You may know this week’s guest by many names. Mr. 305, Mr. Worldwide, or more likely, the one and only Pitbull. Yes, the Grammy winning superstar, education advocate and entrepreneur sat down with Bob for a live conversation in his native Miami at the POSSIBLE conference. Before gaining all his titles, Pitbull was simply Armando Christian Pérez, a kid soaking up the colorful cultures of his city. Growing up, he was exposed to diverse, bustling, and at times unstable environments on the streets of Miami. Yet despite any hardship, Pitbull credits his city with giving him the skills to succeed in music and business. In fact, he’s leveraged his creativity and keen business sense to develop a number of independent ventures, including creating his own record label, Mr. 305, Inc., co-owning the Trackhouse NASCAR racing team and creating the Voli 305 vodka brand. Plus, he uses his international superstardom to give back to his community. Through SLAM! Charter schools, Pitbull is revolutionizing education and giving kids in underrepresented communities the opportunities he didn’t have. Listen to hear about these endeavors and more, and stay tuned to learn how he got the name Pitbull in the first place.

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Ryan Seacrest is America’s favorite host. He’s been on the radio since he was a teenager, but it wasn’t until he came on all of our TV screens in 2002 as the host of American Idol that he became a constant presence in American households. That big break propelled him to other roles, like hosting E! Red Carpets, Live with Kelly and Ryan, and will soon become the new host of Wheel of Fortune. All the while, he’s been on the radio in Los Angeles, and as the host of the syndicated show On Air with Ryan Seacrest, recently celebrating his 20th year on KIIS-FM. All this plus producing ventures that have brought us phenomena like Keeping Up with the Kardashians make it seem like Ryan can be in multiple places at once, and is definitely the hardest working person in showbiz. As Ryan tells Bob, he’s had a relentless drive to find success since he was a kid in Atlanta falling in love with radio. Listen to hear how he dropped out of college at 19, moved to Los Angeles, and turned that determination into a storied career. Plus, hear how a key encounter with Dick Clark helped him hone his hosting persona and why interacting with people–from connecting with contestants to his meaningful philanthropic ventures–is what keeps him going.

To learn more about the Ryan Seacrest Foundation, please visit www.ryanseacrestfoundation.org.

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You’ve probably been entertained by entrepreneur and filmmaker Andrew Jarecki even if you didn’t realize it. He co-founded the business everyone used in the 1990s: Moviefone. His list of accomplishments also include co-writing the theme song for the hit TV show, Felicity, directing the Ryan Gosling film, All Good Things, and directing and producing the documentary, Capturing the Friedmans, which won 18 international prizes and earned an Academy Award nomination. He’s probably best known for directing the Emmy-winning HBO series The Jinx: The Life and Deaths of Robert Durst, which will be back with Part Two this year. Andrew sat down with Bob to recount how he got Moviefone off the ground and changed the industry forever; the major pivots and innovations behind the production of his films; and share how his parents influenced his career. You’ll get a sense of the unique skills that have enabled him to turn curiosities into successes, and have fun along the way.

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