In today’s episode, I sit down with Barry Oberholzer, an entrepreneur, former intelligence operative, licensed helicopter pilot, and host of The Flying Felon. Barry shares how his experience in prison inspired him to build a platform centered on redemption, accountability, and the lessons found in failure. We discuss how interviewing celebrities in a helicopter encourages vulnerability, helping guests confront fear and speak openly about addiction, financial loss, injury, faith, and recovery. Barry also reflects on the common qualities he has observed among people who successfully rebuild their lives, including accepting responsibility, finding strength through faith, and developing the determination required to make a meaningful comeback.

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In today’s episode, I sit down with Brian Rose, an American-British podcaster, political candidate, former banker, and founder of London Real. Brian shares why he walked away from a lucrative banking career to build a media company before podcasting and personal brands became mainstream. We discuss overcoming the fear of other people’s opinions, improving through consistent action, and creating lasting relationships through long-form conversations. Brian also explains why engaged communities matter more than impressive follower counts, how charging customers increases commitment, and why media becomes more valuable when connected to a meaningful product ecosystem. He also shares lessons from censorship, controversy, and building investment ventures in Dubai.

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In today’s episode, I sit down with Dave Portnoy, the American businessman behind Barstool Sports, to talk about building a media company from the ground up. Dave shares how he left a stable sales career, launched Barstool as a free newspaper, and handled nearly every part of the business himself. We discuss hard work, timing, audience loyalty, brand voice, scaling without losing identity, and why criticism can sometimes strengthen a community. Dave also explains how organic ideas, fast reactions, and a willingness to keep experimenting helped Barstool grow from a local publication into a major media brand with a fiercely engaged following.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.