Episode 113: Micro-acts of mentorship for women — with Rebekah Bastian

Rebekah Bastian is the CEO & Co-founder of OwnTrail, an online platform that connects, mentors and empowers women as they share their personal and professional journeys and experiences. Previously, Rebekah was Vice President of Product and Vice President of Community and Culture at Zillow. She is the author of the book “Blaze Your Own Trail,” a contributor to Forbes and a frequent speaker on social impact, career navigation and corporate diversity.

During this episode, you will hear Rebekah talk about:

• How she grew her career at Zillow, and how her experiences there helped inspire her to write her book and create OwnTrail
• Why so many women are still not getting the mentoring support they need, and how OwnTrail helps address this problem by providing access to “micro-acts of mentorship” that women may not otherwise receive
• How OwnTrail is different from other online networking sites
• Why it’s important for women to share both their personal and professional journeys with each other

Find out more about OwnTrail at www.owntrail.com and on social media: @owntrail on Instagram, @OwnTrail on Twitter, @BlazeYourOwnTrail on Facebook and OwnTrail on LinkedIn.

Learn more about Rebekah at @rebekah.bastian on Instagram, @rebekah_bastian on Twitter, and Rebekah Bastian on LinkedIn.

Rebekah and Carolyn have published their own OwnTrails! See what they look like here and here.

Watch the video of this interview on YouTube!

Subscribe to the FREE Beyond 6 Seconds newsletter for all the latest news and updates about my podcast!

The episode transcript is below.

Carolyn Kiel
Today, on Beyond 6 Seconds,

Rebekah Bastian
There’s all these experiences we go through where we feel like we’re the only ones going through them because they don’t get talked about as much. So we can feel really isolated in our experiences when in reality, they’re shared amongst so many different women.

Carolyn Kiel
Welcome to Beyond 6 Seconds, the podcast that goes beyond the six second first impression to share the extraordinary stories and achievements of everyday people. I’m your host, Carolyn Kiel.

Did you know you can watch the video of this episode on the Beyond 6 Seconds YouTube channel? I posted the videos of my most recent episodes there, just go to YouTube and search for Beyond 6 Seconds. Also, while you’re there, please click the red subscribe button under the video and then click the little bell icon so you never miss a video. Thanks so much. And now here’s my interview with Rebekah.

My guest today is Rebekah Bastian, the CEO and co founder of OwnTrail. Previously, Rebekah was Vice President of Product and Vice President of community and culture at Zillow. She is the author of the book Blaze Your Own Trail, a contributor to Forbes, and a frequent speaker on social impact, career navigation and corporate diversity. Rebekah, welcome to the podcast.

Rebekah Bastian
Thank you for having me.

Carolyn Kiel
I’m so happy to have you here today. Tell me a little bit about OwnTrail, what it is and what inspired you to start it.

Rebekah Bastian
Yeah, so OwnTrail is a platform that’s really kind of reimagining what mentorship means and how it plays out for women. The goal is really reaching all women. We know that currently about 75% of women aren’t giving or getting the mentorship that they want. And we believe that when they say they want to be giving or getting mentorship, it’s really kind of shorthand with some problems that need solving. And those really kind of on one side of the equation lie around the fact that we need to see people who look like us in the places we aspire to. And we really want to understand the authentic journeys behind you know how different people get to where they get because we can really start to doubt ourselves and feel like we might be getting it wrong or like we need to know where we’re going without really understanding what those nonlinear journeys look like. On the flip side is also the fact that we want to be able to give back to those coming up behind us, but can’t always say yes to every coffee chat. And, and, you know, it just it doesn’t scale, the traditional one on one mentorship isn’t scaling. And frankly, it’s just leaving women behind. And so the way we’re solving that is by creating this platform in which women can share what we call micro-acts of mentorship, which is, I know you’ve done this, which I was really excited to see, but it’s being able to share the trail that you’ve blazed through life as a series of interconnected milestones. And when we combine all those different trails from all these different women with the different identities they hold and experiences they’ve had, it becomes this content based network that can really provide the insight and inspiration and guidance that we believe women are looking for when they say they’re looking for mentorship. So really being able to see all the different ways that someone might have navigated a situation I’m going through right now or all the different journeys women might have taken to get to a point I aspire to and using that to really fuel our journeys from inspiration into action.

