Rapper, entrepreneur and community leader YG sat for a brand new episode of “Assets Over Liabilities” alongside hosts Rashad Bilal and Troy Millings. The West Coast icon gets candid about learning the music industry, Nipsey Hussle’s mentorship, building a brand and creating wealth through real estate and cryptocurrency.

YG grew his notoriety as an artist by marketing his music at house parties from San Diego to Los Angeles. “Toot it and Boot It” was his breakout hit in 2008, which he uploaded to Myspace. “I was in and out of jail at the time,” he recalled, “and my people were throwing ‘Free YG’ parties and all type of ghetto shit. Real guerilla style. We just did what we [thought] we needed to do and that was just be outside.” Considering his start as a party promoter and as a teenager who was helping his mother pay bills, he’d built a loyal following for being the source of fun. “It was a vibe,” he said.

YG wasn’t initially seeking a record deal but when he was in jail, his mother called to tell him executives were reaching out. “Aww man, this shit happens when I go to jail. I’m like, ‘Man! Fuck, I just blew it!’” he said laughing. He got out early and two months later, he signed his first deal with Def Jam due to the momentum created by his friends and loyal fans. “It was a fucked up situation … fucked up deal, and that’s what turned me on to being involved on the business side. Who I am today started because of the fucked up situation I got in when entering the music business.”

His first contract was a single deal with five album options for $25,000. “12-5 when I signed and 12-5 six months later. Man, I used to rob houses and get that money,” he reflected. The part that turned him off was that together with DJ Mustard, who was on fire at the time, he created a unique sound that the label didn’t think would work nationally. “I was turning in these albums and they said, ‘Nah, these ain’t albums.’ So I took them and was like, ‘Fuck ya’ll’ and then I put them out for free. My video – I’ll go fund everything for the project and go put it out for free on HotNewHipHop and shit like that,” he explained about his foray into entrepreneurship. “I’d go tour and do shows off the music, and then the songs end up blowing up and the radio end up playing it organically,” the rapper went on.

YG was observant and learned how radio worked by talking to independent DJs and marketers. To keep his songs in the mix show format, he spent $25,000 to “work the records” in 2011. For full impact circulation, however, an artist could spend anywhere from $500-$750,000 per song.

His mixtape 4Hunnid Degreez inspired his highly recognizable brand 4Hunnid, which began as a streetwear clothing line. “This brand really represents the street,” he asserted. “I’m about to do a lot of shit for people that don’t get thought of like niggas in jail doing time, mamas that been victims of, like, their sons [dying] to gang violence. I’m about to do a bunch of programs like that and it’s all funded by the brand. And it’s going to be around long after me.”

He then went on to discuss how Nipsey Hussle stayed on him about creating a legacy that will outlast him. “Me and Nip, we would link, we would talk and he always ended up talking about the shit that mattered,” YG recalled. “We’re two rappers, two gang members linking up talking about real shit.” He reflected on the impact Nipsey had on him at a young age. “I’m like 21. This nigga four or five years older than me so he talking to me. I’m like, ‘Bro what are you talking about? You ain’t trying to hit this drink right quick?’” he said laughing. “He really got me thinking.” YG validated Nipsey’s mentorship down to the inspiration for his mixtape cover design, comparing the album art for 2011’s The Marathon Continues and 2012’s 4Hunnid Degreez.

He then talked about brand deals, endorsements and other investments. YG likened his participation in cryptocurrency to gambling, “That’s just side shit. That’s like going to Vegas,” he said. With an interest in television, he discussed a reality show pilot “Stimulus Package,” which was supposed to be similar to Diddy’s “Making the Band” but for business. He and partner Dave Gross decided to put a bunch of up-and-comers in the same house so they can work together to achieve their goals. “We did a pilot. You know how you can be a kid from the ghetto, but you have dreams or goals of making it out, but you don’t have the resources?” he asked. “Well, we put them in a house and basically whatever resources ya’ll need, ‘What’s up?!’ It was like bootcamp at the same time.” The participants had to workout, eat well and live an overall positive life.

The conversation then moved on to his shoe brand, 4Hunnid Block Runners. YG was hands-on in the process, identifying the manufacturer, testing the leather and fully funding the production. “It was an idea that me and my team came up with and we executed it and now it’s moving,” the businessman said. Not only is he proud that a guy from “the ghetto” has his own shoe, but he paid it forward to the people of his community. “For the first drop,” he said, “we did a giveaway to the homeless.”

YG added, “I’m from the streets. I’m selling $200 shoes. They sold out in 8 minutes. I don’t need your [corporate] stamp of what’s cool. I also gave shoes to niggas who were doing life in prison but got out due to the laws changing.”

Went the hosts asked YG about his first big purchase, he revealed that he was tight with his money because he was spooked to lose it. He’d blown money from the street activities he was involved in, so when it came to real money from his music he wanted to be wise and spent his first million dollars on a house. “When niggas was like, ‘Yo bro, why you not buying watches and all those chains?’ I was like, ‘Man, fuck all that. I’m trying to keep this shit.’”

Watch this week’s episode of “Assets Over Liabilities” in the video above to learn more about how YG got his first two artists on 4Hunnid signed with Epic Records and how Nipsey Hussle got him involved in cryptocurrency