What Tech Entrepreneurs Could Learn From Chamillionaire

Chamillionaire is experimenting with new technologies to build relationships with his audience, get feedback on his product quality, and to market his music all the way to the top of iTunes.


On why you should be an entrepreneur,


“A lot of people do what they have to do. You want to get yourself to a position where you can do what you want to do.” -Chamillionaire

Last night I co-hosted a dinner at Soho House in Los Angeles with some of the most senior people in the media industry with executives from Disney, Fox, Warner, media agencies and many promising tech & media startup CEO’s. The topic was “the future of television & the digital living room.”

With all of the knowledge in the room the person who stole the night wasn’t even on a panel. I had called on Chamillionaire from the audience and asked him to provide some views on how artists view social media, why they use it and where it’s heading. He was riveting.


He stood up, grabbed the mic and gave a heartfelt overview of his experiences in experimenting with new technologies to build relationships with his audience, get feedback on his product quality, and to market his music all the way to the top of iTunes. To stay the crowed was “wowed” was an understatement. He received that only round of applause of the evening.

While many were floored by his insights, I wasn’t in the slightest. I’ve known Chamillionaire for a couple of years and I’ve never been at a tech event where he HASN’T upstaged everybody with his marketing insights.

So it was my great pleasure to host Chamillionaire on This Week in VC this week talking marketing, entrepreneurship, old media and, of course, music. We also talked about getting more young African Americans interested in entrepreneurship & technology. I hope many of you can take the time to watch the interview–I promise he doesn’t disappoint. You can click the image above or this link.


Here are some take away’s:

1. On failure, trial-and-error & confidence: He did a lot of experimenting early in his career. As a teenager he experimented with writing & producing his own rap music and received a lot of feedback from elders that he had a talent with words.

He began producing and selling “mixtapes” of his music. He studied the errors that other people had made and tried to improve on them. He made many of his own mistakes. But he was street smart and hustled. He started selling the mixtapes out of his trunk and even gave away some of his music. He wanted to create awareness for himself to generate marketing buzz and demand and then get the retail stores to pay wholesales prices for his cds.


“All the failures that people get so scared of is what I did. It made me confident about what would work. Confidence doesn’t come from being a ‘know-it-all,’ it’s because I’ve done this 10 times already.”

What things did he experiment in the early days when there was no Facebook, Twitter or even MySpace to promote oneself? He used online services such as SHOUTcast, which was online radio that allowed him to play his own songs, interrupt a song, do a commercial break and connect with fans. [It sort of reminds me of the new generation of innovation that is happening around user-controlled terrestrial & Internet station Jelli.]

2. Authenticity – I asked Chamillionaire why he thinks he connects so much with people at tech conferences. How does he always wow a usually skeptical crowd? He said that he finds that people here are often speaking in big words or jargon–and that doesn’t connect with a lot of people. Cham studied early in his career how to hold the microphone, how to project his voice, how to watch the audience and pay attention to what interested them.

He said that he noticed a lot of tech entrepreneurs don’t speak into the mic, don’t project their voices with confidence and aren’t necessarily paying attention to the mood or energy of the audience. I had written a blog post on exactly this–how to not suck at group presentations–and what he said reminded me a lot of this post.


3. Marketing Innovation – Too many entrepreneurs are great product or technology people and lack the knowledge, skills or even desire to figure out how to market their products or themselves cleverly. Some other entrepreneurs who went down the MBA, consulting or banking routes without working at a startup are certainly book smart but haven’t always refined the street-smart skills needed to be an effective entrepreneur.

Chamillionaire has tried so many marketing angles that when new technologies emerge he has a strong sense on how to use them to best marketing himself and his business. In his early career he realized the importance of email lists. He would do anything he could to capture people’s email addresses because he knew that they served as a valuable tool for future marketing purposes.

His email list became his power. He would occasionally give away free music in exchange for email addresses. He created his own domain and gave out email address with the nomenclature. This was in the 90′s. It created viral buzz because other fans saw the email address and wanted to know how they got it. He was trailblazing.


He would try initiatives like announcing that a new cd was going to drop at new year’s. He had a website and put up a timer / countdown for the new year’s release. People would then call stores and ask if they had his album. He would get a call from the stores asking about a new album coming out. He created demand. Sometimes he didn’t even have the product when he announced it but the hype would get him focused on what he had to produce.

There are many analogies here for software development. I often tell teams that you need to create product deadlines that are semi-public (or maybe board commitments) that help you focus on shipping product. You may have to cut scope but nothing gets you more focused and the creative juices flowing than a deadline staring you in the face.

Businesses like TopSpin Media now professionalize campaigns for musicians to capture email addresses, build social-media audiences and sell products directly to consumers (and many other artist-to-fan direct initiatives). Cham learned this on his own because he had to–he didn’t have a label. So when Twitter, Facebook, YouTube, Ustream and other social websites became popular he has ideas for how to use them to authentically build a relationship with his audience.


