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.
Author
Alexa Curtis
Category
Podcast website
Latest episode
May 19, 2026
Where to listen?
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Episodes
What Is The Love List & Moving Back To Connecticut Life Update 19.05.2026 54:37
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 servi...
Everyone Says They Have a Brand, Almost No One Actually Does With John Sampogna 04.03.2026 45:17
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 experie...
Building New England's #1 Luxury Matchmaking Company The Love List 23.02.2026 23:50
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 s...
Solo Episode: This Is What They Don't Tell You About Being an Entrepreneur (+ Life Lately) 17.06.2025 22:45
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,...
Why Connecticut Is The Best State In America 04.06.2025 50:46
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. N...
Side Hustles That Work: Vending Machines 09.04.2025 14:33
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 !
Etsy Closed Down My Small Business: PSA To Entrepreneurs 02.04.2025 26:11
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...
John Mayer's Ex-Makeup Artist Spills Secrets—Meet the Beauty Mogul Behind By Rosie Jane 26.03.2025 46:00
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 chiefswag...
Solo With Alexa: How To Cold Pitch & Network With Confidence 12.03.2025 28:46
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!
Architect Dara Huang On Getting In Front Of People With Cold Pitching, Designing For Cartier & More 05.03.2025 44:56
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 201...
Broke In A Basement To Boxing King With Rumble Boxing Co-Creator Andrew Stern 19.02.2025 49:56
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...
Are Unpaid Internships Worth The Effort? & How To Become A Journalist With Fortune's Emma Hinchliffe 12.02.2025 48:39
Emma Hinchliffe is a senior writer at Fortune, where she covers women in business and gender issues across business, politics, and culture. Emma and I met at SLUSH, one of the best conferences ever in Helsinki. Emma worked her way up from the school newspaper to landing an internship at USA Today to now being a senior writer at Fortune. Filmed at Metro Podcast Studio in NYC. Get a Chief Sw...
Taylor Capuano, Cakes Co-Founder On Ditching Her Side Hustle & Landing On Shark Tank 29.01.2025 16:48
What happens when passion meets relentless hustle? Taylor Capuano, the powerhouse co-founder of Cakes Body , takes us on her wild journey from fitness fanatic to CEO of a booming wellness brand. In this exclusive episode, Taylor spills the tea on: 🔥 Her unexpected "Aha!" moment that sparked Cakes Body 💥 The fitness secrets that transformed her followers' lives 💡 The social media strategy that t...
Nicole Hockley, Co-Founder of Sandy Hook Promise On Gun Violence & School Shootings 22.01.2025 41:07
I was honored to sit down with Nicole Hockley, Co-Founder of Sandy Hook Promise in Connecticut. On December 14th, 2012, Nicole lost her son Dylan in the Sandy Hook shooting. She's made it her life decision to eradicate school shootings and bring awareness to gun violence. The organization has so far prevented 16 and counting school shootings across the country. As the co-founder and CEO of the Sa...
The Shocking Truth Behind Your Fast Fashion Clothes With Tiffanie Darke, Former VP at A&E Networks Turned Sustainability Expert 15.01.2025 38:57
Tiffanie Darke is the former VP at A&E Networks and now a sustainability expert and author. In this episode we cover why fast fashion is going to completely ruin the environment over the next 10 years, what happens when you buy from fast fashion companies, and the reality behind cheap clothes. Plus, ways to solve this problem especially if you can't afford to buy more expensive clothing regularly....
Celebrity Trainer Kit Rich: Does Weightlifting Bulk You, Benefits Of Creatine, Training Celebs & More 08.01.2025 59:47
Kit Rich is a renowned fitness expert, celebrity trainer, and entrepreneur based in Los Angeles, California. She has gained recognition for her personalized approach to health and wellness, emphasizing balance and sustainability. Beyond fitness, Kit has pursued her passion for storytelling. In October 2023, she completed her debut feature film, "Isabel's Garden," which she wrote, directed, and pro...
