September 28, 2020

Swimwear CEO Natasha Oakley’s strategies to success

  • Natasha Oakley has been an entrepreneur since graduating high school, when she founded her own production company out of her native Australia.
  • Now with an Instagram following that tops 2 million, her business savvy has taken social media by storm.
  • She cofounded Monday Swimwear with a $30,000 loan, and it’s now a multimillion-dollar brand.
  • Oakley has used her business savvy to invest in startups, real estate, and more. 
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Natasha Oakley’s start as an entrepreneur came right after high school, when she began running her own production company out of Hawaii, Los Angeles, and Sydney in her native Australia.

“By the time I was deciding whether to go to college or not, I had started my own production company and was producing video and photo campaigns for brands in Australia and the US,” she said. The visually oriented business produced content for other brands and individuals, mostly around upcoming collections, weddings, and commercials, she said.

She had worked several retail and administrative jobs throughout high school, but said she always felt she would combine creativity with entrepreneurship. “Painting, photography, and videography were passions of mine, so I always knew I would work in a creative field that involved one of these mediums,” she said.

Growing up surrounded by entrepreneurial parents — her mother owned a real estate agency and her father a private investigator — an ambitious mindset was instilled in Oakley from a young age.  “This was something I couldn’t learn in a classroom,” she said. 

These days, she boasts over 2 million followers on Instagram and, along with cofounder Devin Brugman, runs Monday Swimwear, which has grown from a $30,000 loan into a multimillion-dollar brand in less than a decade.

But 2012 marked a big change in her career, and it was all about a blog, called “A Bikini A Day.”

Best friends, Instagram, and ‘A Bikini A Day’

That year, Oakley met Brugman, who was hired on as a production assistant. Now best friends and business partners, Oakley said the swimwear-modeling blog was “a small but growing business, the perfect starting point for both us.”

“Our photography skills are what gave us a point of difference on Instagram right out of the gate. ‘A Bikini A Day’s’ content was next-level at the time. We produced professional imagery and immediately saw interest from swim brands because that was rare back then — Instagram was more of a social platform than a business platform back in 2012.”

Oakley said she started her Instagram account when the platform first launched, “and it was a completely different world. Devin and I grew a large following from sharing a very raw version of our lives. A lot of people were inspired by our friendship, our travels and our journey, and we always showcased it in such an organic way.” Now, the platform has “opened doors for me that never would have opened before social media existed,” she said. 

The platform also played a huge role in scaling up Monday Swimwear, allowing Oakley and Brugman “to collaborate with other talent, influencers, and creatives.”

She said there is something “more honest, transparent, and inspiring about social media marketing,” saying that old-age marketing was “so one-dimensional and you never knew what was really going on behind the brand.”

Oakley’s business interests, and her personal career  

With Instagram on Oakley’s side, her blog’s following grew. And so did her plans.

By 2014, she and Brugman launched Monday Swimwear.

Monday obviously remains a major focus, but Oakley said she’s “also focused on my personal career and brand, which involves partnerships and ambassador roles with large Fortune 500 companies and small brands alike.” In addition, Oakley said she is investing in companies outside Monday.

She declined to disclose specific partnerships or investments, but said “it’s really inspiring to also be able to work within other categories like health and wellness, beauty, and fashion which I am just as passionate about as swim.”

She’s also invested in real estate.  “I’ve always loved real estate and have followed the real estate market,” she said. “In the last few years, I’ve invested more in real estate, purchasing homes in Los Angeles as my personal residence, and as investments.”

Her words of advice for entrepreneurs

Subscribing to the “trust the process” mindset, Oakley shows no signs of slowing down, and says taking risks and understanding her worth freed her to broaden her horizons beyond her Australian hometown.

“Owning my own business came naturally to me and happened so organically that I really have always lived a ‘love what you do, and you won’t work a day in your life’ kind of life. Moving overseas or to a new city never intimidated me, so travel was one of the main experiences that led to me finding my calling,” she said.

“Working in a lot of different industries and jobs helped me to find what I wanted to do. The more you try ,the more chance you have of finding something you love!”

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