4. Customer Feedback – Chamillionaire regularly seeks public feedback from his fan base. In the early days that was from releasing mixtapes. More recently it has been by putting free early releases of songs for free on Twitter. He said that the labels have a standard marketing plan that they say has worked in the past for other musicians. Cham is very skeptical of the one-size-fits-all approach

He said he learned what his fans wanted through the trial and error process.

“Not everything works for everybody. I tested so many things to see what works. Labels just had a marketing plan for everybody. but it didn’t work for everybody–it was just a plan …”

What is good? There are a million opinions about what is good. I just wanted to know what people wanted to hear from ME.”


5. Raising Capital–The VC equivalent for musicians is getting signed by a major label. I have always told entrepreneurs that to get VC interest you need scarcity value (in addition to a great product). People want what they can’t have and VCs are no different. The most potent entrepreneur is the one that doesn’t NEED your money.

So cheeky Chamillionaire went to Universal wearing the tags from every other label he had visited. While this blunt approach wouldn’t work with VCs a more subtle version actually does. What Cham said to Universal in his initial meeting was that he wasn’t wearing all of the other label tags just to rub them in Universal’s face, he wanted to make a statement:

“I just want you to know that I’m perfectly comfortable leaving here without a deal.”

6. On JFDI (play on Just Do It) – Chamillionaire talked a lot about social media. We talked initially about ustream. The labels said he could do live streaming himself but they didn’t want him to stream any music or videos since ustream wasn’t paying them. Reminds me of how the networks today announced they were blocking their video content from being shown on Google TV. Universal tried to push him to another site that had cut a deal with the label. He was frustrated because he wanted to be where the fans were:


“I was just trying to give the fans what they wanted and what they wanted was ustream.”

He did it anyways and didn’t ask for permission. By putting up his music free on ustream he ended up driving his song to the number one spot on iTunes (which obviously generates money).

“It would be successful and after it was successful nobody would say anything.”

This was obviously music to my ears since my personal philosophy that I’ve written about is “it’s better to beg for forgiving than to ask for permission.”

7. On What Next?


First, Chamillionaire is up front about the fact that he is trying to get out of the label contract he has with Universal and he’s holding back from producing music until he does. He said that most artists “chase checks” and he actually wants to do what’s right for his audience. He says that labels impede on your creativity, don’t allow experimentation and flexibility. He’s holding back for now, but he’s clearly studying what’s going on in technology

“I look at Zynga and all the games they have and how addicting it is and I think “there’s got to be a way to connect. A way to do music this way.”

We also spoke a lot about “free” as a metaphor to build future value. He spoke about his Grammy-winning song Ridin’ (as in Ridin’ Dirty) and how the labels wanted to extend life of song by getting somebody famous to remix the song. Cham had other ideas. He got people to do bootlegged mixtapes in new york, france and new zealand. He wanted to be bootlegged even more. The song spread globally.

He was fine with the bootleg–it helped build and audience and helped him globalize. It allowed him to do big shows down the line in places like Norway & Dubai. Anyone who knows the industry knows that artists make way more money by performing and selling merchandise than off of their albums (where the studio prevails). So it was almost like Chamillionaire already knew the Zynga model–give away the game and sell other things. He actually did it before Zynga was huge.


I told you this guy was smart.

“I can do so much more than rap with the rest of my life. there’s so much more in this world. I know that young people who look up to me are watching a show like this and they’re paying attention. I want to start feeding this stuff out so that the younger generation will start getting it and paying attention to this stuff ” [technology, marketing, business].

“I’m learning so much, I’m so advanced–ahead of so many other people, I don’t know a better way to serve my music [than by mastering technology]. I study it every day.”

7. On African American Youth?

Chamillionaire would like to see more young, urban, african americans aspire to things other than basketball or rap.


“They’re trained to think that it’s “the only way out.”

It bothers him. He wants people to know that it’s cool to be knowledgeable about business and technology.

“Technology is power. It’s so hard to do it in an over-saturated rap market. I just want to do the right thing and tell young people straight what they need to do.”

“They say the ‘game is to be sold and not to be told.’ Well I just ‘tell it.’ If you’re a young & up and coming rapper and you don’t know what tunecore is–you should know it.”

“The future of the world is in the palm of the tech community.”

Reprinted from Both Sides of the Table

Mark Suster is a 2x entrepreneur who has gone to the Dark Side of VC. He joined GRP Partners in 2007 as a General Partner after selling his company to He focuses on early-stage technology companies. Follow him at

About the author

I grew up in Northern California and was fortunate enough to have computers around my house and school from a young age. In fact, in high school in the mid-eighties I sold computer software and taught advanced computers