Amy Cuddy on How Your Body Language Defines You, What People Do Wrong On Dating Apps And Confidence 01.01.2025 1:04:38
In this inspiring episode, I sat down with Dr. Amy Cuddy, a renowned social psychologist, bestselling author, and TED Talk sensation, whose talk on body language and "power posing" has captivated millions around the globe. Amy shares her groundbreaking research on the science of presence and how small changes in body language can transform confidence, influence, and connection. Join us as we explo...
Kelly Cutrone, CEO & Founder of People's Revolution 18.12.2024 59:15
I went up to Kelly Cutrone at a Starbucks when I was 14-years-old and in NYC. At the time, she was fully focused on her PR firm, People's Revolution, putting together some of the most prominent and famous fashion shows at Lincoln Center at the time. I ended up getting an internship with Kelly, and catching up with her felt so full circle for me since she's truly an icon in the industry. Now, she'...
Mimi Ikonn, Intelligent Change Co-Founder on How To Meditate, Handle Separation, And Selling Her First Company 11.12.2024 55:14
I was quite sick when we filmed this so my voice is not 100%! Mimi Ikonn is an entrepreneur, author, and co-founder of Intelligent Change , a company known for its transformative tools like the Five Minute Journal and the Productivity Planner . Born in Baku, Azerbaijan, and raised in Toronto, Mimi's journey embodies creativity, resilience, and a commitment to personal growth. Alongside her husban...
Co-Founder of Medik8 Daniel Isaacs: Secrets Dermatologists Don't Want You to Know 27.11.2024 48:05
Medik8 , one of the fastest-growing skincare brands in the market, co-founder Daniel Isaacs joins as a guest on Dare to Be Fearless this week! Medik8 is an award-winning, science-led brand making skincare full of smart, safe ingredients, including retinal, vitamin C and SPF. The brand is approved by derms, doctors, and beauty editors alike due to the simple fact that they deliver results without...
Loren Gray, Captivating 53M TikTok Followers, Pursuing Acting And The Business Of Influencing 20.11.2024 55:34
LOREN FUCKING GRAY EVERYONE! Joins Dare To Be Fearless today for a captivating episode about Being fearless, exisiting as a young person with 53 million TikTok followers, building a sustainable career as an influencer now actress, and so much more... Use code CHIEFSWAG10 for 10% off your first order at chiefswagofficer.com Connect with Alexa on social media ( Instagram & TikTok )
How To Cold Call, Handle Rejection And Drive Traffic To Your Brand 06.11.2024 39:16
How To Cold Call, Handle Rejection And Drive Traffic To Your Brand, with Alexa Curtis. Connect with Alexa below: Chief Swag Officer Sponsor this show at https://www.passionfroot.me/alexa-curtis Subscribe to Stay Fearless or Die Trying here . BUY A MEDIA LIST OR MEDIA KIT HERE !
Sam Budd, CEO of Buddy Media Group: ADHD As A Founder, Steven Bartlett And Resilience 30.10.2024 1:04:29
Samuel Budd is the founder and CEO of Buddy Media Group, an award-winning independent social and influencer marketing agency. With over a decade of experience in launching and scaling global marketing agencies, Sam has led performance and acquisition strategies for renowned brands such as Apple, Aviva, Procter & Gamble, Spotify, and Bacardi. He's also an angel investor and co-founded Social Change...
How The Fashion Industry Helped Amanda Beausoleil Overcome Self-Harm (Founder of Sira) 16.10.2024 29:19
Amanda Beausoleil is the Founder and Executive Director of SIRA, a nonprofit that helps people recover from self-injury through an effective and powerful peer-group support model. Amanda struggled with self-injury for 15 years. She found recovery through a self-injury peer support group in New York. In 2019 she left the corporate world and a longstanding career in fashion working for the industry'...
Behind Bars: From Connecticut To Prison To HBO With Ian Bick 09.10.2024 41:13
In this gripping episode of Dare To Be Fearless, Ian opens up about his harrowing experience of being locked up and the profound lessons he learned during his time behind bars. Join us as he takes you on a journey through the challenges, the camaraderie, and the unexpected moments of clarity that transformed his life. Ian shares candid stories of resilience, personal growth, and redemption, reveal...
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