Michael Walker: All right. I'm excited to be here today with my new friend, Jesse Lacy.

So, Jesse is the founder of a company called On the Savvy, which helps develop tailored marketing strategies to help artists grow their fans, engagement, and connection with their audience. They focus specifically on targeted advertising and content planning.

Nowadays, I feel like this is one of the most important leverage points for you as an artist to grow your music career online—actually figuring out how to build authentic relationships with your fans and how to get smart, or might I say, savvy, about building digital marketing funnels and campaigns to be able to grow.

So, I'm really excited to have him on the podcast today to talk a little bit about current strategies, what's really working for indie musicians, and helping them build a successful music career.

So, Jesse, thank you so much for taking the time to be here today.

Jesse Lacy: Thanks for having me.

Michael: Absolutely. So, to kick things off, I'd love to hear just a little bit more about your story and the founding of On the Savvy. How did you find your way to helping artists connect with their fans?

Jesse: I was a touring musician for many years, and I worked in PR for a while. Around that time, I worked in world music. I also worked with CD Baby. I actually worked on their first conference, which was kind of fun.

I started out as a touring musician, going from city to city. I played over 600 shows across the country. So, I know what it’s like to play an empty venue just as much as a packed house.

I toured for many years, moved to South Korea, and while I was there, I was establishing the groundwork for On the Savvy. Then I moved to L.A. and started helping artists here and there. About two years ago, I officially started On the Savvy.

The whole goal is helping artists understand the tools they need to succeed in the modern industry. Nowadays, it's not just about the song—it's an entire brand that needs to be promoted. So, we help artists not only understand how that works but also develop a process to make it happen.

Michael: Awesome. Yeah, I think about that a lot—the idea of having the tools and knowing how to use the tools.

Because the tools are really important. If you're trying to cut down a tree and you only have your hands versus if you have a chainsaw, you're a lot more able to actually cut down the tree if you have the chainsaw. But you also need to know how to use the chainsaw, or else it could be really dangerous.

So, it's great to have instruction manuals and guidance—like what you're talking about—to help artists use these tools effectively.

I'm curious. Having been an artist yourself, played a lot of shows, and having the experience of being an artist while also working with a lot of artists to help them grow their music, what are some of the common challenges or patterns that you see artists struggling with in today's music industry?

Jesse: I would say the three main ones I see often are:

First, scams. Artists are dealing with a lot of scams. If you're an artist, you're probably receiving messages in your DMs about how someone enjoys your music and wants to put you on a playlist for a certain amount of money. And it's constant. I get them as well because I'm also an artist. So, I think that’s a major issue.

Second, and this is on the artists, but I think a lot of them have unreasonable expectations, especially when starting out. We live in an industry where more songs are released per day than per year in the '90s. There’s just an overwhelming amount of music out there.

The song itself doesn’t have as much impact as it used to. You need an entire brand. You need a personality that people can actually identify with. And that takes time—it takes time to build relationships with fans.

Having the right expectations helps, and it also helps you avoid scams. Anything that promises quick results—quick likes, quick streams, quick anything—is a red flag right off the bat.

Lastly, standing out in the industry. I think the way you stand out is by how you uniquely connect with your audience—what makes you unique as an artist, what makes what you do interesting to people, and how you actually perform.

The bread and butter for an artist is going to be live shows. That’s where most of the money is, and it's also where you can have the biggest impact. But it's not just about going on stage and playing a song well. There’s a ton of talent out there, and many artists perform their songs really well.

The key is creating an experience for people.

Because honestly, the difference between music as a hobby and music as a career is this: as a hobby, you're doing it to entertain yourself. As a career, you’re doing it to entertain others.

Your job is to entertain the people who come to see you perform.

Offering a unique experience when you perform is what brings people in—and what keeps them coming back. It gives them a reason to invite others. That’s typically how connections happen.

People buy merch, go to shows, and create memories. And when they buy merch, they’re taking that memory home with them.

Michael: Good stuff. Awesome. So it sounds like the three biggest challenges or misconceptions are:

One, just understanding the landscape itself and the amount of scams artists have to be careful about when someone reaches out—things like playlist marketing and DMs.

Two, having expectations set correctly so that you're in it for the long term and not expecting overnight success, which can also be an indicator of a scam.

