Often, our jobs just don’t fully reflect the kind of skills and capacities we are made of. They can be limiting and tend to keep us from growing and reaching the life we truly want. Take control of your career as Rich Redmond brings over to the show serial entrepreneur, Jimmy Pemberton, to talk about his inspiring story of taking his own career and income by the reigns—beginning from working at the legendary DiCenso’s Drum Shop to eventually starting his own digital marketing consulting company and music education service platform, Lesson Squad. Jimmy also discusses the need to change the narrative about multipreneurship, wear a ton of hats in this day and age, and design for the lifestyle you want and not the career you want. What is more, he then taps into celebrities on social media, being involved with film and TV, and the reasons why Boston is underserved for entertainment. Discover a ton more insights in this conversation as Jimmy reminds you that when you can’t find a job, create one!
Jim, let’s get into this, a longtime friend of mine and a killer drummer. We’re not talking about basic four life count. We’re talking about a serial entrepreneur. My friend, Jimmy Pemberton. What’s up?
Thanks for having me, guys.
Jimmy, tell us all about you. Remind me in my T-Rex brain that is getting worst and worst because Alzheimer’s does run in my family, we met many years ago.
This is a story that I love telling because the story is so bizarre. It was Friday, I’m sitting there and I was looking for something to do. None of my friends were around and I saw a friend of mine, James Murphy, a killer drummer was hosting a drum clinic an hour away from me. I was like, “Screw it, let’s go.” I got my car, go up there and I watched James Murphy put on his killer clinic. After, we’re catching up and talking. He introduced me to his young pupil who is Jeremy Gold. My first time ever meeting Jeremy Gold. The second thing he brings up to me is like, “Do you go to Nashville?” At that time, I was doing back and forth as an artist and I was like, “Yes.” He’s like, “Do you know Rich Redmond?” I was like, “No.” He’s like, “You need to know him.” I get home and I google you. The first thing that comes up is a picture of you wearing a shirt that I designed. I had a short stint having a custom t-shirt operation. There was this shirt that said, “I like girls in heels,” that through some other way made its way to Los Angeles and in a store and you happen to pick it up.
How small of a world would it need to be that you being an entrepreneur developing this clothing line, developing this shirt, somehow from a musician wearing it and ends up at the wasteland in LA on Melrose and I buy it?
That’s when I reached out to you and we started talking on the phone. I ran into you once at Red Door in Nashville. You were up here doing a clinic with James Murphy and Dave DiCenso.
That was an event at the Stephen King’s Salem’s Lot.
Salem Witch Museum, the Satan church.
I didn’t know what I was getting thrown into. Someone says, “Do you want to play your drums in front of a group of people, say a couple of words of wisdom and be a fundraiser?” I’m like, “Yes, sign me up.” I’m there with DiCenso, who’s a monster. Both these guys, James Murphy playing in the Blue Man Group in Boston and they were shredding. They played 32 notes for every one of mine.
You were great, especially as far as personalities and diverse playing were a great mix.
We kept in touch over the years and you kept coming to Nashville. You’re a New England kid through and through, and you would be coming to Nashville because you were like, “I’m going to try to crack this nut. I’m going to play with these recording artists.” You were doing business there and you always had this mindset of, “The businessman drummer.”
Since day one, that was a definite thing. I started to learn everything to play drums more. Being in high school, it was like, “Do you want to be able to play in shows? You need to know how to book the show.” I learned how to do that. “Do you need money to keep this thing going? How does this work? Merchandising and ticket sales.” As I got older, I started to tour in my late teens and this was during the MySpace era. We started to go out on college runs and I was part of the team that was running the MySpace for the band, selling the tickets for the off dates, selling the merchant online, building the whole thing. That’s where I got my business chops was from, “If I do these things, it allows me to play drums more.” That was the equation.
Have other passion or skillset bringing in the money, which would afford you the ability to play drums and to play with whoever you want no matter what it paid.
That’s definitely where I got it. To make the long story short, it went from doing the bits of touring, recording and then building up a teaching career because that was goal one and like, “Can I make a good living just with drums?” I got to that but I didn’t have any days off. I was like, “Where’s this going to lead?” In the music space, I started to do a little bit of consulting, but then a drummer friend of mine said, “I need to introduce you to Bret Siarkowski.” At that time, Bret was at the Game Show Network running their mobile app division. He was running their research and development thing. I met with Bret for twenty minutes and he was like, “Do you want to consult for Game Show Network?” I was like, “Sure. I’ve never done this before.” He’s like, “You’re creative, you’ll be fine.” That was my start into that. When I saw what I could make money-wise for that, that’s when that other thing shifted where it was like, “If I can build another vertical of revenue and make sure I’m working for myself, I can play drums for whoever I want.” I’m in control of the drum path at that point.
This is something that always reminds me of our friend, Nick Ruffini, with the Drummer’s Resource. He’s always talking to his guests about, “Should we feel guilty if we have to work a day job? Should we feel guilty if we have other interests outside of drumming?” which comes up a lot. It’s that guilt factor. This is something that Jim McCarthy of Voiceovers.com has a lot of thoughts and feelings on because he started as a drummer, still has drums, still plays drums and he’s got a bunch of my gear that I gave him over at the house there that he’s playing it Hot for Teacher. He’s all sweaty because he finished the intro of the Hot for Teacher. He created all these other verticals and revenue streams. With Jim being involved in all these things, he’s always been my Yoda and my muse, always gives me advice about how to handle business.
There’s a silo congruency in what you’re doing. There’s always a creative part of you being engaged in order to keep the motor running for the drumming.
