A special bond exists between Prince fans online — especially those who have been congregating, sharing their love of the Purple One and interacting with the man himself through his decades of digital evolution, from AOL's early chatrooms to the modern-day hum of Twitter. Much like Prince would gather his die-hard fans IRL at Paisley Park for last-minute, late-night dance parties, he spent the last 20-plus years finding the most cutting-edge ways to connect his art to his fans online.

Prince was an early adopter, it turns out, and the tech journalist and entrepreneur Anil Dash has been following him online from the very beginning. I knew Anil would have a lot of insight to offer about Prince's online life; what I didn't expect, and was delighted to learn, is that he's even traded a few AIM chats with the man himself.

When Anil Dash was visiting the Twin Cities recently, we got together to chat about Prince's secret computer nerd life and our shared grief. Find a transcript of many of the highlights of our chat below, and check out the Prince Remembered podcast for our full conversation.

Andrea Swensson: So I’m trying to think of the right way to introduce you because I know you through Twitter; we’ve developed a Twitter friendship and you are a huge Prince fan. But that’s not what you do for a living.

Anil Dash: No, not yet. I wish it were.

You’ve developed this real love of Prince that is so palpable, and I think of you almost as a historian of Prince’s relationship to technology and to his fans. How would you describe your relationship to Prince and his music?

Everybody has that story, if you’re my age, of being a kid and seeing these songs come out and change your life. I definitely remember hearing the muffled sounds of "Controversy" through the door to my sister’s room when I was a kid, and that’s forbidden and I wonder why. That was definitely there. And then for everybody who grew up in the ‘80s the music was omnipresent and it’s amazing. Back then the thrill of going and digging through the crates to find – was there one of these 12” singles that was still in print, and doing that.

And then the interesting thing for me at the age that I am is, I came out of high school and was really into technology. I was making little apps and the web came out right as I got out of high school and into college, and I ended up dropping out of college because I loved the Internet so much. And the first thing I found was the Prince community online, because he had done — he’d changed his name and had done the interactive CD-ROM, and a lot of fans were like, I’ve got to go out and upgrade my computer to be able to run this thing. It wasn’t like "download this off the app store" and you’re off and running. It was like, this is a process, and literally I remember there was a news group, which was a sort of discussion forum on the Internet before the world wide web was even existing, and people being like, I have to install a sound card in my computer so that I can play Prince’s interactive CD-ROM, and what the hell do we call the guy now.

So this community was forming together, really forged in this crucible of understanding technology. A lot of people don’t know that around this time – I think the same month that he changed his name in June of ’93 – the Prince news group was formed. And these discussion were going on. There were Internet services for chat and things back then. Prodigy was one of them. It was one of the first places there was a weekly Prince fan chat. As Prodigy faded, AOL took over and it moved to AOL. The room was called "Paisley Park," and there would be a Prince fan chat that started on Monday nights, but it started going longer and longer as more people joined, so it would be a little easier doing the weekends, so we moved it to Sunday nights. And after we had been doing it a couple years – ’94 and ’95 – these other mysterious handles would start to show up in the chat room. The Emancipation album didn’t come out until ’96, but the names on the AOL accounts were like bedIscream, and there’s this song on Emancipation – “In This Bed I Scream.” So it’s like this sort of tip-off of this thing that’s going on, and a couple other handles were like npg2000, and one was henna2000, and Henna was Mayte's dog at the time. And people would sort of piece it together, like isn’t that her dog’s name? And it was like, Who are these people?

The moment I think it clicked for a lot of us – there were a couple dozen fans that would be there every week and talk about, literally at that point, like how do you say the symbol, and what does it mean? And is he ever going to put a record out again? What is going on with this guy?

It was a confusing time in his career.

Yeah, and keep in mind this is only two years after he’d had huge hits like “Diamonds and Pearls,” so he was a very mainstream act. He hadn’t really faded that much. And right before that he’d had “The Most Beautiful Girl,” which was like one of his biggest hits that he ever had. And so he was seen as a very current artist, and never more inexplicable. Like right after the name change but before it had ever been explained, before he had given any context to it at all – and people genuinely thought he was disturbed, like he was off. And so the fans were like, What happened? This guy, 10 years ago, was the biggest thing in the world, so what’s going on?

