connected with online, and that's a pattern that continued all the way through to the end of Prince's life.

Anil Dash: If we look at the last couple of albums and tours that Prince did, things the album cover artwork were illustrations that he licensed from fans. Even the clothes on his body were based on artwork that fans had created that inspired him. That's something really powerful, to think about the idea that collaborative relationships, creative relationships can happen online. And it gets back to the fundamental optimism a lot of us had about technology in the first place. By getting on the internet, we were going to find people that we could share our ideas with, or who'd even make our ideas better. I love that Prince was able to discover that he could let people in, and even collaborate with them because technology is going to make that possible. And I think that's a great lesson for us that it was especially possible if we started in that idea that we should own and control the way our information and our ideas are shared out in the world.

Anil Dash: That's it for this episode of Function. If you missed the last part, you'll definitely want to check out part one of our two-part discussion of Prince's use of technology. And check out the episode I did of the podcast Switched On Pop. We took a deep dive into the ways Prince used technology to create his music. That's it for this week on Function. We'll be back next week with a brand new episode.

Anil Dash: Function is produced by Bridget Armstrong. Our Glitch producer is Keisha TK Dutes. Nishat Kurwa is the Executive Producer of Audio for the Vox Media Podcast Network, and our theme music was composed by Brandon McFarland. Thanks to the whole engineering team at Vox, and a huge thanks to our team at Glitch. And you can follow me on Twitter @AnilDash, but you should also follow the show @podcastfunction, all one word. Please remember to subscribe to the show wherever you're listening to us right now, and also check out glitch.com/function. We've got transcripts for every episode up there, apps, all kinds of stuff to check out about the show. We'll be back next week and we hope you join us then.