Michael Walker: Yeah, all right. I'm excited to be here with my new friend, Michael Tolle. Michael is the founder and director of operations at Mello Music Group, hailed by Forbes as the most successful new indie rap label of the decade. That's some pretty high praise.

He's the executive producer of over 200 albums, collaborating with legends like Brother Ali, Pete Rock, and Joell Ortiz. He's a powerhouse in sync licensing, with music featured by brands like Apple, Gatorade, and HBO, plus Grammy-nominated production credits with Lizzo.

So today, I'm excited to have him on the podcast to talk a little bit about content, or at least consistency. Especially nowadays, with the state of the world and the music industry—how easy it is to create music in a home studio and put it out there—how do you really cut through the noise and stick around long enough to actually achieve meaningful success and results?

You're a person who knows a thing or two about that. So thank you so much for taking the time to come on the podcast today.

Michael Tolle: Thank you. You guys just had on one of our friends, Terry Cole, the other day.

Michael W: Okay.

Michael T: Fellow Ohio label that started around the exact same year we did.

Michael W: Okay, awesome. That was a great conversation. Well, let's dive into it. So, for anyone connecting with you for the first time, could you share a little bit about yourself and how the record label started?

Michael T: Sure. So originally, I was going to school thinking I wanted to be a writer—write novels and maybe be a professor or something like that. I was studying writing, working on it, learning to tell my story. But during that process, like a lot of college kids and young people, music was a huge part of my life.

Diving into that, it just became more and more of my life, and I wanted it to be more and more of what I did. So after I graduated, I was working on applying to grad schools, trying to get an MFA. In the meantime, I was still super involved in music—just creating it and having fun with it as a consumer, a fan.

When 2007 happened and everything kind of fell out for people, I had an opportunity to start doing more with music. That led me to dropping our first release in 2007, though I had been planning it for a few years, working on things. It was a fortuitous time to jump into it with the shift to digital, where a lot of the majors had all this overhead—offices, A&Rs—and they weren't ready for the digital transition yet.

I didn't have those liabilities in terms of assets and fixed costs, so I was able to be really flexible and roll with the industry at a time when it was still developing. That was during the digital distributor wars of the early days.

So that's kind of where the business started. But my first music interest started as a kid growing up in Ohio—middle class, divorced parents, latchkey kid. My older brother was a music video director, one of the early ones.

Seeing him off in L.A. from a distance—we weren’t close because this was before cell phones—I would get a VHS tape in the mail from my big brother to the family, showing the stuff he was working on. That gave it this shine, and I knew I wanted to be involved in that in the background. That was behind everything I was doing.

Michael W: Cool. Yeah, it’s really interesting hearing about the state of the music industry at that point and the advantages you had because you were an early adopter and a fast mover in the digital revolution.

It seems like one of those things—kind of a David and Goliath situation—where independent artists or startups can move faster and take advantage of the lay of the land.

So, I’m curious about your perspective, having benefited from being part of that wave of going digital. Right now, there’s maybe a comparable wave happening with technology and AI. Maybe it’s fundamentally different because AI can replace certain roles that musicians used to do.

At the same time, you could see it as making things easier—eliminating overhead and past limitations. So I’m curious to hear where you fall on the line with these tools. Do you recommend that people lean into AI, or do you think it's something we should shy away from?

Michael T: I think calling it AI is sort of a disadvantage because it gives it this robotic, futuristic feel. Anyone who grew up watching movies is going to feel some stress from that, as if it’s some otherworldly thing. But calling it a new program or a new tool is really all it is. It has a lot more capabilities, but ultimately, it's just another tool.

One of the things I really believe in is that you don’t feel lost in your work. It’s when you're resting on your laurels and things are going well that you don’t know where you belong. But when you're actively working, tools like AI naturally come up. You use them when you need to—whether it’s ChatGPT, video editing, or whatever else.

Musicians are creating with it too. Once you start using it, it doesn’t feel as threatening. It is more accessible, which raises the bar in terms of proving your skill set. There may be concerns in the future about AI-generated music that people like, but I don’t think most people in music need to worry about that—as long as they keep creating. We'll let the legal channels sort out what AI is trained on and how it’s used.

