Interview with Music Industry Executive Jack Isquith

by Alex Cosper

Conducted July 28, 2015 on Facebook

Alex: Ladies & gentlemen, today I'm with Jack Isquith from New York. He's currently the Senior VP of Strategic Development & Content Programming for the music streaming service Slacker Radio. I first met him in the 90s when he did promotion for A&M Records while I programmed KWOD. He's also worked for Epic/Sony & Warner Bros .. As a digital music expert he has been a commentator on national TV & in high profile publications. Jack, thanks for joining me.

Jack: Hi Alex.

Alex: Jack, it's been years. Great to talk with you again. Before we get into your background, tell us what you do for Slacker.

Jack: I run Content & Programming ... and lean in on strategy. In English, that means doing the licensing deals with the labels and publishers, and leading the charge on our content strategy.

Alex: Does that mean you help curate stations for the platform?

Jack: Well, Kevin Stapleford, our head of Programming, still lets me program a few.

Alex: Another point I want to bring out early in this interview is you've been on TV shows like the Today Show to talk about digital music. You've also been interviewed by CNN, NPR, Rolling Stone, Billboard, Wall Street Journal, Reuters and USA Today. Congrats on all that.

Jack: I have been outed as someone who will take almost any excuse to talk about this stuff. From the time I was a kid, I have been obsessed with music and especially radio, and I fell hard for the internet, so there you go.

Alex: We'll talk more about Slacker, which is just down the road from where I live in San Diego. Let's talk about how you were involved with music at college radio. Was that at UCLA or in New York?

Jack: It was actually WCDB-Albany NY. Godforsaken weather, and long dark winters probably created a perfect storm for a bunch of music obsessed kids to take a shot at making great non-conventional radio.

Alex: So how did you wind up in the music industry from there?

Jack: Lots of mentors came out of that station ... Russ Rieger, who is now an investor at Magna and also managed the Replacements, Diarmuid Quinn who runs Kobalt Recordings, Craig Marks from Billboard (& Slacker), Joe Trelin at NBC Universal. I had a choice out of college ... radio vs label. Radio = Boondocks. Label = NY/LA. I choose Labels.

Alex: What was your first label job and where did it lead? My first job was working for Joel Webber who was a manager, and had a little label called Uptown Records. Our big record was The Dominatrix Sleeps Tonight. Joel, RIP, was a passionate, towering, intimidating entrepreneur ... he also was a co-founder of the New Music Seminar. I learned a lot.

Jack: Eventually, I went to the majors (Polygram & then Sony), doing College Radio and then Rock Radio promotion through the late 80s and into the 90s. I met you when I ran Alternative Promotion & Marketing for A&M. A&M was a great label in those days ... at least I thought so.

Alex: I clearly remember our conversations when you were at A&M. You always stood out as someone who cared a lot about music. Thanks for bringing Soundgarden, Sheryl Crow and Gin Blossoms (to name a few) to my attention. Credit also goes to the SF rep DJ Ennis at the time.

Jack: DJ was a star! And of course, had the best nickname you could have for a guy walking into a station. I remember you also had a unique sensibility for a Programmer. You were really knowledgeable, but also had a sense of humor about the whole thing. An existential programmer ... that's what you were, Alex. I really loved commercial Radio ... especially 'alternative" back then. That helped.

Alex: Thank you. I thought of myself as someone who didn't get into radio to learn the biz, but to make it better. As you may recall, I was an early believer in Sheryl Crow's first record. How important were alternative stations to launching careers back then? She was one of the main survivors of the 90s.

Jack: It's hard to overestimate just how important the format was for many artists through the 90s. These stations played new music in aggressive rotations, and routinely took chances on sounds and ideas that pushed boundaries. And they were good stations ... well programmed ... with passionate and large audiences.

Alex: Kevin Stapleford, who you work with now, had an influence on my KWOD programming when he programmed 91X in San Diego with Michael Halloran on his team. They brought a lot of creativity to the format, as did Richard Sands at Live 105, who appears in the picture with you, DJ and Sheryl Crow.

