Winston “Win” Coleman, better known by his artist name Win Cant Lose, is Bay Area’s “one man band.” The Oakland native is not only a rapper and producer, but also founder and CEO of CANT LOSE Entertainment.
His work has been featured on popular shows such as “Love & Hip-Hop: Atlanta,” “Shameless,” and “It’s Always Sunny in Philadelphia.” His recent single “Can’t Lose Flow” has amassed over 1.5 million streams on Spotify and counting– ultimately proving that there truly is no losing with Win.
From a young age, Win Cant Lose was enticed by the musical stylings of rappers such as Ma$e and 2Pac, motivating him to write his first rap lyrics by the age of eight. Determined to make a career out of music, he moved to Los Angeles to study engineering at the LA Recording School. In 2013, he went on to write, produce and mix his first full-length album, Druglife: The Green Print, Vol.1, followed by 2014’s Drugs & Dreams: The Greenprint, Vol. 2, both of which featured Grammy nominated artist and producer Ca$Hpassion.
After taking a brief hiatus, Win came back stronger than ever. He performed as an opener to PnB Rock’s “Catch These Vibes’ tour, which featured Lil Baby as a co-headliner. The two month long, 40-show tour became the catalyst for Win’s heavier production work and industry involvement. In 2020, he opened a recording studio in North Hollywood, California and started his record label CANT LOSE Entertainment the following year.
Three of Win’s recent singles including “Cant Lose Flow” and “Pop Out” have been released under the artist-friendly label. As of 2022, CANT LOSE Entertainment has signed other artists such as fellow Oakland native, 25 year-old 4EVAGRIM, and 17 year-old MyCousinJ from London.
There’s more “winning” in store for the one-man band, with a new full-length project coming out soon.