We need to consciously change the narrative because many people are coming up, they don’t know what the new lifestyle is. I feel like not only do we need to change it, but we need to glorify the new narrative and celebrify that because I feel people will be ten times happier and they’ll get to do more cool stuff. If you think about Jared Leto, Pharrell or any of these guys. they’re all pluralist already. You don’t think about it like, “I wonder if Jared feels guilty from the ‘90s onstage with Thirty Seconds to Mars versus when he’s on a film set versus when he’s working with a tech startup.”
That’s where it has to go for drummers. One, there’s so much more value. There are already drummers doing it like Chris Kimmerer who owns The Brown Owl. He has his hand in real estate. He crushes things. That’s what makes his passion for hockey and the things he has going on in that vertical as well. That’s amazingness and he played drums and crush it. It’s the same with you. How do we better tell that story so it’s not like, “I’m a drummer, but I also do this?” It needs to be a collective narrative.
It’s a matter of confusion of the market is what you’re talking about, which is something that I’ve battled with since getting into self-entrepreneurship and self-employment. A lot of my background is voice over, video, radio, podcasts and things of that nature. At the same time, I am a partner and own an electrical lighting trade conglomerate that’s starting to develop. A lot of people are like, “Did you do all this? How does this come in?” I said, “I know I get it. It’s confusing.”
Jimmy and I talk about it all the time. How do we take all these things that define you as a creative being? Jimmy, you’re the perfect example of a guy where art and commerce are constantly meeting. For the neophytes out there or the people that don’t know about consulting that are interested in that, what does that entail? What does consulting mean?
That can be a little bit ambiguous and it’s how you define your services for yourself. When it comes to me, it depends on what it is. It could be on anything from building an audience or following on social media. It could be also consulting on building out content for social media, business development, or creating the right partnerships. I even do things like Think Tanks where a company will hire me to come in and do three meetings that are about 1 to 2 hours long. I present a whole deck on everything on where they need help and then give them all that information and then offer them the support, but then you’re out, they want you for that one brain dump and to move it forward. It can be anything and that’s what makes it beautiful. If you get known for 2 or 3 services under your consulting umbrella, that’s where you’ll build some consistent revenue.
Can you list out the silos that you have and what are you working on? I know there are a lot of victories that you can celebrate here publicly, a couple of which you’ve dragged me along with you during the process, which is awesome.
One complete vertical for me is a consulting company that’s been a blessing. I’m a consultant for The Game Show Network, specifically on their mobile apps and even in the instrument manufacturers. There’s KHS that has a whole suite of brands. I’ve done some work with them and continue to do so. There’s a great company called Overtone that was acquired by Unity that’s in the video game space. I worked with them for two years on their product and I had a bunch of fun there. Consulting is one main vertical. I have a tech startup called Lesson Squad that Rich is involved in and as the whole COVID thing happened, that started to take off and it was timed by accident with a release of the new part of our platform. That has gained a ton of traction there.
The other thing that comes into play is working with TV and film. I have an animated series, Benny Beats, that’s in development with Studio71. We have a great writer involved in the project, Chad Murphy. We’re seeing where that lands and I’ve been out doing those pitch meetings, seeing where Benny’s Home will be. Also, I have an agreement with a company called Litton Entertainment to do a Saturday morning network show called Drumming Up. I got into that space and a great guy named Larry Aidem is part of what’s called Reverb Advisors. I signed with them to do from here forward any of my entrepreneurship endeavors or TV and film endeavors in collaboration with them.
That’s something to keep you busy and you’re thinking in drumming, you didn’t have a day off. I remember if you do two church services on a Sunday and then your circuit band plays Thursday, Friday, Saturday, and then you had church on Wednesday night, and then you might play with a big man, do commercials or teach a drum line. It’s like you work every day.
That part of the drum career thing for me was crazy. I was up to almost 50 students a week on top of 2 to 3 gigs a week. I was having times when I was going out for those three gigs traveling, coming home and I was filling any other space in between. I was helping out at DiCenso’s drum shop where that’s one of the places I was teaching and where I grew up and got my foundation in this whole industry. The cool thing about this, as much as it’s crazy and there’s a lot going on, I got to a point where I could hire some people on the consulting side and build out a team and do that. That helped. If I want to take three days and go play drums or playing with friends in New York and we’re doing a record, I can jump in the studio, it’s all there, fly down to Nashville and do whatever. Those opportunities open themselves up in a big way.
Time management has got to be crucial for you like pre-planning. Are there days that you’re doing everything that you have to do or is it each day you’re putting out fires? I’m assuming you’re dealing with the things that need to be attended to the most right then and there.
I went through a period of life where it was too much. If I was switching gears too much, my brain couldn’t handle it. That included if there was traveling involved too and trying to go from consulting brain to creative player brain. That’s where I’d get somewhat messed up depending, and everything shifted. Now, I run a crazy morning routine that involves a bunch of other things like waking up, getting hydrated, cold shower, journaling, and exercise. By 10:00, I have my first meeting of the day or my first meeting that’s always on the books with my co-founder at Lesson Squad, Josh Hoffman-Senn. That’s the first thing of Lesson Squad. It’s like, “What do we need to do?” We’re checking, “Are there any fires to put out?” It’s always the question one. When it comes to consulting clients, that stuff is always scheduled throughout. It could be a couple of hours that day or it could be that I’m checking them with two guys who are working on a client that I’m overseeing. I run by the calendar on my phone. Let’s get onto that IP conversation. I have questions that I want to get your thoughts on.
