Brian Buckmeyer

Diddy was in the middle of a successful run with Danny Kane on his MTV show Making the Band, and he was getting ready to release the debut album of Atlanta rapper Young Jock. But Diddy wasn't happy with the label's recent performance. He said publicly that he was trying to get things back on track. So now he had another up-and-coming artist he wanted everyone in the room to meet. Cassie Ventura.

Diddy was in the middle of a successful run with Danny Kane on his MTV show Making the Band, and he was getting ready to release the debut album of Atlanta rapper Young Jock. But Diddy wasn't happy with the label's recent performance. He said publicly that he was trying to get things back on track. So now he had another up-and-coming artist he wanted everyone in the room to meet. Cassie Ventura.

That day, she wore her long, dark hair tucked behind her ears and big gold hoop earrings. She dressed casually, with little to no makeup. Combs was in his late 30s. He sat at the head of the conference table while 19-year-old Cassie was at the other end. She was there with a producer she'd been working with. They'd released a song you've probably heard of called Me and You.

That day, she wore her long, dark hair tucked behind her ears and big gold hoop earrings. She dressed casually, with little to no makeup. Combs was in his late 30s. He sat at the head of the conference table while 19-year-old Cassie was at the other end. She was there with a producer she'd been working with. They'd released a song you've probably heard of called Me and You.

To this day, Me and You is the track Cassie is best known for. A song that would go on to peak at number three on the Billboard Hot 100. A song that stayed on the charts for about six months. In other words, back in 2006, Cassie's song was one of the country's most popular singles.

To this day, Me and You is the track Cassie is best known for. A song that would go on to peak at number three on the Billboard Hot 100. A song that stayed on the charts for about six months. In other words, back in 2006, Cassie's song was one of the country's most popular singles.

For me, this song brings back memories of being 18 years old and driving around with my friends in my mom's car. It was the kind of song where if you heard it on the radio, you'd tell your friends, yo, turn that up. It was this song that caught Diddy's attention.

For me, this song brings back memories of being 18 years old and driving around with my friends in my mom's car. It was the kind of song where if you heard it on the radio, you'd tell your friends, yo, turn that up. It was this song that caught Diddy's attention.

He told everyone gathered at the conference table that the song had been haunting him in nightclubs and that he thought Cassie had a personality that, quote, the whole world could fall in love with. Before Bad Boy released a remix, Me and You was already an underground hit, even without the backing of a big record label. Cassie Ventura had built up a fan base DIY style.

He told everyone gathered at the conference table that the song had been haunting him in nightclubs and that he thought Cassie had a personality that, quote, the whole world could fall in love with. Before Bad Boy released a remix, Me and You was already an underground hit, even without the backing of a big record label. Cassie Ventura had built up a fan base DIY style.

The secret ingredient was early social media. Remember Myspace? Myspace was only about three years old at the time. It was the beginning of social media for millennials like me who grew up in the 90s and early 2000s. My profile had posts about soccer players I liked, like Ronaldinho, Zizou, and Henri, and some of my favorite music.

The secret ingredient was early social media. Remember Myspace? Myspace was only about three years old at the time. It was the beginning of social media for millennials like me who grew up in the 90s and early 2000s. My profile had posts about soccer players I liked, like Ronaldinho, Zizou, and Henri, and some of my favorite music.

I probably posted a picture of me working my after-school retail job at Hollister. I hope to God that picture doesn't still exist. Today, it's pretty common for artists and influencers to get famous off of social media alone. But when Cassie was starting out, it was pretty new to release music without a label, to build connections directly with fans without going through a gatekeeper.

I probably posted a picture of me working my after-school retail job at Hollister. I hope to God that picture doesn't still exist. Today, it's pretty common for artists and influencers to get famous off of social media alone. But when Cassie was starting out, it was pretty new to release music without a label, to build connections directly with fans without going through a gatekeeper.

Here's Cassie and the producer she'd been working with, named Ryan Leslie, talking about this in a video blog.

Here's Cassie and the producer she'd been working with, named Ryan Leslie, talking about this in a video blog.

And that's when the major labels came knocking, including Bad Boy Records, Sean Combs' company. As an attorney, I can tell you that the terms of any deal like this are usually private. We later find out Bad Boy reportedly offered Cassie a contract to make 10 albums. That was huge and also pretty unusual for a new artist without a proven track record.

And that's when the major labels came knocking, including Bad Boy Records, Sean Combs' company. As an attorney, I can tell you that the terms of any deal like this are usually private. We later find out Bad Boy reportedly offered Cassie a contract to make 10 albums. That was huge and also pretty unusual for a new artist without a proven track record.

I could only find a couple of examples like this, including the 10-album deal a teenage LL Cool J reportedly got in the 1980s with Def Jam Records. Just think about it. Here's Cassie. She's at the very beginning of her career, only a couple years out of high school. And one of the biggest record labels in hip hop and R&B offers her a chance to make not just one, but 10 albums? That's crazy.

I could only find a couple of examples like this, including the 10-album deal a teenage LL Cool J reportedly got in the 1980s with Def Jam Records. Just think about it. Here's Cassie. She's at the very beginning of her career, only a couple years out of high school. And one of the biggest record labels in hip hop and R&B offers her a chance to make not just one, but 10 albums? That's crazy.