Reynolds has donned many hats. His 25% majority stake in fledgling Mint Mobile led to a substantial windfall when T-Mobile acquired the startup for $1.35 billion after just four years. Between 2017 and 2020, Mint Mobile's revenue increased by nearly 50,000%, with many subscribers signing up because of Reynolds. In 2020, he sold his Aviation American Gin brand to Diageo for $600 million after acquiring an ownership stake in 2018. His venture Maximum Effort, an advertising agency, produced viral ads for brands like Match, Mint Mobile and Aviation Gin.