The Timeless Branding of Ms. Lauryn Hill

Braven Greenelsh
  /  
CEO & Founder
November 27, 2023

Do you know who the first woman to win five Grammys in one night was? Or who is among only 29 women who have a Diamond-certified album? Part of an exclusive club of only 92 artists with Diamond status? Ms. Lauryn HIll, that’s who!

I had the pleasure of attending her 25th Anniversary show featuring The Fugees and special guests Nas, Lil’ Wayne and B Real.

Establish and live by values that resonate with your true beliefs. Authenticity should be the foundation upon which all brand decisions are made.



During the show, I was struck by the realization that Ms. Hill is not only a musical titan, but also a masterclass in branding. Despite The Miseducation of Lauryn Hill being her only full-length album, her career approach offers invaluable lessons for both corporate and personal branding.

Although she’s been questioned for her personal artistic decisions, these criticisms overlook the powerful narrative of her work and how it continues to resonate deeply with audiences. 

In the summer of 1994, I first heard Ms. Lauryn Hill on a mixtape my cousin brought me. The track was, “Vocab.” And it was an awesome song. It still is. 

Ms. Hill was almost an afterthought on the Vocab track. But shortly thereafter, when The Score came out, she was center stage.

Following two Grammy wins with the Fugees, anticipation was high for their next album. But Hill blindsided the world with a big fat slap in the face releasing her debut solo album, The Miseducation of Lauryn Hill. The album would forever change hip-hop. I listened to every single lyric of that album. I was so into the music, the poetry, the history, the vulnerability...And it changed me. A little at least.

With this album, Ms. Hill became the first female artist to win five grammy awards in one night. Her acceptance speech at the Grammys—declaring the triumph of hip-hop in a traditionally pop category — was historic. She not only kicked pop’s door in, on behalf of hip-hop, she made sure no one ever looked the other way again (source: Tidal).

Ms. Hill’s next statement was one of silence and authenticity, choosing to prioritize family over fame—a decision not universally applauded, especially by those who stood to profit from her career. Though she stepped back from the public eye, save for an MTV Unplugged album and sparse guest appearances, her impact only magnified. The love from her peers and fans only solidified her influence, with her monthly Spotify listeners reaching 20 million and The Miseducation of Lauryn Hill reaching 10x Platinum.

Twenty-five years later, she emerged with a feature on Nas’ King’s Disease, delivering verses with undiminished fervor and truth.

”Now let me give it to you balanced and with clarity

I don't need to turn myself into a parody

I don't do the shit you do for popularity

They clearly didn't understand when I said I get out apparently

My awareness like Keanu in The Matrix

I'm savin' souls and ya'll complainin' bout my lateness”

What can Ms. Lauryn HIll teach about leadership while building a timeliness brand?

  1. Be Fearless: Iconic brands are built by leaders willing to make tough, sometimes unpopular decisions and challenge the norm. Too many CEOs play it safe. To create something legendary, you must be fearless.  
  1. Keep it Real: Brand integrity is about authenticity. Establish and live by values that resonate with your true beliefs. Authenticity should be the foundation upon which all brand decisions are made.

  2. Be Honest with Yourself: CEOs need to acknowledge their brand’s and business’ shortcomings. Embracing and addressing these gaps can lead to genuine improvements and trust. 

Ms. Hill continues to fill stadiums and inspire, even without the convenient trappings of celebrity. A multifaceted icon—artist, poet, mother—she remains a beacon of integrity and proof of a band’s power when grounded in authenticity.

CEOs and leaders, take note of Ms. Hill's unique path. Observe, learn and consider how her authenticity and steadfastness can be a a template for success in your endeavors. 

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