Jack Dorsey, co-founder and ex-CEO of the formerly great Twitter, has shared his take on the long-running “dinner with Jay-Z or $500,000” meme.
In comments provided to GQ’s Chris Heath, as seen here, Dorsey pointed to the innumerable bits of “wisdom” he’s been able to amass through knowing HOV.
“The meme—half a million dollars or dinner with Jay? Like, that is real,” Dorsey said. “Every moment I’ve had with him, every story I could tell, is really just a compounding realization around how much wisdom he has. A lot of it’s through experience, but a lot of it is just instinct. I haven’t met a lot of people with that.”
Dorsey went on to praise the 25-time Grammy winner as “this ultimately wise individual” with acute observational skills and an uncanny ability to offer unique insights, later likening him to a teacher.
“I don’t think people realize how deep it is,” he said. “You get it only through these small snippets in the music or maybe a speech or an action. But if you put the whole corpus together, it’s pretty impressive.”
Jay himself has spoken about the relentlessly memed dinner-or-money proposal in the past. In a 2023 interview with Gayle King, he urged those who might find themselves faced with this purely hypothetical conundrum to “take the money,” arguing that any advice they might cull from a dinner can instead be found in his lyrics.
“I wouldn't tell you to cut a bad deal,” he said at the time. “Take $500,000, go buy some albums, and listen to the albums. It's all there if you piece it together and really listen to the music for the words.”
Dinner debates aside, fans are in agreement that 2026 may end up being the year that Jay decides to drop a new solo album. At the very least, he would appear to be rounding the bend on being open to the idea, as evidenced by his return to the stage.