Let’s take one of your offerings. You could take the idea of being a drummer. I fancy myself a drum educator. You’re a drum educator. You took that idea, executed on it, got picked by Benny Beats. It is this great animated character and if people follow you on Instagram, they could probably go back and see some posts and stuff. You’ve never been shy about throwing opportunities and creating opportunities for your friends. You’re like, “You’re Steve, the Snare Drum. Can you please voice Steve the Snare Drum?” I would send you a read for Steve the Snare Drum and you have any consulting for Lesson Squad. These are great things where you’re not afraid to spread the wealth. We even had a three-person company for a while called GPR Creative and we managed some music acts. We learned a lot and our partner, Jeremy Gold, got big and famous. You got big and famous.
I call this entourage effect. I grew up on that HBO show, Entourage, which half-ruined me, but the half was like, “I get it. Take care of your people and vice versa.” That’s the actual fun of it. I hate when people say, “Don’t work with your friends.” I’m like, “If you don’t want to work with your friends, you have the wrong friends.”
Don’t mix business and pleasure. That’s all we do.
I’d say flip that. If you don’t think that you want to work with the people who are your friends, get new friends. I would mix business with pleasure all day. Us doing that GPR thing, and this is a huge thing. We were doing that work with a great artist, Lindsey Highlander. We got a lot done in a very interesting space. The big thing that I’ve learned about things like that, or even as different projects move ahead, and you think this one’s going to go over the line first, but then it stops and then this one goes over the line never kill anything. People kill things too much. They go, “That’s done.” I never say that’s done. I say, “That’s here for now until an opportunity comes.” Let’s say you, me and Jeremy needed to reunite because some artist opportunity happened for the three of us. We wouldn’t think twice, we do it. That’s why you never completely kill something unless it was a bad experience. Other than that, keep everything open because you don’t know.
It’s like you had a scrimmage game going at all times over at your place.
Everything to me, it’s always the way I visualize it. It’s a line item. I try to keep them and I’m stealing this from a great interview that’s on Complex with the founder of Span. He learned how many balls he could juggle before one fell. I’ve done the same thing. I know that I can have no more than four verticals going on at one time or something will be bad. This is how I categorize it. I have drumming in this thing where I always keep that going. Even if I’m not doing a ton of it, it’s always there. I then have the startup Lesson Squad and I bucket everything that’s TV and film because it’s the same headspace as that piece and then consulting.
Going back on Benny Beats, I’m going back to that because we’re both products of music education, Jim’s a product of music education, and our friends at Nashville School of Rock Franklin are the sponsor of our show. Jim, what comes to mind when you see Jimmy?
It’s because of diversifying his skillset, capitalizing and identifying the areas that he can monetize it, understanding that we’re probably not in a world where you can monetize this and be mega-successful at one thing anymore that people need to be okay with this multipreneur aspect of life. I can appreciate that. That’s one of the things I preach to voice over people, and I consult with a lot of different voice over students. All they want to do is get in front of a mic and read. I’m like, “You should probably learn how to produce your own stuff and learn how to mix your voice with music beds and produce spec spots so you can prospect with people and do all these different things that you should learn how to do.” This is contrary to the elitist voice over people out there. Making your own demos, they hate that notion.
I’ve made all of my own demos up and that’s how I’ve gotten my work. It’s always been out of the real stuff that I’ve done. That’s something you have to do. I can appreciate that aspect that there’s somebody else out there that is doubling down on their skills, gifts, and talents, and figuring out different ways to juggle a lot of things in the air to see which one goes. It’s almost like what you used to talk about, Rich, coming to town and playing with how many bands in one year?
Twenty-nine bands were my record.
You had no scheduling conflicts but you understood. It was like playing the lotto. One of these things has got to go.
Ninety-nine percent of those people have left the music business. They were like, “I’m going back to Des Moines, Iowa or Fargo. I’m going to work for my dad’s company.” It’s not a bad thing but it’s that gumption of that follow through and that stick-to-it-ness, pumping your chest, facing that rejection and falling in love with that rejection. What do you guys think that the world changed in a way where we have to wear so many hats? If I was playing drums at the level that I’m playing at in the ‘80s and ‘90s with Studio 54 and the velvet ropes, playing drums was enough back then. Being a consultant wasn’t enough back then. What changed in the world that now we have to wear many hats and be great at all the hats? How did that happen?
It’s technology, as things got automated, mixed with an industry’s failure to progress or to innovate all the way through. You look at the whole Napster situation. What should the industry have done? They should have acquired Napster and not sued it. Even look at live streaming, somebody in the music industry, call it Sony or Warner or whatever. They should have been building live streaming for musicians at scale, making certain deals with the labels. That should not have come from where it’s coming from now like Facebook, Twitch so they lose again. It’s that type of thing for music specifically. Other than that, I’m trying to think what was the different thing there.
In voice over, Jim, the tools you need to be allowed entrance into that field are so much more affordable.
The barrier to entry has come down for sure.
The competition goes up. If that starts to split, that’s where one person can’t take all the cake.
It’s amazing to see how the industry is becoming somewhat commoditized because you’re going to have your Kias, your entry, low-cost talent out there, and there’s a ton of them. You have the upper talent, the elite talent that I talk about that I always manage to piss off by sharing my ideas because they don’t like the notion of having to drive down rate. For people that are getting into it, they think making $20 for reading something is amazing. They might’ve been at Walmart being a greeter. $20 being made in five minutes to them is going, “This is incredible.” You’ll get the elitists that go, “You should’ve paid $250 to $500 for that project.” That’s all well and good because they don’t know how to negotiate yet. They’re not that good yet. The elitists don’t realize that it’s good for them because it’s setting them apart even more so.