Jack: These folks were easy to respect ... they are remarkable people ... if you talked to Kevin Stapleford, Richard, Halloran, Kevin Weatherly, Lewis Largent, Tom Calderone, Kevin Cole, Sean Demery, Mcguinn, you ... these people were all incredibly smart, interested in music AND media, could talk books, movies, life. It's no surprise so many of these people transitioned well to digital and succeeded for years after. They were really talented.

Alex: Yes, it was as if alternative meant something beyond music - as if it were a modern counter-culture. Lots of corp consolidation eventually drowned that out, but it was fun while it lasted. After A&M you moved on to other labels at a time when the music biz went through big changes.

Jack: I went to Timebomb/Rebel Waltz with Jim Guernoit. Jim may be the single smartest music exec I worked with. He saw around curves, and taught me a lot about artist management.

Alex: Who were some of the artists on that management roster?

Jim: Jim managed No Doubt, Social D, Beck, The Offspring ... he had a huge role in the format.

Alex: Pandora came on the scene in 2000 then Spotify launched in 2006 followed by Slacker in 2007. Wasn't that enough streaming services? Now there's too many to name.

Jack: It seems that way to some of us, Im sure. But I think for the general public, it feels both new and exciting ... and confusing. For listeners it is an embarrassment of riches.

Alex: What sets Slacker apart from the other music streaming services? What I notice are the various theme-driven curated stations.

Jack: We have a definite POV. A voice. We celebrate that whole idea of "Voice" on 2 levels ... we have really talented DJs who literally host and bring the human voice to the digital music experience, and we have "voice" in the way we contextualize music.

Alex: Now that Apple is the biggest company in the world and has the money to do whatever they want, does that have any impact on Slacker and the direction it takes? Are there ways to innovate beyond all the redundant ways streaming is done?

Jack: Whether it's things like The Best Ideas In Music History or it's sister station The Worst Ideas In Music History, or 66 Songs That Changed Everything ... we are always letting the audience know our take on things, and encouraging a conversation. Lets talk Apple ...

Alex: Does Slacker compete with Apple on any level?

Jack: We think Apple entering streaming is good news. They may help mainstream the idea of streaming, and may teach a segment of people there is another way to get to music. At this point, it's hard to say we are competing with Apple. We are much more focused on the audience that is disatisfied with the 18 minutes of commercials an hour, no-skip button, and super tight playlist of terrestrial music radio.

Alex: I'm curious to see which streaming company is the first to let users pick their own song by song playlist as opposed to starting with artists and narrowing down the playlist with ratings from there. Do you foresee a day when voice-acitivated playlists will take over? In other words, you just tell your smartphone the song you want to hear and there it is. Does that tech exist already?

Jack: It does. All I can say is please stay tuned ... if you will indulge me ... i'll take this full circle ...

Alex: Yes, please, I want to know more.

Jack: I think the streaming music world in some ways brings things full circle for those of us who grew up with some of the great alternative radio of the 90s ... That radio, at least for a few years, was a combination of taking the technology of terrestrial radio and breaking a bunch of radio and music rules to innovate and bring a humanity to listeners that had not necessarily been heard before.

Alex: Long live out of the box thinking. I know for a fact that it works.

Jack: That's what Kevin & I are aiming to do at Slacker. We are a challenger with a challenger's mentality to inject some daring and rule-breaking into what streaming music can be. Hence the crazy themed stations, the sensibility of experimentation ... the hiring of some, uh, unusual hosts ... and just the general mandate to shake things up in the name of music, entertainment and engaging an audience that we think wants something newer and smarter.

Alex: Awesome, Jack, you've given us interesting insight on your career and the music streaming biz. Jack, thanks for this interview, which will join this list of interviews.

Jack: Thank you Alex, for keeping the flame burning for great radio, and for giving me the chance to tell people about Slacker. Really, thanks again.

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