Living Legends. Photo by D4 Nguyen.

We all know it’s hard to get your music noticed and grow a fanbase in today’s content saturated world. Have you ever thought about how much harder it would have been to make a living with your music as an independent artist WITHOUT the internet and social media? Or how about without powerful computers (desktops, laptops, smart phones) to conveniently record and produce music from home?

In this blog, I want to share some key lessons we can learn from DIY independent music artists from the 1990s, specifically in the underground hip hop scene in the United States. Even if you don’t listen to or make hip hop / rap music, you should be able to learn something and gain perspective that applies to you today.

The Back Story / Context for this Topic

Feel free to skip down to the next section if you want to get right into the lessons. I share some of the historical context about this topic and include my personal connection to the independent hip hop scene beginning in the early 2000s.

Compared to present times, a lot has changed since the 1990s when it comes to the music industry, technology and even culture.

Before the internet became a household consumer good, many soon-to-become-big-name artists across the U.S. were able to hustle from the ground up starting in their local scene and launch their music careers. Many stayed independent while some got signed to record deals or even started their own labels.

For these hip hop artists, their origins often involved selling albums / mixtapes out of their trunk or their backpacks on the streets to random passersby.

Instead of recording demo tapes to submit to the major labels, they dubbed their own tapes or burned CDs to sell directly to customers in their local area.

As the internet became more accessible from home, we can see the DIY independent music scene really flourished in the early 2000s and into what we have today.

Yes, the gradual decline of CD sales due to the rise of online music “piracy” also started around this time and would become a major road bump for independent artists. However, you can argue that illegal file sharing networks also helped get their music exposed to new fans that would eventually buy their music and pay to see them live.

This DIY movement in music was important because it challenged the commonly held belief that you need a major label to grow a fan base and make a living as an independent musician.

I’ve been fortunate enough to be able to work with some of these independent artists from this period and see how they think and operate. These are the same underground hip hop artists I essentially grew up listening to and becoming fans of for over 20 years. My understanding of independent music is based on being fans of their work.

I was originally inspired to write about this topic when I saw independent rapper The Grouch on the SteeBee WeeBee show a few years ago. During a time when the internet was still in its infancy stage, The Grouch shared some cool details in this interview about how it was like to promote and sell your music independently before the internet.

The Grouch is a hip hop artist originally from Oakland who has been putting out music independently for over 25 years. He is a part of a bigger hip hop crew Living Legends. My client Eligh is a part of the same crew and makes up the other half of the long time recording duo The Grouch & Eligh.

Among their music peers, the Living Legends crew in California were considered the most DIY / independent hip hop artists at the time. They literally handle everything themselves from throwing their own shows, recording their own music, making their own tapes and selling on the streets.

It is said that Master P, one of the most successful independent hip hop artists and entrepreneurs, actually learned and was inspired by the Bay Area artists like Too Short and E-40 who in turn inspired the likes of The Grouch and Eligh.

Most of you reading this probably don’t listen to underground hip hop, which is okay. I’ll be referring to hip hop artists because that’s the scene I got into in college and shaped my identity. As I have written in my About page, it was my passion for underground hip hop that ultimately led me to create a music blog for independent artists in the first place.

Although a lot has changed since then, I wanted to share 9 important lessons from the 1990s independent music grind that still apply today. You might not listen to hip hop, but these lessons can be applied to any genre of music. After all, we see the DIY ethos practically start with punk rock subcultures as early as the 1960s.

For further visual context, there’s an excellent Netflix series called Hip Hop Evolution that covers the beginning stages of the genre and how many artists in different parts of the U.S. got started independently. I highly recommend it as I think it’s important to understand the history of independent music if you’re trying to make it as an independent.

1. Selling physical products / merch is essential.

The biggest source of income for independents during the 1990s was selling physical music, like cassette tapes and CDs. With larger profit margins, that’s what really allowed independent artists to sustain financially.

One of the big pioneers of this independent spirit of selling out of the truck was Oakland rapper Too Short who offered to record a personalized shoutout on his music tapes in the 1980s. He charged $20 for this custom tape and it blew up.

