The music superstars are making moves in the world of elite horse racing, as buyers get a shot at owning a piece of their Breeders’ Cup contender, Listenupshance.
Hip-hop, high stakes, and horsepower are coming together in Kentucky as Lil Wayne and Lil Yachty continue to make their mark on the world of thoroughbred racing.
On October 28, the prestigious Keeneland Championship Sale will offer an exclusive opportunity to purchase a 25% ownership stake in Listenupshance, a Grade 1-winning racehorse backed by Run Fast Racing, the celebrity-connected ownership group featuring Lil Wayne, Lil Yachty, and Latin music star Rauw Alejandro.
The timing couldn’t be more exciting. Just three days after the auction, Listenupshance is set to compete in the $2 million Breeders’ Cup Sprint on October 31, giving a new investor the chance to join the ownership team ahead of one of the sport’s biggest races.
From the Recording Studio to the Racetrack
Led by music executive Adam Kluger, Run Fast Racing is helping introduce a new generation to a sport traditionally associated with established racing families and wealthy investors.
By bringing influential names from music and entertainment into thoroughbred ownership, the group is creating a cultural crossover that goes beyond the racetrack.
And Listenupshance isn’t relying on celebrity connections alone.
The four-year-old sprinter has already proven himself against elite competition, winning the Grade 1 Bing Crosby Stakes and the Grade 2 Santa Anita Sprint Championship. With those victories behind him, he heads into the Breeders’ Cup as a serious contender.
A Million-Dollar Precedent
For prospective buyers, the opportunity comes with an intriguing recent example.
At the 2025 Keeneland Championship Sale, Michael and Jules Iavarone purchased a 25% interest in Bentornato for $1 million. Three days later, the horse captured the Breeders’ Cup Sprint, transforming their investment into an unforgettable championship moment.
This year’s invitation-only auction takes place at the historic Castleton Farm in Lexington, Kentucky, bringing together prominent owners, investors, and racing insiders during Breeders’ Cup week.
Beyond Listenupshance, the event features a curated selection of elite racing and breeding opportunities, with the historic Castleton property itself also scheduled to go under the hammer.
A New Era of Celebrity Ownership
For Lil Wayne and Lil Yachty, horse racing represents another chapter in their expanding business interests and cultural influence.
From music and fashion to increasingly unexpected investments, today’s hip-hop stars are finding new ways to extend their brands beyond entertainment.
Run Fast Racing is part of that evolution, combining celebrity appeal with a more accessible approach to experiencing the sport.
Whether Listenupshance delivers a championship victory or not, the attention surrounding the horse demonstrates how the worlds of entertainment, luxury, and competitive racing are increasingly intersecting.
And with the Breeders’ Cup just days away, all eyes will be on what happens next.
The Keeneland Championship Sale takes place October 28, 2026, at Castleton Farm in Lexington, Kentucky. The Breeders’ Cup World Championships follow October 30–31 at Keeneland.