Carolyn Kiel
Right oh that’s really interesting. Yeah, I have had a chance to check out the platform and even build my own OwnTrail. And it is very different than say, you know, looking at someone’s resume or their LinkedIn profile, which tends to just be the major milestones from a professional level, but the OwnTrail is really holistic, in that it incorporates a lot of personal milestones, professional milestones, education, and really a whole host of other things. And it seems like that was very intentional in the way that you put that together. Is that something you found really helps women in networking and building those mentorships?

Rebekah Bastian
Well, you know, it’s really the fact that our personal and professional lives are so intertwined, you know, so trying to separate them out, you know, essentially kind of sells our experience short, it’s not realistic, even though surprisingly, most platforms and conversations do tend to think about them as separate things. So yeah, for us, integrating personal and professional was really important. And you know, like you said, it’s easy to see these kind of picture perfect end results on different social media or media and you know, and see what the final accomplishment is. But in reality, the things that really make us who we are, that I think are really the most character building and the most, you know, that gives us the most success in life is the obstacles that we’re able to navigate, what we make it through and what those journeys really look like behind the the final win. And so we’re really trying to embrace that level of authenticity.

Carolyn Kiel
Yeah, that’s really important. And that’s one of the things that motivated me to start this podcast is to not always just present the finished product, the highlight of everybody’s career and personal lives because it is just so much more complicated than that when we’re trying to find success and build our careers and the rest of our lives. So that’s really interesting.

Rebekah Bastian
Yeah. Absolutely. Yeah.

Carolyn Kiel
Cool. So before you started OwnTrail, you had a multi year career at Zillow. You know, you had a variety of positions. And I’m really curious to learn how the work that you did at Zillow helped inspire and lead you to start OwnTrail after a couple of years.

Rebekah Bastian
Yeah, definitely. So I was there for 15 years, and most of that time was spent in product leadership. And then the last few years I spent leading community and culture. And so I, you know, I would say that both my experience and my passion really lie at that intersection of product strategy. So you know, how you solve user needs and delight users through really meaningful products, and social impact and equitable systems. So really thinking about, you know, how we can leverage products to solve social issues, to create more equity in the world to really, you know, essentially bring people together. And so that is definitely the foundation of what we’re building OwnTrail with. The gateway experience for me was really writing this book, that led to OwnTrail. And so that was something that I did on the side while I was at Zillow, not with the intention of leaving to start a company. But just because it seemed like it’d be fun to write a book. And so Blaze Your Own Trail is this interactive exploration of women’s life paths with really, you know, kind of similar goals, it’s really trying to embrace the idea that there is no one right path and create solidarity in the shared experiences that we have as women. And so it’s this choose your own journey format, which means you the reader are the person going through the storyline. And at the end of each chapter, you make a decision, and that tells you what chapter to go to next. So essentially, the whole table of contents is a big decision tree. There’s all these different paths, there’s 19 different endings. And, you know, it spans personal professional life, and it’s really trying to recognize that our decisions won’t always you know, be, the outcomes won’t always be predictable, things won’t always go as planned. We don’t always know where we’re headed, but you know, and we’ll make it through tough things along the way. But we’re strong enough to make it through and we’re going to be okay. And we’re going to find our happy ending through through any of those. So I wrote the book and had signed with the publisher. And at the point where I was waiting for it to come out is actually when I started building what I thought would be a book launch website. But it pretty quickly took on a life of its own and evolved into what OwnTrail is now.

