How Natasha Oakley & Devin Brugman Turned a Bikini Instagram into a Global Brand

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: instagram.com/tashoakley

Follow Devin: instagram.com/devinbrugman

Follow Monday Swimwear: instagram.com/mondayswimwear

Shop Monday Swimwear: mondayswimwear.com

Book Recommendations:

Excessively Obsessed by Tash Oakley a.co/d/aski91P

The Power of Now by Ekchart Tolle a.co/d/8DeuoAV

Sex at Dawn by Christopher Ryan a.co/d/2ZiptCN

Good Morning, Monster by Catherine Gildiner a.co/d/3ud8vUW

Attached by Amir Levine and Rachel Heller a.co/d/ivLtVkS

Only Love Is Real: A Story of Soulmates Reunited by Dr. Brian Weiss a.co/d/4nVFYrT%20%20

The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary Results by Gary Keller and Jay Papasan a.co/d/4LEoWHX

The Diary of a CEO by Steven Bartlett a.co/d/iS1jwER%20

Shop my look from this episode: shopmy.us/collections/1898265

Follow me: instagram.com/valerialipovetsky

What we talked about:

01:00: Swim Week in Miami04:00: 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

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