Rebekah Bastian on The Orbit Shift Podcast

S02E42

Rebekah Bastian, CEO & Co-Founder of OwnTrail on building diversity and inclusion in startups

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Rebekah Bastian, Co-Founder, and CEO of OwnTrail talks about her journey, building diversity and inclusion in startups, the need to refresh ‘tech mafias’ and building her startup OwnTrail

Today companies not only want to focus on profitability but also create a positive social impact. With consumers identifying strongly with brands that are committed to the greater good, profitability and positive social impact have become intertwined.

In this episode, we speak to Rebekah Bastian, CEO, and Co-Founder of OwnTrail and an award-winning writer who is a strong advocate of such an approach to company building. Rebekah talks about her journey, building diversity and inclusion in startups, the need to refresh ‘tech mafias,’ and building her startup OwnTrail.

Edited Excerpts

Q. Rebekah, tell us about your journey

Rebekah: I graduated with a master’s in mechanical engineering, and I was in Microsoft for a couple of years doing product management. After that, I was one of the first employees at Zillow, and I spent almost 15 years there. 

I started as an entry-level Product Manager and then grew through my career working on different product areas until I was Vice President of Product. And then, for my last couple of years there, I was the Vice President of Community and Culture. Working on creating equitable systems internally for employees and also leveraging that to create social impact through our products and our business decisions. 

This intersection of product strategy and social impact is where my passion lies, and it’s what I brought with me when I started my own company about a year and a half ago called OwnTrail.

Q. What problem are you solving with OwnTrail?

Rebekah: OwnTrail is a peer support system for women. Its foundation is women sharing their authentic life paths, which we call trails. 

The problems we’re solving are the systemic problems where women are not supported through their personal and professional lives. Women oftentimes don’t see people who look like us in the places that we aspire to be, and we exist in this world of social media that doesn’t take into account the intersection of our personal and professional lives and the authenticity that we need in order to feel connected and confident in our paths. 

By women sharing their authentic trails- where they’ve been and where they’re going on OwnTrail; we’re connecting women in a way that moves from inspiration to action in supporting each other through our lives. 

We have over 1000 trails and a team of six. We’ve been working on this for about a year and a half now. 

Q. Do you hope to build a social media network with OwnTrail?

Rebekah: No, we see ourselves as the anti-social media. While there are some similarities in terms of people sharing and connecting with each other, we see that there’s so much toxicity and so many issues that arise from social media, namely the media model. 

This model is where advertisers are the ones who are paying, and anyone that’s sharing on social media is being sold to these advertisers. The company’s incentives there are to keep people on the site for as long as possible, to make them feel inadequate, so they want to stay longer, come back more, and buy more things from the advertisers. It creates these unhealthy dynamics. 

With OwnTrail, we see it as being that any time spent on the platform makes people feel better and more supported. We’re not focused on trying to get the most eyeballs or sell people’s data in any way. The business model for OwnTrail is that it’s free to everybody, and anyone can share their trail and find inspiration in the trails of others. And then we have programming built on top of that, that women can pay for. We have cohort-based programming and other programming in the works that drives value, which then drives revenue.

Q. What advantages do diversity and an inclusive culture bring to a startup? 

Rebekah: It’s essential to have employees that represent the people that you’re building products or solutions for. When you don’t have that, there are huge misses that happen. There’s lots of research that show that having diverse perspectives and experiences leads to better decision-making overall. 

There’s also the fact that it’s the right thing to do. We live in a world where opportunities are not equitable, and there are different systems at play that hold some people back and privilege others. So companies that have the resources to do so or have the opportunity to do so should be creating every opportunity they can to change some of those impacts. 

Q. You’ve spoken about the need for companies to refresh their networks and move away from the ‘tech mafia’ mindset. What are your thoughts on this? 

Rebekah: If you take an ecosystem that is not as diverse as it could be or not as equitable as it could be, or not as impactful as it could be, and then you try to replicate that with the same people, you create closed networks or closed systems that replicate the negatives of these systems.  

What happens with a lot of the tech mafias that you see forming is that they tend to be a less diverse set of people from these companies. They tend to fund each other, hire from each other, and often build products that serve others like them. There’s a missed opportunity for more impact and systemic change there. 

There’s so much opportunity for positive impact, and there’s so much opportunity to change existing systems that aren’t serving everyone that it’s a little uncreative when people aren’t trying to constantly expand outside of their existing networks and systems they’re part of.

Q. How can founders measure diversity and inclusivity within their organizations?

Rebekah: You can look at the representation of different identities within your workforce. This varies by country but focusing on the US. It’s possible to keep track of ethnicities and gender identities. You can also look at veteran status and age, and then there’s also geography, especially as we’re looking at more distributed workforces. You can also measure the identities that your employees hold at all different levels and functions within the company. 

It’s also important to be doing different forms of surveying or finding out directly from employees what their experience is to get more of a sense of belonging and this level of engagement of employees within the company. For example, suppose only certain identities of employees feel a strong sense of belonging. In that case, those are going to be the identities that are able to speak up the most, do their best work, and feel the most supported in sharing their perspectives. So you could have a diverse employee base, but if not everyone feels comfortable contributing, you’re not going to be reaping the benefits of that,

Q. What would be your one piece of advice to a young entrepreneur?

Rebekah: It’s all about the team. You’re not going to be able to do everything yourself. Recognize where you need complementary perspectives, skills, and people. Sometimes that means hiring them onto your team, and sometimes that means people that are advisors or other people that you’re able to lean on outside of your company.

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Join the Freshworks for Startups Program and unlock superpowers to run your startup. Eligible startups can claim up to $10,000 in credits on our intuitive, scalable and affordable software suite. We also offer white glove onboarding, mentorship, market access and resources to help startups scale faster.

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