Company Spotlight — Own Trail

Products by Women
Jul 2, 2020 · 4 min read

Funding Raised: $250k

OwnTrail is reimagining and scaling mentorship to serve all women. Through micro acts of mentorship, we are creating a powerful tool for understanding the many paths to and from the major milestones in our lives, helping a diverse range of women see people that look like them in places they aspire to, and creating a bridge from inspiration to action.

What problem is your startup solving?

Women worry about our paths through life, and we need to see people who look like us in the places we aspire to. We also want to be able to give back to those coming up behind us. While those problems have traditionally been short-handed needing mentorship, we know that 75% of women aren’t receiving or giving the mentorship they want to be.

Where do you see the company in the near term and long term?

OwnTrail is creating impact on the individual level by helping women to find the inspiration, guidance and confidence to combat inequities, own their narratives and achieve their aspirations. We will also create systemic change as we build the largest database of women’s life paths. We will be able to share data that has previously been unavailable about the experiences and barriers that an intersectional array of women face, so that all of the institutions, corporations and elected officials that make decisions about women’s lives can do so in a more informed and intentional way.

VC, Angel or Bootstrap? And why?

We bootstrapped entirely through our beta launch. We recently raised a small pre-seed round with some incredible angel investors, and we’re staying extremely cost-efficient to make that last as long as possible!

Your proudest achievement so far?

We recently passed 750 registered users and 300 published trails through purely organic growth. These are of course early startup numbers… but on the entrepreneurship roller coaster, it’s important to celebrate the wins! And beyond the numbers, we’ve been really proud to see the level of authenticity and vulnerability being shared by womxn, about the meaningful milestones in their personal and professional lives. It feels like our vision is coming to life with every trail that is shared!

Who are your role models or mentors?

I’ve had so many people in my life that I admire in different ways, that have given me advice and inspiration. At the same time, I’ve never had a single formal mentor. That’s a big reason behind creating OwnTrail — I hear women asking often about how to find a mentor, and I truly believe we can’t get everything we need from a single person. There is so much power in seeing people who share our identities and experiences and in understanding their journeys.

When you’re considering partnering with another person or business, what factors are deal-breakers for you?

Shared values, divergent backgrounds, and complementary skill sets are all really important. This applies to the people I work with and the organizations that OwnTrail partners with. So I guess the deal-breakers would be people or organizations who don’t believe in our same core values (authenticity, inclusivity, transparency, growth mindset and safety), and beyond that I would definitely prefer partnering with those that bring new perspectives, identities and talents to the table.

How do you keep your employees (or team members) keen and motivated?

We’re solving some really important problems in innovative ways, so we’re all motivated by the impact we can make and the challenging work. When you hire and partner with amazing people and are working on interesting, mission-driven problems, it just takes collaboration, transparency and trust to keep everyone feeling excited.

What’s the one piece of advice you’d give to other women entrepreneurs just starting out?

Surround yourself with great people, channel bravery in the face of fear, and get ready to work harder than you ever have. Successful entrepreneurs are brave, brilliant and resilient… and so are you!

Rebekah Bastian

Rebekah Bastian is an entrepreneur, writer, artist, tech executive, mentor, wife, mother, and an aerial acrobat. She is the CEO & Co-founder of OwnTrail and was previously vice president of product and vice president of community and culture at Zillow. Rebekah is the author of Blaze Your Own Trail, is a contributor to Forbes, and is a frequent speaker on social impact, career navigation, and corporate diversity.

Products by Women Journal

Since its inception in 2019, Products by Women has strived to create an inclusive community that offers women to connect and learn from peers from around the world, get matched with recruiters, and network with mentors to accelerate their career.

Products by Women

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Diverse global community for women in innovation and tech

Products by Women Journal

Since its inception in 2019, Products by Women has strived to create an inclusive community that offers women to connect and learn from peers from around the world, get matched with recruiters, and network with mentors to accelerate their career.