Likeable rapper Donnie in the jet-set lifestyle of wealthy people who – often very young – have amassed an enviable fortune thanks to their unusual talent and entrepreneurial spirit. In this candid and revealing show, we watch Donnie casually immerse himself in the lives of football stars, YouTubers, rappers, influencers, models, top entrepreneurs, musicians and social climbers to see if these stars are really all about the money - or maybe for something completely different. While Donnie marvels at the luxurious life of his hosts, he fully enjoys their enormous villas, expensive cars, jewelry, designer clothes, trips to Dubai and the seemingly carefree existence that seems to come with it. While Donnie observes all the excess, he tries to find out what it really feels like to be so rich and whether money really makes you so happy.