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...
Jun 17, 2025•23 min
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 epis...
Jun 04, 2025•51 min
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 !
Apr 09, 2025•15 min
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 he...
Apr 02, 2025•26 min
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!...
Mar 26, 2025•46 min
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!
Mar 12, 2025•29 min
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 2013, Dara founded Design Haus Liberty, an international architecture and design practice based in London,...
Mar 05, 2025•45 min
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 him with an idea, and from there the creation of Rumble began. Follow Alexa on social media at...
Feb 19, 2025•50 min
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 Swag Officer microphone cover at chiefswagofficer.com with the code CHIEFSWAG10 ....
Feb 12, 2025•49 min
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 took her from unknown to unstoppable Whether you're a fitness lover, aspiring entrepreneur, or just lo...
Jan 29, 2025•17 min
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 Sandy Hook Promise Foundation, Nicole works every day to protect children from gun and school violence....
Jan 22, 2025•41 min
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. Follow Alexa on social media at @alexa_curtis on Instagram and @alexacurtisunfiltered on TikTok...
Jan 15, 2025•39 min
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 produced, showcasing her multifaceted talents and dedication to creative expression. In this discussion...
Jan 08, 2025•1 hr
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 explore her journey from overcoming personal challenges to becoming one of the world’s leading experts on...
Jan 01, 2025•1 hr 5 min
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's focused on helping creators like Anna Delvey (yes, that Anna) reinvent the narrative behind being a...
Dec 18, 2024•59 min
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 husband, Alex Ikonn, she has built a brand that empowers individuals to lead intentional and fulfilling lives...
Dec 11, 2024•55 min
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 compromise. The brand has already garnered celeb fans, including Hailey Bieber and Rosie Huntington-W...
Nov 27, 2024•48 min
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 )...
Nov 20, 2024•56 min
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 !...
Nov 06, 2024•39 min
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 with Steven Bartlett, a creative media agency. Use code CHIEFSWAG10 for 10% off your first orde...
Oct 30, 2024•1 hr 4 min
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’s most respected brands (Saks Fifth Avenue, Tory Burch, and Coveteur) to take the peer support group...
Oct 16, 2024•29 min
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, revealing how his past experiences shaped his present. You’ll hear about the friendships forged in unlikel...
Oct 09, 2024•41 min
Forbes 30 Under 30 Cadana (payroll system) Co-Founder Ameer Shujjah came to America and started a business that's generated major revenue and press. The world's largest payroll platforms and talent marketplaces use Cadana's APIs to build compliant hiring products in Africa, Asia, and Latin America- but the greater question is how hard is it for immigrant founders to scale and build businesses, and how do you get your parents to support your dreams from across the world? Connect with Alexa below:...
Sep 25, 2024•36 min
Darren Marble is a serial entrepreneur, investor and executive producer of Going Public, a show similar to Shark Tank. We connected on X in April and he has advised me through some highs and lows in business as a young founder. His background (college dropout!) is remarkable, and he and I have some unique thoughts on how to go about cold pitching, landing investors and building a brand on X (Twitter). Shop Chief Swag Officer with a special discount code for fans of the show using the code FEARLE...
Sep 18, 2024•41 min
Surprise, I started a new company earlier this year. It's called Chief Swag Officer , and we make custom foam and microphone products for creatives. I've been keeping this a secret for months and I'm finally ready to dive into how this scaled and was created. Shop Chief Swag Officer with a special discount code for fans of the show using the code FEARLESS here ! Connect with Alexa below: THE PERSONAL BRAND E-COURSE IS LIVE! Get it here! Sponsor this show at https://www.passionfroot.me/alexa-curt...
Sep 11, 2024•54 min
April Uchitel is the former CEO of Violet Grey, a content and commerce company inspired by Hollywood’s beauty culture. Prior to joining Violet Grey, April was a founding member and the chief brand officer of the digital shopping destination Spring and the EVP of global sales for Diane von Furstenberg. Now, she is the founder of The Board, a large consulting group that focuses on helping small and big businesses scale. Connect with Alexa below: THE PERSONAL BRAND E-COURSE IS LIVE! Get it here! Sp...
Sep 04, 2024•53 min
If you want to know how to scale a million dollar brand through marketing, this episode is for you. Oliver is an entrepreneur, speaker and co-founder of Flight Story, a 120+ strong global marketing and communication company founded alongside Steven Bartlett (Diary of a CEO). Flight Story exists to keep brands at the forefront of what’s possible - through a range of strategy, content, communication and media services. For over a decade, Oliver has been at the forefront of digital marketing and tr...
Aug 28, 2024•59 min
Alex grew up in the SF Bay Area where the definition of “hotness” was dictated by “beautiful” people in popular magazines and TV shows. His entire childhood, he felt trapped in his fat body and hated how he looked. That was until he realized what he had been taught his whole life was a lie. Hotness was more than perfect abs and bulging biceps, it was an attitude. And that he had! Alex is also a Professional Opera Singer, an industry that he thought would be accepting of his fat body. Boy was he ...
Aug 21, 2024•1 hr 7 min
Justin Brooks has spent his career freeing innocent people from prison. With You Might Go to Prison, Even Though You're Innocent, he offers up-close accounts of the cases he has fought, embedding them within a larger landscape of innocence claims and robust research on what we know about the causes of wrongful convictions. Buy You May Go To Prison Even Though You're Innocent here . My biggest passion project aside from helping you be fearless is helping kids whose parents were incarcerated. Anot...
Aug 14, 2024•59 min
This episode covers trauma, anxiety and depression. Please watch at your own risk. Opening up about the years of trauma my family endured when I was growing up that is the reason I started my blog. When I was 7-years-old, my dad disappeared. What transpired was 5 years of hell based on two false confessions he signed under duress as an undiagnosed diabetic, who was put through the corrupt justice system and left to rot in a prison until he was released. My biggest passion project aside from help...
Aug 08, 2024•31 min