Those people aren’t necessarily going to buy that gear and stick with it. They might get that one opportunity that comes out of nowhere. Let’s face it, we all know that there’s maybe that initial bit of luck or a door being open, but to stay in that room, you got to keep showing up with the goods and be continually developing personally and professionally. Otherwise, forget it. It’s just a fluke.
What I don’t get is that you’re never going to hear about Brad Pitt being upset that Rich Redmond is trying to get into acting. He’s never going to be upset about that because he’s Brad Pitt and he commands a certain price. The thing is being able to create yourself into a person of interest to the point where you can package and sell it, and ‘sell it’ is the most operative word, and be able to close deals.
It’s been interesting to watch in the acting space. They’re already getting to this point, but it’s getting more with live-action where it’s like, “Who is going to bring more eyeballs to the film? Is it the tried and true star?” Brad Pitt’s a bit of a different level, but that will also shift as these years go on or is it so and so on YouTube that has millions of viewers every week? It becomes a game. If you look at what happened with Will Smith, he wasn’t doing much until he joined Instagram and YouTube and started putting out web content. That brought him back into pop culture, at least in my opinion. What was his big film in that gap? There wasn’t any. Now, you’re seeing him get more, but you’re seeing now. He’s relevant to the entire market again because of that.
There’s one element that he’s doing that a lot of the elitist actors are not. From what I could see, he truly engages with his audience, which is very important. If you’re an actor or a celebrity and you don’t engage with your audience, people are going to pick right up on that and the paradigm has changed.
Look at Will Smith and Ashton Kutcher, two serial entrepreneurs and highly successful people. Will Smith was a rap star who knew Quincy Jones. Quincy Jones got him to a sitcom. He didn’t have any acting or comedic training. He was natural and it worked great. It moved him up. Ashton Kutcher, a male model and a super nice guy. He had opportunities come to him. He got that ‘70s Show and had no idea how to land a bing bong boom. I listened to his thing on Marc Maron and he’s like, “I had no idea about the poetry and rhythm of sitcom acting. I learned on the job as I was making the money.” As he was making his money, he said, “Let me continually be a humble student of life.” He learned all about tech, startups and made a fortune.
He has been able to reinvest in himself and do great things. I’ve learned that Sean Penn is responsible for the majority of the COVID tests in the United States. He bought them with his own money and is giving them out. Those COVID tests at Dodger Stadium are because of him. We’re talking about TV and film. Jimmy, you were at playing drums and acting. It’s the same thing. In the movie Love, Weddings and Other Disasters directed by Dennis Dugan, starring Diane Keaton. Tell us a story. How did this happen?
I was on set for four days. It was super fun. I got to play drums with some cool people that you’ll see in the film. That was a big thing. Overall for me, I answered an email from a casting office here. I was like, “I’ll send in my bio,” and they called and said, “You’ve been approved for it. You need to be available on these days.” I showed up and did it. The first day on set, I sat in holding for six hours doing nothing. I called another actor friend of mine and I said, “You never know how it’s going to be. Go see.” I get there and I sat there and then they had me at the very end of the day after sitting and holding on all day, just like you would on a gig, take the drums out of a van and walk them into a venue.
I did that on the last music video I filmed for that band The Fell. I was like, “This is where we’re going unload the van.” I’m like, “I can do that.”
The other days on set were all playing scenes and I get there and because the props is bringing in the kit so you don’t know what you’re showing up with. I brought a pair of sticks just in case and you get up there and they didn’t send me any of the music prior. They’re like, “Cue music,” and I’m like, “Does anybody know what this track is. Can I look through on a chart?” The guy who is the MD on set comes over, “No one sent you the music?” We’re like, “No.” We did it and it was great. It worked out.
Oddly enough, him and I were talking and he’s like, “Do you know who played drums on this?” It was Chris Kimmerer. I spent the next on and off days. It was one of those crazy times where I was doing too much of this switching gears. I was getting on a set at 5:00 or 6:00 AM and sometimes earlier, and then I would leave set after doing a full day or more and I was going to New York for meetings for other TV stuff. It was craziness but it was all good stuff and it was super fun. I’m excited for the film to come out because I got to perform with some cool people that you would know some relevant names. For me, the benefit beyond getting paid to play drums in a film and do that and check that box was more watching a film get made.
Weren’t there some other opportunities that happened before that too or you were playing drums in the films?
There were some things that came up. Nothing that I got. There were some things that I got put in for, but it didn’t happen. They’re all on the West Coast. Perfect thing to fall in love with rejection is the name of the game.
The message I’m getting from you is, the audition process was almost like a hobby.
It was literally one of those little things where I wanted to go check. I’m a huge lover of TV and film. I was like, “I have to put drums in a thing.” I got fortunate with this one where I get to perform with other musicians with careers. The people I’m performing with are principal actors in the film as well. That was cool for me where I was like, “What an added bonus to be doing it and have that go on.” Watching how they shoot things, I learned so much about like, “They’re setting the camera. They’re going to catch this now. They’re putting one behind me to catch this. We’re resetting.” In video village, they’re watching everything for continuity. If I could have had a pad and note or if I could have my phone on me onset, I would have taken notes all day.
