Skip to content

Blaze Your Own Trail with Rebekah Bastian

Listen to the podcast here

If you want to hear more about women helping women, this episode is for you! We explore the intricate lives that women lead -- with circuitous paths or “trails” that aren’t necessarily the most linear. In this discussion, Rebekah Bastian, whose personal and professional roles include author, tech executive, mother, wife and aerial acrobat invites women to help one another through mentorship, support and solidarity.

As the CEO & Co-founder of OwnTrail, Rebekah invites women to share their experiences, hopes, fears, and dreams as we connect with, support, mentor and lift one another up. We discuss diversity, inclusion, and how through community and collaboration we can change personal and professional dynamics for the better, shatter glass ceilings and achieve more.

Rebekah Bastian previously served as vice president of product, and vice president of community and culture at Zillow. She wrote the leadership book, Blaze Your Own Trail, is a contributor to Forbes and is a frequent speaker on social impact, career navigation and corporate diversity. Please follow the links below to learn more, and to create your OwnTrail.

Build Your Own Trail: https://www.owntrail.com

Blaze Your Own Trail, by Rebekah Bastian: https://www.amazon.com/dp/B07Y422NWF?ref=KC_GS_GB_US

Rebekah Bastian’s Linkedin: https://www.linkedin.com/in/rebekahbastian/

Support Care More. Be Better. https://www.caremorebebetter.com/donate Care More. Be Better. is not backed by any company. We answer only to our collective conscience. As a listener, reader, and subscriber you are part of this pod and this community and we are honored to have your support. If you can, please help finance the show. Thank you, now and always, for your support as we get this thing started!


Transcript

Corinna Bellizzi: Hello fellow do gooders and friends i'm your host Corinna Bellizzi a social entrepreneur who is passionate about social impact and sustainability, over the course of the last year we've all spent more time in social media than I think many of us would like to admit. We've used it to connect with one another and replace a lot of personal interactions that we were having before in person we've been living a zoom lifestyle. With happy hours remote from our friends and we've begun exploring new ways to connect that's what we're going to talk about today a budding enterprise that is helping shift that is helping shift the dynamics of how women connect with one another to network seek advice grow their tribes and build the future they want to. So, to talk about today to talk about that today i'm joined by Rebecca bastion Rebecca is a renaissance woman of sports, who is an entrepreneur a writer and artist a tech executive mentor wife mother and even an aerial acrobat. She's the CEO and co founder of own trail and previously served as the Vice President of product community and culture and zillow. Rebecca is the author of blaze your own trail she's a contributor to forbes and is a frequent speaker on social impact career navigation and corporate diversity and sort she's just the kind of person that we want to get to know welcome Rebecca.

Rebekah Bastian - OwnTrail: Thanks so much for having me.

Corinna Bellizzi: Now, before we talk about your company and your book, I want to hear about your activism path, ultimately, I like to better understand what really got you started and trying to have a stronger social impact.

Rebekah Bastian - OwnTrail: yeah it's it's a great question I guess it depends on kind of how you define social. And from from the standpoint of what we're doing with trail in terms of really to creating systems to support intersections array of women in the workplace and in their lives that's something that I think has has really blossomed for me as i've moved further until leadership and mentorship roles in my own journey. And just hearing about the different experiences that women have that and that tend to be very common in universal and I think there's a lot of systems at play that can impact our lives and everything from not seeing people who look like us in the places that we aspire to, and then how that can impact how decisions are made about our lives and what belief systems are held about us and then there's the. kind of the impactor effects of that has in terms of how we might feel like we're not enough for not getting it right that we're supposed to be following some some perfect path that we're not on. And so I think those observations and just hearing countless stories from women that have experienced and the impacts of some of those systemic issues is really what led me to. do work when I was at zillow from moving from product leadership into Community and culture, which was an organization that I started there and then what's really driven me to write my book and to start own trail as well and. you know I think along the way, and that's why I said depends on how you define social impact, but you know i've also been really passionate about just how. Technology and products can be leveraged to create social good and i'm solve social issues, and you know when I was at zillow I really channeled a lot of that into the housing and homelessness space, because that was so relevant to our core competency there, and now that I own shall we We really are lucky enough to be. Building a tech platform and a product that is centered on that that mission centrally as it relates to supporting women through their lives so it's it's exciting to think about the leverage that technology, plus impact can make.

