Rebekah Bastian: Opening to Possibility [Built in Seattle Ep. #41]
2 min read

Rebekah Bastian: Opening to Possibility [Built in Seattle Ep. #41]

OwnTrail CEO & Co-Founder, Rebekah Bastian, talks about opening to possibility, assessing risk, and blazing your own trail.

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There's no "right" career path.

Rebekah is a role model in blazing her own unique path.

On paper you see that she was employee ~20 at Zillow, PM to VP in 15 years, author, and founder. Like many successful people, she has an impressive resume.

But Rebekah says that she never had a masterplan. It was never a straight line.

She says that we all need to normalize the real journeys that people take through career and life. And that's especially important for woman who don't have as many examples or positive points of comparison.

Rebekah is building OwnTrail to help woman normalize their experiences and learn from others. Their platform advances women by helping members share their paths through career and life.

With seed funding and an all-star team, OwnTrail is growing fast and serving an important mission.

Rebekah shares her story on this episode of The Built in Seattle Podcast.

Episode Highlights

  • How she joined a 20-person startup called Zillow.
  • The journey from PM to VP of Product over 15 years
  • Why she built an "Equity and Belonging" program in 2017.
  • How writing a single guest blog post led to writing a book.
  • Why she has avoided a master plan in blazing her own trail.
  • How "accidental entrepreneurship" pulled her away from Zillow.
  • Why your goal shouldn't be to avoid all pain and failure.
  • How designing the book launch website led to the idea for a company
  • The 3 questions she asks to make big decisions.
  • Why LegUp is her Seattle business role model.
  • Why Laura Clise is her Seattle leader role model.
  • Why she wouldn't give her 20 year old self any advice.

Rebekah Bastian Bio

Rebekah Bastian is an entrepreneur, writer, artist, tech executive, mentor, wife, mother and aerial acrobat. After 15 years at Zillow, with roles including vice president of product and vice president of community and culture, Rebekah is now CEO & Co-founder of OwnTrail.

OwnTrail is a peer-to-peer support system that drives meaningful personal and professional development for women. Through OwnTrail's proprietary technology, women can own and share their authentic stories as Trails, see people who look like them in the places they aspire to, and empower each other to navigate obstacles and opportunities. In line with this theme, Rebekah published her first book, Blaze Your Own Trail, in February 2020 with Berrett-Koehler Publishers.

Rebekah serves on the Board of Directors of Bellwether Housing and the Advisory Board for the University of Washington School of Mechanical Engineering. She is also an advisor to technology startups, a respected thought leader and community partner. She writes articles in multiple publications including and is a frequent speaker at conferences and community events. She has been recognized in the Puget Sound Business Journal 40 Under 40, the Inman 33 People Changing the Real Estate Industry and the Female Founders Alliance Champion Awards. Rebekah earned her Masters of Mechanical Engineering from UC Berkeley and Bachelors of Mechanical Engineering from the University of Washington.