Do you guys know the story of Steven Schirripa? He is an actor. He’s the guy who played Bobby Bacala on The Sopranos. Back in the day, he was the entertainment director at the Riviera Hotel and Casino in Vegas. As a hobby, he would go out and audition for acting jobs on his lunch break. Look how that panned out. He landed his first film with one of the Flintstones movies and it took off from there. He got a secondary role in The Sopranos, but substantial.
Many people say, “This is how it’s done so this is how I have to do it.” Forget all that. This comes down to a huge belief thing that I had, “Never design something to pinpoint the career you want. Design to the lifestyle you want.” Because that could change the career or the way that the career facilitates itself for you. I see a lot of guys who’s like, “This is what I want to do for a living.” They go and they get it and they go, “I love my job,” but then they hate the life that it requires for them to have around it. Where if they had designed a little bit more for lifestyle, then the job might’ve looked different or they might’ve negotiated something differently going into whenever the job is. Maybe there’s someone out there that they like being on a film set once a year. That’s what they keep in mind. It’s a different perspective, but I like coming for a lifestyle versus a job title.
You’re setting up a lifestyle for yourself that you like. You’re single. You don’t have anybody telling you what to do. You got your space and got cash in the bank. You’re a creative person. You’re making money from your creativity. The thing is that I don’t know any of your hobbies. I only see you working all the time 24 hours a day. Are you still working out with Ryan? We’ve done that workout together.
I’m working out with you and I was like, “I had been working so hard to get in that shape to do that workout.” You come in and you kill this thing and I’m like, “How? I’ve been doing this for months.” You crushed it. That blew me away that day.
That guy is good because it’s a full-body workout where you’re doing kicks, sparring, plyometrics, and resistance training, but then you go out and you’re swinging the sledgehammer on the tires and then you’re moving the NFL thing across the concrete. That’s my kind of workout. You have such an amazing essence. You’re so focused and time managed. You also have the spirit of positivity. A lot of people are like, “You got to move to Manhattan. You got to live like a rat. You got to move to Los Angeles and get six roommates.” You’ve had amazing things happen come to you in Quincy, Massachusetts.
It is the craziest thing from all the music stuff this happens. They shoot films here in the spring, summer, a little bit of fall. I happened to get the one drum gig for the feature film that was being shot that needed a drummer. Even the way I got into the other projects like getting the animated series off the ground and moving in a forward direction. I was meeting with an amazing guy, Chris Lynch, who at the time was running Reverb Advisors. He’s the CEO of a great company AtScale. I’ve met with him to talk about Lesson Squad. He was like, “What else do you have?” When I showed him the animated series, he’s like, “A great guy, Larry Aidem, will be here in a couple of weeks. I’m going to get you a meeting with him.” Larry at the time was living out West, but also in New York. I got lucky where these things seem to happen.
It’s that thing also where no man is an island and you definitely have these true believers that have opened doors for you and you keep them close. We need the help.
It takes a team and time. Many people forget about the time, me included. Patience is a jerk. I’ve learned to be patient but it’s the thing where you can see where the dots connect, but you don’t know how that timing’s going to unfold. You have to keep it going forward. The games change. A good example is playing drums. If you do want to play drums and tour, you are 100% better off moving to New York, Nashville or LA, because a lot of the bus call, you have to physically be there. If you’re playing in the digital realm, you can do whatever you want.
Let’s say you only want that part. In my case with the drum stuff to be a percentage of your career, though that means I have to be in New York, Nashville or LA a percentage of the time, or have a presence there enough to make enough happen for whatever fits that lifestyle or that career that I’m looking for. That’s something I hope that more people know and explore that they can do that. I was looking at Chance the Rapper and what he did out of Chicago. He didn’t move, didn’t go to one of the meccas. He’s in a secondary market and crushed it.
You’re going to see that happen and I have crazy predictions too. Boston is a city that is underserved in entertainment. We do get the tax credit for TV and film. You got on the music side and dance. You have Berkeley which also has the conservatory attached. You then have Harvard and everything that comes with that. You have MIT. It’s the area in the country with most schools per square mile. You got a whole youth market. It’s like the craziest thing to me, where I feel as more comes in, there’s more to be done here.
It’s an epic city culturally. The fact that you were there, you’re going to be in line way ahead of everybody else.
Jim, you had this crazy idea you’re going to tell us.
You and I have talked about it before. It hearkens back to putting Rich in situations and scenarios that he may not be familiar with. The NFL thing brought that back to mind. You and I have talked before about doing a series of videos of you doing things nobody would expect you to see like changing a tire, maybe describing what is going on in a professional sport?
These guys right here in the black jersey are up against these guys in the yellow jersey. It seems like the yellow jersey guys are running one way and the black jersey guys are running the other way.
Going hunting would be hilarious too. This also goes back to when we did your documentary and I talked to your parents and they interviewed them for the film. They said that you were at a game and you were doing the drumline and everything. You were so concentrated on that they asked you who won the game and you said, “I don’t know.”
I was always worried about getting my parent a little speed up. I would’ve definitely done some stuff differently in my youth.
I was thinking that there’s an opportunity there for you to do things that people would never expect to see you do. It’s entertaining and hilarious.
I would love to add something that came in my mind as you were saying that, amongst that brilliant idea, what I would pay to watch you do is to be a date commentator. The two people go on a date and you’re on another table with a microphone and you’re telling the audience what you think is happening on the date.
This can be another whole dating thing. Dating shows are popular.
Picture having somebody watch it and then the crowd at the same point is going to watch. Do they agree with you? Do they disagree? At the end, you put the two people who are on the date in separate things and interview them and you see how you’re commentating worked out because you’re reading their body language. We can go a lot of ways with this, but I think you would crush it.
