Billionaires are a relatively new phenomenon, yet their influence is immense. Some billionaires hide in the shadows, and others are at the forefront of our society. With the advent of social media, the reach of billionaires at the forefront has expanded exponentially. Some sport their fancy lifestyles, some preach their views on the world, and some share what it takes to become like them. With 2.562 billion monthly YouTube users and millions of views for any video with or about billionaires, the reach the highly wealthy have is immense. So many are watching, raising two questions are the viewers watching with the intent of learning how to become a billionaire themselves or are they purely focused on entertainment value? Additionally, what purpose does speaking to the masses through YouTube serve for the wealthiest individuals in the world? This paper will attempt to answer these questions and dive deeper into the billionaire YouTube landscape. There will be a discussion of the immense power of billionaires, what it means to be one, and an analysis of a select few of America’s wealthiest individuals. Hopefully, this will give a better perspective on the wealth-based social media landscape.