Not many people can say they’ve attended both an Ivy League school and one of the most elite music institutions in the world, but Jake Cassman can. After two years at UPenn, he transferred to Berklee to pursue his musical dreams; a decade later, he’s worked as a radio host, music publication writer, booking agent, wedding band manager, songwriting teacher, music director, and performer of everything from dueling pianos to improv comedy. He also works with the LA-based music education program LOUD, and his indie-rock band Drunken Logic has released three critically acclaimed records, one of which is currently in development to become a musical. In our interview below, Jake tells me about the process of turning an album into a stage production, navigating the different chapters of a music career, and the immense value of Berklee’s alumni connection.
Tell me what first drew you to music to pursue it as a career?
My parents say that even before I could walk, I would crawl over to their stereo speakers and pull myself up to listen, so I guess it pre-dates any memory I have. But I think the moment it really clicked for me was the first concert I ever went to—Green Day at what’s now Oracle Park. I was 14 years old when they put out American Idiot; they were my favorite band, and since I lived in the Bay Area I went to that show a year later. There were 47,000 people, and Jimmy Eat World and Flogging Molly were the other two bands on the bill. I’d always loved music, but it wasn’t until I saw that show that I thought, “I think that’s what I want to do. What could possibly be better than what those guys are doing right now?”
Why Berklee? I didn’t feel like there were many options for a popular music program. I started out at the University of Pennsylvania, where I was majoring in political science for two years, and then I started majoring in music because I could take music theory instead of calculus. I had a band and worked for three different radio stations while I was there, but it was never serious. I wanted music to be a huge part of what I was doing; I wasn’t finding it there, and I realized increasingly that all of this stuff I was writing on my own wasn’t going to see the light of day while I was at Penn. I realized I was going to have a serious regret if I had this idea, this notion I wanted to pursue, but didn’t take a chance. So I took a chance. Berklee was the only school I applied to transfer to, and I got in. I think school at Penn ended on May 8th, 2010; I started at Berklee on May 16th and went year-round for about five semesters.
What were your favorite experiences at Berklee?
I did the Cultural Diversity Leadership Retreat in the fall of 2011. It was a bunch of really thoughtful, interesting people from every background you could imagine, going up to a cabin in New Hampshire for three days and having a blast. It was a really nice time, and I got one of my best songs out of that weekend. I also worked for three years as a booking agent at The Red Room at Cafe 939 with Jackie Indrisano and Michael Kramer. I learned so much from them. In the time I worked there, I think we booked The Civil Wars, Hozier, The Lumineers, and several other acts before they blew up. It was a blast.
I think the best experiences are the ones you’re forced to have and don’t realize when they’re going to pay off. I was a vocal principal, and one of the first classes I had to take was an R&B vocal lab. It totally kicked my ass. I didn’t have that kind of control and I’d never tried singing like that. Now from doing piano stuff I lean into my Marvin Gaye side whenever I can, because the first vocal run I ever improvised was on “I Heard it Through the Grapevine,” and I just wrote a song for whenever the next Drunken Logic record comes out that’s leaning into those kind of vocals as well.
I moved to LA two years ago, and there’s a wonderful alumni community out here. I’m probably seven or eight years older than you, but I still have questions, concerns, and ideas that I don’t necessarily know how to communicate. I can get in touch with people who are further along than I am and have had the experiences that I want to have, all through the alumni office. It’s a wonderful thing to have going all the way back down the line. The alumni connection is one of the most valuable parts of the Berklee experience, and it’s nice that it continues afterward.
Who are your musical influences?
I became obsessed with Frightened Rabbit’s record The Midnight Organ Fight in college, and I think in high school too. That album had a huge impact on how I write and what I write about. It’s funny how Berklee changes you, too—if you told me when I first got there that I would be listening to country music and taking business classes, I would have laughed you out of the room, but I realized over time just how valuable that was. Now I listen to Jason Isbell all the time; he’s someone whose writing I really treasure and like. As far as influences on my music in particular, there’s this band called Dawes from LA that I’m very obsessed with; Frank Turner is another guy I listen to a lot of. But really, I like anybody who is inventive in the way they write their music and is also trying to say something in a unique way—I spent one night listening to all three Portishead albums; I’ve spent nights listening to Kendrick Lamar, Run the Jewels...whoever it might be. I’ll listen to anybody. That’s one of the great things about Berklee, too—that you can’t help but be exposed to all those different types of music.