Michael W: Mm. Awesome. Yeah, I like that a lot. It reminded me of an analogy I’ve heard before—it’s important to always be moving forward, to have momentum. It’s like riding a bike. If you’re resting on your laurels, like you said, or just sitting still, it gets really hard to balance, and you end up falling off the bike.

But it sounds like what you're saying is that as long as you continue to show up and use these tools to work and move forward, it's like riding a bike—you maintain balance by staying in motion. That’s an interesting way to put it. I hadn’t really heard that perspective before.

Michael T: Yeah, and from a personnel standpoint, it's tough. You have to be willing to adapt and allow people to adjust. When we started, it took a room of 20 people to do what digital distributors can now offer with just one person. That was the advantage.

Likewise, if you have a team of videographers and other specialists, you need to adjust their compensation because there’s always a new kid out there who can do it all on their phone. You have to adapt to that and compensate people accordingly.

As you get older and more established, there's an expectation that you’ll always be the big player hiring top-tier professionals. We have people approach us, asking for $40,000 for a music video. But those big-budget video days are gone for most people—it’s not even close. They see us as a big label and assume we have the budget.

It’s a reminder that you always have to stay scrappy and focus on what’s needed in the current marketplace. There's so much content out there now that refining what you truly want to work on is crucial.

Michael W: That makes a lot of sense. So it sounds like what you're saying is that in order to be competitive, part of the market is that you have to compete with what other people are doing for the prices that they're doing it. And so with these tools, it's a double-edged sword in some ways in that it's going to make it a lot easier to record high-quality content.

And I'm curious, mindset-wise, I feel like one of the blocks that a lot of people have, or fears and concerns—and I mean, it's totally valid—but it would be great to hear your perspective on folks who are concerned about AI replacing some of those roles. Those paying jobs that people have relied on as a source of income, for videos and for all different roles.

How do you view these tools, and what would your response be to someone who's like, "Well, we shouldn't use these because people need this for their jobs, and AI is evil, and we should never use it?"

Michael T: If you're working in AI, that is your job, so use it. If you're working in something else, you use it just as much as needed.

Artists are sometimes being forced to act like a label themselves, forced to do their own marketing, forced to do all this stuff because of the DIY push over the last decade or so. But when they remember they’re artists and do what they do, that's all they need to do. They don't need to be threatened by any of this. It's just, like I said, the refinement of what you're doing and whether it helps you.

As a musician—though I'm not creating music like that myself—these tools are coming into your production skills. But the one thing is, AI is always trained on something, so it can't be trained on your life experience unless you give it to them. Your own life experience is always going to be unique.

I think so many people already use ChatGPT to write most of the bios and journalism. And you can see right away—if you've been involved in the industry and working with indie artists—I can read these little write-ups from ChatGPT and immediately tell: "Okay, you stole this phrasing from Jeff Weiss at The LA Times, you stole this one from this writer." Because I've been there for 20 years, reading these articles that it's trained on, seeing where it’s pulling this stuff from.

The problem with that is, it sounds okay. It works on a surface level, but the depth isn't there. And that doesn't resonate with people. Whereas when you dive in and try to say something generative—which maybe AI will catch up to soon, but not yet—you're going to have something that resonates a little deeper.

That’s true for the artists too. But even as a business, you're going to be able to offer something in a textural layer that's a little more important.

I think I mentioned my brother in videos earlier. His work early on had a sort of life experience and grit to it that resonated and stood the test of time. If you look back at his videos, they still move you in a way that people adopting the newest technology and making something glossy and fast-cutting don't. It gets washed away.

Just like when we all started on Instagram long ago and they had those little borders or frames around the pictures—I don't know if anyone still remembers that—but it quickly looked dated, whereas in the beginning, it was new.

So if you're doing your own thing, it's going to stand out and be unique.

Michael W: Awesome. So it sounds like what you're saying is that one thing AI can't really do right now is have a soul and that characteristic of unique expression that you can add to it.

While it is a very powerful tool, if you use it as a tool to streamline workflows—using it like you would use any other tool—then it’s valuable.