So these folks from Paisley Park that we knew were inside somehow started coming in and talking to the chat room. And the moment that jumps out would’ve been in January of ’95. I don’t remember which of the handles it was – it was just sort of casually like, "Yeah, Prince is working on this medley of all his songs because he’s going to retire Prince at the American Music Awards." And we were like, "What do you mean?" And they’re like, "Prince is dead." It was confusing; he hadn’t used this sort of rhetoric. And lo and behold, less than two weeks later he does this really great American Music Awards performance where they play what became the "Purple Medley" single. They played like a three or four-minute medley of all his greatest hits under the name Prince, and then literally his name changed to a symbol. They did this whole voiceover. It was exactly as this mysterious AOL account had laid out. And there was no way — there were no leaks. It was not in the press, in the media. None of us were connected to newspaper people. These days, if it would happen on social media it would’ve been in the newspaper the next day and vetted or verified or confirmed or denied or whatever, but we were like oh my gosh, this person’s there. They know. They called it. And it was just stunning.

https://www.youtube.com/watch?v=L9lQcwAclgQ

It was funny too because I think a lot of us were fairly young, and you wanted to poke the person next to you and be like, "I think this is Prince." It was a really crazy moment. It’s funny because there were people there who I was in these chats with 20-some years ago who I’m still friends with. Some them are like senior at Google, have gone on to these amazing careers, and because we were all teenagers or early 20s, you’d grow up and get married and have kids and all that stuff and have a career. And to sort of reconnect in recent years on Facebook and Twitter, as you do with your old classmates or whatever, was really interesting. And then as that reconnection happened in the last couple of years I was like, did I half remember this wrong?

"Were we in a chat room with Prince?"

Yeah. And I’d saved transcripts from a couple of the conversations, and after he passed I said to my wife, “I think I have an IM conversation with Prince in 1986.” And my wife, who knows me for like 15 years, she’s like, okay? And I had sent a note of condolence to Mayte. We had just connected online because she knows I'm a fan or whatever. And then just as a sort of follow-on, I was like, by the way, a lot of us fans have been wondering for 20 years now, was this really you? And she was like, "Oh yeah." And it’s like, "What about this other name?" And she’s like, "That was Prince."

So which one was him?

It was the way he used the name, so I’m trying to remember. She was like, it depended what times. Like the handle he’d use — this is something he did many times over the years, like we’re this broad collective and we’re from this voice that is Paisley Park or the NPG or whatever. It’s not like it’s over there – that person in the corner is the one writing it. But we know who’s going to approve everything before it goes out.

And then the other interesting parallel to this is that he had 15 or so websites over the years that he started up and abandoned after his attention wandered. And me being a geek – my background is I work in social media and sort of help create a lot of social network and social media tools. And so I knew the tech folks because I’m in tech. And so I would reach out to the web folks, people like Sam Jennings, who did a lot of websites over the early to mid 2000’s for prince; Scott Addison Clay, who did the Lotus Flower site, and things around that era. And even earlier people. I just kept in touch with them because we were Internet nerds and also Prince fans.

One of the things I don’t think people really realize, is a lot of the folks who were engineers and studio staff at Paisley in the mid-‘90s went on to form Bitstream. And Bitstream was one of the first Internet service providers in the Twin Cities, and later for all of Minnesota, and became very important. And Michael Koppelman and a bunch of people that were over there were, in a real way, pioneers of the Twin Cities Internet scene too. And so my worlds intersected. There was nothing that could’ve been more compelling to me – the two things that I was really obsessed with: the Internet and Prince.