And three, learning how to cut through the noise, stand out, and make music in a way that connects with other people—so you're entertaining them and not just entertaining yourself.

I have to say, I was debating whether to even bring this up, but for obvious reasons, this reminds me of something my friend Rick Barker said that really stuck with me. He was like, "Music done for your own sake or entertainment done for your own sake is like music masturbation." There's nothing wrong with entertaining yourself, but it takes on a greater meaning and purpose when it's not just about you.

Out of those three, the one I’d love to hear more about is that last one—how it relates to what you mentioned earlier. I hadn’t heard it put that way before—more songs being released in one day now than in an entire year in the '90s. In that kind of market, where there’s so much music and it’s harder to cut through, I’m curious what you’ve found really moves the needle. What helps artists go from scratch to building a real, engaged fanbase and a sustainable career they can depend on?

Jesse: Yeah, I think it’s focus. The average artist needs to have focus on goals that actually make their career work.

There are essentially four ways to make money in the music business as an indie artist:

1. Live shows—ticket sales.
2. Merch—and let’s face it, most indie artist merch is sold at shows. You might sell some online occasionally, but for the most part, merch is sold at shows.
3. Crowdfunding—which can also be a way to sell merch if you’re clever about it.
4. Getting your music placed—sync licensing.

Since it’s all about focus, if an artist or manager puts together a long-term strategy that doesn’t lead to one of those four revenue streams, the artist isn’t going to make money.

As far as making money on streaming platforms, I know some people do, but for the vast majority, it’s not a reliable stream of income. So figuring out live shows, how to present themselves, how to entertain their audience, and who their audience is—these are really important questions for an artist or management team to answer.

The other thing I hear often is artists saying they’re "marketing" their music when what they really mean is they’re trying to promote their music. It’s important to understand the distinction between marketing and promotion.

Promotion is short-term—it’s pushing something out there, getting the word out. “We have a new song,” “We have a tour date.” It’s making a post to build awareness.

Marketing is a much larger umbrella, and promotion is just a piece of it. Marketing includes everything that happens before that—artist development, defining the audience, branding, copywriting, and determining what kind of promotion to use. There are multiple types of promotion.

For example, playlisting is a form of promotion—not my favorite one because it's so easy to scam. Performing a live show is also a form of promotion.

That distinction is really important. Most artists think they’re marketing, but they’re actually just promoting. And those short-term efforts tend to run out of steam when they don’t have a long-term marketing strategy.

Michael: Interesting. Okay, cool. So the difference between marketing and promotion is that promotion is more of a short-term tactic. It’s powerful, but it’s a subset of marketing, which, as you define it, is a broader approach to bringing your product to market.

Part of marketing is also product development itself—figuring out who you are, your brand, your identity, and what products you’re offering. Then, you apply that to your promotion strategy by putting it in front of people.

In terms of marketing and promotion, I’m curious—what are some of the biggest mistakes you see artists make? Say they’re just getting started and want to promote or market themselves and grow their audience. What are the most common patterns of mistakes you see?

Jesse: The biggest mistake that I see on a regular basis is they go to YouTube, find a guru, and try to copy it. They copy templates, try to do it themselves. We're in this whole industry where everything is DIY. In doing that, it's like—you don't go to YouTube to figure out what kind of illness you have. You're not using it to diagnose people.

They are going to YouTube essentially to find out a way to do it. And I would say that if you're not in a position to hire a professional to help you actually develop your marketing strategy, you're really putting yourself at a disadvantage. You’re possibly just going to drop money on ads or boosting without putting together the entire marketing strategy.

You're going to end up wasting money and probably not even really getting much out of it. You might get some streams, but a career—there's a lot more that goes into marketing than just promo. A lot of artists, when they start doing their own ads, think of it as promo.

They use it to market a song, but they’re not trying to build an audience on the platform for retargeting, for example. They’re not utilizing tracking tools to actually get data about who's interested so they can essentially prompt and educate the AI that the ads manager is using.

Another mistake I see often is artists that just play their songs at shows. They go up there, play their song, and then they ask me to go see them do the exact same show down the street or on the other side of town. It's like, "Oh, I just saw that show."

