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Michael, entertainment is a family business for the Lippmans, between your brother Terry, who worked with you throughout the 1980s, Nick and your son Josh, director of video content at iTunes. Did you steer them towards the industry or did it come about organically?
Nick: Funnily enough, it was my wife who pointed out that Michael and I could really compliment and learn a lot for each other if we worked together. And that's really how it started.
Michael: I believe I'm the luckiest guy in the world to have been able to work with my two sons and my brother in the same business. At the same time, I wasn't the greatest father because I was always on the road. So now that I have the opportunity to see them every day and work side by side, it's been incredible. Nicholas is my best friend today.
Nick: Yes, I would say that's a fair statement.
Who was your mentor, Michael?
Michael: Clive Davis, whom I worked for running the West Coast of Arista Records [during the mid 1970s], really made an impact on me. I never saw a man work that hard and that long every day. He'd be in the office until nine or 10 o'clock and then would have dinner. He inspired me to put in the time.
Nick, is there a lesson you learned from your father early on that you still apply today?
Nick: Don't pretend you know something when you don't. Michael always said, "There's no such thing as a dumb question," and "Never be scared to ask." Also, "If somebody tells you they know everything, run away."
Michael, you have developed a reputation for being tough. Where does that come from?
Michael: From caring!
Nick: Really, it comes from love of the artists. You have to wake up and want to kill for your clients. Michael doesn't take no for an answer. When people push back, he pushes back harder. And with record companies, who might have 20 or 100 artists...
Michael: ...And you're fighting 10 other managers. I want more time, attention and money spent on my artists than the nine other guys. So I created this persona that people respected and slightly feared and hopefully, if things went the right way, I got what I wanted.
Can you give an example?
Michael: One day I get a phone call that Bob Hope on the phone. He said, "Melissa Manchester is scheduled to perform on one of my TV specials and they just let me know that there is not enough time for her to do the two songs that you've asked for. So I've called to ask you if you would cut one of the songs."
And I said, "Mr. Hope, I appreciate your call but she had a hit single, which I want people to know her for, and she's got a new single out just when your show is airing, and it's important to us to do two songs, so I'm gonna stick with two songs." And he goes, "But I'm gonna cut my monologue, so she should cut her song." "And I go, 'Look, I'm sorry, but we're not cutting any songs.'" And I hung up the phone.
If I'm gonna play television -- and there wasn't a lot of television in those days -- play the hit and the new potential hit. So it's meaningful.
And what happened?
Michael: It was two songs.
David Bowie was the first act you managed. Did you know he was sick?
Michael: No. He kept it very quiet. It was very sad. I loved him, my wife loved him. I'm very proud of the many "firsts" we had together: my first big photo shoot was with him; he was the first ever white artist on Soul Train; he had a No. 1 single with "Fame"; he starred in the movie The Man Who Fell to Earth, which I put together.
He also lived with you for a time. What was Bowie like as a roommate?
Michael: David was always very easy -- as a person. He was incredible to talk to. He taught me a lot about fashion, art and photography. All I wanted to do was learn from and help him.
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You have spent more than 20 years managing Rob Thomas and Matchbox Twenty, and 30 for George Michael. To what do you credit these long relationships?
Michael: They know I'll go fight on their behalf and I will tell them the truth. If they run ideas off me, I never say, “Sure, it's fine,” and do something that will hurt them. And I've continued to bring new stuff to interest them.
You first started representing George Michael as he was about to leave a popular group to take a stab at a solo career. What was your outlook at the time? Did you see the move as a big risk?
Michael: I fell in love with the album, Faith, like most of the world later did. He looked great and this voice was like nothing I'd ever heard. I wanted to make him the biggest thing in the world. And that's how it turned out.
Through the years, George has toured less and less. Why is that?
Michael: He doesn't have a desire to be in front of people like Elton [John]. He'll say, "I just can't do that." He's a homebody. He wants to rejuvenate. I'm looking forward to when he performs again.
What does that mean for your roles when George isn't active?
Michael: There have been over 20 synchs this year for his music, including movies like Key & Peele's Keanu and Deadpool.
Michael: There have been over 20 synchs so far this year for his music, including movies like Key & Peele’s Keanu and Deadpool. Even when he's off, it's crazy how much interest there is in him around the world. We have to weed it out.