There's a book I read recently that was comparing AI and how technology disrupts markets and labor. It kind of answered that question of, "Well, what about all the people who lose their jobs?" I thought the point was fairly well made: 90% of people used to be in farming because that was the need of the time. Then these factory machines came along, and now it's less than—I don’t know—like 10%, 5%.

A lot of people lost their jobs, but there are all these new jobs that didn’t even exist before. Jobs that you couldn’t even imagine, like being a full-time creator with videos, content, and streaming. These things have opened up.

I feel like that aligns with your way of putting it. As long as you just keep showing up, keep growing, learning, and adapting—using these tools as they’re valuable to you and others—you can go along for the ride.

New jobs and different opportunities come up, but certainly, it's changing the landscape of what’s actually needed. And many of the jobs that were needed before aren’t needed in the same way anymore.

Michael T: Yeah, I’ve mentioned this in other places, but before industrial optimization, tools were really important to craftspeople. They had their own spirit, their own soul when you look back at old literature.

When those were thrown out for efficiency so that we could all use the same tool at the same factory, something was lost. But even today, whatever tools you're most comfortable with, you will produce better-quality products with them.

Whether that’s the microphone you know how to record with or the particular production machine that you're good with—knowing that tool is what makes you an expert at it.

I think the same thing will happen with AI. You give my parents some of the AI tools we use, and they don’t get the same results we do. It’s all about learning your tools as they grow.

Michael W: Yeah, that's a great point. Learning how to use the tools is just as important as having the tools in the first place. I feel like the tools are extremely important themselves. If you're racing to cut down a tree against someone that has a chainsaw versus someone that has just their fingernails, then the chainsaw is going to give someone a huge advantage, even if they're not great with it. But if they don't know how to turn it on or how to use a chainsaw, it can be very dangerous or less effective than someone who actually knows how to use a hacksaw to cut it down. So it does seem like you need the tools, and you also need the education or the knowledge of how to use those tools.

Michael T: One thing about having been in business for a while now that I've noticed is, every year, every quarter, every six months—whatever it is—whenever I go back into that strategic vision or that planning phase, or just sit with a piece of paper and write out what I'm trying to do, I realize I've been doing the same planning for 20 years, since before I had a label. For five years, it's always been a little more refined and a little more reflective of reality. I learn more, but it's much like when I watch good film directors.

You watch Michael Mann's Manhunter, and then you watch Heat 10 years later, and it's the same movie but done really well. I think that remembering that—you can get knocked off your horse, you can get sidetracked, you can make bad decisions and lose everything—but if this is your career, if this is what you do and what you love, you'll come right back and use that to your advantage.

That's one of the things I think artists have a challenge with right now. When you're young, maybe you're being sold constantly on stardom, success—get in quick, make it all. No one's reminding you it's a career. You're a musician for life. If your goal is just to get rich and quit, I probably don't want to hear what you have to say. But if your goal is to make good music, express yourself, and live and do this forever, those are the kinds of people I want to be involved with. And that's timeless.

Michael W: Good stuff. We were joking backstage before we started this about the power of now and being timeless with the last name Tolle. Speaking to that concept of consistency—showing up and being willing to weather the storms, the ups and downs, and not just expecting quick, instant wins—how would you encourage someone who's listening to this or watching this right now?

Maybe they really need to hear a message about sticking through and seeing it out. Maybe they're questioning, Do I really have what it takes to be successful? Let's say, for context, they've released their first song, maybe three to five songs, but haven't had a big breakout yet. They're not making enough money to be sustainable, and they're wondering, Should I keep doing this? Is this even possible for me? Or should I go back to working a different job and give up on my music?

What would your recommendations be for someone to think through their long-term vision?

Michael T: I hate to say this, but if you're questioning yourself, you might be in the wrong place. The people I know who have been at it and continued—we all doubt ourselves. We have those moments. But those moments are so few in comparison to even when you have that thought, shaking your head and getting back to what you love.

If you're pushed out of it—if you're trying to make a financial living from it and that's all you want to do—then I understand. If you can't do that, it's tough. But I've seen so many artists who thought that's what they were going to do, had to go back to a job, and thought it was the end of the world. But that job ended up freeing them up to truly be creative again, and they came back more successful because of that.