Everything that you’re doing for your community in LA is incredible, and it’s obviously a passion of yours. What advice would you give to people trying to find the intersection of their music and their other passions?
Right now I’m kind of in a crossroads spot myself. It actually looks like I’m going to go back to school in the fall and get a masters’ degree in community music education, because that’s what’s important to me—but it’s also cause I’ve been doing a lot of part-time work jobs and cover gigs. I got hired at Howl at the Moon right out of school; that was my first job, and then I ran wedding bands in New England for four years. I did a lot of different work, and after turning 30 two months ago, I’m finding that I’m a little burned out from the instability...the idea that looking for work is a full time job in and of itself. I’m trying to make changes to my life around that, but I also remember what it was like when I first graduated Berklee, and I had the energy for that and loved that.
So I guess that I’d say two things: the first is that if opportunities of a certain type keep coming to you, there’s usually a reason for it—there’s something that people see in you or a skill that you have that people want you to provide them and the world. For instance, I pushed back against teaching for a long time, because I didn’t think I wanted that to be the crux of what I did as a professional. But I found that more and more, it’s something that I am actually passionate about, and I’m currently designing an online songwriting class for the LOUD program, because we need some kind of online programming at the moment. That said, I’ve never worked as, say, a one-on-one lessons teacher. I never practiced piano as a kid, and I would feel like a hypocrite asking them to practice their skills all the time. So I always resisted being a teacher on that level, but at the same time I keep getting asked to teach and finding these opportunities to teach, and since I enjoy it and people want me to do it, I want to pay attention to that.
The other thing I’d say is, don’t be afraid of your definition of success or what you want to do changing over time. You should absolutely go and do that thing that seems like it’s the dream job when you leave school, and after a few years—maybe even a few months—check in and see if that still means what it did to you. I worked at Howl at the Moon four nights a week for two and a half years, and I still do some dueling piano stuff here and there, but I can honestly tell you that I could go the rest of my life without ever playing “Don’t Stop Believing” again. I’m at that point now. Those shows are fun, you get to meet some really tight-knit groups of great musicians, and you have to memorize hundreds of songs, so it’s a great opportunity to learn how pop music is constructed. But at the same time I’m very sick of it, and I don’t want to do that week in and week out for the rest of my life. So when that happens, don’t be afraid to realize that and take a chance on yourself again.
That is fantastic advice—especially as so many of us are feeling pressured to constantly create in the midst of this quarantine.
Right now we’re all in the same room, day in day out, and especially with creation you need inspiration. There’s not that much of it when you’re distant from people, not to mention the anxiety and all of that. I think this a great time to work on something you’ve already started, but I think the real explosion of creativity is gonna come when we all actually get to hug each other. However, I also want to say that you shouldn’t be afraid to write honestly about this sort of thing. My last semester at Berklee was when the Boston Marathon bombing happened, and someone (a great musician who I’m still Facebook friends with) wrote an inspirational song about how we’re going to keep on running. I think she still plays it at the yearly marathon parties and stuff as part of her career. That’s all well and good; there’s a place for that motivational stuff, and I think OneRepublic already put out a song that’s being trumpeted as being about the coronavirus crisis and all that. But there’s a song on my most recent record called “Last Week” about how long it took to get back to normal in Boston, and how weird and anxious and traumatized we all felt by having something like that happen in our neighborhood, on our campus. And that’s an okay thing to write about, too, you know? You can worry that nobody’s going to want to listen to that right now, but eventually they will. People are going to want to remember what this was like, the good and the bad. You shouldn’t be afraid of trying to dig into that dark side.