And so I started archiving it because I realized he – it’s funny, because for as meticulous as he was about how to present himself or his music, he was also very haphazard. I think he saw it as sort of like how back in the day the record stores would have those cardboard rectangles the size of an album cover they would use to promote it, and they put them up all over the record store, and then at the end you’d throw them away, like who cares. I think he saw the websites a little bit like that – it’s going to promote this album and then it’s going to go away. And on the very first website, thedawn.com, one of the first things he posted – clearly the site had been tied to all the things that were going on 1996 – he got married in February; the last significantly promoted Warner album, Chaos and Disorder, came out; and then Emancipation came out in October and was supposed to be obviously tied to the birth of his child and all these things. And he started setting it all up in advance of the wedding; thedawn.com was initially promoted like it was going to give the details of his wedding. That was like the teaser.

They put up the program for the wedding, and it was this beautiful romanticized story of Prince and Mayte meeting each other, and what their relationship was about, and it was very sweet and stunningly personal. It was like this view into his life. And then being geeks, we’re like, what else is on this site. So we started poking around, and in those days if you would just sort of type in the address of a website and leave the web page off it would show you the other files that are part of this web server. And we just started finding stuff. There was tons of stuff. And one of them was this letter called “Message from The Artist.” And it was stunning. It was in plain English. He wasn’t using a picture of an eye for the word “I.” He spelled out the word “for” for the first time since before Controversy. It was incredible. He reproduced the press release he’d put out in late ’95 about wanting to sever his contract with Warner Brothers, which had gotten some pickup then. In those days we were still reading print magazines to get that news. And then he wrote a first-person letter from Prince about why he changed his name, what his issue was with the record industry. It was so rare for him to make a public statement not in music, that was vulnerable. And he was like, "I was a young kid of 17 when I agreed to this recording contract, and I made mistakes." And still, it almost takes my breath away because you never heard something like that from him publicly; he could be extremely vulnerable in music, but that was almost a different character.

Do you think he wanted that to be found? He’s so in-control.

I don't know. What happened is we found it, and that was actually when I had the one and only AOL chat conversation I had with him. I said, "We found the letter. I beg you to put it out. The world needs to hear this." I still feel that way. And he just said, “In time.” He kept up the mystique even in chat. And then a couple weeks later they put out this edited version of it that was from the NPG – the dawn staff – and it was like “we feel” – and I was like who’s we? Ain’t nobody else over there that’s got a contract with Warner Brothers. What are you talking about? And it was sort of emotionally gutted, like they’d removed the really compelling parts. But I saved the old version. There were other things I wish I’d saved. At the time we didn’t think he was going to take the website down.

So some of those materials I had held onto for 20+ years, and I just felt after he passed, the thing that casual fans never saw was the amount of self-awareness. When he put aside the artifice of being this magical mysterious elf that generates funky sexy music over here, he was just a guy who was obviously extremely passionate about his music, but had this broader mission about what the industry was going to be and how he was going to be respected as an artist, and said it in plain English sometimes, and said it straight to us and the fans, and told us in direct conversation with fans. And that 2-way conversation with fans continued through the whole second half of his career for the last 20 years of his life.

And on to Twitter.

Yeah, and on to Twitter. On the day he passed I had a series of tweets eulogizing him, which I think a lot of us did, and in one of them I said I never got a chance to really meet him, but he had direct messaged me on Twitter a couple times and we chatted, whatever. And like anybody that has a bunch of followers on Twitter, there’s a bunch of folks that hate me and like will look for any excuse to criticize, and they were like you’ve lost you mind; like that is impossible. And I’m like, the reason I mentioned it is not because I thought I was that special. It’s because it was really common, and people didn’t realize.

That happened to me. I did a little sketch of him at the Dakota and he saw it online and reached out. That was kind of the beginning of my relationship with him.

