In this week’s episode, Valeria sits down with Natasha Oakley and Devin Brugman, best friends and co-founders of Monday Swimwear, for an honest and energizing conversation about building a business, growing through friendship, and redefining leadership.
In this week’s episode, Valeria sits down with Natasha Oakley and Devin Brugman, best friends and co-founders of Monday Swimwear, for an honest and energizing conversation about building a business, growing through friendship, and redefining leadership. Natasha and Devin open up about the rare bond that has held them together for over a decade, one built on unwavering trust, shared values, and deep emotional loyalty. They reveal how they’ve come to trust each other even more than their romantic partners, and why that unshakable connection is the foundation for everything they’ve built. The trio also explores how they launched a globally recognized brand without formal fashion training, what it means to lead as women, manage teams with heart, and stay grounded while scaling a company. From navigating dating in your 30s and freezing eggs to staying obsessed with work and each other, this episode is a love letter to ambition, authenticity, and choosing the people who lift you higher.
Follow Tash: https://www.instagram.com/tashoakley/
Follow Devin: https://www.instagram.com/devinbrugman/
Follow Monday Swimwear: https://www.instagram.com/mondayswimwear/
Shop Monday Swimwear: https://mondayswimwear.com/
Book Recommendations:
Excessively Obsessed by Tash Oakley https://a.co/d/aski91P
The Power of Now by Ekchart Tolle https://a.co/d/8DeuoAV
Sex at Dawn by Christopher Ryan https://a.co/d/2ZiptCN
Good Morning, Monster by Catherine Gildiner https://a.co/d/3ud8vUW
Attached by Amir Levine and Rachel Heller https://a.co/d/ivLtVkS
Shop my look from this episode: https://shopmy.us/collections/1898265
Follow me: https://www.instagram.com/valerialipovetsky/
What we talked about:
01:00: Swim Week in Miami
04:00: How Tash and Devin first met
07:00: Building a business on friendship and trust
12:00: The secret to their communication style
14:00: Managing team dynamics with empathy
20:00: The Bikini A Day origin story
24:00: Designing swimwear that actually fits
31:00: Choosing partners
34:00: How Monday Swimwear became the standard
38:00: Dating in your 30s with clarity
41:00: Freezing eggs and taking the pressure off
47:00: Opening a store and staying playful
51:30: Wellness habits that keep them grounded
54:00: Advice for aspiring influencers
56:00: Running a brand that lasts
Sydney-born and LA-based, Natasha Oakley is an internationally celebrated entrepreneur, super influencer, and model, renowned for her natural beauty, beach-chic style, and commitment to promoting positive body image. In 2012, Natasha co-founded A Bikini A Day with her best friend Devin Brugman, which quickly rose to prominence as a leading marketing platform. Their success paved the way for the launch of Monday Swimwear in 2014, where Natasha now serves as CEO. Building on this momentum, she and Devin expanded into activewear and everyday essentials with the launch of Monday Body in 2023, with Natasha also leading the brand as CEO. Natasha’s diverse career spans roles as a model, presenter, designer, producer, and author. In 2020, she co-founded The Pilates Class, an online fitness platform that has achieved multi-million-dollar success and a global following. In 2024, Natasha released her first book on business, sharing her insights into entrepreneurship and brand building, which was met with critical and commercial success. She is widely revered for her business achievements and her ability to turn creative vision into thriving global brands. Her brands have earned international recognition, establishing Natasha as a pioneering businesswoman and influential figure in the fashion and wellness sectors. Through her hands-on approach, she ensures that every endeavor reflects her personal values, solidifying her role as an inspiring role model for young women around the world. Maui-raised and LA-based Devin Brugman is an internationally recognized entrepreneur, swimwear model, and fashion/lifestyle influencer. She is known for her natural beauty and effortless style, and her authentic approach to social media has gained her a loyal and devoted following. In 2012, Devin co-founded 'A Bikini A Day' with her best friend Natasha Oakley, which quickly gained prominence as a leading marketing platform. Their success led to the creation of Monday Swimwear in 2014, a highly successful swimwear brand. Building on this success, Natasha and Devin launched Monday Body in 2023, expanding into activewear and everyday essentials. Devin’s diverse career includes roles as co-founder, model, travel expert, speaker and designer, showcasing her versatility across various media platforms and industries. Both Monday Swimwear and her personal brand have earned global recognition, establishing her as a pioneering businesswoman and influential figure in the fashion, home and wellness spaces. Devin’s thoughtful approach ensures that her work resonates with her personal values and identity, solidifying her as a true source of inspiration for all women who view her content.