Carolyn Kiel
Wow, that’s really interesting. And you know, you mentioned starting in Product Management at Zillow, and then, you know, your career kind of moved towards, like the culture related types of topics. You know, we talked about diversity and engagement and community and at your last few years at Zillow, your career really evolved into that particular area. Was it an interest that you developed while you were doing product management? Or how did that enter the picture with your career?

Rebekah Bastian
I was Vice President of Product and had an incredible team with some really amazing directors reporting to me and found a little bit of bandwidth through that to start doing some more side projects, so I actually spent probably a good three or four years doing side projects that were really around, you know, how do we create social impact through our products? How do we get more diverse representation into our tech org? How do we really foster this culture that’s been fantastic from the beginning, but you know, as we grow and scale as a company, how do we keep that alive and growing? And then it really was kind of an a-ha moment where I just realized one day, like, literally one day that you know, whenever friends asked me about, you know, what’s cool at work right now, I’m talking about all my side projects, those are the things that I’m really most excited about. And so I started having some conversations with with leadership and pitching this idea of creating a team in the space that brings these different areas together. And I think because I had really proved myself in these areas, through doing it on the side and and some some really good results from it, and because we are in a place where we were really ready to to grow and invest in the space more as a company, my timing was was really good with it as well. And I was able to get the go ahead to start this team. And I think the best thing I did was really hiring an incredible team of people that that were experts from all different areas to run with this work and who ended up being really amazing. I would still be there right now if it weren’t for discovering this complete calling to be building OwnTrail, but it was a really cool experience working with that team.

Carolyn Kiel
Did your interest in networking and mentoring tie directly into the culture work, or was it sort of a realization that you had after doing this work that, you know, hey, mentoring and networking is a critical part of this, and that, particularly women in general are sometimes at a disadvantage when it comes to that?

Rebekah Bastian
Well, I mean, I’ve just since I’ve been in leadership and mentorship roles for you know, probably over a decade now, I just had enough conversations to realize that there’s some really common themes there. And it oftentimes is women who reached out to me to talk and I think it is because it is important and oftentimes when we’re looking for mentorship or for guidance to reach out to somebody whose identities we share, and I think that’s a reason that I end up talking with a lot of women, but the common themes really are talking with all these women who who worry about their paths through life who think they’re supposed to know where they’re going, and how they’re going to get there and hoping they get it right. And, you know, also the fact that there’s all these experiences we go through where we feel like we’re the only ones going through them, because they don’t get talked about as much, sometimes something that’s more taboo in nature, or people feel embarrassed about. And so we can feel really isolated in our experiences, when in reality, they’re shared amongst so many different women. And so, you know, I wove a lot of data into the book, into Blaze Your Own Trail. And we’re really trying to create this platform that is powered by community but but really powered by data to really kind of create that sense of solidarity around what these shared experiences are and how all these different paths fit together.

Carolyn Kiel
So OwnTrail is it currently in beta right now or is it fully launched?

Rebekah Bastian
Yes, we launched our beta site in February. So it’s fully available to everybody. It’s OwnTrail.com and anyone can go on there, and anyone who identifies as a woman can share the trail that she has blazed and everyone can can browse through those trails. Women can choose to use their real names, or stay anonymous with a screen name depending on you know, kind of what their comfort level is with that and, and we do still have the beta tag on it. We’re actually in the last week of a crowdfunding campaign right now, that is giving us the fuel to kind of do the the last push of features to get us from beta into our full production release, which, you know, it’s essentially a logo change, but it’s also the mentality of like, you know, like, we’re really it’s official we are we are out there. This is our, this is the platform that that we’re gonna be growing from here.

Carolyn Kiel
Yeah. So, in the show notes, I’ll add a link to my own OwnTrail and like I add one to yours if that’s ok with you.

Rebekah Bastian
Absolutely.

