5 Top Serial Entrepreneurship Lessons From Jay Z’s Appearance On Kevin Hart’s Talk Show

A full-length Jay Z interview is as rare as a Jay Z album these days, but that didn’t stop the iconic hiphop star come entrepreneur from sitting down with the comedic legend Kevin Hart in a thrilling interview on his Hart to Heart talk show airing in July. Kevin Hart’s masterful navigation of the conversation took us away from the usual gossip that one would expect from a Jay Z interview and took us into the mind of the man who has achieved unprecedented success considering his background and the limitations he has had to overcome.

If Jay Z’s business acumen and intelligent moves in the VC space were ever in doubt, we could have recourse to the endorsement that a young Jay Z got from none other than the veteran investment legend Warren Buffet 12 years ago after the two had a brief chat that left Buffet impressed; “Jay is teaching in a lot bigger classroom than I’ll ever teach in. For a young person growing up, he’s the guy to learn from,” said Buffet to Forbes.

Buffet’s predictions were spot on as Jay Z’s shrewd business moves soon skyrocketed him into the billionaire space, making him hip-hop’s first billionaire. Over the last two decades, Jay Z has built RocNation from just a label to a business empire with roots in many industries; talent management, fashion, sports, cognac, film, and real estate. The rapper also owns about $425 million in cash and investments via his Venture Capital Firm, Marcy Venture Capital, and over $50 million worth of real estate property. Jack Cornell, an investment real estate broker, describes that path to fortune as, “The most graphic example of how serial entrepreneurship should be done.”

Picking The Right Opportunities

Jay Z has been known to pick quite a few great deals in his time. He was one of the earliest investors in UberUBER
, a move that has been credited as contributing majorly to getting him over the $1 billion mark, but for the rapper, it’s all about having a discerning ear. During the talk show, when talking about family and others propositioning him for business deals and investments, Jay Z stated, “I try to explain to them that it doesn’t work that way, money is not just given away, and no one just gives you opportunities. If it sounds too good to be true, it probably is.” Cornell describes Jay Z’s path to fortune as a clear blueprint and admits to being inspired by Jay Z’s success.

According to Cornell, “Entrepreneurship is tough enough without expending yourself on a business that you should never have gotten into in the first place. Some deals are dead on arrival, and we would probably see through the shiny exterior if we look beyond our desire to make money. As a broker, I maintain the same attitude towards picking the right real estate deals for investors. Sometimes an investment isn’t only about the return profile, it’s about the fit and level of comfort for an individual investor. Every long-term success comes from buying correctly and the critical analysis upfront in the selection.”

Cornell is a well-known name among investment real estate brokers. With clients spanning coast to coast and internationally, in the most lucrative investor/broker/developer networks. Cornell’s team at SRS Real Estate Partners, has sold over $10 billion of Commercial Real Estate since 2018. In 2021, Cornell brought in one of the largest commissions in the firm’s history, selling a 400,000 sq ft industrial manufacturing facility in North Carolina. Cornell branched into the growing oil change industry, acquiring a famous brand franchise rights for Take 5 Oil Change in the state of Utah. He then went on to co-found Jack Graham & Co, a social media marketing agency alongside popular talent manager and marketer Graham Kramer.

Jeff Bezos, the famed owner of AmazonAMZN
and The Washington Post, was recently asked about entering a bid for the Washington Commanders with Jay Z in an interview with CNN. “Yes, I’ve heard that buzz,” Bezos said. “I grew up in Houston, Texas, and I played football growing up as a kid… and it is my favorite sport… So we’ll just have to wait and see.”

In his Rock & Roll Hall of Fame former U.S. President Barack Obama said on Jay Z’s impact, “I’ve turned to Jay-Z’s words at different points in my life, whether I was brushing dirt off my shoulder on the campaign trail, or sampling his lyrics on the Edmund Pettus Bridge on the 50th anniversary of the Selma march to Montgomery,” Obama said. “Today Jay-Z is one of the most renowned artists in history and an embodiment of the American dream, a dream he has helped make real for other young people like him.”

“So let me be one of the first to welcome Hov, the kid from Marcy Houses … as an official Rock and Roll Hall of Famer,” he continued.

