Dare To Be Fearless with Alexa Curtis

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. May 19

    What Is The Love List & Moving Back To Connecticut Life Update

    I have been WAITING to film this one. Today I'm sitting down to talk about two things I get asked about constantly — what is The Love List, and yes, I moved back to Connecticut. We're getting into all of it — the business, the move, the why behind everything. Grab your coffee, get comfy, and let's catch up!  For more on The Love List, please apply at jointhelovelist.com. We offer matchmaking services and events throughout New England, with new cities launching soon. We encourage everyone to apply, because if we have a mutual match in a city, we will absolutely connect you! Grab your swag on Chief Swag Officer with the code CHIEFSWAG10! Follow Alexa on social media on Instagram and TikTok.

    55 min

  2. Mar 4

    Everyone Says They Have a Brand, Almost No One Actually Does With John Sampogna

    CHIEF SWAG OFFICER IS LIVE ON BSW!   It's a huge week for the brand. Shop all of our swag on BSW here! Use the code CHIEFSWAG10 on Chiefswagofficer.com ---------------------------------------------------------------------   I sat down with the CEO and Co-founder of Wondersauce in this episode to talk about branding. John is a seasoned entrepreneur, investor, and CEO with over 15 years of experience crafting award-winning strategies, digital experiences, and campaigns for renowned brands such as Golf.com, Nike, L'Oréal, Scott's, Sixpenny, NYC's Brookfield Place, Chandon, and Grubhub, among others. Inspired by his generation growing up with the Internet, Sampogna was among the first in his field to embrace social media as a creative tool for growth, earning recognition on Business Insider's list of "30 Most Creative People in Advertising Under 30." His insights have been featured in various media outlets, including Glossy, Adweek, CNBC, Marketing Brew, Ad Age, Yahoo, and Digiday. He has also appeared on globally ranked podcasts, as a judge for prominent industry awards, and on stages like the Brand Innovators Summit at the US Open. Today, he leads a team of over 100 technologists, creatives, strategists, and producers as the Co-Founder and CEO of Wondersauce, a business acceleration agency that partners with brands poised for change to achieve their next stage of growth. Under his leadership, Wondersauce has earned a spot on Inc. Magazine's Inc. 5000 list of America's Fastest-Growing Companies, built a roster of premier Fortune 500 clients and innovative startups, and was officially acquired by Project Worldwide, an advertising holding company.   Follow Alexa on Instagram here and TikTok here. Find out more about John and Wondersauce here.

    45 min

  3. Feb 23

    Building New England's #1 Luxury Matchmaking Company The Love List

    DARE TO BE FEARLESS IS BACK. And this time, we're not holding anything back. Answering your questions about building this matchmaking company, the age demographics and services we offer, and how many couples have fallen in love so far! Between scaling Chief Swag Officer and growing The Love List, life has been nonstop. I've relocated to Los Angeles to build both companies simultaneously — while still spending a ton of time in Connecticut meeting so many of you in person, hosting events, and expanding The Love List into new destination cities like Boston. This season is about what it really takes to build multiple brands at once. The wins. The chaos. The travel. The pivots. The behind-the-scenes decisions no one sees. If you've ever wanted to build something big while juggling everything else in your life — this is for you. Apply for The Love List and jointhelovelist.com! Follow Alexa on Instagram here and TikTok here

    24 min

  4. 06/17/2025

    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

  5. 06/04/2025

    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

  6. 04/09/2025

    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

  7. 04/02/2025

    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

  8. 03/26/2025

    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
See All (218)

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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