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  • Writer's pictureJustin Delaney

What we can learn about branding from Vanilla Ice

Updated: Oct 1, 2018

I wrote a book about startups, but the current state of entrepreneurship books has made me reluctant to release it out into the world. It is a Billy Graham world right now, and I just do not want to be a part of hat part of entrepreneurship. It feels to inauthentic and strained; the world is filled with faux-entrepreneurs and wannabe Gary Vee's and all of them have a book. I don't want to add to that dumpster fire. I don't want to publish a book or create a personal "entrepreneurial brand". I just want to write and start companies. Fuck the dumb shit.

All of that said, I will occasionally share a chapter here on my site. The first is an entry about Vanilla Ice - a crash course in branding.

Chapter Sixteen - Branding

At my church growing up in Plano, Texas, there was this guy named Tommy Quon. He was an Asian guy with some serious swagger, a nice car, and a wife who looked like a model. Urban legends swirled around him. There were rumors that he was Vanilla Ice’s father, or manager, or both. There were whispers that he had a fleet of luxury cars, and that he made Vanilla Ice who he was.

The year was 1991. In hindsight, it all seems like the work of pre-Internet imaginative teenagers. Yet, every urban legend about the guy eventually was proven true, except his being Vanilla Ice’s father. That was ridiculous.

Robert Van Winkle was born in Dallas, Texas and spent time in Florida as a kid. He moved back to Texas around the age of sixteen and dropped out of school. He was an excellent breakdancer and motorcyclist. He also loved to rap.

At age nineteen, Van Winkle performed at a club called City Lights in South Dallas and was granted a sort of residency due to his immense talent as an MC. He began to nail his performances, and, he opened up for bands like Public Enemy and N.W.A. in the late ‘80s. He was living a new variant of the American Dream.

Vanilla Ice was born.

About a year into his gig at City Lights, he was stabbed five times outside of the club.

It was in the hospital that the owner of City Lights, Tommy Quon, signed him to a record deal. Quon used his earnings from the club to finance Vanilla Ice’s early career and album. It took them two years to record Ice’s first studio album, To the Extreme.

Most radio stations passed on playing the album’s first single, but a B-side titled “Ice Ice Baby” caught the ear of a DJ in Atlanta, Georgia. It became a staple on Atlanta radio. Even in 1991, Atlanta had the ability to make or break a young rapper. Quon spent $8,000 to quickly create the now iconic video for “Ice Ice Baby” in response to that modest success. You may remember the video—with the stupid baggy pants and the ‘80s Dallas skyline in the background. And that haircut.

To the Extreme was Vanilla Ice’s first studio album and became the fastest selling hip-hop album of all time with 11 million copies sold.

In many ways, the wall that Run DMC and Aerosmith metaphorically took down in their classic video for “Walk This Way” did not come down until Van Winkle dropped “Ice Ice Baby” on suburbia. Hip-hop was fast tracked to dominate the music landscape for decades. It broke through in a way that had yet to happen.

Timing. Perspective. Preparation.

Back to Tommy Quon. He was not a musician, but he was an excellent businessman. He knew how to brand, and his timing was impeccable. In Vanilla Ice, he saw the future, and like any entrepreneur, he used his platform to take a measured risk. He started with a studio recording, and when customer feedback was good, he moved on to a music video. Classic escalation of concept.

There is one key reason why it all worked. Vanilla Ice was a greatly consistent, near-caricature (in hindsight) brand. Plus he solved a problem.

The problem? The suburbs needed a bridge to rap and urban culture. N.W.A., Ice-T, and lots of other rappers were historical and great but ultimately too intimidating and polarizing for white America to get behind.

My parents were not going to listen to “Fuck the Police,” but they would listen to “Ice Ice Baby.” Sure, kids like me, we would grab N.W.A. and Ice-T tapes at the mall and hide them from their parents, but the parents were dismissive and protective. With the “Under Pressure” Bowie riff and the harmless baggy pants, Vanilla Ice was rap at its most accessible. It was like a cartoon advertisement for rap, but it was just catchy enough to set the world on fire. Even though the second verse of “Ice Ice Baby” describes a drive-by shooting, and yet, the world accepted the track as vanilla enough for the mainstream.

Vanilla Ice was rap culture’s fait accompli. After “Ice Ice Baby” stormed the U.S., everything changed. In school, teachers encouraged rapping as a form of presentation. During NBA games, rap beats were played. On TV, in increasingly uncomfortable formats, people would rap things. I lived through many of these painful cultural moments personally.

Rap became legitimate and safe.

“Rolling in my 5.0 with my drop top down so my hair can blow.” He was no Rakim, but he tore down the wall. He shattered rap’s ceiling. His music was not great, but his timing was.

