Tee Grizzley shows off his winning ways. Still celebrating the runaway success of his breakout single “First Day Out,” the rising Michigan rhymer unveils the creative video for “Win.”

The clip plays out like a journey through Grizzley’s rise from a dilapidated crib, where a piece of wood on top of a milk crate works as a coffee table. It shows his early beginnings, recording music inside of a home studio, looking out into abandoned houses, and eating food where insects roam.

But the flip side of this is also present in “Win.” In between scenes of the struggle, Tee flexes cash inside and outside of his mansion. Although he’s still the same — playing cards, making phone calls, and grubbing on some food — the perks are much greater. Instead of home cooked eggs, it’s Benihana. Instead of a broken down Mustang, it’s a fleet of fancy rides.

Lil Durk makes a cameo in the video, hanging out in Tee’s mansion. The duo is set to collaborate on a joint project soon. Last month, Grizzley announced the news on Twitter. “Y’all gone love when me and @lildurk drop our project,” he wrote.

“Win” follows recent Grizzley collaborations with Jeezy (“Cold Summer”) and Meek Mill (“Beef”).

Watch Tee’s victorious transition unfold.