Carolyn Kiel
Because I’d love to give people the visual and if I can figure out how to add a visual into this video, I’ll put mine up there as well. So I want everyone to be able to see what this is. So it it’s called OwnTrail because it’s literally it’s your own trail. And it literally looks like a visual trail of significant milestones that are personal and professional. And I’m fascinated when you talk about the data behind it. So you know, we’re putting in whatever you choose to share, obviously, as much or as little as you want. And then if there are several different women doing that, it seems like there’s a lot of potential to potentially match up people who have similar experiences, and things like that. So is that part of the the data engine that you’re building behind it? How will it match people up or connect those conversations?

Rebekah Bastian
Yeah, definitely. So it’s very data driven, both on kind of the individual level and in aggregate. So on the individual level, like you’re saying that it’s the power is really in being able to say, you know, these are the trails of women that are, you know, maybe similar to yours that you can identify with and find that solidarity and shared experience. And these are the trails of women who are in places that you might aspire to, or you know, to give you some wisdom of where you’re going or how you might get there, you know, and really having it be personalized and tailored to your own experiences and to your aspirations. And then in aggregate, as I was writing the book, and weaving a lot of data into that, what I discovered was that there’s some huge gaps out there in the data that we know about women’s lives. You know, there’s a few annual reports that come out about like women in the workplace and stuff, but there’s really big gaps, especially when you’re trying to look at it intersectionally and understand what women experience based on the different identities that they hold. And so as we get more and more data in OwnTrail, what we’re able to do is really provide data about what women experience in their lives and you know, that intersection with the different identities they hold and hopefully that can really help create some systemic change. You know, if everyone who’s making decisions and policies and supporting women through their lives and you know, everyone in all these different sectors and, you know, imagine what, what good could be done if we better understood what women are really experiencing in their lives across the full spectrum of personal and professional. And so we’re really excited to put that out there and be the leader in everything about women’s lives.

Carolyn Kiel
Wow. Yeah, absolutely. That is wonderful. What kind of stories have you heard through OwnTrail? Do you have any cool anecdotes or results of people who have made connections or otherwise found it to be helpful with their lives or careers?

Rebekah Bastian
Yeah, yes. I mean, the stories are totally what fuels us because it’s so amazing to hear. Like, we’ve had a lot of different women reaching out both about the experience of creating their trail and how you know, really the act of reflecting on and owning our story and our narrative is so powerful in and of itself. Hearing from a lot of women about just the power of seeing women’s trails that they can really identify with and the real authenticity and vulnerability that we’re seeing there. There’s stuff being shared about just everything in life from from workplace issues and accomplishments to you know, relationship issues and mental health and childbearing and infertility and travel and mourning, and just, you know, all of the richness of life is really encompassed into these trails. And it’s incredible. And it really does provide that sense of solidarity and inspiration. And we actually we just launched a feature a couple weeks ago now called conversations that lets women now ask and answer questions on trails and dig deeper into because what we’ve heard is that some women were starting to reach out to each other on other platforms to like hear, I want to hear more about your trail! Tell me more about this. And so we’re really we’ve pulled that part of our roadmap in pretty quickly because we’re like, oh, these conversations need to be had. Women want to be connected with each other about this. And so we have that. And it’s really cool to see now how people are connecting about the shared experiences.

Carolyn Kiel
Yeah. And I was wondering if people kind of made those connections beyond the trail and I’m sure that that sounds like it’s one of the wider goals and with the adding of the messaging and the conversations feature, it definitely makes it easier to reach out to anyone on the platform and just ask questions or connect or you know, ask anything that you might want.

Rebekah Bastian
Yeah, yeah, it’s really you know, it’s a content based network, as opposed to a profile based network. So it’s not about like racking up the most friends or followers or likes, right? It’s not that kind of winner takes all model, because we think that’s the reason that so many platforms don’t have the authentic journey is because that kind of profile based network doesn’t really foster that. So when it’s about content, the most powerful thing there is authenticity, it’s about those shared experiences and about what we’ve been through and the commonalities that come from that. And so it’s not just about connecting is like, oh, we’re part of a network now, you know, but it’s really about like, how our stories connect and intersect and the network that comes from those stories.