Some important things to remember if it's not working: Expand your education. Make sure you're surrounding yourself with people who are better than you. Not just in the I'm going to go read Malcolm Gladwell type of way, but in the be uncomfortable type of way. Recognize that maybe you aren't good enough yet, and work with people who are better.

When you work with people who are better than you, you usually have to pay to play. It's education. When I started the label, I had no business being a record label owner, so I had to pay. That meant I had to work a side job to fund the label that I loved. I think artists need to do the same thing. If you need to learn something, you're going to have to pay for lessons from someone better. If your business skills are off and you need a manager, you have to bring something to the table for them—or an attorney who can give you some context.

It's really important to remember that you might have to go work a side hustle, but pour that money into your career because that's self-investment and career investment.

Michael W: Oh—

Michael Tolle: Again, ask yourself if you see yourself being a musician in 20 years. When you look at the truly great musicians, they're still outperforming at 60. They didn't stop. They still love it. They're still working. You should want to be doing that.

Michael W: That's great. Yeah, I appreciate you saying that. So, first of all, just kind of calling out—if you don't believe in yourself, if you don't believe in your music, if you don’t have that level of dedication, then it's unlikely in the first place that you're going to be able to weather that storm.

Because it really does require a huge amount of confidence, belief, and wherewithal to keep going and to know that you're doing this for the long term. Yeah, absolutely.

But also, the point you made about surrounding yourself with people who make you feel uncomfortable and stretch you to a bigger level—I feel like sometimes it's kind of trendy right now to hear the opposite side of that coin, which is, "Don't compare yourself to other people. Just be yourself. You're perfect exactly as you are."

And, you know, there's some truth to that. On a deep level, you are enough. You're yourself, and it's okay to be yourself. But then, on the level of growth, personal development, and improvement, surrounding yourself with people who are better than you feels uncomfortable. Comparing yourself to people who are further along than you makes you feel uncomfortable.

But that discomfort can also drive you to be better—to rise up to the level that actually deserves to be in the same room as those people. So I appreciate you calling that out and hopefully inspiring people to be okay with surrounding themselves with people who make them feel a little bit uncomfortable.

Michael T: Well, I would say I may be damaged, right? A lot of us may be damaged. We're products of capitalism. And if you're involved in this—I'm not saying it's necessarily healthy to never feel satisfied. Contentment is really important. So if you can't find any contentment within that discomfort, there's a problem.

I often talk with my wife. We sit there and say, "Look at these people we know who are so happy, doing the exact same thing they've been doing for such a long time." And that isn't something I have.

It's not because I want to achieve so much more. I don't have some weird drive like I did in my twenties. But I just like the process of growth, and I know that process is uncomfortable.

I do recognize that, as Americans in particular, we are very productivity-driven. We're very success-driven. We're sold so many things that are in our subconscious that we don't even realize. It's important to unpack that and make sure you're doing it for the reasons you want to.

And it's perfectly fine to have hobbies that don’t generate income. When I started, I was trying to be a writer. I thought I'd be teaching. I was running a tutoring and educational company for professors with kids here on sabbatical. That was how I paid the bills. I loved it.

I was lucky to get to read literature, write stories, and teach people. But the music thing kept taking more and more time. It just wasn't making the money that would support things. The teaching company was paying for this. There was a point when I was putting 50 hours into one and 40 into the other, and I wasn't sleeping. I was living on energy drinks.

I had to choose which one. And music became that thing.

So, I don’t know. That drive was there for me, but I don’t know if it needs to be for everybody. I think there’s freedom in realizing that music can also just be fun.

Because I do want to remind musicians—it's art. In my genre, particularly in hip-hop, there's a competition that isn’t always healthy. I like to view it as art and expression.

And it’s not going to be timeless if you haven’t shared something truly deep from within your life—if you're not vulnerable, if you're not living and experiencing.

It’s also important to remember that monetary success doesn’t measure your art’s value.

Michael W: That’s great. Yeah, so what you're saying is that it's important. It's okay to be ambitious and to want to achieve goals and really go for it.

But you have to temper that with balance, with being content, and with appreciating what you have—which can be easier said than done. Especially in our society, with capitalism in general, there's consumerism and a drive to do more and be better.

So learning how to ride that balance is an important thing to play on the edge of.

