The Grammy-award winning artist owes a lot to the women in his family. They helped him to focus on the right things when he was younger, he says on the "The Tony Robbins Podcast": "Those are the women that built me — my grandmother, my aunt and my mother."
"Do you see where you're going to be?" he remembers they would ask him. "Do you see the opportunity you have in this country? Do you see how you can take advantage of this freedom that you have?"
Pitbull's mom reinforced the message by playing Tony Robbins' motivational tapes while driving him to school. It was the last thing the teen wanted to listen to, but "it would subliminally get to me," he recalls.
Pitbull's second advance was significantly bigger: $50,000. Again, he spent it on cars, he tells CNBC Make It: "I went to the chop shop. I bought three cars. I knew they would be get me from A to B, B to D, D to Z and Z back to A. That's all I needed. I didn't need rims. I didn't need chains. I didn't need none of that."
He spent the next two years saving the majority of his earnings so he could invest in his first property.
When it comes to spending money, "it all depends on what you want to do and how you want to grow," says Pitbull. He himself enjoys giving it away, since that's how money really can buy happiness. Otherwise, he says, "if you think money is going to make you happy, you are completely, completely confused."
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