Corinna Bellizzi: Well, I have to say i've spent a bit of time playing in your platform myself. And as a mom of two who's had a couple of bumps along the road you know just that life will throw at you. I found that building my own trail on the site got me to think about what i'm doing or where i've been and the things i've accomplished a little bit differently. And so I was actually more willing to share some things that I might otherwise not like I wouldn't put on linkedin or on my resume per se. I will give you a, for example, I had a very close friend to was killed in a random attack. And that was in the middle of this relatively new job I made the choice to leave it because I just needed to be in my Community I needed for my mental health and mental space to be home. And I found it liberating, to be frank, to be able to put that down on paper in a way, or in the digital paper space. To just kind of acknowledge that this was something that happened in my life that I had to work through that I think if anything. actually makes me a more rich individual and shouldn't take away from my career trajectory just because, after seven months of being at a company I needed a break.

Rebekah Bastian - OwnTrail: yeah it's so powerful and I completely agree like experiences like that make you a stronger they make you oftentimes more empathetic and compassionate and there's just there's. It gives you a new appreciation on on life and a lot of ways to, and I think that um you know that I think one of the things that we kind of discussed early on, is we're building own trail is, do we assign value judgments to these experiences, you know because. That is obviously probably one of the worst things that's happened in your life and so it's it's really negative, but then there's also positive effects that have come from that in terms of who you are and your your strength and your understanding of life as well, and so you know we decided know that we shouldn't have value judgments, because things can be you know, there can be two truths that the same time, or those values can change over time as well. And I really appreciate that you shared that and I think hopefully. That came from you know a lot of the hypotheses we've had around how we build on trail in order to create a safe place for authenticity and how that differs from a lot of the kind of winner take all dynamics that are commonplace on on most social media platforms so.

Corinna Bellizzi: Well, and visually when you look at your own trail it's not like there's a linear path right. So, like when you log on to the site you add these different experiences, you had through your life both personal and professional and it shows us kind of winding circuitous path, which is more like how actual life happens right. We don't walk in a straight line from birth to death really there's all sorts of things that happen in between, so I just think even from a visual perspective it's very interesting. So i'd like to know a little bit more about what drives the company and and what your vision is of own trail how it can serve the Community and help women.

Rebekah Bastian - OwnTrail: Yes, we have, we have a pretty big vision, you know it's we we are creating this peer to peer support system to have to help women support each other in our journeys and that support starts with the inspiration that comes from sharing our trails really owning our own narratives and seeing the trends of other women and being able to see the ones that may be matched your same identities or experiences millions, a way of seeing people that you identify with both in the situations that you might be going through right now, and the ones that you aspire to. And, and then building out the the ways that women can be deeply connecting with each other and supporting each other, we have. A peer cohort program called trail guides were women who really want to take that connection and working towards their aspirations to the next level can join together in groups of six to eight women that are that are carrying it based on really meaningful differences and some shared goals and values as well and that's that's a fantastic way so far that we're seeing for for women to really move from inspiration into action, as they support each other. But then we have this really big vision and also about changing the various systems that may have held us back and and part of that is in you know. Moving or shattering the glass ceilings that that wouldn't might be experiencing through the empowerment and support that they're that they're providing to themselves, and each other on the platform. But then also we're we're collecting this incredible data set of you know understanding what women experience in their lives and looking at that, from a really intersection standpoint of the different identities that we hold. And we can fill in gaps in data that are that have been there for a long time, and that really impact the way decisions are made are the beliefs, that are held. And when I was working on my book blaze your own trail I leave a lot of data into that story, and so I. Experienced firsthand how much data is missing or is you know, not even statistically significant or is biased, or you know there's just huge gaps there and so we're really excited that by creating this really impactful platform of story sharing that we can also provide that data in aggregate to change the various systems that impact us.