In Houston, Texas, DJ Screw would sell $15,000 worth of mixtapes a day in the mid-1990s. He made seven-figures a year selling tapes out of his house, his car trunk, and at car shows. In 1998, he opened a shop just to sell his mixtapes!

As for The Grouch, he talked about how he would go to local record shops around the San Francisco Bay Area in the 1990s and sell a bulk of his CDs at $10 a piece and make about $7,000 each store.

Getting paid opportunities to do live shows wasn’t as accessible for independent artists back then. So if you were relatively unknown and not getting airplay on the radio, you had to have physical products to sell.

The need to sell physical products is no different in today’s music climate. Although with streaming platforms, the average fan doesn’t need CDs, vinyl and cassette tapes to listen to music. But the need to have some kind of physical products to sell is still necessary.

This is where understanding branding comes in. You need to know what merch to make for your target audience.

One of the big challenges with merch for independent artists is having the money to front for the production. Making products in bulk like vinyl, CDs, shirts and sweatshirts can be costly.

Thanks to advancements in technology, dropshipping services like Printful, make it easier for creatives to sell merchandise without any upfront capital or pay any costs to get items made.

Key Lesson: Build your brand and always try to have products to sell online and during live shows.


2. Keep pushing out music – make more music, more money opportunities.

This should come at no surprise. The more music you put out, the more opportunities you have to make money from it and to grow an audience. Specifically, more physical products to sell. Obvious right?

As mentioned earlier, the profit margins from CDs during this time was what allowed independent artists to flourish financially.

Within a major label system, there’s a lot of bureaucracy and process when putting out music. For independents, there’s no such thing so use to your advantage.

The Grouch knew that they couldn’t sell 100k copies of an album without the financial backing that a typical record label could provide. But he would have a better chance of selling 10k copies of 10 different CDs.

Over 20 years later, these underground artists have large catalogs with over 20 albums worth of music. To put into perspective, just with The Grouch and Eligh alone, they have 38 released albums combined, which doesn’t include any albums as a crew and features for other artists.

Was flooding the market with too much music a bad thing? Nope, fans ate it all up. Even now, no fan is going to tell their favorite artists to stop putting out so much music. It’s basically a necessity for emerging artists in today’s music industry.

Nowadays, with relatively less of a demand for products like CDs and tapes, putting out a lot of music isn’t necessarily going to earn you more money with streaming as the preferred method for music consumption. With streaming royalties so low (roughly 3,000 streams will be equivalent to what you make from selling a $15 CD), it’s not possible for the average independent artist to sustain from it alone.

However, putting out more quality music has an exponential effect. Pushing out more songs won’t necessarily mean you’ll generate cash in the short term, but each one will give you a chance to blow up with proper marketing. It gives you more “content” to promote yourself and get discovered.

Even though not all songs will be a hit, it will be added to your back catalog and accumulate more streams over time as your fan base grows. As the saying goes, old music is always new to someone. And if one of those songs take off or goes viral, it’ll definitely help lift the rest of your discography.

Key Lesson: Keep creating and pushing out new music consistently at a pace that works for you. Every new release you put out is another opportunity to blow up, sell merch, earn sync licensing opportunities and earn passive income with a growing catalog. The idea is to put high quality music as often as you’re capable of and to continue to show progress with each release.


3. Have the ability to record and make music from home.

The ability to make music at home is drastically different than how it was in the 1990s. Not only was equipment more expensive, it sounds much more complicated using things like an ASR-10 and SP-1200 sampler.

Recording and producing music at a professional studio is pricey. If you’re able to do it from home, you can save a lot of money and potentially accomplish a lot more.

For The Grouch, he was doing 4 track recordings at home and using music samplers to make beats. In the 1990s, you didn’t have affordable DAWS (Digital Audio Workstations) on portable laptops and free education on how to use them like on YouTube.

Lot of these hip hop artists at this time were teenagers so buying $2,000 – $3,000 recording equipment was relatively more expensive to them.

Take advantage of the technology today to record and make music from home. Russ is a great example of a modern DIY artist. In this video, he talks about putting the “gym” at home.