Currently you’re turning Drunken Logic’s most recent record, The Loudness Wars, into a musical theatre production! What inspired you to do so? Well, I suppose the fact that American Idiot was my favorite album growing up means that this was all bound to happen eventually! It’s funny because I definitely thought of myself as a rock-and-roll guy trying to make a serious album. The Loudness Wars is our third album, and it was always a concept record. It’s very much political; it’s contemporary. It was really an attempt by me to try and find empathy for someone whose political views I thoroughly disagree with. So I tried to create a character who was perhaps older and more conservative, maybe a little bit more thrilled about this more MAGA thing than I was, and trying to explore what that person’s life experience could have been in a way that didn’t sell them short. The rule I had was to find empathy, not sympathy. That’s half the album, and the other half is somebody coming from my perspective, and the concept is that they trade off songs.
When marketing the album for an indie release, I came up with this really great plan—we made custom action figures to mock a GI Joe thing, they’re on the album cover and featured in the music videos. We made a music video heavily inspired by the movie Network, which was very political and, I thought, on-point. When we put it out, it ended up being highly controversial, which is always interesting. The video is a satire and it ends with these two action figures who have been made into cable news hosts killing everyone in the newsroom, basically. And within ten days of shooting it, someone sent pipe bombs to CNN and there was a litany of mass shootings. There were a lot of people who, somewhat understandably, were unwilling to touch that. But on the other hand, to me, I thought it just got more real. It made me feel artistically vindicated even if it didn’t really get the word out.
I really believed in the album and what I was trying to say with it, and I wanted to try a new way to say it. I’ve been working more and more as a music director at Second City Hollywood, an improv club, and it’s been a blast. I’ve also recently completed their conservatory program as a performer, and I’ve been working with some people who really liked and admired and saw some of the shows they put together there, and I thought, “I would love to do that.” The idea was to expand The Loudness Wars to four characters, with two on each side, and turn that into a show at the Hollywood Fringe Festival, which is hosted in LA every year. You get discounted tickets for theaters, and they let people with really barebones productions put something together. So I’ve been working hard on that script for about six months now and we’ve had a few table reads; obviously the music’s been more or less completed since the album came out. The show was supposed to happen in June and it’s been delayed till October for obvious reasons, but it’s an exciting new thing to be working on.
What advice would you give to beginning writers?
I would try to show whatever you’re working on to as many people as you feel comfortable with before putting it out there. Always be aware of what you don’t know and try to pick up things from people who know a little better, but who also understand you and what you’re attempting to do. I’ve literally never written a script before; this is a completely new thing for me. It’s gone through several different iterations already—I’m hopefully going to get to work on draft ten tonight, and ten is the low number. It’s changed a lot. Your idea is going to change, especially in a project like this. I think in music, it’s much easier to keep a little bit of control of the project and what it means to you because you don’t need as many people to make it. You can just do it with you and your producer, you and your band, or whatever the setup is. The lowest common denominator is a little higher on some other projects where you need a production team, a cast of actors, a director, and etcetera going down the line.
What I’ve learned over time is that there’s certain things in the show that might make sense to me, but if they don’t make sense to the people I care about and am working with, then I need to go back and revise them. The whole point is that this is supposed to affect an audience as well, not to mention the people I’m trying to create this with, because at the end of the day I can’t do it all myself. So get as many revisions as you feel comfortable with. But at the same time, just because somebody gives you a note doesn’t mean you have to take it. Go in with the confidence to say “no, I like that. I understand where you’re coming from, but I’m not going to change that just to appease you.”
How do you #getinthegroove?
I work a lot in improv now, and one of the things I’m trying to incorporate into all the classes I teach—even the songwriting sessions—are improv warmups. I’ve never been somebody who does a lot of vocal warmups before I perform; my usual routine is to go for a run or get some sort of exercise before I perform, so that I have full lung capacity. But there’s a lot of really stupid, silly improv games that get you in a space where you’re receptive to the crazy ideas your brain has, and to saying them out loud instead of just thinking too much about them, which is something I’m always guilty of even to this day. I love getting to a place of being physically loose but also mentally loose, and being ready to chase something that’s funny or exciting with good people on stage. So just getting in a room and being silly with others is always a good way to warm up.