An Interview with Rebekah Bastian, CEO of OwnTrail

If you have been following my interview series, you already know that my biggest goal is to provide a place of inspiration and motivation for my readers. One of the reasons I reached out to Rebekah Bastian was because I had read one of her LinkedIn posts regarding the challenges of being a woman who’s hustling to get funding for her startup, OwnTrail. Since I spent nearly a decade in the tech startup scene, I felt a great deal of empathy for her and decided to reach out to see if she’d be interested in being featured on my blog.

Rebekah Bastian OwnTrail

Truth be told, when I was a part of the tech startup scene, it was heavily male-dominated both in the boardroom and in the C-Suite — and not much has changed. I remember presenting my marketing plan to board members and the rest of the executive team at a startup I was a part of back in 2015. Not only was I the youngest executive on the team, but I was also the only woman minority. I’ve never been one to rally the “girl power” expression, but this was certainly the first time I experienced the same shit so many women have in the workplace. 

Before I could begin my presentation, one of the oldest board members (who happened to be a wealthy Caucasian male) asked me to give my career background. After I finished, he followed up with, “Do you have kids?” At the time, I didn’t and answered, “No.” He then responded, “That’s the only reason why you’ve been so successful in your life so far.”

Being so young then — and that was well before the #metoo movement with tons of women coming out facing the same misogynistic culture — I really was taken back and speechless. However, I did leave the company shortly after that and went on to run my company full-time.

That said, this interview is just so authentic and also addresses the challenges that exist for women in the workplace, especially women-founded companies. More specifically, as highlighted in a recent article on CNBC regarding Bumble’s IPO

In 2020, as U.S. venture-backed start-ups raised record amounts of capital, funding to female founders fell to a three-year low, according to data from Crunchbase. Seeing more “role models” like Wolfe Herd take their companies to IPO can help, said Anu Duggal, founding partner at the Female Founders Fund.

“Often women … aren’t taken as seriously,” Duggal said. “I think what she’s proven is that you can put women first and you can build a huge company behind that.”

With all of that said, let’s dive into Rebekah’s interview:

1. What’s your story?

I left a 15-year career at Zillow to start OwnTrail, after writing a book on the topic of women blazing their own trails. While at Zillow, I served as VP of Product and then VP of Community and Culture, and my skills and passions really lie at that intersection of product strategy and social impact. I’m all about community: I’m involved in the Seattle tech, affordable housing, and circus communities, and the community of trailblazers that have been part of our OwnTrail journey has been phenomenal! I love creative outlets (writing, art, aerial acrobatics), and live in the Ballard neighborhood of Seattle with 5 boys (2 sons, husband, puppy, and geriatric cat).

2. What inspired you to start OwnTrail?

I’ve definitely had my own non-linear path, and I’ve also had the opportunity to connect with countless women, and there are some themes that emerged for me. There are systems at play that can hold us back — from not seeing people who look like us in the places we aspire to, to not being at the tables where decisions are made that impact our lives, to societal belief systems that sell us short. Because of those systemic issues, we often feel like we’re not enough or that we’re “getting it wrong”. We started OwnTrail to solve these problems by creating a peer-to-peer support system for women that is structured by our authentic, non-linear life paths.

OwnTrail Founders
Rebekah and her Co-Founder, Kt

3. What was the biggest challenge you faced when you started OwnTrail?

Fundraising was harder than I expected. It’s definitely a space where there are still major biases at play, as evidenced by the 2.3% of venture funding that goes to all-women founding teams. That being said, we also ended up with the most supportive, mission-aligned, diverse group of investors we could have hoped for. So it was challenging, but also ultimately rewarding. I wrote up some observations about the experience here.

4. What motivates you to jump out of bed every morning?

The puppy needing to pee 🙂 But seriously, the work we’re doing at OwnTrail is beyond motivating. Like, when I have a few minutes to myself, I want to be doing work because I’m so excited about our purpose and vision. I feel lucky to be able to work on something that feels so meaningful, especially when there’s so much going on to get discouraged and frustrated by.

5. How do you see the importance of content playing a role in helping you grow OwnTrail?

Authentic content is the foundation of OwnTrail. It’s what connects women with each other. Rather than traditional social networks, where people are trying to build up the most friends/followers/likes, OwnTrail uses shared experiences to create meaningful connections. That leads to the authenticity and inspiration, and the power of women supporting each other as they work towards their aspirations.

6. What’s your favorite quote and why?

So many quotes inspire me! So to answer this question, I opened up a treasured book of illustrated quotes by Jade Purple Brown, Words to Live By. Today, I’m going with this one, since it’s so core to what we’re building at OwnTrail: “If you don’t like the road you’re walking, start paving another one.” – Dolly Parton 

dolly parton quote

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