Someone takes a photo and he wants to use it, and he would reach out, and it was a 2-way creation. And the one that – it gets to me even thinking about it now – the one that got me was the night after his last show in Atlanta. A fan had tweeted him her review of the show, and it was. like, "I’m still on the cloud floating over this." And the end of her tweet-length review was “I’m transformed.” As he was wont to do, he would quote-tweet people in a way that was not at all how Twitter re-tweeting is supposed to work. He would excerpt things. He split her quote into two tweets, and the one on its own said, “I am transformed.” And so many people retweeted that after he passed as a eulogy to him, and that the words people remembered him by were him amplifying the words of a fan in response to his art — I think that exemplified what his use of these technologies to connect really was about. It was very mutual and very 2-way, and not the mystique and not a manufactured pop star persona, but somebody who really genuinely connected with hundreds of people all over the world over decades of time, and that we all loved and respected him enough to also keep that confidence, to sort of say that’s fine, that’s for us, and I don’t need to shout it out to the world.

I have two short stories to tell you that I think you’ll appreciate. One of the times that I was at Paisley Park, he invited a bunch of press there, like every publication here in town, and he called us all back to his studio. And I’d been back there before, but this was the first time that there was door open on the way to the studio. So I’m walking down the hall, and I look to my left, and it’s this enormous room with two desks, equally spaced, in the middle, and two men at computers, and nothing else. I was like, "Is that where he tweets?" It just looked so stark.

The tweet factory. I picture them in those clean room bunny suits – like everything is disinfected; don’t touch. This is where the tweets happen.

And then another time, the time I really got to speak with him one-on-one extensively, he had this musician that he had flown up from Australia to come hang out. This young kid – he was like 19 – he was talking about how he was staying at Paisley Park, and in the mornings they would get up and go on Twitter together and just sit at the computer and Prince would tweet out links to his Soundcloud or YouTube or something, and then just read the responses. And that was like a part of the creative process.

I did this talk – so half the reason I came to town was to do this talk at IO festival. It’s like an arts and design festival, and they talk a lot about the cultural impacts of the technology that we create, and I opened the talk – because I wanted to explain this idea of Prince as a geek — I opened the talk with a clip from Graffiti Bridge, the opening credits. The scene is Prince is in bed with a beautiful woman – Jill Jones – and his muse strikes and he hops out of bed because he hears his angel. And what happens is Prince gets out of bed with Jill Jones, who was beautiful, and he’s supposed to be naked, like he wrapped a sheet around himself, and he sits down – and keep in mind this is a movie he wrote, directed, performed, did everything himself, this is a character he wrote himself. He sits down at a Mac 2SE computer that’s in his bedroom and starts clicking around this eight-inch black and white screen with a giant track ball, like the nerdiest input device that’s ever been created. He looks like a NASA engineer. It’s the least cool thing. And he still has the full Prince hair, circa 1990, the big long mane, and Jill Jones comes up and is kind of like yeah, I think I’m going to go dance at Morris’s club, like it’s just like very Prince thing going on in the background, and his song is playing and he’s like theoretically composing “Can’t Stop This Feeling I Got” on this old Macintosh.

The crazy thing about it is to me – keep in mind this is filmed in ’89, so there are still like Revenge of the Nerds sequels being made at that point. Like computers were not cool. Bill Gates was not cool. Steve Jobs was not back at Apple. This was not a moment when you were like, "This is me just hanging out on my Mac clicking around on my track ball." Like that was not a thing. And it’s the front of the movie. There’s a naked woman in bed; he hops out to get on the computer. I don’t watch Graffiti Bridge a lot, and on re-watching it was like an epiphany, because he did not see it as separate from his life. He did not see it as different than picking up his guitar. He did not see it as different than sitting down at a piano. He did not see it as more off-putting to a beautiful woman to sit down at the computer than to pick up his guitar. It was all of a piece. And the closing credits to Graffiti Bridge – it’s him at the same Mac, like the end of the story after the bad guys are defeated and Prince wins and love triumphs, he’s like, "let me click around this Mac and look at some other songs I wrote." There’s a million times during the production of Graffiti Bridge somebody should’ve pulled him aside and been like, "Hey boss, we got to have a conversation. This isn’t your best work." But of all the things that he was like, "Yes, this is my vision when I have total artistic control; this what I’m going to create — I just want the world to know I’m geeking out on this computer right now."

Find more stories about Prince on our Prince Remembered podcast, and find all of our Prince coverage here.