You may still use a professional recording studio to record the final mixes, but all of the early demos and mixes can start from home to save money.

Key Lesson: Because it’s much more affordable and accessible now, independent artists need to be able to make, record and/or produce music from home.


4. Word of mouth is still important. Otherwise, meet your fans where they’re at.

Back in the days, you discovered new music from either the radio, TV or from a friend. Your friend likely gave you a dubbed tape or a burned CD from another friend’s sister’s cousin’s older brother.

Today, word of mouth is still a popular way of learning about new artists whether it’s a friend making a personal recommendation or you seeing a social media post about it.

On the flip side, getting exposure to new potential fans in the 1990s was a different story. Because many of these local artists weren’t getting coverage from traditional media like TV, magazines or radio, they had to depend on doing things in person and hopes that would lead to word of mouth recommendations.

For the Living Legends crew, they took it to the next level. The Grouch talked about how they would save up money and periodically check flight prices at a local travel agency. The tactic was to find popular artists in the same lane and physically follow their tour routes. They gathered up whatever money they could scrap together to fly to different cities (and even countries like the UK, Germany and Japan) to promote their music and sell tapes outside of these shows. Because of their persistence, these artists would often let them be the openers and get direct exposure to their target audience.

It was a totally different time culturally where now soliciting random strangers on the streets is no longer as effective today.

Fortunately, you can get people’s attention and put your music in front of people without having to do any traveling because of the internet. We now have the option of running hyper targeted Instagram Ads to fans of artists with a similar sound from the comfort of our homes.

Key Lesson: Know who you are artistically and where to find your target audience, whether it’s in person or online. Build your fan base off similar artists in your lane. Use all the tools you have at your disposal, even if it means you have to pay, to get your music in front of the right people.


5. Use your money wisely. Investing back into your music career.

You hear it all the time. Treat your music career as a business because that’s what it is. For businesses to grow, you need to invest money into it and not blow the money you earn on things that won’t further your career.

When The Grouch was a teen, his day job was delivering pizza. The first day he got a credit card, he maxed it out as you would expect a teen would do.

You might think maybe it was for clothes, going out or some form of entertainment. Not at all. He bought an ASR-10 to make music from home. Although he went into debt, it was an important investment for his music career and his close peers.

To tie in with the previous point, The Grouch would grind by selling tapes on the streets so his crew could have money to buy plane tickets to promote their music at shows from popular groups like The Pharcyde. It was well worth the investment as they eventually got noticed and opened for these artists. This is a great example of reinvesting the money you make for the long term growth of your career.

You can argue that there are a lot more distractions to waste your money today and that the cost of living is higher, but if you really believe in your music, you’ll make the right decisions. For more on this, I wrote a blog on the top things you want to invest back into your music business.

Key Lesson: Don’t expect you’ll make any substantial income directly from music early in your career. You’ll have to invest your own money that you’ve earned elsewhere, like a day job, to grow your business.


6. Team up with other independents.

Being an independent artist doesn’t mean you have to do it all by yourself. Being a part of a crew, artist collective and/or community is a big advantage.

I’ve talked about having a community mindset in a previous blog and it is certainly applicable here. A lot of these independent artists worked together with others in the same area or city. Many developed their own crews or collectives so they could collaborate and even release albums together. It made a lot of sense back then because resources were limited and you were more likely to get further by teaming up with others.

The Grouch and Eligh are a part of the California hip hop crew The Living Legends. Crews like this were very common all over the United States in the underground scene.

Being a part of a music crew may be more of a “hip hop” thing, but you can still incorporate this concept even if you do any other type of music. Find other like-minded artists you can befriend and collaborate with musically. Maybe even become really good friends. It’s all about building a network with a community-oriented mindset.

Key Lesson: Don’t take independent music literally. Find other artists and musicians to work with and integrate yourself in different communities (in person and online) that make sense for who you are and the type of music you do.


7. Fill a need that’s lacking or do it better. Innovate.

One of the reasons why these DIY artists were able to win over fans is because they offered something unique or different. These underground movements were often providing alternative sounds the mainstream didn’t want to shine a light on, hence underground. For many, it was countercultural.