Michael T: Well, I wish we, as a culture, valued music differently than we do right now. Because I think music should just be a regular part of life.

When I grew up, we were not musicians in our household. It wasn’t a regular part. Dance wasn’t a regular part of our life.

When I married, my wife’s family all played instruments. They’d play at dinner. They’d sing. It was a part of their culture, which was cool.

It wasn’t about 20-year-olds saying, “I want to be a musician.” You don’t see 35-year-olds saying, “You know what? This corporate career isn't as fulfilling. I think I want to be a traveling musician.”

And that’s a shame. Because they maybe have the financial knowledge and understanding, and they could bring some management skills to being a semi-successful musician—maybe making 50 or 100 grand from music instead of thinking, "I have to be a pop star and make millions."

When you're 15 or 20, you want to be an NFL player, an NBA player, a pop star. You want to be at the top of whatever you’re going for.

But by the time you hit 30, you realize, "I want a comfortable life. I want to do the things I love with my time."

And I think music hasn’t been sold enough to people as something you can do that in. You can have a very good professional career without being a star.

Michael W: That’s a great message.

It’s funny—when you described that persona of a mid-30s, approaching-40 musician deciding to go for it, that literally describes my business partner now.

He started as a client of our company. His name’s Eli Lev. He’s an amazing human being. He used to be an educator. He transitioned in his mid-to-late thirties. Now, he’s full-time with his music.

He’s not a massive artist, but he’s full-time. He’s doing his first international tour right now—he’s in Europe—and he’s living that life.

And, yeah, it’s exactly like you’re saying. It's possible to have that lifestyle and be successful in a different way. You don’t have to be a household name.

So, for anyone listening or watching this right now, if you had to share one piece of advice—if you could go back in time to your most challenging moment, when you really needed some help or advice—what would you tell yourself and why?

Michael T: I mean, those moments continue to happen, right?

But every time I’ve faced a truly daunting challenge—when my career was in peril, which happens from time to time—two things helped.

First, just work. Not with people. If you can, shut everything off. Take as much time as you need to do private work so you reconnect with why you're doing it and what you're doing.

The second thing—reach out to the people you have in your circle. And listen, even when they don’t give you the best answer.

When I started, I wasn’t close with my brother, who was successful. He didn’t even know I was running a record label. At a certain point, I thought, "Man, if I had these things, I could really break out."

So I decided, for the first time, to ask for a little bit of money. Looking back, it wasn’t much at all. And he said no.

And I wish I hadn’t done that. But at the same time, when people say no, it makes you realize, "Oh yeah, I have to do this myself."

If it’s a good idea, I’ll find a way to make it work. If someone had given me that money, I probably would have lost it and never learned how to generate income.

Even today, when I'm around a lot of people, I leave wondering, “Did I actually work?” But it’s those quiet moments—when I get four, five, six hours alone—that answers come. And they come through work, not just thinking about it.

Michael W: I don't know. I just thought in my head—uh, is it Taylor Swift? Like, "I'm the problem, it's me."

Michael T: Yeah.

Michael W: It's good. I mean, it seems like that's where the worst self-growth really can happen—when you turn inward and take responsibility for where things are at. Even if there's an element of truth, like, "Oh, this other thing happened," or, "There’s a circumstance where this person did this thing." Sure, it did. But what are you going to do about it? And how did you contribute to it? Taking ownership of that.

So, I'm curious—you seem like the kind of person who has a great mindset around goal setting, staying consistent, and continuing to show up and work through challenges when they come up. What does your visioning process look like? What does your planning look like?

I mean, we're not approaching a new year—it is the new year at the time of recording this. It's a fresh start, and a lot of people are thinking about what they want to be different this year, who they want to become, and what their goals are. So I'm curious, what do you do on a regular basis—whether that's weekly, monthly, or yearly—to set those plans and stay consistent?

Michael T: Early on, I did a lot of goal setting, a lot of lists, a lot of planning—meaning 20 years ago. And that process has just been natural. I'm a natural list-maker. I see my daughter making lists, and I realize it's maybe just a part of us. My dad, in his house, has little pieces of paper with lists. That’s a kind of goal setting in a way.