Carolyn Kiel
Oh, yeah, that’s an interesting way to think about it because you’re right. All the other social networks are about like, how many followers do I have or how many likes, but this is, you know, you can appreciate someone’s platform. There’s a button for essentially a like, I think it’s called appreciate.

Rebekah Bastian
Appreciation, but it’s private, though. So it’s not like other people can see like, oh, they’ve gotten more appreciations than I have, right? But it’s more just like this, this private nod of solidarity of appreciation between two women, that doesn’t have to be like a big, like, Who’s racking up the most? Yeah. Yeah.

Carolyn Kiel
It’s kind of a more one on one type of conversation or connection through that, because you’re really focusing on the person and the content of their journey. Very very good. So you know, you mentioned that you with OwnTrail, it entered beta in February, obviously, you were running before that. And, you know, we’re recording this in August and obviously 2020. It has been quite an unusual and difficult year, especially for I would imagine someone who’s starting out with with a startup and trying to grow a brand new business. What’s it been like for you and for OwnTrail? Have you noticed any change in the way people use it? Or I’m just kind of curious what it’s been like in this very unusual time.

Rebekah Bastian
Yeah, I mean, we first launched in February. So like that, that was the beginning. We haven’t we didn’t have a lot of before to compare it to. But I think the way that we have OwnTrail structured is really conducive to what we’re going through right now. In that, you know, it’s fully virtual. We’re about helping women make it through hard things. And we happen to be pre revenue right now. So we don’t have the financial hit, but so it actually like it’s not I mean, it’s hard to know what the trajectory would have looked like without a pandemic, but it’s not been so bad. And I will say that it’s been so satisfying and fulfilling to work on this right now, you know, at a time when we all want to just feel like we’re able to do something with the uncertainty and the chaos and the issues that we’re seeing in the world. And so I’ve really been enjoying working on this. I don’t know if you’ve seen them coming and going but I have my co founder and VP of engineering. The three of us are all in my garage here as a little pod together. And so we’re able to be working together and It’s just it’s been a really cool experience. I’m also, I have two young children and just dealing with all of that has been nuts. So I’m not saying it’s an easy time, but OwnTrail has probably been the most fulfilling part of it.

Carolyn Kiel
Right, that’s really cool. Since OwnTrail is largely focused on mentorship and mentorship for women, and you know, you’ve had your own amazing career with career growth and you really had an opportunity to build. Do you have any mentors who kind of stand out in your mind as being like incredibly influential or helpful to you to kind of help you along and any stories, a story or two you’d like to share about someone who’s helped you grow in your career?

Rebekah Bastian
Well, so not to sound ungrateful because there’s been so many people that have helped me through my life and my career and that, you know, I actually feel completely lifted up by community, but it hasn’t been like, I haven’t had like that single mentor that’s been like, Oh, this is my mentor. This is the person that has all the answers for me. You know, it’s, and that’s really like why we’re building OwnTrail in the way that we’re building it, I think we all agree with that. And the more women that I talk to the more that’s kind of, that’s more common. You know, some people have definitely had great mentors, and certainly great sponsors, I’ve had that as well. But even under the best, you know, circumstances, for one on one mentorship, you can’t get everything you need from a single person. And so our philosophy is really that it’s the culmination of all the different experiences and advice and journeys. And also, you know, I think that there’s this kind of misconception that mentorship is this one directional relationship where there’s like the mentor and the mentee. And the mentor gives the mentee advice or whatever, you know, and I think, both in my life, the way that things have played out and in, you know, the way that we’re building OwnTrail, there hasn’t been necessarily a separate mentor and mentee. And you know, these neatly categorized roles. It’s more like we all have a story to tell. And we all have more to figure out and we are both. We are both the mentor and the mentee, and I think in a really great relationship, that’s how it plays out, is you’re there for each other, you learn from each other, you support each other, you both have different experiences that you can share. And that’s really how we’re trying to build OwnTrail so that everyone is both of those roles together.

