The Last Mixed Tape

Stella Lefty is having a moment, in more ways than one. The newly minted country-pop star’s debut album Long Way Home has reached the US Billboard Top 20, while her breakthrough single Boston became a viral hit earlier this year.

On the surface, it’s the modern songwriter’s dream: a young artist writes a song, shares it online and suddenly millions of people are listening.

Except Stella Lefty’s story has a second chapter. Born Stella Lefkofsky, she is the daughter of billionaire entrepreneur Eric Lefkofsky, the co-founder of Groupon and founder of Tempus. Her background quickly became part of the conversation surrounding her rise, turning what might otherwise have been a straightforward success story into another argument about nepotism, privilege and authenticity in popular music.

And then came Boston. The song attracted criticism over its similarities to Noah Kahan’s Stick Season, with Kahan ultimately receiving a songwriting credit. Suddenly, Lefty’s rise had become a collision point for several of the biggest arguments surrounding music in 2026: industry plants, authenticity, inherited wealth and the suspicion that some artists are simply being given opportunities that others have to fight for.

But is Stella Lefty actually a nepo baby? And perhaps more importantly, are working class artists being squeezed out of the music industry?

The Last Mixed Tape is hosted by Stephen White, and is also available on Spotify and Apple Podcasts.