5 of My Favorite Interviews I Did at Boston Music Spotlight

I’m an entrepreneur again, which has gotten me reminiscing about the first business I started, Boston Music Spotlight.

In 2006 my friend Rory and I started an online music magazine that would give a picture of what it was like to be a music fan in Boston, focusing on great local bands right next to major touring acts. Rory had enough experience to know that publicists would take us seriously if we acted professionally, and I had so little money that I would cover any show and interview any person in order to get free concert tickets, so we were a perfect fit.

Since we weren’t successful in traditional terms like “making money,” today only a portion of www.bostonmusicspotlight.com exists online in the way back machine, but it lives on in all the experience we gained and all the memories and cool experiences we got to have before we were old enough for someone else to hire us and give us that experience. When we started getting front-row photographer passes Rory figured he should learn how to be a photographer. We got hundreds and hundreds of concert tickets in exchange for our promise to attend and review the shows.

And I got to talk to musicians of all kinds about music, which was awesome.

Well, mostly awesome. In my mind, the first two interviews I did—with Craig Finn and Tad Kubler of The Hold Steady—went something like this:

I got better over time through sheer repetition, and usually I’d be interviewing several artists a week and reviewing shows every few nights. If a publicist or label was going to send you tickets to see the Foo Fighters, they were also going to ask you to cover some other artists they represented, which meant there was always someone to talk to or a concert to see.

I talked to so many people I’m now one degree from Kevin Bacon (interviewed him and his brother Michael about their band). Today, this interview experience comes in handy for the Kind & Funny Soul Search, a two-hour long dive-deep interview that starts every project we do and lets us learn all the really juicy stuff in order for us to discover a brand’s true target audience and personalized story.

While I haven’t gotten to talk to a Beatle yet, I did get to talk to a Beach Boy. Brian freaking Wilson. Pet Sounds. I was bummed when he gave me one-word answers to what I thought were engaging questions, but a few years later I saw him do the same to Zooey Deschanel. Knowing I had something in common with her made me feel better:

Talking to Brian Wilson wasn’t my favorite interview, though. Here are 5 of my favorite experiences:

1. The time I made Rainn Wilson laugh

This was in a pool interview when Rainn was promoting the movie The Rocker (which I like). I remember it was a pool interview where several journalists interview one subject together and take turns asking questions because 1) it was in-person at a fancy hotel near Beacon Hill and I was in the room with “real journalists” and 2) one of those “real journalists” in the pool later published a Q&A where they made it sound like they asked my question and I wasn’t too sure about the ethics of that and I wanted to sue them or something but we didn’t know how to sue someone without spending money that we didn’t have, so we didn’t do anything.

Anyways, Rainn was talking about how he had just finished filming his part in Transformers: Revenge of the Fallen and I asked him, “What was it like to work with Optimus Prime?” and the actor who played the immortal Dwight Schrute laughed at something that came out of my mouth and responded with something like, “He was great. Huge trailer though.”

Great comedy partner, that Rainn Wilson.

2. The time I asked Darius Rucker about his country career

Darius Rucker was incredibly friendly, which made me comfortable enough to ask my optional question. Usually these questions were either weird or pointed or controversial somehow, and I learned that there was an art to when, and sometimes if, a question like that could be asked given that I usually had between 5 and 15 minutes on the phone with a person depending on their schedule.

In this case things were going well, so I went for it and asked him if this Burger King commercial was secretly the reason that he went on to start a solo country career:

If I recall correctly he laughed and did not say yes, but also didn’t say no, because Burger King jingles are fire. (Sing it with me now, “BEEEEEEEEE KAYYYYYYYYYYY …”)

3. The time Peter Gammons said “Fuck”

The preeminent baseball reporter Peter Gammons also played a mean guitar at his annual “Hot Stove, Cool Music” charity event. By the time this interview happened I had enough experience to not be starstruck (this became easier the more unfriendly famous people I talked to), and I was pleasantly surprised by how nice and engaging and just plain fun he was. He told me story after story about music, baseball, and anything else that came up during our conversation.

The best story was about Dustin Pedroia.

The Red Sox had recently beaten the Colorado Rockies in the World Series, and in Game 1 the 5’7” Pedroia had done this against Rockies pitcher Jeff Francis:

The way Peter Gammons told it, before Game 3 Pedroia was stopped by security while going into the players’ entrance at Coors Field, allegedly because they didn’t think he looked like a major leaguer due to his small stature, and Pedroia kindly suggested that Rockies security “Ask Jeff Francis who the fuck I am.” Hearing that story delivered in Mr. Gammons’ venerable voice was a real treat.

4. The time I told Scott Hutchison of Frightened Rabbit I loved his music

I got a press copy of Frightened Rabbit’s The Midnight Organ Fight and I became obsessed with it, and still am. In 2018, after a decade of loving the band, Kelly and I and friends traveled to Scotland to see the 10th anniversary celebration of this record in Frightened Rabbit’s hometown of Glasgow, which tragically would end up being the last show the band would play before Scott’s death. I still feel sad about Scott a lot, and I am profoundly grateful that I can recall this personal opportunity I had to tell him I loved his music.

5. The time I talked to the Young@Heart Chorus

I loved talking to people about music, but over time I learned that music journalism isn’t just that, and I began to experience an internal Almost Famous-style conflict as I moved from Patrick Fugit’s bright-eyed idealist toward Philip Seymour Hoffman’s jaded cynic:

Ultimately I didn’t want to not like music anymore, so I decided to step back from the time I was spending with BMS, but not before I worked on an extended piece about the Young@Heart Chorus, speaking with several chorus members out of the group of singers aged 75+ prior to their powerful show at the Somerville Theater.

I say powerful because, well:

For this group, it was just so plainly evident that music brought them joy. They weren’t after fame or fortune, they just wanted to sing with their friends.

At Boston Music Spotlight I didn’t find fame, or fortune, but looking back now I sure am glad that I got to do something cool with my friend.

Thank you to Rory Flynn, the visionary leader who made it all happen, and everyone else who poured some of their time and passion into Boston Music Spotlight. Rock on.