Carolyn Kiel
Yeah I mean, that makes a lot of sense. And you’re right. I think sometimes there’s this perception that you really need this one person who you stay with as your mentor for years and you kind of follow them around or they have, you know, you have significant amounts of time that you spend with them. But really, a mentor can be maybe someone you meet with for 20 minutes or just for like one or two months, or someone who gives you advice or who you know online and maybe never meet in person. It’s really just so varied. And it sounds like OwnTrail is really helping to open up more opportunities for those types of relationships so people can learn from each other.

Rebekah Bastian
Yeah, exactly.

Carolyn Kiel
What are your big goals for OwnTrail once you get out of beta and like fully launched? Where do you see it evolving? And what do you still want to build into it and achieve with it?

Rebekah Bastian
Next, we’re working on aspirations. So you know, women right now are able to share where they’ve been in life. We want people to be able to share where they want to be going just as a way of really putting it out there into the universe, but also that will help us as you know, kind of a machine learning platform to better provide the the tools and framework and structure to help people get where they want to go and connect with people that can help them get there. We’re hand building kind of a way for both people who want additional guidance as they navigate OwnTrail and the people who want to be able to help with that to connect with each other in this kind of peer to peer model. And so we’re working on that right now as our business model. But ultimately, like the big vision is that OwnTrail is the place where all women can go to both connect with each other, find the confidence that they need to deal with anything they’re dealing with and aspire to anything they want to aspire to, have the tools to do so, and that we’re able to really blow open how the world views and supports women in a way that creates more intersectional gender equity across the board. So big goals, big aspirations for us, I’m putting it out there into the world. Because it’s you know, it’s something is, this is what we’re working towards. And we just have so many ideas and visions for getting there. But it’s also a very consumer driven strategy. We really want to know how people are using the platform, what they need, and really let that drive where we’re going as well.

Carolyn Kiel
Yeah, that’s that’s really fantastic. Wow. OwnTrail you said is up and running. And really, it’s open to anyone who’s a woman or identifies as a woman. How can people either get in touch with you if they want to learn more about your work with this or how can they try out OwnTrail on their own?

Rebekah Bastian
Yeah, so everyone who identifies as a woman should definitely create their trail on OwnTrail.com just O W N T R A I L. Everybody out there should reach out to the women in their lives that are inspiring to them and ask them to share their trails on OwnTrail because it really is, we’re growing organically based on you know, women empowering women, women inspiring women, and so everyone has someone that that inspires them. And so getting more of those trails up on the platform, OwnTrail and myself are both on all of the different social platforms. So you know, people can definitely follow along and reach out on their favorite platform there. And yeah, I, I read every single trail that comes through. So I’m just so excited to get to know more about the journeys of your listeners.

Carolyn Kiel
Wonderful. And I’ll put links to OwnTrail.com and the social media links in the show notes of the podcast so people can find it there too.

Rebekah Bastian
Perfect. Thank you.

Carolyn Kiel
Rebekah, thank you so much for being on my show. You know, as we close out, is there anything else that you’d like our listeners to know or anything that they can help or support you with?

Rebekah Bastian
I mean, I think sharing OwnTrail with friends and sharing your trails is the biggest thing. I think our crowdfunding campaign might be closed out by the time that this goes live, but that is quite all right. But yeah, just helping spread the word. And remembering that there’s no one right path, you know, I would just hope to leave your listeners with with the confidence of knowing that we’re all on these wild winding journeys and you’re just staying open to possibilities can lead to some really cool things. So, enjoy that.

Carolyn Kiel
Wonderful. Thank you so much.

Rebekah Bastian
Thank you.

Carolyn Kiel
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