That sounds like a great offering.
We should pursue that and drumming roulette. I had this idea before where you get some heavy hitter drummers, and it could be any instrument but for drummers. This could be a nice little video series. Somebody coming to Nashville, they get in front of their peers and these heavy hitters like Kevin Murphy, Ben Caesar, Chris McHugh and all these other guys, they sit down at a set of drums and it is a drumming roulette. They have to play four songs and they have no idea what the songs are. It’s based on interview question. It’s not like you’re going to throw a complete curveball at them. It’s based on what music did you listen to that you would like playing growing up? I always said that I could sit down and I could play Carry On Wayward Son. I could play a whole host of songs because that’s what I used to do. I still have the muscle memory.
There’s something there. There’s a certain niche web show thing that could happen there. That is becoming more and more a thing. If that’s a beat, you can take it to a Drumeo or a DrumChannel, and you created this expanded offering for them beyond education or interviews.
Even the entertainment and the education part of it comes in with the reactions from the judges, “Here’s what you could have done better.”
There’ll be those iconic moments when a song comes up and one of the judges played the song, the originator of the song. Imagine having to do a Police tune in front of Stewart Copeland, which I’m sure Josh Bresette has. There’s something about doing it in front of the guy that did it.
Jimmy, going back with this Harvard Incubation Program and launching Lesson Squad and then all the cool things that have come from Lessons Squad. Take us down that trip from coming up with the concept of what it is to getting it to where it is now.
The concept is relatively several years old. This is a great example. This is going to run into the whole sitting on things. I was teaching and I was having a lot more luck teaching than some of my peers. At the time, Twitter had started to take and this is pre-Instagram, I was able to build a crazy teaching roster to the point where I was giving students to other teachers. It started to hit me. I was like, “I know how to use these digital tools from playing in bands, being on the road, and figuring things out.” There are all these other educators that didn’t go that road and don’t know how to use these tools. I was like, “What if we could make the tools for them?”
That was the first idea that I jotted down. My next step was to do a proof of concept completely non-digital. I had other teachers, I was giving them students and they were putting a percentage in my mailbox, literally dropping off an envelope of cash to me because I helped fill their roster. I was like, “Here’s what we’ve learned. If we give the teacher students and they don’t have to handle X amount of the work, they will pay for that convenience.” I was consulting at the time for a venture back startup called Cosmo that Josh Hoffman-Senn, who co-founded Lessons Quad was the founder of that company. I was telling him what I had been doing and he was like, “Do you want to help making that digital?” I was like, “Yes, I do.”
We did the first V1 and we launched that and we put some teachers on there and then we started testing. At that point, Josh had taken a break from the startup and had started going to Harvard Business School. Since he was at HBS, he applied for us to be in the Harvard Innovation Labs and Venture Incubation Program. That’s how we got in there, which was amazing. I don’t have a college degree. For me, to be able to roll on to the Harvard campus and check things out, be in that community, and see how it thinks and operates was amazing. I was impressed, which I would say expected to be, but by the culture that they had, it was from what I was exposed to.
It’s amazing the way that in the program, we were in other companies rooting for each other. The way that they so openly networked was great. We got into it two separate times. We took two years and the whole time Josh was in grad school and we tested everything with Lesson Squad. From lessons to then, “Can we add this piece of tech and expand it to be nationwide? Can we add retail?” That became a big thing. We did our testing and got our full foundation there. For me, that was a whole experience. More or less learning from the culture and Josh was kind enough where I got to even go sit in on a class at HBS, which was a whole experience where they give you the case to say, “If you’re going to come to the class, here’s the case.”
You have to read the case and then go in and participate. Those two years were crucial because it allowed us to make all the mistakes that you have to make when building a company, you have to try everything. Thankfully, it ended up to where we had things. When we launched the whole foundation, everyone in the industry, as we started showing to all these instrument manufacturers and major retailers, there wasn’t anything to poke holes in. It was like, “That’s a great foundation. Let’s start working together.” We even made this rule, any manufacturer that would show Lesson Squad to, we would never try to sell anything. They had to ask, “How can I use this?” That would validate that we have something worth using.
We’re still an early-stage company and figuring that out, but that has been a roller coaster in growth, but also the occasional dumpster fire like, “The tracking link for this retailer isn’t working. This happens here. You had 50 new people sign up in the last hour.” There’s this all different stuff that you’re always thinking about and that’s also the fun of it. It’s the fun of the ride, but the Harvard Innovation Lab and their Venture Incubation Program is crucial. If I could tell anybody who’s starting a company, this is a common saying, fail fast. It’s the truest thing. Go make all the mistakes you can and try everything as early as possible. At that point, it will be the most inexpensive and you can take that knowledge. You’ll get quicker until your actual product.
I have to keep in mind, especially with the big dot side of things, the company that I’m a part of. In the beginning, we would hit stuff that I would feel embarrassed. I can’t believe that this is going to make us look bad. That’s going to happen over and over again, you don’t realize that in the beginning until it happens. Once you realize that even Amazon screws up and makes themselves look bad, it’s okay.
