Dare To Be Fearless with Alexa Curtis

Hosted by Alexa Curtis

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222

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Sep 2026

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About the show

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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60 recent

September 23, 202644 min

Gina Simm, The Love List Host & Connecticut Icon

Gina Simm is a Sales and Digital Marketing Executive at iHeartMedia, podcast host and producer with more than 20 years of experience in media, sales and marketing. She is the co-host and producer of the Welloff Podcast, where she brings a bold, honest and no-BS perspective to conversations about health, wealth, relationships, purpose and living a top-shelf life. A breast cancer survivor and passionate breast cancer advocate, Gina brings real-life experience, resilience and plenty of personality to every conversation. She is also a cheer and tumble coach, entrepreneur and lifelong Boston sports fan who believes in working hard, taking chances and never playing small. Whether she's behind the microphone, building a business, coaching athletes or connecting brands with audiences, Gina brings energy and authenticity everything she does. Follow Alexa on Instagram here and Tiktok here . Join The Love List here !

September 2, 202627 min

No Shame, Just Facts: A Conversation About Reproductive Health with Planned Parenthood

Reproductive health is a part of women's health throughout every stage of life, yet so many of us still have questions about what preventative care we actually need, when we should be getting screened, and what our options are when it comes to our bodies and our healthcare. In this episode, we're having an open, honest, and judgment-free conversation with Jennifer Love, a certified nurse midwife and Lead Clinician at Planned Parenthood of Southern New England. With more than 20 years of experience in reproductive healthcare and over a decade at Planned Parenthood, Jen brings a science-based, evidence-based, and patient-centered perspective to some of the most important topics women need to understand. We're breaking down cervical cancer screenings, including what Pap tests and HPV testing actually look for, why routine screening matters, and what women should know if they've been putting off an appointment. We're also talking about STI testing and treatment — why someone can have an STI without symptoms, how testing works, and why getting tested should be viewed as a normal part of taking care of your health rather than something associated with shame or judgment. And we're having an honest conversation about abortion care, including the differences between medication abortion and procedural abortion, what each experience can look like, and how healthcare providers help patients understand their options and make informed decisions about their care. Most importantly, this conversation is about access, education, prevention, and empowering women to feel comfortable asking questions about their own bodies. Whether you're overdue for a screening, wondering when you should get tested, trying to understand your reproductive healthcare options, or simply want reliable information from a medical professional, this episode is designed to give you straightforward answers without the stigma. No shame. No judgment. Just facts — and a reminder that taking care of your reproductive health is taking care of yourself.

August 12, 202657 min

He Bought a Building for $1… and Bet on New Haven: David Salinas

David Salinas is a serial entrepreneur, investor, and one of the people helping reshape Connecticut's startup and innovation scene. In this episode, we sit down with David to talk about the unconventional decisions, risks, and vision that led him to buy a building in New Haven for just $1 —and what he saw in the city that others didn't. We dive into how David transformed that opportunity into District , a thriving entrepreneurial and innovation ecosystem in New Haven, and what it really takes to build something from the ground up. From entrepreneurship and real estate to investing, failure, taking massive risks, and betting on Connecticut, David shares the behind-the-scenes story of how he built his businesses and why he continues to invest in the state. We also talk about what it's actually like to be an entrepreneur in Connecticut, why New Haven has so much untapped potential, how to recognize an opportunity before everyone else does, and the lessons David has learned from building multiple companies. In this episode: • How David bought a New Haven building for $1 • The story behind building District New Haven • Why he decided to bet on Connecticut • The realities of being a serial entrepreneur • Building businesses from the ground up • Taking risks when the outcome isn't guaranteed • Real estate, startups & investing • What David sees happening in New Haven next • Advice for aspiring entrepreneurs • The mindset behind turning an unconventional idea into a major business Follow Alexa on Instagram here and Tiktok here . Join The Love List here !

May 19, 202654 min

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 .

March 4, 202645 min

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 .

February 23, 202623 min

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

June 17, 202522 min

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 !

June 4, 202550 min

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!

April 9, 202514 min

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 !

April 2, 202526 min

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.