I’ve had dinner with Jay-Z, but is it worth passing on $500,000?

Jay-Z attends 2020 Roc Nation brunch,
Jay-Z attends 2020 Roc Nation THE BRUNCH on January 25, 2020 in Los Angeles, California. (Photo by Erik Voake/Getty Images for Roc Nation)

A viral meme has been circulating across the internet about whether you should take $500,000 in cash to invest as you see best or have dinner with Jay-Z where he could, presumably, give you wisdom and put you on game to help propel you to multi-millionaire or billionaire status.

I have been in the culture media business for over two decades, and in that time I’ve interviewed and hung out with Jay-Z on many occasions. The man is smart and funny and dinner with him would be a great time. I’ll never forget the time we were backstage at a Destiny’s Child concert in Philly, waiting for them to finish so that he could hang with his then-girlfriend Beyoncé. There were about eight people with Jay that day and we were seated on some couches with about 30 minutes left until Bey came out.

Kelly Rowland, Michelle Williams, Jay Z, and Beyonce Knowles,
Kelly Rowland, Michelle Williams, Jay Z, and Beyonce Knowles attend the 2005 NBA All Star Game at the Pepsi Center on February 20, 2005 in Denver, Colorado. (Photo by Mark Mainz/Getty Images)

While we waited, Jay took over the moment and led us all into a song. He pointed at one person and told them to make a rhythmic sound. Then he coached another person to come in behind the first one, adding to the beat. Then he pointed to another person and another, bringing everyone in, making everyone feel comfortable and a part of the moment. Soon there was this big, weird, funky beat being driven by eight people, including me, where we were making percussive whoops, or claps, or dings, or table bangs or whatever you could think of. Everyone was smiling and into the creative musical session that ended in Jay doing a cool little freestyle on top of it all and then concluded the beat. It was fun!

During another time, we were on a private jet flying somewhere. Fried chicken wings and red wine were being served on the aircraft. I remember holding my glass with my fingers gripping the bowl of the glass rather than the stem, prompting Jay to ask me, “You know why you’re supposed to hold the stem and not the bowl?” I could tell that he loved that he, from the ‘hood, knew more about this high-falutin cultural minutiae than a guy from the middle-class suburbs. He finished his thought: “Because your fingers apply heat to the wine that can change its flavor.”

There’s also the time when we played Guts, which was then Jay-Z’s favorite game. There were nine rich men sitting around a table ponying up thousands of dollars a hand to play a game where you’re dealt two cards. You decide whether or not to stay in the hand based solely on your two cards and reading other people’s faces. If you lose, you must replace the pot all by yourself — the pots were routinely $3,000, $5,000, or $10,000. I have no idea why I was playing. I was not rich.

Jay-Z.(Photo by Slaven Vlasic/Getty Images for Sports Illustrated)

By 11 p.m. I was down $5,000 and I was freaking out. But I thought I was in good shape when I got dealt two Jacks. I was the only one in the hand when it was Jay’s turn to decide whether or not to stay in. The pot was about $3,000 — which was pennies to him and a lot of money to me. But I’m a fool. He looked me over, trying to decide if I was bluffing. We had been playing for hours and I had not bluffed once. At the time, I was working on a Rolling Stone cover story and I said, “If I beat you, I’m putting it in the story.” Jay replied, “But will you put it in the story if you lose?” He stayed in. I proudly put down my two Jacks. He looked at my hand with this condescending, dismissive look that essentially said, ‘That’s cute,’ and my heart sank. He laid down two queens and reached out to rake in the pot while I asked someone if I could borrow $3,000.

So fun.

During another time with Jay-Z, we broke bread in the Hamptons once at a big table of 10. Aaliyah was sitting across from me. I was talking to her and getting lost in her beauty when someone at the other end of the table made a condescending joke about wearing flip flops as if that was the corniest thing in the world. Then they realized that I was wearing flip flops, but that I hadn’t said anything. Dame Dash started dissing me, saying what do you do when someone disses flip flops and you’re wearing flip flops? Jay was at the head of the table, laughing uproariously, making Dame’s joke seem even bigger. Having Jay-Z laugh at you in front of a bunch of people is so … fun!

One last story. It’s November of 2007 and then-Senator Barack Obama is in New York for a round of fundraisers. He does one at the home of a famous record executive and both Jay-Z and I were invited. The space was so crowded that it took minutes just to wade through the sea of people and get away from the door. As I was trying to do that, Jay and Beyoncé came in behind me. I turned to say what’s up. Jay said, “Yo family, do me a favor. Do my cufflinks?” He was in a tux and when he held up his wrist I could see he had a silver cufflink in his hand and empty eyelets at the end of his shirt. I thought to myself, ‘What? I’m not your butler.’ I glanced at Beyoncé as if to say, ‘Shouldn’t your woman do that for you?’ He looked at me as if to say, ‘I said what I said.’ I thought, ‘He’s done a solid giving me a ton of interviews over the year and it’ll only take a second. I don’t want to say no. Screw it.” So I took his cufflinks from his hand. I tried to put the link through both holes at once so it’d be done faster, but, I found out, that’s harder to do.