But I think I've reached a new understanding in the last couple of years that I think is pretty important. It's not my idea—I forget where it's from—but learning the difference between an objective and a result is really important. Sometimes we put things like, "Make a million dollars," or we put measurable things as the goal instead of an objective without a measurable thing to it. It's more of a mission, more of a purpose.

It’s hard to come up with one that matters to you, but if you can, then you have your key results under it—how you measure that. So, if I say I want to be one of the most respected indie music labels, what does that mean? How do you measure that?

The nice thing about setting an objective like that is that it can inspire others in your organization. They can't measure it, so you get to define for yourself what that means. And that's important. You can put your key results—like, for me, we have 200 records in the catalog. I don't know if that's good. I don't know if I need 10,000 or if I should have 100 that I'm more focused on. But for me, I've chosen what my metrics are going to be.

So, having the difference between setting objectives and then the key results that tell you you're there is crucial. It also allows for conversations—whether with employees, artists, or just people you know—so you can explain why you're there. Instead of just having a mission statement, you have an objective: "This is what we're trying to do."

And they don't get to define that for you. I would keep it personal. I would keep the key results personal—people don’t need to know how you measure your own success. That will keep you driving toward it.

At this stage, I literally use an app called Mentee, where I have a checklist of everything I need to do. I call it my daily rituals. If I do these things, they'll help lead me to the key results. And if I do the key results, they'll help lead me to the objective.

So, I look at it every day as kind of a balance sheet. Some days I get all of it done, some days I get 50% done. But overall, I can tell if I had a good week or not from that. And it also reminds me that the purpose of these actions is that objective.

As a label, we went through phases where we were just trying to put out more stuff or just get more. Now, I’m in a phase where I’m trying to reduce and do more for the people I’m working with, but with less quantity.

Michael W: Awesome. Yeah. I really like that.

It sounds like having a North Star—it gives you guidance. If you have an objective or a mission statement, you don’t necessarily expect to reach the North Star, but it gives you direction.

If you start there, you also need to figure out specific results and measurements that help track progress. It’s like having mile markers that let you know if you're moving in the right direction.

So, it's a nice way to make sure you're inspired and progressing, but also having personal checklists and to-do lists. If you know that showing up and doing X, Y, and Z will help you accomplish meaningful steps toward that bigger goal, it makes the process clearer.

Michael T: Yeah. I worked through this idea with someone who had recently become a real estate agent. After doing that for a few months, they realized it was a big landscape with a lot of people doing the same thing, getting the same advice—like, "You should do open houses," or "You should canvas neighborhoods."

So everyone’s getting the same information. And if you ask most people what their goal is, it's probably a monetary level or how many houses they want to sell—which, if you break it down, is still a monetary goal.

But when I shifted them to the idea of actually wanting to be one of the premier architectural real estate agents—because that’s their passion, houses with architectural value—then they started setting objectives around that.

They realized, "Well, I need to be more involved in learning the history, joining groups, and connecting with people who are involved in this field." And suddenly, they became a more interesting person to talk to. They started attracting clients who were also interested in that topic.

Naturally, people want to list houses with someone who shares their ethos. It gives them a purpose, and it makes the work fun instead of just randomly doing anything to make money—which usually doesn’t work.

Michael W: I like it.

Oh, Mello, this has been a fun conversation. I feel like "Mello" encapsulates the conversation—mellow, but also driven and mindset-focused, which I appreciate.

For anyone listening or watching right now who’s interested in connecting more or seeing if your services would be a good fit, what’s the best place for them to go to learn more?

Michael T: Our website, mellomusicgroup.com—Mello with no "W." Also, our Bandcamp to hear our music. And, of course, our socials—we’re everywhere as Mello Music Group.

Michael W: Awesome.

Yeah, I just realized I called you "Mello" unintentionally because your name appears as "Mello," but it’s Michael—which I shouldn’t have a hard time remembering.

Michael T: Yeah. It’s funny—people used to call me "Mike Toll," and the anagram of that is "Melo Kite," which means "a message from Mello."

Michael W: Wow. There you go, man.

Well, Michael, it's been great connecting today. Thank you for coming on the podcast, and I look forward to talking to you again soon.

Michael T: Thank you. I appreciate it, Michael.

Michael W: Yeah.