Corinna Bellizzi: Well, I think that's an important point something i've been thinking about a bit over the years, to which is the gender pay gap. I think, often the excuses thrown forward are that women choose jobs that are paid less than general like there are fewer women on an executive track as a, for example, and a lot of that has changed over the years, we have countries like Norway, where 50% of CEOs seats are occupied by women. And yet, in the American sphere that's let's just say far less far fewer women are lower percentage in those positions of power. I think, largely because of the fact that we have set up a system with a lot of excuses for example Oh well, it's because during her childbearing years she spent less time working, therefore, she wasn't climbing the ladder. i've heard all of these arguments from people that I know and respect in my life that honestly feel a little bit like their mansplaining to me, in some cases, and I really don't like that word but it fits here so. I just wonder if you could comment on that, and if you think that own trail could be part of the solution for that, from a data perspective, like gathering what really makes. This compensation pathways so different when women are earning at best 80 cents on the dollar to men, generally speaking.

Rebekah Bastian - OwnTrail: yeah I mean it's it's so it's so complex and so you know there's there's both the data around what women experienced in their careers, and you know there's a significant number of trails that experience that share having issues at work, and those are often times being. You know treated poorly or even you know, harassed in the workplace or being being overlooked for opportunities and promotions right and so those those are really commonplace and there's obviously the the bigger kind of societal issues that may lead women to certain careers that have different ranges and then of course we've seen very clearly this past year, what has been true for a long time, which is the the penalty that mothers experience in the workplace and how they're kind of the, the first to go when things get rough like the pandemic we've been experiencing here and.

Rebekah Bastian - OwnTrail: See the stats we've seen this year really celebrating and so that the data is one piece of it is just really understanding what's happening there, what women are experiencing and everything from you know milestones about self doubt and and the imposter syndrome which you know I think is is less of a syndrome and more systemic issue. And, and you know everything to kind of the experiences that we have really tangibly in the workplace. And so yeah being able to highlight that data is one thing, but then also you know, creating that support system for women to really revisit well. What is it that I really want right because that's that's kind of the first question is that sometimes we think we're supposed to be on a certain path where we're supposed to be in a certain place in our lives and it's. You know it's not really serving us and there's so many familial and societal and other forces that kind of lead us in directions that that aren't the best for us oftentimes so really understanding what you want, but then also having the. The confidence and the the bravery to go after those things that we really want and that's something that a strong support system and a framework for moving from that inspiration into action can really help drive and so that's that's we're trying to kind of tackle it from from both ends of the problem there.

Corinna Bellizzi: So it sounds like you're creating a platform that also cheerleaders women.

Rebekah Bastian - OwnTrail: The cheering each other, you know the the connections being made, particularly in the travel guides cohorts and but also you know we've been rolling out more features recently just on the free platform as well for connecting and having conversations and sending messages. But and it's it's amazing the power that comes from women supporting each other and from you know both the solidarity of our charity experiences, but then the inspiration from seeing all the different paths that other women have taken to get where they are.

Corinna Bellizzi: yeah, so I would like you to dig a little bit deeper for me and talk about these cohorts and how they're run. Like one of the questions that came up for me is, is there a particular person that's nominated as a leader that's running that cohort is that. Even an employee of own trail, or is it just another person from within the Community, it just be helpful to I think understand what that looks like.

Rebekah Bastian - OwnTrail: yeah so we just launched this at the end of last year, and so we have five cohorts that are currently running and right now we are facilitating them ourselves my co founder katie and I are day with facilitation we came up with the the framework and the activities, with the help of a woman cheyenne Chen who. has done a lot of great career coaching frameworks and. And kind of digging into the neuroscience behind a lot of coaching and so she helped us create. Both individual activities that that women reflect on and do themselves and then group activities for bringing those reflections back together with with other Members. And so yeah we're facilitating them now, but we're actually exploring kind of what this looks like as we scale it, because what we're realizing is that the most impactful pieces of the program are. The activities and conversations that are happening and the connections being made and so we're looking at having more of a peer guided kind of model and and even self guided options going forward.

