"Anyone who's embarking on entrepreneurship sets themselves up for a lot of fires, a lot of fear, [and] a lot of anxiety. But if you're really a true entrepreneur, then the ability to bounce back from those fires or situations is ingrained in you." - Alexa Curtis Alexa Curtis is a serial entrepreneur, former Radio Disney host, and the founder of Chief Swag, the number one customized microphone pop cover brand. Starting her journey at age 12 with a fashion blog while being relentlessly bullied in her small Connecticut hometown, Alexa made the daring decision to move to New York City alone as a teen. Through cold emails, fearless pitching, and what she calls "productive naivete," Alexa built a career in media and entrepreneurship that included launching "Fearless Every Day" on Radio Disney, speaking at corporate events, and building multiple businesses. In April of 2025, Alexa experienced one of the internet's most brutal cancel culture moments when a tweet about running a half marathon went viral for all the wrong reasons, garnering 9 million impressions and even death threats. Rising from those ashes, and focusing on her “be fearless” mantra, Aleexa launched Chief Swag Officer from an Etsy shop while in an airport in Zurich, turning her lowest moment into her greatest comeback. What we explore in this episode: (04:00) Navigating bullying (08:05) Body image, social media toxicity, and advice for parents navigating digital pressures (15:53) How a cold email changed everything: Landing Radio Disney with a BCC pitch (20:06) The viral tweet that became a nightmare (34:04) When and why every entrepreneur needs a lawyer (42:16) The aha moment: From canceled influencer to e-commerce founder (45:21) Alexa’s daily fearlessness practice: Small steps outside your comfort zone Connect with Alexa: @Alexa_Curtis on IG chiefswagofficer.com Connect with Nathalie: AllOverAgainPodcast.com @AllOverAgainPodcast LinkedIn
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