The Cowboy Rapper Who Made History With $50 and 60 Minutes

In 2018, 19-year-old Montero Hill had a problem. He wanted to make music, but everything was working against him. His parents didn’t support his dreams. His sister had kicked him out of the house. He had no money, no connections, and no clear path forward.

Most aspiring artists would have given up. Hill did the opposite—he got resourceful.

With $30, he leased a beat online. It was a simple, country-tinged melody that caught his attention. He found a local studio that offered “$20 Tuesdays” to fill their slowest day of the week. In under an hour, he recorded vocals for a song that mixed country and rap in ways the music industry had never seen.

But Hill—who performed under the name Lil Nas X—knew recording was only half the battle. Without a marketing budget, he turned to TikTok, creating memes and content around his track. He didn’t wait for radio stations or record labels to notice him. He built his own audience, one viral post at a time.

The song was “Old Town Road,” and it defied every rule the music industry had about genre, marketing, and artist development. It became a cultural phenomenon that nobody could categorize but everyone wanted to hear.

That $50 investment became the second-highest-certified song in American music history. It earned Hill a Columbia Records deal, two Grammy Awards, and 17 platinum certifications. More importantly, it proved that constraints don’t have to be limitations—they can be catalysts for innovation.

While major-label artists with unlimited budgets stuck to proven formulas, Hill’s financial limitations forced him to experiment, to think differently, to create something entirely new. His resourcefulness became his competitive advantage.