Corinna Bellizzi: It sounds almost like some of my MBA courses. So you know you do activities you come together, you discuss projects and things like that, too, so.

Rebekah Bastian - OwnTrail: An hour in and kind of the fluctuating between individual and reflection and activities and then the group sessions as well, and being able to switch back and forth between those can lead to some really interesting ideas and experiences.

Corinna Bellizzi: So I had an experience, just yesterday, since launching the podcast i've had a variety of people reaching out to me who are interested in social impact in some way right and this one woman just sent me a note on linkedin and she said to me, you know i'm struggling finding my path. I feel like this is what you're doing is what I want to be doing, but I don't know how to approach working in this space i'd really love for you to take some time with me and perhaps we can discuss it through. And it just seems so of the moment and so perfect for this conversation today because I think that often it's really intimidating to reach out to somebody in a space. That comes from a position of power or experience, where you feel like well heck they're just going to say no, or i'm never going to hear back. But the reality is it never hurts to ask right. And it just reinforced, for me, the need for something like own trail out there to help empower women to be a part of that to understand that this is a platform that is essentially built to enable you to build your own track and reach out to other women who might have had similar experiences, or who are living the life from the outside of what you'd like to do or we're doing professionally what you'd like to do.

Rebekah Bastian - OwnTrail: yeah and that that exact scenario was a big part of what drove us to to build on Shell, which is that. And you know and that's great that she reached out to you and and that you're open to sharing your experiences with her and the truth is that your path to where to where you are right now is one of you know, an infinite number of paths, probably, or at least a really large number of pattern to where you are so her learning about your story, yes, is valuable, but also she should see She should be seeing a lot of different trails that lead there in order to really both realize that there's no one right path there and to blaze her own. And you know you can say yes to every coffee chat or question like that, but what you end up doing is kind of telling the same stories and. Life lessons over and over again, and so that in itself isn't as scalable right, and so the idea with own trail is that. And you can put your chill out there, she can see that she can learn about your overall journey and then, when you to do talk she'll have really specific questions about that, instead of spending the time with just the kind of overview of your path or she asks you those questions on own child and your answer might be able to reach countless other women that had a similar question or that that would have been wondering that you know.

Corinna Bellizzi: So are the questions and answers, then on trails are those public or do you set the settings for those.

Rebekah Bastian - OwnTrail: yeah so the conversations on trails are viewable by everyone that has logged into own trail and and then we also have private messaging now so if there's something that you know really more personal that she wanted to ask you about your trail and kind of. Take it out of the public view, then, then you can do that as well.

Corinna Bellizzi: cool so I know you're in beta right now. But you're really getting ready for this next leap and growth, with new investors on hand, and so I just I would love to hear a little bit about how you've measured success as you get to this point. And how you for see the next couple of years, playing out how you'll measure success as you continue forward.

Rebekah Bastian - OwnTrail: yeah and we actually just had our one year birthday so maybe we should it might be time to take it off soon you know it's like when you have a huge vision and you're working on pieces of it is time it's like wait it's not the full thing yes it's um but yeah you know the vision really is scaling out we've been growing fully organically, which has been really powerful because everyone that that ends up on it and trail is really excited about the the vision and what we're building and really into this authentic sharing that that we're curating here and we're really excited to grow out what is essentially this content based network. And and turning it in Thomas kind of a neural network of life paths that is really the foundation of the connections being made and the support being generated by all of the women in our Community and so, you know, moving more into the kind of data science piece of it, as we understand how all these trails relate to each other and how our experiences, you know what I can be the most relevant or inspiring or kind of solidarity, giving trails or experiences to your own and how do we connect people in really meaningful ways where it's not trying to rack up the most likes or followers but it's really about connecting over those shared experiences in a really authentic way. And so, you know as as we grow over the next several years where it's it's really with that, as our North star is growing the stories deepening the connections and then really moving into action, as women navigate their their journeys together.