It’s a part of it. I’ve been on the retail side of things. I was in the industry since I was 16 or 17 working on a drum shop and figuring things out. I had all these relationships from when I was a kid. That’s when I started meeting these people. For the first time, the industry and some of these long friendships I’ve had, I even calling Rich to advise. You never want to look bad or risk a relationship on it. I have this extra attention thing where I’d be calling my co-founder Josh, “Is it almost done? Is this fixed yet? We can’t have it like this because my heart’s going like this.” I’m more asking it to myself and he assures me very nicely as the co-founder that he is. I’m freaking out and he’s asking, “What’s going on?” I’m like, “I’ve had these relationships since I was a teenager and this is the first time that I’m putting this certain level of risk out there.” Exactly to what you’re saying, you are going to look bad at times, but I don’t think you’ll ever look bad as you think you do unless it’s something catastrophic. Be sensitive about it because it’s how you’re going to make a better product and the better decision. Emotionally, it might suck a little more.
It’s an amazing offering and the site is live, LessonSquad.com. You can use it if you’re a person or a parent that wants to get lessons for any instrument. You could find an instructor. If you’re a teacher, it’s a great way to have your schedule filled, find more students. The eCommerce and all that stuff is handled through the site. Not only that, you look up my profile and you’re going to see a list, a picture, and a quote about every product that I use and recommend. If you’re a teacher and you have your little lessons store, Jim can teach lessons on Lesson Squad. He can recommend the Rich Redmond drumsticks, the Black Sheep Beater, FUNdamentals of Drumming for Kids, all these products that he uses and he might make a little taste from purchasing that product.
We literally took the old brick and mortar model, which was lessons in the back retail on the front and put it in the power of the end-user. That was the big thing. It was how do we make the day-to-day musician win? I got to the point where I was teaching, gigging but I had no days off and I had reached the ceiling. It’s like, “How do you improve life for those people? Here are the digital tools. Here’s another revenue stream.” In my opinion, they should have been making the hallway, but now that we can help bring that to light. The truth of the matter too, it’s then a win for the retailer because they’re getting your influence on their sales which is huge. The other part, it’s also a win for the manufacturer. When they have artist relations, we allow them to see the value of their artists’ roster. They’ll see the list. They’ll see how many page views artists are getting, how many product clips, how many sales and if they teach or not. Artist relations has never had that dataset before. We look at it like we’re enriching the entire industry and helping progressive forward.
It’s identifying a problem and solving it. It’s sales 101.
We do several random questions of the day.
Number one, would you rather go back to age five with everything you know now or now know everything your future self will learn?
My gut reaction was I would love to know everything from here forward now because I’m excited on where things are going in, even though it was a crazy time in the world. If you look at the tech advancements across the board for every single industry, it’s fascinating. I would love to know where that’s going because it would bring me a certain peace of mind. I would love to know the health care industry as a whole like, “Do I need the hip replacement or are you injecting me with some stem cells?” There are things like that to think about where I’m like, “Where does this net out?” I got to a point in my life where I was like, “I can see 40.” This is an interesting time to look and get some perspective. Thinking about it in that way, I would love to know everything that’s ahead of me because I’ve already done the back. If I’m going back and win because I have all this other knowledge, yes. I like where I got to. If I could get the advantage going forward, that’s the bet I would take. How about you guys?
Moving forward, it’s like getting a glimpse of the future. A little bit more certainty and accuracy in what you can make play out.
I have two questions for both of you. My first one is, as you’ve seen the industry change, what do you not like that’s happened and what do you like that’s happened? Apply this to you as a whole. I don’t want you to one vertical it as you as a drummer. Think about all the things you do and you’re passionate about, both of you. Let’s say in the industry, you can apply it to anything. What’s one thing that you’re like, “Thank God this happened. This is awesome.” It’s one thing where you’re like, “I wish this didn’t happen or what would be to solve for it?” As we share stuff back, I always think about what’s the sixteen-year-old looking at? They have all these digital tools. They’re going to be some great filmmakers when you see what some of these kids do on TikTok alone or YouTube. I think about all those things.
For drumming, you had the Napsters and all the file-sharing which virtuously impacted the recording industry to where recording artists, if they want to be relevant and have a fan base that will last 5, 10, 15, 20, 25 years, they have to put the emphasis on getting in the bus, going and taking live music to the people. As somebody who was a drummer that records and tours, you don’t have to put all your eggs in the recording thing. It’s a great icing on the cake. The thing that I tell the kids to go for is like, “Get a gig, align yourself with some artist that’s not afraid, that wants to take the music to the people.” That worked out great. I’m with a bunch of guys that love being on the road and love going to do that thing.
I love the fact that there are as many outlets and channels for people to consume content, which means it’s a great time to be a writer, production, producer or actor, which trickles over into voice over and other creative things. You have Amazon, which allows guys like us to become authors and not have to go and be published by Penguin Press or Random House. We are some giant conglomerate. We could self-publish things ourselves, get our message out there, and then being a speaker for Fortune 500 companies for a reason, and they’re always going to need their teams and their people to be motivated and lifted up. For the things that I do, there isn’t a better time in human history. I have to do all 4 or 5 of them to make it all work.
Luckily, they all crosstalk and they all cross-pollinate. This COVID thing comes along. Every revenue stream that you have is online, which is a horrible feeling to think to yourself, “I’m not going to be able to pay my mortgage. How am I going to pay my credit card bill? How am I going to feed myself or my family?” Sometimes you’re only on one revenue stream. That can happen and we’ve watched it happen. It’s terrifying. Jim, I don’t know if you feel a little bit of that along those lines.
Where I am in my life, I’ve benefited from everything that’s happened. I’m not regretful or wishing something not to have happened because everything I could do is pretty much online. The whole COVID thing steered more business my way because more people now want to do podcasts. I can produce them, help them, and coach them. While they’re pulling all their advertising budgets from traditional media and things of that nature, they’re now realizing, “I can have control over all of my messaging, put it out to my audience and they’ll resonate it or not resonate with it.” It depends on how it’s put out there. It’s been beneficial for me. I thought when COVID hit, it was one of those things where I was like, “I’ve been building this thing for several year. Now it’s going to hit a stonewall.” It’s been great.
