Jack Harlow and Drake have a budding friendship that is equal parts wholesome and hilarious to watch grow.

The two rappers were on vacation together in Turks and Caicos a few months ago, and Drake recently joined Jack at the Kentucky Derby following the release of Harlow’s sophomore album, Come Home The Kids Miss You. Drizzy is also featured on the project.

While the two looked like they had a great time, Harlow revealed during a recent visit to The 85 South Comedy Show that he lost a considerable amount of money betting with the rap giant at the horse race.

“I did, I lost a lot of money,” Harlow said after being asked if he bet on any horses at the Derby. “I just told Drake I would bet what he bet, so I copied him.”

Elsewhere in the interview, Harlow talked about what it’s been like becoming friends with Drake, who he said “taught” him how to rap.

“That’s what’s a real gift to this shit [hip-hop],” Jack says at the 34:30 mark of the video above. “Drake is one of the people who literally taught me how to rap; him, Wayne, and Kanye. Now, to be cool with him is the biggest gift. It’s better than $10 million. There’s no price tag on meeting somebody who taught you how to do it, and them saying, ‘Yo, you’re dope.’”

Watch the full episode of The 85 South Comedy Show with Jack Harlow up top.