Dare To Be Fearless with Alexa Curtis

Alexa Curtis
Dare To Be Fearless with Alexa Curtis

Join Alexa Curtis, serial entrepreneur and former Disney host, as she dives into the exhilarating world of startups. From sharing inspiring success stories to candidly discussing the inevitable challenges faced by entrepreneurs, each episode explores the essence of fearlessness and resilience needed to thrive in the ever-evolving landscape of entrepreneurship.

  1. JUN 17

    Solo Episode: This Is What They Don’t Tell You About Being an Entrepreneur (+ Life Lately)

    In this episode of Dare to Be Fearless, we're getting real about what it actually takes to be an entrepreneur. From behind-the-scenes challenges to unexpected breakthroughs, I’m sharing the raw, unfiltered truth about building a business — and giving you a life update along the way. Whether you're just starting out or deep in the grind, this episode is packed with honest lessons, mindset shifts, and encouragement to keep going (even when it’s messy). If you’ve ever questioned whether you’re cut out for this path, this one’s for you. Use code VIDCON on chiefswagofficer.com for a discount off of your first order! Follow Alexa on Instagram here and TikTok here!

    23 min

  2. JUN 4

    Why Connecticut Is The Best State In America

    This might just be one of the funniest and most fun episodes we’ve ever recorded. A few months back, I was filming another pizza review in my home state of Connecticut when a guy named Tony unexpectedly jumped into the shot and shouted, “Get this girl a job!” That moment went viral—and the internet instantly fell in love with him. Thanks to one of you, someone tracked him down and connected us. Now, he's officially a guest on the podcast! I’d call Tony a true Connecticut legend—and in this episode, we dive into everything from growing up in this underrated state to what makes the people here so real and unforgettable. If you’re new here: I’m Alexa Curtis, a content creator and mental health advocate born and raised in Connecticut. From building my career as a teen entrepreneur to connecting with changemakers across the country, I’ve always believed there’s something incredibly special about this place—and this episode is proof. Whether you're from Connecticut or just curious why it’s so close to my heart, you’re in for a ride. Let’s get into it. Follow Alexa here and here. Shop Chief Swag Officer here with the code CHIEFSWAG10!

    51 min

  3. APR 9

    Side Hustles That Work: Vending Machines

    This week, one of my best friends Nick joins the show to discuss one side hustle that I'm particulary intrigued by: vending machines. Can this $17K investment make you into a millionaire? Buy Chief Swag Officer mic covers at chiefswagofficer.com with the code CHIEFSWAG10 for a discount off of your first order! Follow Alexa here!

    15 min

  4. APR 2

    Etsy Closed Down My Small Business: PSA To Entrepreneurs

    Chief Swag Officer is alive on our website chiefswagofficer.com and thank gosh it is because Etsy closed down our store! It's been a chaotic week in business working to get our shop fully optimized online so people know where to buy us. But we went from 20+ sales a day to not even 2 (because of Etsy's SEO) so I've learned a lot about business this week. PSA to aspiring and current founders: you always need a website. Support Chief Swag Officer on our website and social media, and follow Alexa here! Use the code CHIEFSWAG10 for a discount off of your first order.

    26 min

  5. MAR 26

    John Mayer’s Ex-Makeup Artist Spills Secrets—Meet the Beauty Mogul Behind By Rosie Jane

    Welcome the most fearless Rosie Jane Johnston to Dare To Be Fearless this week! Rosie is the founder of the #1 clean perfume brand in the world, By Rosie Jane, sold at stores like Sephora and Nordstrom. Prior to founding BRJ, Rosie was a celebrity makeup artist who did makeup for celebrities like John Mayer and more.  Buy Chief Swag Officer customized microphone covers and accessories on chiefswagofficer.com with the code CHIEFSWAG10 for a discount off of your first order!

    46 min

  6. MAR 12

    Solo With Alexa: How To Cold Pitch & Network With Confidence

    Solo episode with Alexa about how to network like a fearless and confident boss. In this episode, she covers: Cold Pitching  How She Landed Her Radio Disney Show  How To Find And Scout Emails  and leaving London for a bit.  Want Chief Swag mic covers? Use the code CHIEFSWAG10 now!

    29 min

  7. MAR 5

    Architect Dara Huang On Getting In Front Of People With Cold Pitching, Designing For Cartier & More

    I met Dara Huang at an event in London last year when I first moved to town. Dara is one of those people who lights up the room she walks into.  As a Taiwanese-American architect and designer, renowned for her innovative contributions to contemporary architecture, Dara was born in Florida to Taiwanese immigrants, where she pursued a master's degree in architecture from Harvard University.   In 2013, Dara founded Design Haus Liberty, an international architecture and design practice based in London, with additional offices in Hong Kong. The firm offers a wide range of design services across residential, commercial, hospitality, and retail sectors, establishing itself as a tastemaker and game-changer in the industry. On a personal note, Dara was previously engaged to British property developer Edoardo Mapelli Mozzi, with whom she shares a son, Christopher Woolf Mapelli Mozzi, affectionately known as "Wolfie." Despite their separation, they continue to co-parent amicably, with Wolfie also being the stepson of Princess Beatrice.  Follow Dara on social media here. Follow Alexa Curtis here. Buy Chief Swag Officer microphone covers here!

    45 min

  8. FEB 19

    Broke In A Basement To Boxing King With Rumble Boxing Co-Creator Andrew Stern

    Andrew Stern is the Co-creator of Rumble Boxing, one of the most popular boxing studios in the world that is now a franchise model. Andy is the President of Talent & Programming Globally for Rumble Boxing, where he oversees over 100 studios & 1,000 Rumble Boxing Trainers. He was hustling out of his parents basement after high school and through college before the other Rumble founder approached him with an idea, and from there the creation of Rumble began.  Follow Alexa on social media at @alexa_curtis and @alexacurtisunfiltered on TikTok. Buy Chief Swag Officer microphone covers with the code CHIEFSWAG10 at chiefswagofficer.com

    50 min
See All (215)

4.9
out of 5
70 Ratings

About

Join Alexa Curtis, serial entrepreneur and former Disney host, as she dives into the exhilarating world of startups. From sharing inspiring success stories to candidly discussing the inevitable challenges faced by entrepreneurs, each episode explores the essence of fearlessness and resilience needed to thrive in the ever-evolving landscape of entrepreneurship.

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