Business is All About Service

“It is important to be result driven, but place service at the forefront of your business.” Explains Cornell. Cornell’s insight into the power of a service-oriented attitude is echoed by Jay Z in his interview; “In the beginning, it’s about your circle, those that grind it out with you, but then you have to turn back and say to yourself, what else? How else can I be of service?”. According to the Roc Nation legend, Roc Nation’s growth is driven by a strong desire to serve others and to give something tangible back to the next generation. Cornell adds, “That’s the best way to provide value. When I am genuinely helping people meet their objectives and needs, and going above and beyond my duties, I am getting a double dose of fulfillment.”

This is by no means a new principle of entrepreneurship. It is common knowledge that the greatest inventors and businesspeople have been those who saw a problem and created a solution to serve the people dealing with it. However, there are only few people who have replicated that in many diverse industries.

Roc Nation co-founder Jay Brown said on Jay Z in 2018 “I think the legacy you 
create…is built on the people you help. It’s not in how much money you make or what you buy or anything like that. It’s about how many people you touch. It’s in how many jobs you help people get and how many dreams you help them achieve.”

“Jay always knows how to influence you to be the best version of yourself,” Brown says of Jay Z. “He doesn’t look at it as working relationship—it’s a partnership, a family atmosphere—and it’s a culture that can’t be purchased.”

At the 4th annual Milken Institute Summit in Abu Dhabi last week, Brown echoed a similar sentiment.

“Being a superstar is not just having a hit record or something. What do you stand for? Who do you touch?” He emphasized, delivering an impassioned speech around the Roc Nation stable, particularly Rihanna.

Duplicating Success

In response to Kevin Hart’s question about how his consciousness shifted from just achieving personal goals to building generational wealth and impact, Jay Z said; “When You achieve that goal that you thought was unattainable, you have to stop and ask yourself, How can I duplicate this?.” Jay then described how he has had to create a template for success in the music industry and hand it over to some other artists who have gone on to replicate his successes. Two of Jay Z’s mentees, Rihanna and Kanye West, have also gone on to become Billionaires (though Kanye West recently lost the moniker), following his path by investing away from music. The success of these two mega stars proves that Jay Z is not just duplicating his successes in his businesses but also in people.

“The heartbeat of an entrepreneur is that he is never satisfied,” says Cornell. “A serial entrepreneur doesn’t start businesses or make investments for the money; the money is only exciting because it proves them right. It’s about the thrill, the conquering of an industry, and the ability to take your success template and replicate it in a totally different industry.”

On September 25th Apple Music, the NFL, and Roc Nation announced that Rihanna would be the headline act for the Super Bowl Halftime Show at Super Bowl LVII, on Sunday, February 12, 2023, in Glendale, Arizona.

In a statement after the announcement, Jay Z said on Rihanna, “Rihanna is a generational talent, a woman of humble beginnings who has surpassed expectations at every turn. A person born on the small island of Barbados who became one of the most prominent artists ever. Self-made in business and entertainment,”

Rihanna has had immense success so far in the business world with ventures including Fenty Beauty, Savage Fenty and now Fenty Skin.

Curiosity and Respecting the Process

“These are all years of work that are just coming to fruition at the same time, Ace (Ace of Spades Cognac) is 15 years in the making, and Dusse (D’Ussé VSOP Cognac) is 10, We come from a hustler’s mentality, so we were forced to either give up or make our own lane. So, I became curious, you have to stay curious.” Jay Z made this statement in response to Hart’s question about when he realized that the business success was beginning to surpass his hip-hop stardom. Curiosity is at the root of every entrepreneur’s ability to identify opportunities.

Loving The Project

When asked how he picks his ventures and businesses and what is next for the icon, Jay Z responded rather succinctly; “All these things are just extensions of what we love. We love to drink champagne, so we own a champagne company. We love to talk about sports, so we go and start a sports bar (40/40 Sports Bars). Ownership in a sports team is only natural; we will figure out a way to do it.”

A wide view, and examples of making the most of opportunities, places entrepreneurs like Jay Z on the top spot of role-models and inspirations for young adults and kids. To see that finding yourself on one path in life and career doesn’t exclude succeeding on another one, is an important message.