They’re missing the point—it’s not really just the song. I don't really know who they are yet. That relationship takes time. I have to be introduced to you. I have to think about it. Then I have to hear it again. It's a process—just like when we meet people. You don’t just trust somebody outright when you first meet them. I typically don’t buy things from strangers either.

When an artist tries to convert the moment they meet someone, it actually does the opposite. I think it makes people want to go the other direction.

Putting on an amazing live show—an amazing live show—is stories, it’s props, it’s a cohesive thing. It’s not just going up there and playing. And then, having a way that I, as a listener, can connect—

The average listener works a job. They work nine to five or they have some other job. They’re working probably 30, 40 hours a week. So when they go to see a show, they're not going to understand you as an artist. They are going because they’re trying to relax. They're trying to decompress from their lives. They don’t play an instrument—or maybe they do a little at home, but it’s not really their thing the way it is for you.

So quite literally, they’re going to be entertained, to live vicariously through you as the artist or whatever brand you’re actually presenting. Or maybe they want to be you in some facet. And I think that’s true both online and live.

I don’t think we live in a time period where the average artist—some artists can, there’s always an anomaly—can just play live shows and that’s it. We live in a time where you have to keep in touch. And the way you keep in touch is through social media, through an email list—essentially by being top of mind wherever your audience is.

People hang out on social media—that’s why it’s relevant. People hang out on Spotify—that’s why it’s relevant. So becoming relevant on those platforms, as well as live, is really going to be part of the entire marketing strategy.

Michael: Good stuff. Yeah. A couple of things come up based on what you're saying.

One, I’ve definitely seen people who, in the short term, hope to save money by doing things themselves. I’ve worked with artists who have spent tens of thousands of dollars on different types of campaigns—radio campaigns, playlist campaigns, ad campaigns—without really knowing how they were set up.

Ironically, they could have actually saved a lot of money if they had started with the right foundation and learned properly. You know the Abraham Lincoln quote about sharpening the saw—cutting down the tree? It can be counterintuitive.

If you just invest a little bit of energy here, it's going to make everything a lot sharper so you can actually get a lot more leverage from it.

So with that in mind, I'm curious—what are a few ways to sharpen the saw that you've seen working for artists right now? If they were going to go in and do this on their own—let’s imagine an artist is starting from scratch.

They have a song, they feel really proud of it. And let’s say the song is actually really well done. They have a cohesive brand and a good identity. But now, they’re looking at how to actually get this launched—how to start building their community.

What are some ideas or ways you’d recommend they get started?

Jesse: I would say they need to be very aware of their budget. Whatever amount of money they put into creating the actual thing—if they were to bill it out in hours—is probably how much they need to spend on marketing.

Not just putting together their social media content, but having an ad strategy. Meta is a free platform, but it’s optimized for people who run ads. So by running ads, you’re actually using the full service.

That would be one example. And if you don’t have an ad budget, I would recommend getting your live show—well, you should be doing this anyway—but getting your live show to a point where it is spot on.

It’s not just about having a good song. Again, we’re in a saturated market. We don’t need more songs—we need more reasons to listen to your song. A great live show is one example.

I would really narrow down who your audience is. Not to limit your reach, but so you truly understand who these people are.

I'll give an example—I have an artist from Nashville. His music is kind of like Black Keys meets Mumford & Sons. I work with all types of genres, but this particular artist—

Michael: I’d enjoy listening to that.

Jesse: Yeah, it’s good stuff.

Michael: What’s his name?

Jesse: His name is James Freeborn. Very good. Yeah, yeah. I've known him for a year. We actually went to college together. But anyhow, the audience that did best for him was not the Black Keys, it was not Mumford and Sons, it wasn't the Lumineers. It wasn't anything really to do with the music industry at all. It was people that drive Subarus. These are called psychographics.

So when doing marketing, I focus a lot more on psychographics than I do on sheer demographics or interests. When you think about it, the type of person, on average, that is going to listen to music that is somewhat introspective probably has a dog. On the weekend, they put their dog in the car and drive up into the mountains to go hiking. And they're probably driving an Outback Subaru.

By marketing to that, you're tapping into their lifestyle more than you are just... I mean, they already have the Black Keys, and they can go listen to the Black Keys for free on Spotify. So they don't need the B-grade Black Keys. That's not your selling proposition—that you sound like the Black Keys. Your selling proposition is that your music rocks while you're driving up into the mountains in your Subaru.

