The song "Pillionaire" by Syph Flips is about the hustle and grind of a young person growing up in the streets of the United States. The lyrics talk about getting rich off selling pills and wanting a luxurious Richard Mille watch. The song also references living a "trap life" and dealing with the loss of friends and loved ones. The artist expresses the struggles of the streets and the desire to succeed despite the hardships, while also flaunting the lavish lifestyle that comes with the drug trade. The song captures the reality of life in the streets and the determination to make it out and thrive. Overall, "Pillionaire" tells a story of resilience, survival, and the pursuit of success in the American urban environment.