The Man That DISCOVERED & Built Jay-Z & Kanye West!
Key Takeaways
- Ownership is everything. Dame Dash's core philosophy is that you should never work for someone else when you can build your own. He regrets not retaining more ownership in his early ventures and teaches others to prioritize equity over salary.
- Dash discovered Jay-Z when no record label would sign him. After being rejected by every major label, they decided to do it themselves — founding Roc-A-Fella Records and building a hip-hop empire from nothing.
- The loss of Aaliyah was the hardest moment of Dash's life. Her death in a 2001 plane crash devastated him and fundamentally changed how he viewed life, mortality, and what truly matters.
- Dash's Harlem upbringing shaped his fearless mentality. Growing up in a tough environment taught him to never back down, always express himself authentically, and refuse to conform to others' expectations.
- Generosity without boundaries can destroy relationships. Dash reflects on being too generous with Jay-Z and others, learning that unreciprocated generosity breeds resentment rather than loyalty.
- He has shifted from a business-first to an art-first mindset. Dash now believes that creating for passion rather than profit ultimately generates more authentic work and sustainable success.
From Harlem Drug Dealer to Hip-Hop Mogul
Dame Dash opens with the raw story of his childhood in Harlem. Kicked out of school multiple times for challenging authority and refusing to conform, Dash was dealing drugs by age 16 — not out of desire, but survival. He describes how this environment forged his relentless independence and his refusal to let anyone else control his destiny.
Dash's earliest formative memory is being embarrassed at nursery school at age four. Rather than internalizing shame, this experience taught him to stop caring about others' opinions — a mindset that would define his entire career. He credits both his parents' mistakes and their love with shaping who he became.
Discovering Jay-Z and Building Roc-A-Fella
The heart of the episode is Dash's account of discovering Jay-Z's talent and the founding of Roc-A-Fella Records. After shopping Jay-Z to every major label and being rejected by all of them, Dash made the decision that would change hip-hop forever: they would do it themselves. With almost no resources, Dash's hustler mentality and Jay-Z's raw talent created one of the most iconic labels in music history.
Dash describes the early days of selling CDs out of car trunks, the breakthrough success of 'Reasonable Doubt,' and the rapid ascent that followed. He discusses the business decisions — both brilliant and flawed — that built the Roc-A-Fella empire, and the eventual fallout with Jay-Z that still resonates today.
Loss, Legacy, and Reinvention
The conversation takes an emotional turn when Dash discusses the death of Aaliyah, his girlfriend at the time. He describes her loss as the single most devastating experience of his life — one that fundamentally altered his understanding of what matters. The grief, he says, never fully goes away, but it taught him to value every moment and relationship with a depth he hadn't previously possessed.
Dash also discusses his evolution from a business-oriented entrepreneur to an artist-first creator. He believes that focusing on creating authentic art — film, fashion, music — rather than chasing money leads to better work and, ironically, more sustainable success. He points to the fact that many of the artists he mentored now have more money than he does, which he views as a testament to his teaching rather than a failure.
Notable Quotes
"I never worked for anybody in my life and I never will. Ownership is the only real freedom."— Dame Dash, On his philosophy of ownership over employment
"Every label said no to Jay-Z. Every single one. So we built our own. That's how Roc-A-Fella was born."— Dame Dash, On founding Roc-A-Fella Records
"Losing Aaliyah changed everything. You think you understand life until someone you love is just... gone."— Dame Dash, On the death of Aaliyah
"I was too generous with people who didn't deserve it. Loyalty should be earned, not assumed."— Dame Dash, On the fallout with business partners
"Society is programmed to make you scared of success. They teach you to conform rather than create."— Dame Dash, On independent thinking
"I don't make art for money anymore. I make art because it's who I am. The money follows the authenticity."— Dame Dash, On his artistic evolution
Frequently Asked Questions
What did Dame Dash say about Jay-Z on Diary of a CEO?
Dash revealed that every major record label rejected Jay-Z before they founded Roc-A-Fella Records together. He also discussed regretting being too generous with Jay-Z and the eventual fallout of their business relationship.
What episode of Diary of a CEO is Dame Dash on?
Dame Dash appears on Episode 192 (E192), titled 'The Man That DISCOVERED & Built Jay-Z & Kanye West!' Published November 3, 2022, with over 6 million YouTube views.
What did Dame Dash say about Aaliyah?
Dash described losing Aaliyah in a 2001 plane crash as the hardest moment of his life. Her death fundamentally changed how he views life and mortality, teaching him to value every moment.