I tried to push the first cufflink through once, failed, then again, missed, then a third time, and missed again. Each time I had to start all over. My embarrassment slowly grew — I wanted to do this quickly and not risk someone see me doing Jay-Z’s cufflink for him. And with all of this flooding into my mind it’s getting even harder to get that little link into the little holes and it’s all taking way longer than I wanted to and then Jay-Z said, “Hurry up.” ‘Damn,’ I thought. ‘I’m doing you a favor at risk of my self-esteem and you’re saying “hurry up” like I work for you or something?’

Jay-Z and Beyonce,
Jay Z (L) and Beyonce attend the “China: Through The Looking Glass” Costume Institute Benefit Gala at the Metropolitan Museum of Art on May 4, 2015 in New York City. (Photo by Mike Coppola/Getty Images)

I finally got it in and walked away but before I did, I smiled at him and gave him a pound because hey, it’s Jay-Z.

My sarcasm and my cherry picking of these stories from the time we’ve spent together, is meant to be funny at my expense, not Jay-Z’s. He’s got a big ego but he’s truly fun, smart, cool, and a good brother to hang out with. He can say wise things and he retains enough humility to truly listen to others. He’s a good dude and a people person who’s fun to argue with because he likes to mix it up and he knows when to laugh to diffuse the moment. I say all that to say having dinner with Jay-Z would be fun even though he’ll probably tease you here and there.

That said, Jay-Z is not some business genius who knows secrets that can make the difference between you becoming wealthy or not. He used capital and relationships based on people wanting to associate their brand with his cool factor to sell products and make deals that have in turn made him wealthy. He made Rocawear and D’Usse sell because fans trust his taste. He was allowed to invest in Uber and buy major artwork and create Tidal and sell it to Square because time, and again, people, have thought that being in business with him would result in his cool factor rubbing off on their brands or their investments.

Jay-Z’s done well by making others want to be in business with him and making an audience of young men trust him. This is not a road you could travel and there’s nothing he could tell you that would help you do that.

Of course, Jay-Z would tell you that you should’ve taken the $500,000. That’s more valuable than dinner with Jay-Z. The path to wealth isn’t opaque; it’s just that most people don’t know the roadmap and don’t have the capital to invest nor the time to wait for those investments to grow. They have to use the dollars they made today to fend off tomorrow’s bills. But people make big money by creating companies that are successful and/or investing in companies that are successful. Some people get to wealth via a salary but very few.

Jay-Z and Warren Buffett attend the grand re-opening of Jay-Z’s 40/40 Club on January 18, 2012 in New York City. (Photo by Theo Wargo/Getty Images for Berk Communications)

If you suddenly had $500,000 to invest you should look to buy income-generating real estate — a place that has tenants so you’re getting rental income while the value of your investment is rising. You should also invest chunks of it into Bitcoin and Ethereum and blue-chip stocks like Apple, Google, Microsoft, Amazon, and Tesla. All of that would lead to your $500,000 multiplying in value over the subsequent decade. If you can take that $500,000 and put it into investments for many years then it’ll balloon into wealth. Either that, or, if you have the passion and the acumen, you can use a large chunk of that $500,000 to start your own business and work 80-100 hours a week at making it into a success. If it blows up maybe one day you’ll have people investing in your company. 

The point is, there isn’t some magical formula that only the wealthy have — as if they can whisper it to you and then all of a sudden you have the cheat code on how to be wealthy. A lot of people seem to believe that the wealthy know something they don’t, but the truth is that the wealthy are people who took capital and invested it in strong financial vehicles over several years (or they inherited it.) Warren Buffett (a business friend of Jay-Z) says it’s not about timing the market, it’s about time in the market. You don’t need Jay-Z to tell you that.

And the thing that’ll really bake your noodle is, even if you don’t suddenly inherit $500,000, if you can take a slice of your income every month — maybe $250, maybe $500, no more than $1,000 — and invest it in a few of the elite financial vehicles I mentioned (Bitcoin, Ethereum, Apple, Google, Microsoft, Amazon, Tesla), invest it no matter what, rain or shine, up or down, and don’t sell for five to ten years, at the end of that time you’ll have a lot of money. Not to mention, building Black wealth is the key to building Black political power in the future.  


Touré is the host of the podcasts Toure Show and Democracyish and the podcast docuseries Who Was Prince? He is also the author of six books.

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