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Dare To Be Fearless with Alexa Curtis

Dare To Be Fearless with Alexa Curtis

Written by: Alexa Curtis
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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.All rights reserved Economics Leadership Management & Leadership Social Sciences
Episodes
  • What Is The Love List & Moving Back To Connecticut Life Update

    What Is The Love List & Moving Back To Connecticut Life Update
    May 19 2026

    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.
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    55 mins
  • Everyone Says They Have a Brand, Almost No One Actually Does With John Sampogna

    Everyone Says They Have a Brand, Almost No One Actually Does With John Sampogna
    Mar 4 2026
    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.
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    45 mins
  • Building New England's #1 Luxury Matchmaking Company The Love List

    Building New England's #1 Luxury Matchmaking Company The Love List
    Feb 23 2026

    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
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    24 mins
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