Natasha Oakley, Co-founder of Monday Swimwear & TPC: Starting a Business With Your Best Friend, How to Know if You Should Start a Business, Protecting Against Burnout, & More

Natasha Oakley, Co-founder of Monday Swimwear & TPC: Starting a Business With Your Best Friend, How to Know if You Should Start a Business, Protecting Against Burnout, & More

On today’s episode I am speaking with Natasha Oakley, co-founder of Monday Swimwear and The Pilates Class. We start off discussing how her and best friend, Devin Brugman, took their online blog “A Bikini a Day” and turned it into a multi-million dollar brand, Monday Swimwear. We dive into tips for creating a business with purpose, working with your close friends, the not-so-glamorous side of being a business owner, burnout, and much more! Tash also has so many more tips and stories in her new book, Excessively Obsessed, which you can buy now! Enjoy!


To connect with Tash on Instagram, click HERE.

To connect with Tash on Tiktok, click HERE.

To connect with Monday Swimwear on Instagram, click HERE.

To shop Monday Swimwear, click HERE.

To shop Tash’s Book, Excessively Obsessed, click HERE.


To connect with Siff on Instagram, click HERE.

To connect with Siff on Tiktok, click HERE.

To learn more about Arrae, click HERE.

To check out Siff’s LTK, click HERE.

To check out Siff’s Amazon StoreFront, click HERE.



This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.


Go to boncharge.com/DREAMBIGGER and use coupon code DREAMBIGGER to save 15%.



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 2026 Future You Project: Hotter & Healthier with Skin Foods, Beauty Sleep, & Nutrition

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20 Tammi 54min

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2026 Glow Up Series – The Business Playbook: Tools Every Brand Should Be Utilizing, How to Build a Scalable Company, Securing Funding & More

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2026 Glow Up Series – Becoming Your Healthiest & Hottest Self

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On today’s solo episode, I’m back with Part Two of my 2026 Glow Up Series, and we’re diving into what it actually takes to become your healthiest and hottest self. I break down my current wellness rou...

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2026 Glow Up Series – Goal Setting, Manifesting & Vision Boarding Deep Dive

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