A lot of these Bay Area hip hop crews had artists representing different types of styles, voices, identities and personalities that attracted those who didn’t feel they could resonate with what was being offered in the mainstream.

In the west coast for example, the dominant sub genre played in the mainstream was gangster rap that glorified things like drugs, objectification of women, violence and money.

Music from California underground crews like The Living Legends and Hieroglyphics and SoleSides (Quannum Projects) was quite the opposite. Their songs had a more lighthearted vibe with relatable substance that the average person could relate to. More importantly they were innovative.

Here’s an audio clip with Andre 3000 of Outkast, who currently have the best selling rap album of all time, talking about how influential and innovative the Hieroglyphics Crew was on him personally but for hip hop in general at the time.

Of course, you don’t have to be a gangster to like or listen to gangster rap, but these independent artists from the 1990s provided multiple alternatives to what was readily available on the radio or TV.

To be fair, it’s a bit harder to fill a need in music today because of how the internet has already opened so many doors for artists around the world that typically wouldn’t have been given a chance by a major label. It doesn’t help that that the 1990s wasn’t as musically diverse and intertwined as it is today. But it’s not impossible to create your own lane today by doing something different as we’ve seen artists like Post Malone, Lil Nas X and Hobo Johnson do it in more recent times.

Key Lesson: At the end of the day, people seek connection with others who are like them. Music is powerful because it taps into our need to connect and relate with others. Find your niche. It doesn’t always have to be something so obscure or specific that no one occupies. But find something that is most authentic to you. Also, don’t be afraid of trying something new or experimenting with a new sound.


8. Be adaptable, diversify and experiment.

Society, culture and technology is always changing so don’t ever get complacent with what currently works.

The biggest source of income for independents in the 1990s were tapes and CDs. Touring was optional as a way of bringing extra income and engaging with fans.

The rise of MP3s and music piracy would eventually disrupt this business model dependent on record sales and begin a drastic shift towards digital music.

The Grouch says he was a go-with-the-flow guy so he wasn’t opposed to this change. Although it affected the money he would make in the short term, it also would help get his music out to more people and created a demand for other income sources down the line.

This line of thinking also applies to social networks, platforms and apps. MySpace was once the top social media platform for music, but others like Facebook, Twitter and YouTube would overtake its place.

Key Lesson: Don’t get too comfortable with what is currently working for you. You never know what is around the corner that can threaten it. Always keep an eye to the future and be open to trying new platforms and technologies. If there’s something new that’s getting some buzz, don’t be afraid to experiment.


9. Embrace the entrepreneurial spirit. Develop your hustle, start the grind.

Despite how accessible it is to build a music career independently today, there’s still a desire to get signed by a record label. Why? Because there’s a lot of work and resources that goes into being a full-time artist that many don’t want to deal with.

Regardless if you want to earn a record deal or not, you still need to build the foundation of your career on your own. This requires an entrepreneurial mentality and dedication.

All these artists I’ve mentioned and many more independent hip hop artists during these times embraced the entrepreneurial spirit. Chances are they didn’t think of themselves as businessmen or entrepreneurs but that’s what they were. They got their hands dirty in the different aspects of the music business and made it work with the limited resources they had. Failure was not an option for them and they stayed persistent.

With so much competition today, it’s easy to get discouraged, especially when you’re not seeing much success early on. It’s up to you to develop yourself to become a well-rounded artist. It starts with embracing the entrepreneurial spirit and persisting through all the challenges.

Key Lesson: If you’re an emerging artist, it’s hard to be purely an artist. Your best chance to make it is to get involved in as much of the business building and marketing as you can. Understand that failure is a part of this journey and learning from them is the best way to progress in your career.



There’s always going to be a debate about which time period was actually harder to be an independent artist in. Was it before the internet where it was more profitable selling tapes and CDs, but potential for exposure was very limited? Or in present times with streaming and social media platforms where income directly from music is limited but you have the ability to grow and scale your music worldwide?

I would love to hear what you think!

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