Corinna Bellizzi: yeah so one of the things I noticed in navigating my own trail, for example, is that there isn't like a space for dates. And I first was like well why would you leave dates out entirely because there's no endemic space to say Oh, I was at this particular. Job from this time to this time, so I I realized and even thinking that through that it was probably intentional. So I wanted to get your viewpoint on how you've architected the type of information you encouraged to be shared on the platform and why you might leave information like that out.

Rebekah Bastian - OwnTrail: yeah so the dates when we actually went pretty deep on this discussion we kind of the reason that we were leaning towards no dates, but at the end of it is that a lot a lot of times we don't remember specific dates and things more in chronological orders, you know just less of a mental barrier to get the milestones out onto the trail and and then also it's it's a level of information that's not necessarily as helpful and understanding someone's journey but can disclose more kind of like agent timeline stuff that that people don't necessarily want to. And at the end of the day it was actually not a completely. clear decision to us, so we did what we do a lot of the time which is we've been really intentional from the beginning about building out this community in this movement with the the women that are part of it, and not for them. You know, we see it as really a Community effort, so we have a lot of channels in place to ask questions and get feedback and discuss questions like that, and so we put it out to our Community and there's a pretty resounding. Answer yeah we like it without dates and so that that was kind of the deciding factor there.

Corinna Bellizzi: Well, I like that I also think that led me to be more open to share a job that otherwise might have left off my resume. As a, for example, right like well, I was here and then this big thing happened and I needed a break so. I think that's really kind of lovely I also as a 40 plus women look at my you know history of employment and I start to consider Do I need to include the year I graduated from my undergrad school. Do I need to include more than the last 10 years of work experience I don't want to seem like an old hag.

Rebekah Bastian - OwnTrail: I mean it's so funny too because it's like some some more recent say career milestones might feel less impactful to you, whereas like you know, I was bartending and a dive bar when I met my husband and I put that on my child and that was you know 20 years ago, but that was a very painful very momentous right. Job For that reason, and just because of like the experience of bartending and undergrad yeah. So that one made it on, and so it doesn't have to be like, and I think that's that's kind of the the mental space that we're in when we're creating a resume oftentimes is like, will you put the most recent things. You know you put more more effort or more highlighting is in the most recent things and that's not always you know, looking at the trail of what's what's brought you to where you are that's not always the rubric for it.

Corinna Bellizzi: You see, now I need to go back and update in on my archaeology digs and stuff like that — you know this stuff I did an undergrad the the idealistic path of as a child wanting to essentially be Indiana Jones and then pursuing it from an educational perspective. And realizing I wasn't independently wealthy who's going to pay for my PhD this isn't something that gets a lot of funding.

Rebekah Bastian - OwnTrail: Well, and I think that one of the things that can be so inspiring to others also is to say, like to be able to see This is where I thought I was headed, and this is where I ended up and they were totally not in line with each other and i'm so glad it turned out this way or you know or not, or whatever it is, but I learned from it and I think that you know when you look at kind of initial aspirations and then where they went and seeing the non linearity there can be really powerful.

Corinna Bellizzi: Well, it just reminds me to have when I was having to make an argument to my parents for the degree path they wanted to pursue. At that time I wanted to be an English major and just go pursue academic studies and literature and my dad was pushing hard for something a little bit more practical, he said, what about biotech you love biology i'm like when I hate math. So the compromise was anthropology which led to archaeology which is you know really kind of bridging towards the sciences, because I studied forensics and physical anthropology and all that, but then, what do I do when I graduate. I went into sales i've led multinationals sales teams, I was able to pay off my college debt, the thing that he was most concerned about by being in a completely different work environment that ended up being my reality right. yeah so it's I think so true that there is just no path is exactly linear and the people who pursue life that way, perhaps are telling that story on linkedin perhaps or telling that story on own trail but i'm betting that there's a piece that isn't being told.

Rebekah Bastian - OwnTrail: yeah or you know, a piece that you wish was there, too, I mean it's definitely it's possible to follow and mostly linear path, but oftentimes it's because we're we're not staying open to the other possibilities that that might have been more fulfilling so yeah.

