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Rebekah Bastian: Finding your OwnTrail 


Rebekah’s journey has taken her from Copenhagen to Santa Fe, from music to mechanical engineering, from Microsoft to Zillow, and now to being the co-founder and CEO of OwnTrail.  

Growing up with deeply-in-love hippie parents, Rebekah's childhood was filled with artistic expression and scientific curiosity. She developed a love for music and became a talented oboe player, even earning the title of best-in-state. However, her life took a turn for the worse when she experienced debilitating panic attacks at 19. With the help of prescribed medication, a change of scenery, and time, she overcame this difficult period in her life.


Rebekah's journey through higher education was not without its challenges, even failing college due to personal struggles. But she didn’t let this deter her. She quickly picked up where she left off, including working odd jobs like bartending at various bars and clubs, and completed her undergraduate studies.  

Rebekah went on to earn a master's degree in mechanical engineering from UC Berkeley. Her first job after grad school was at Microsoft, where she worked on the legacy product, Outlook. It was here that she got married, just before starting her job at Zillow. At Zillow, Rebekah's career took off. She worked on the company's first mobile app and eventually became a Program Manager.


As her team became more self-sufficient, she took on more side projects, including ones focused on maintaining and enhancing the company culture, promoting diversity in tech, and solving social issues around housing. Through these side projects, Rebekah became more connected to her local communities, particularly around homelessness, tech, and diversity. “I finally realized that all the side projects I had been doing were really where my passion lay.” She also began taking on advisory roles for women-founded start-ups and non-profit organisations.  

Rebekah started aerial aerobatics when she was about 30 and instantly fell in love with the sport. “I found my creative, physical and social outlet all in one.” she says. Writing also became a passion of hers, and she eventually wrote a book called Blaze Your Own Trail, which inspired the concept of OwnTrail. 

As she thought more deeply about the problems women face when navigating their paths through life, Rebekah realised the potential for a platform like OwnTrail. She shared the idea with her friend Carolyn, who is now the VP of Engineering for the company. Rebekah then met her co-founder McBratney, who helped complete the puzzle for building the company.  

Now, as the CEO of OwnTrail, Rebekah is fired up to keep building an impactful platform for people to visualise and navigate their life paths. Her ultimate goal is to take the money from a liquidity event and reinvest it into under-estimated founders who are building AuthenTech companies. She sees the potential for community building and redistribution of wealth & power using Web3, aiming to get more women and people of colour into this space early on.  

Rebekah's journey has been full of ups and downs, but through it all, she has remained resilient and passionate about making a difference in the world. Her story inspires others struggling to find their own path in life. With OwnTrail, Rebekah is helping people blaze their own trails and reach their full potential.

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