Michael: Super interesting. So it sounds like what you're saying is that with this particular artist, when you were testing campaigns, the best-performing audience you found was not even something you normally would think of as related to the music. It was actually just a profile of the people that would listen to that kind of music but in a different way.

It's funny. I'm just like you—we run a lot of campaigns, and we've always run split tests, exploring different audiences. We've had the same experience where sometimes, I don't know what it is, but an audience you’re not expecting will outperform everything else. And that's why we run the tests.

But it also seems like audiences based on similar artists tend to do pretty well, so it's a good thing to test. It sounds like you tested both approaches. So in this case, the Subaru audience was the winner.

That's a great mindset in general. Hopefully, for people listening to this, they're gathering that they can expand their targeting. It doesn't just have to be focused on the music itself. In many ways, when you're in a different context where it's not just music-related, it kind of makes your music more special.

For Subaru, there's not as much competition, not as much saturation around the music as it relates to Subaru, for example.

Jesse: Exactly. And I think it also informs what kind of merch you're going to create. A lot of times, artists stop being unique when they leave the studio. But that uniqueness has to carry through. Your marketing strategy has to be unique. Whatever makes you unique needs to be what you amplify.

For James, since he’s our example right now—if a lot of your audience is driving a particular type of car, maybe make beanies as a merch item instead of just a t-shirt. Not that t-shirts are bad, but they have to fit the right demographic. Not everyone wears graphic tees. If your audience isn't into them, they’re not going to buy your shirt, and that really cuts into revenue.

By understanding who your audience is, you can cater to them. An artist who's about to release music, they're excited about it, it's a great track—they need to understand who they are giving the music to so they can talk to them at their level.

Michael: Cool. Along those lines, in terms of understanding your audience, what are some recommendations you have for artists trying to understand their fans? Obviously, that's one of the most important things when it comes to building a career, targeting, and building a community.

What are some different strategies or ways that artists can actually build that relationship and get to know their fans on a deeper level?

Jesse: They need to be consistent. The same way you build a relationship in person is how you build a relationship with a fan or a community of fans at scale. You need to be trustworthy and genuine because people can pick up on insincerity—it's all very subtle.

I don't think it's just about having a sales proposition that's enticing. We get bombarded with that all the time on social media—download this, get this webinar, sign up for this offer. What I think really works is being genuine and offering quality and value upfront.

And by value, I mean, yeah, it's the song, but it's also your personality and your stories. It's the stories you share at a live show. It's making sure you've thought it through and that it's a genuine representation of your brand.

Artists sometimes think they need to put on a facade. I don't think that's necessary. There's an element of playing a character to an extent, but it has to be a genuine character. If you try to play someone completely different, people pick up on the subtle cues that it’s not real.

So be genuine, be consistent. We can go down the list of virtues, but just because it's digital doesn’t mean it’s not communication. It doesn't mean there aren’t real people on the other end. You connect with people online the same way you do in real life—emotionally. The only difference is the tools you're using.

Michael: Yeah, so it sounds like it's really just relationship-building 101. It comes down to what makes it possible to build a relationship with another human being offline, even when it's not in the context of your music.

That means being a good person, having good values, finding shared interests, building trust over time, providing value, and being authentic—being yourself.

Maybe a good follow-up question would be about providing value. What are some ways you've seen artists go above and beyond to provide value to their fans?

Especially in a world where, like you mentioned, there's so much music out there. If you share your song with someone, it almost feels like they’re doing you a favor by listening to it, rather than you doing them a favor by sharing it.

So have you seen any creative ways artists position themselves or genuinely provide value to their fans?

Jesse: By being consistent, you become the go-to person for whatever it is. So, like, if I'm feeling really bummed out and I need to listen to something very cathartic, I'm like, "I need to just express this sadness." I listen to Glenn Hansard—he's my go-to guy for that expression.

If I’m feeling good, I'm walking down the street, I know I'm a boss, whatever—I'm going to probably listen to some rock music or some funk music, and I'm going to have a particular artist that I listen to in that genre. I listen to The Pastels quite a bit. I'll listen to The Ramones. If I'm feeling contemplative, I listen to Sting quite a bit.