Nick: My role with George is everything that has to do with technology and the internet … making sure that we are current across the board with the ever-changing ways in which fans communicate with artists and that George is present on all of them. The other night, he called at 2 a.m. wanting something up on the website, so even if he’s inactive, he’s active.
Matchbox has been a consistent touring performer, especially in the last decade. How do you ensure that they’re not looked at as a '90s novelty act?
Michael: Recently, Ken Ehrlich called me asking if Matchbox would do his ABC show Greatest Hits [to represent] the late 90s and early 2000s. The band wasn’t available, but in some respects, I stay away from stuff like that. At the same time, the last tour that they did was with the Goo Goo Dolls and it was incredibly successful – their biggest yet, 18, 19 years in. That's a very '90s package, and while we didn't sell it that way, it worked out well.
Nick: Another thing: the last Matchbox album in 2012 was also their first [Billboard 200] number one. We went very hard on that and built a lot around it to make it all come across as uber-current.
Also on your roster is Ryan Cabrera, who’s currently out on the nostalgia branded My2K tour with 98 Degrees, O-Town and Dream. What are the challenges in reintroducing an artist best known for a decade-old radio hit -- “On the Way Down” reached No. 15 on the Hot 100 in 2005 -- and time on reality TV?
Nick: The challenge is navigating the waters in a modern marketplace where, if Taylor Swift puts out a record, all ten of those songs are on the radio. I have always felt that Ryan was overshadowed musically by the celebrity aspect of [his career], so I felt it was important to go back and remind everybody what an incredible musician he is how much music mattered in his life.
Did being a regular on shows like The Hills or the various Simpson family chronicles help to reintroduce Ryan?
Nick: No. The best example of how ineffective reality TV is are shows like The Voice and American Idol. Who won The Voice? Adam Levine. The biggest person to come out of Idol is Simon Cowell.
Matchbox have been early adopters of emerging technologies, embracing wearable thumb-drive downloads of concerts back in 2008, 360 video in 2012 and now holograms and virtual reality. What’s the thinking behind investing in an experience that allows you to sing and interact with Rob Thomas?
Nick: Looking at VIP packages and realizing that they’re all kind of the same. They don't really provide fans with a once-in-a-lifetime experience anymore. I talked to Michael about finding something where fans were, like, “Holy shit! I got something amazing from Rob.” And they can take it home. We also have a 360 video for fans which puts them in places they wouldn’t have access to, like a backstage dressing room — we’re utilizing technology to that sense of being close to an artist. At the same time, Rob is not actually there, and he doesn't have to worry about his safety. But the fan still gets the awesome feeling of looking at every part of that dressing room — probably more so through VR than you would in real life where you might be nervous. Here is an engaging and interactive way to bring value to that VIP laminate.
Michael: My only thing is it's not a big earning thing for us. There are artists that charge a lot more.
What are the biggest threats to the music industry right now?
Michael: The discouraging economics of streaming. I always considered an album a piece of art, and I used to believe that if an artist made a great record and there was an international market, they could sell more around the world. Now that might happen with a song, but services like YouTube and Spotify are not paying songwriters and artists what they should be. And those companies would not exist without songs and artists singing them. Is there an Andy Warhol today? You could say it’s Damien Hirst, and people are buying his paintings.
Nick: Another issue is the people who are in higher position of power are leaving the understanding of technology and the digital revolution that is shaping our business to forward-thinking underlings rather than learning themselves.
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Nick, having spent time in Silicon Valley, do you sense a divide between north and south and creative vs. product and can it be bridged?
Nick: Silicon Valley wants to be more rock'n'roll and rock'n'roll wants to be more Silicon Valley. There is a really unique, interesting mix to be had if you can remove the ego to serve a greater good. But in my experience up there, music is still very sexy to tech.
TV shows like Vinyl and Roadies, in dramatizing the music business, seem to confirm the myth of the old school, hard-partying record executive. What do you make of how they portray the industry?
Michael: I said to my wife, I've seen more coke in the last couple years in television than I think I saw in the heyday. The truth is, we did throw a lot of parties. You'd have Harry Nilsson, Ringo Starr, Quincy Jones, Dick Clark, Little Richard, George Harrison, Tom Petty ... One night, we had Axl Rose at our house until six in the morning. He wouldn't get out of the pool, and he was naked with two girls. But it was fine, we encouraged that.
A version of this article was originally published in the July 23 issue of Billboard.