Brand + Timing + problem solved = greatness.

“Ice Ice Baby” also adheres to the most important rule of branding—repetition.

He says “ice” over thirty-five times on the track.

The most important thing for brand is consistency, repetition, and authenticity. Unfortunately, Vanilla Ice had some issues with authenticity.

As a white guy practicing in a predominantly not-white game, he already had a target on his back. The late ‘80s and early ‘90s were a time of frequent poseur accusations, and Vanilla Ice checked those boxes, especially when contrasted against fellow “Brothers in Ice,” Ice Cube and Ice-T. As a suburban kid, I remember loving Ice Cube of N.W.A., but being legitimately terrified to cross paths with him. He seemed so hard. I had no such feelings about Vanilla Ice.

Vanilla Ice summed it up perfectly in 1990:

“It’s not about skin color,” he insists. “Rap is from the streets and I’m from the streets. That’s why a lot of people accept me.”

It was about the streets.

He published a biographical account about his “background” coming up in the streets, of which parts were falsified. Of course, getting stabbed numerous times seems like a fair qualification for one’s connection to the street to me, but it didn’t matter. He lied in a book about himself—that was the story. It destroyed his brand, and really his career as a musician. He was twenty-two.

If your brand lies, then kiss it goodbye.

If your brand is inconsistent, then you do not have a brand.

If you do not have a brand, then you will never create long term value.

“Ice Ice Baby” also caught the ear of infamous gangster Suge Knight. Knight, as we know now, is a gangster of a hip-hop icon, and a cautionary tale about the dark side intimidation that takes place behind the stage.

Suge effectively intimidated Vanilla Ice into licensing the publishing rights for “Ice Ice Baby” to his record label. Allegedly, Suge held Ice from his feet off the fifteenth-floor balcony of the Bel Age Hotel until he relinquished the rights to the track.

The rap game.

Suge used the royalties earned from “Ice Ice Baby” to start Death Row Records. That anecdote, along with its place as a MAJOR crossover hit and the first number one hip-hop single, probably makes “Ice Ice Baby” the most historically significant hip-hop track of all time, though it does not get that credit.

A brand attracts.

The Nuts and Bolts of Branding

Branding is a very basic and yet complicated art and science. At its core, it is the essence of your business. When people think of your company, it is your brand that they feel. Every interaction, every word, every image, collectively forms a brand.

Everywhere your brand interacts with a customer needs to have a common thread and theme.

Logo and Name

This is number one. Naming your business is a moment that reflects what you believe it means to the world. Choose a name that fits the character and what you want people to remember. Combine it with a logo to use as a visual shorthand. Someday, people may know your brand so well that they recognize it from logo alone. That is the goal. Create a primary version of your wordmark and logo and then use it everywhere. Do not create many variants.

Vanilla Ice had a perfect name. It both made a new genre more vanilla, and it summed up who he was perfectly—a white rapper.


Choose your family of fonts and stick to it. Make sure every single thing that is ever typed uses those fonts. From email to website to print ads, the fonts need to be consistent. People trust consistent. The mind notices little inconsistencies in brand like an errant font and interprets these inconsistencies as dissonance. Create rules for headings, subheadings, and body text first. Move on from there as necessary. This is an easy best practice. Try to pick fonts that are not too clever or creative, as they will lack a utilitarian function and be difficult to use.

Personifying the Brand

I have been blessed to work alongside some of the greatest people in the world at Menguin and Generation Tux. One of my mentors from before either company existed is a guy named Neil Morgan. Neil is a branding expert and academic who taught at Cambridge, University of North Carolina, and currently teaches at Indiana University. He is one of my luckier breaks as far as collaborators are concerned, and much of my obsession with brand stems from Neil.

One of my favorite exercises that I inherited from Neil is the brand personification exercise. Effectively, you create a fictional individual and create attributes for that individual as though he or she is your brand. If your brand is a person, what is their job? What kind of car do they drive? What do their friends say about them? What are their hobbies? What type of music do they listen to? Are they married? Are they straight? Where are they from?

It can go on forever. The purpose of this exercise is to create an individual that everyone at the company can relate to and understand. From there, everything your brand does must be consistent with how that individual would behave.

As it is difficult to make decisions of consistency with an ephemeral brand, this exercise creates a polymorph version of your brand that is a human. Say his name is Steve. Say a new intern creates a social media post that sounds wrong. You get to say, “Steve would never say this; he doesn't talk in contractions and hates the mountains” or something like that.

By personifying the brand, you make it more real and consistent. But above all else, you get to sound like a crazy person.

<Part 2, Continued, some time...>

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