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. 1d ago

    She Turned Strangers Into Couples on Her Front Stoop. Here's What She Learned About Men ft. Julia Radley

    This week on Dare to Be Fearless, I sit down with Julia "Julz" Radley, founder and host of Stoop Dating, Boston's buzziest dating show. She's on a mission to get singles off their phones and onto a front step. Julia and her team match two singles based on their applications and set them up on an on-camera blind date on a stoop in Southie, which plays out on Instagram and TikTok. The idea came from real life: after moving to South Boston, she noticed that one of the ways people naturally met was by sitting out on a front stoop. She came up with the concept in December 2024, and the show premiered on March 3, 2025. During each date, Julia guides the couple through games and questions. At the end, they clink their drinks if it's a match or sip if it's a no.   The results are hard to argue with. Stoop Dating has received more than 600 applications, and Julia says every couple so far has either swapped numbers or gone on a date right after their stoop date. She's since moved offline too. Stoop Dating teams up with Krissy Bets' STAG Boston to throw in-person dating events, and there are plans to bring the show to every neighborhood in Boston.   We get into why Boston has a reputation as one of the hardest cities to date in, what Julia has learned about men from watching hundreds of first dates up close, and why apps leave so many singles burned out. Julia tried a dating app once and deleted it a week later, saying it made her feel disposable. We also talk about building a business out of a social media idea, putting yourself out there when rejection happens in real time, and what it takes to make dating feel authentic again.  Whether you're single, swiping and exhausted, or just love a good love story, this one's for you. Julia's dream outcome? A stoop marriage.  Follow Stoop Dating on Instagram and TikTok, and follow me at @alexa_curtis.

  2. Sep 23

    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!

  3. Sep 2

    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.

  4. Aug 12

    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!

  5. 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.

  6. 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.

  7. 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

  8. 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!

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4.9
out of 5
69 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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