Jimmy, what are your socials?
If you guys want to get me for lessons, I teach on Lesson Squad.
Even just a gear recommendation I feel are huge. It’s one of those things where if you’re looking for something and you want to know, “What do you use on the road? What do you recommend for a beginner?” they can go through and read the quotes and have an understanding of what you recommend.
Here’s an interesting question based on your answer to the last question. Would you rather be able to see ten minutes into your own future or ten minutes into the future of anyone but yourself? Think about the relationships you could make if you knew other people’s future. Let’s say you run into Steven Spielberg and you want an introduction. You see his future in ten minutes. Maybe you know exactly what he’s going to order at Starbucks.
If I see mine, what if I get nailed by a truck? I could use the ten minutes to save myself. That’s awesome.
That’s a feature film right there, that whole time-bending thing and what would you do? I remember the kid in Stephen King’s Pet Sematary? The little kid went across the road and the eighteen-wheeler came barreling through. It was horrific. When Al Dean started to pop many years ago, you were twenty.
The whole age thing is fascinating, especially within the entertainment industry as far as the way their careers can go this. The more you look at anyone’s career, get ready to ride the wave and enjoy the high as much as the low, because it’s the same thing. I wonder if music will change to a degree with this where you can have these secondary careers that also do other things later. Michael Strahan, a football player, and TV host. When he was younger, he was on that other show Gossip Girl, like Blake Lively. At least to my knowledge, he didn’t do a whole lot or at least it was relevant that I knew of and another hit show. Just ride it. Sometimes that’s the game.
Jim, you didn’t go to college?
Partially, two years.
Jimmy, you were like, “I’m working at the drum shop. I’m going to be a rockstar.”
I went to Berkeley for two weeks and when I first went, I wasn’t ready to study. I learned that day one when I walked in.
Were you still party mode in life?
It wasn’t necessarily the party mode. It was that I had gotten so in love with already being in a band. I was already actively playing. That was a thing where I was like, “I’m playing decent size audiences and I was making a little bit of money.” What got me to go was, I got an audition for a band that was doing the whole college circuit. I was like, “I could either go to college or I could be college-age playing all the colleges.” That was the move. I was nineteen when I got that gig and they were all 27 or 28. I was this young guy behind the drums and they already had experience. I learned a ton from them and that was worth it. Once I’ve received that thing in the mail that said I owed X amount of money and that was on me, I was like, “That’s exciting. We’re never going back.”
We could sit here and have hours of conversations about all the music meeting, the crossroads of entrepreneurialism. I’m happy for you with the cartoons, TVs and the consulting. Thank you for dragging me along. Everybody, check out LessonSquad.com. It’s a game-changer. It is changing the world of music education as we speak. Thank you to both of you guys for being here and School of Rock for being our sponsor. Jim, any parting gems of wisdom?
It goes to show that if you’re willing to understand the work it takes to be put in, you can make it happen. I’m not sure if a lot of people understand that. It’s sad to figure out that 35 million people, all of a sudden, losing their jobs and they’re all like, “I need to find another job.” There are many people in my life that everything’s dried up and I’m going, “Figure something out.”
There some other things that you do where you have a natural talent towards that you could pivot just a little.
Make a little bit of money to make your next mortgage payment. There are many people that are like, “I’m going to go out and interview for jobs.” Go and figure something out. Make it happen.
I have the sentence I love for that and it’s, “Learn to create, not to take.” You take a job because someone has to give it to you. If you create it, it’s yours. That’s the thing that I feel like some people, especially in the bigger conversations, they’re not using their brain to create something. They’re like, “I’m going to go take a job interview.” That’s how they’re thinking. They’re not thinking of, “How do I create it.” I deal with this a lot. If a friend calls me and he’s like, “I lost my job. What do I do? I’m looking at my finances and I’m taking away all of this.” I’m like, “Ask yourself how do you create a little bit of income? You don’t need to cover your whole salary. How can you create $500 a month? We’ll brainstorm on it.” When they turn that on, that’s when the idea is overtaking all day.
We need to create a course around that, how to dig deep into somebody’s psyche to shift their mindset. How many people that I run into that don’t know how to do it.
It’s like, “Create your future now.”
Be your own island, create your opportunities, hang a shingle. I belong to a networking group. Do you know how many people I invite to that that have been out of a job? I say, “Come by. It’s mainly for business people and salespeople.” People that need jobs have shown up before and you never know who you’ll meet, who may know somebody or may need you. How many of them don’t even bother to show up? It’s free. It takes a little bit of effort in getting up earlier. It meets at 7:15 to 9:00 every Wednesday.
Jimmy, I’m a huge fan of you. I hope that all of our readers take the lead and they look you up because you are changing the world. It’s been amazing to be in your solar system.
Thanks for all of your energy. It’s huge. Watching your work ethic is what inspired me to keep it because there are not a lot of guys out there that keep the fire burning like you do and it still is insane. It’s wild. I’m sure Jim can attest to witnessing the same. Jim, thank you for having me. It’s awesome to be learning about you and everything you’re doing. I’m excited to chat more.
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I’ve been a drum instructor in the Boston Area for over a decade. I grew up working at a drum shop and have an immense passion for sharing the joy that is playing this instrument. I speak to college music business programs and entrepreneurship programs and am willing to take on music business students as well!