I have particular artists that make me feel a certain way, that help me express whatever I'm feeling, which is really the value of music—it's articulating feeling and expressing it in both sound and lyric. So if you end up becoming the go-to person for that thing for a person, they're going to become a loyal fan.

That's why it's really important that you understand exactly what you offer as a unique person. You don't try to copy Taylor Swift. You try to become your version of yourself. And obviously, you don't have to ignore industry trends, but the more unique you are—not just creating avant-garde music within a pop realm, which is what we're talking about—you need to know that you're the person that, when I'm feeling sad, I can go listen to your music.

Maybe you're also a poet, so I know that if I'm feeling bummed, I can go to your website. Your website needs to be up always so that I can go and read poetry and feel something. It's really the consistency. You build trust with that consistency.

Michael: That's super interesting. So it sounds like what you're saying is that one way to provide value, as it specifically relates to your music, is to really think through the context and the situation in which someone's going to find the most value listening to that specific song.

By thinking through what they're feeling, what's the intended emotion, what's the response, and what's the situation in their life where they're really going to find that valuable—to feel that or to express what they need to express.

Because you can have a great sad song, but it's not going to be valuable to someone if they're trying to get hyped up for the big game. And then it's like, you put the song in front of them, and it's not valuable, even though it's the exact same song.

But if you find a person that's going through a situation where they need an outlet, they need to express themselves and feel that emotion, and you put it in front of them in that moment—now, that exact same song is actually really valuable to them.

So really, just kind of thinking through your songs—the specific feeling that's being expressed—and also identifying what the moments or situations are in which someone listening to this would actually find it valuable and expressive.

And then maybe positioning and marketing the message around how you promote it to specifically speak to that person and ideally put it in front of them when they're going to find it most valuable.

Jesse: Even when you get away from songs, just—what do you do in terms of content, right? Because essentially, artists have to adopt the fact that they are content creators in 2024, 2025, in this modern industry.

So then, how do you actually deliver that? I would say, if you're funny, be funny on social media. If you are dramatic and you make sad music, you should still be funny a little bit—because humor works for everybody, it breaks the ice—but be vulnerable.

Vulnerability works for an artist who is expressing vulnerability in their music. Just pick a lane and deliver that thing consistently.

As an artist, you have the skill of being creative, so you can see how this connects with your music. Maybe you're kind of a funny guy, but it's also a deflection.

I can't remember his name, but there was this guy who had a whole comedy thing during the pandemic, and he nailed it. He put together this whole thing where he made music videos in his bedroom during the pandemic, and he turned it into a show. I think it was on Netflix. It was very, very good. Many of your listeners probably know exactly who I'm talking about—I just can't remember his name.

By making a cohesive connection between your brand, your music, your content, your communication style, and how consistent you are, you're starting to build a marketing strategy.

Whereas promo is like, "Oh, I'm just trying to go viral with this video because I saw that someone else went viral with a similar video."

Artists—our job is, we're explorers of the abstract and the esoteric. That's what we do. We take those things and express them in our own way. So it's our job to go out there and articulate things that are going to resonate with people following us—people who aren't necessarily thinking about things that way, but maybe we unlock something for them emotionally.

Michael: Good stuff. Yeah, really well articulated.

So Jesse, man, it's been really great to connect and go through some of the foundations of building a real marketing strategy—not just thinking about short-term promo, but actually thinking through what it takes to set the foundation correctly for a long-term, successful career.

I really appreciate you coming on the podcast today to share a little bit about your experience, your ideas, and the things that you see really working right now.

For anyone who's listening or watching this right now who is interested in diving deeper, connecting with you, and seeing what you're doing, what's the best place for them to go?

Jesse: So, onthesavvy.com—that's O-N-T-H-E-S-A-V-V-Y dot com—is where you can see everything I offer as a service. I also have a blog that I’ve been adding to.

I'm also an artist, so if you want to listen to my stuff, go to springowls.com—one season, multiple owls.

Those are the two main spots. You can also connect with me on Instagram if you’d like—send me a DM or reach out through the website.

Michael: All right, awesome. Well, as always, we'll put all the links in the show notes for easy access.

Jesse, thank you again for being on the podcast today.

Jesse: Thanks for having me, Michael.

Michael: YEAAAH!