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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How does one come up with great ideas? Some may think they’re random strokes of genius, but Rob Reilly knows it takes a mix of hard work and creativity–the truest embodiment of math and magic. Now the Chief Creative Officer of WPP, Rob built his stunning reputation on work that is memorable and buzzy, from campaigns for companies like American Express and Burger King to the “Fearless Girl” statue that still stands in Manhattan’s Financial District. These works weren’t strokes of genius. They emerged from decades of Rob tirelessly logging ideas and learning his business inside and out. Listen to hear Rob explain his creative process and reflect on some of the most important moments of his career, from the college party that landed him his first advertising job to the time he took a demotion and pay cut to improve his craft. 

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Country music is the biggest radio music format and Nashville’s Scott Borchetta knows the genre inside and out. He’s the founder, president, and CEO of Big Machine Label Group and the founder of Big Machine Distillery. Scott has signed deals with artists like Tim McGraw, Jewel, Lady A, Zac Brown Band, Thomas Rhett, Florida Georgia Line, and many others.  Scott sits down to talk about his impressive career, from how he discovered his place in the music industry to when he knew it was the right time to go out on his own. His optimism, strategic thinking, and competitive spirit has helped him master music promotion and he feels more energized than ever to take on the next big thing. 

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Audiences love a spectacle, and Kenneth Feld knows better than anyone how true this is. As the Chairman and CEO of Feld Entertainment, he’s an acclaimed visionary when it comes to live, family friendly theatrics. He took over the business from his father, who founded it back in 1967 when he discovered the Ringling Bros. and Barnum & Bailey. Kenneth sat down with Bob to describe how he maintains the company’s core principles, from valuing families above all else to championing live entertainment as a way of bringing people together–even during a global pandemic.

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Kellyn Smith Kenny was born to innovate. From her early years, she was a textbook over-achiever, thriving as both an athlete and a mathlete and joining any additional club she could squeeze her way into. Growing up, she watched her mom run a hospital and her dad contribute to groundbreaking work at Bell Labs, inspiring her to dedicate herself to meaningful work. This well-rounded foundation has taken Kellyn far in the world of marketing. Her resume is stacked with giants of business like Microsoft, Hilton, Capital One, and Uber, where she learned to approach work like she’s captain of a sports team. Knowing the game inside and out and fostering a diverse, cohesive team is of the utmost importance. Currently, as the Chief Marketing and Growth Officer at AT&T, she has continued making bold moves to breathe new life into an iconic brand. She sat down with Bob to explain just how she does it. 

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Join iHeartMedia Chairman and CEO Bob Pittman for the new season of Math & Magic: Stories from the Frontiers of Marketing, starting Thursday, February 29th. This season, Bob sits down with leaders, entrepreneurs, and visionaries across music, film, live entertainment, marketing, and more. 

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Tech pioneer Ted Leonsis is never one to shy away from a challenge. He’s an uncanny trend spotter, from his beginnings at companies like Wang Laboratories and AOL to his current role as Founder and CEO of Monumental Sports and Entertainment. He’s also the ambitious co-founder of investment group Revolution Growth and even did a stint as mayor of a small Florida town. But before college, Ted was a self-described “lazy” student who would just get by. So, what changed? In this conversation, Ted tells Bob about the monumental event that changed the trajectory of his life and ignited his passion for technology. He also explains how a near death experience propelled him to create a list of 101 things to do before he died – a list that guides and motivates him in all aspects of his life to this day. 

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Howard Makler knows how vital small and medium-sized businesses are to the economy. But he also knows not everyone appreciates their value. A successful serial entrepreneur and CEO of Innovation Refunds, Howard is working to make sure smaller businesses are no longer ignored. Innovation Refunds helps small businesses gain access to government funding, along with the knowledge, resources, and technology to succeed. Howard started small too—he founded his first company out of his bedroom at 13 years old—and knows that paths to success aren’t always traditional. Bob sat down with Howard to hear how he went from opting out of college to teaching classes at Wharton. Howard also shares what big businesses can learn from small businesses – and why taking care of your employees should be a priority for every company, regardless of size.

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The world of media is ever-changing — and no one has played it quite like Jacki Kelley, CEO of the Americas and Global Chief Client Officer of advertising giant, Dentsu. Jacki has been at the center of media and advertising for the last 25 years, with leadership roles at USA Today, Yahoo, Martha Stewart Living, and Bloomberg. Her deep understanding of the media landscape has put her in a valuable position to both manage Dentsu’s global portfolio of clients and lead a team that is always looking to where to go next, from exciting ways to use AI, to more precise messaging that powerfully connects with individuals. But what people may not know is that Jacki comes from a fifth generation cattle ranching family and has been a foster parent for more than 20 children. Bob sits down with Jacki to find out how these experiences have shaped her approach to business, leadership, and company culture.

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