Corinna Bellizzi: So if i'm to take the 30,000 foot view with you in your ideal world, what is the impact that own trail would have.

Rebekah Bastian - OwnTrail: You know I want I want angel to be the place where women go to get the support they need across their personal and professional lives, and I want the systems that led us to start our own trail, to begin with, you know the inequities in the workplace or in the home or you know, particularly looking at at the different identities that women hold I want those to become more over time because of the impact that we're making with own trail, but the support will always be needed and relevant and just really growing into that.

Corinna Bellizzi: That's really beautiful So how are you now, as you get this lifting off the ground floor integrating some of that earlier work and diversity and inclusion and just ensuring that that path stays constant with the company.

Rebekah Bastian - OwnTrail: yeah I mean you have to be really intentional about creating intersection of spaces, especially when it's you know kind of a space for women, because what often times happens when you're not intentional about that and it's and you know if there's white able bodied and heterosexual SIS women especially working on a company, then it can end up being a very narrow range of women that it's serving and so we've been been really intentional from the beginning about. And how we hold space for different identities and use those to really enhance the platform and in terms of that kind of seeing people who look like you goal that we have.: And, you know, in the way the partnerships that we create an outreach we do in terms of the woman that we're reaching and so and we're really happy that we have you know essentially more diverse women on own trail than the US population overall right now so it's about 50% women of color and about 15% LGBT Q a identifying and. From 44 states and 27 countries right now for the trials that have been published and then you know we just raised around and our CAP table is is equally diverse and. And you know we're focused on on building out a diverse team so it's. It all takes intentionality but then it's also all very doable you are intentional, you know so and especially when when you're applying that lens from the very beginning, because obviously when when larger companies are larger platforms suddenly say Oh, we just start caring about representation, then it's it's a harder thing to do, but you know when when you're focused on it from day one, then it's.

Corinna Bellizzi: You know I mean they'll rewrite it to just say oh it's one of our core values. And nothing is changed.

Rebekah Bastian - OwnTrail: yeah.

Corinna Bellizzi: No, I hear that so being a platform for diversity and inclusion, I understand it's really geared at women now, but do you foresee a day when it would be for everyone for all sexes and genders.

Rebekah Bastian - OwnTrail: yeah I think I mean it's it's an interesting question that comes up pretty regularly. And I think that having a centered space where identities that have particular experiences, or that are less represented in environments that they're in is really powerful. And so we are focused on women, and you know all all intersection ality of women, to begin with. And that could move, I think we probably you know if we expanded to all genders, we probably still be centering different identities that that needed that centered space and I don't know, and I mean we definitely hear from a lot of men that they're interested in it as well, because I don't think that non linearity in our padding is gender specific and certainly the desire for more authenticity is not gender specific, but there are experiences that. That are unique to to people who identify as women and having that kind of safe centered space, I think, leads to more authenticity as we're seeing and and, of course, being 50% of the population means it's not a super.

Corinna Bellizzi: niche audience either so yeah but you know, at the same time it's also the website and the platform is own trail that seems gender neutral. Yet I mean I totally get an 100% agree that we as women need a space to be able to feel completely safe and like there isn't. Some of the judgment that often can come from the outside of Oh well, what you experienced wasn't sexual harassment or it wasn't this and really you need a safe space, I think, to to feel like you can be very open.

Rebekah Bastian - OwnTrail: yeah exactly and and and you know, like you said it's it doesn't the name the branding all of it like we're very intentionally not being the like pink washed girl boss kind of a. platform. Like that, obviously, is for a small subset of women so we've been intentional about that as well.

Corinna Bellizzi: Well, I would love to invite you to say a few words before we wrap this up if there's anything in particular that you just want our listeners to come away with to resonate with to remember, as this kind of core is they carry on with their days.

Rebekah Bastian - OwnTrail: yeah I mean, I would just say that you've got this you know there there, there is no one right path and you're not alone in in the experiences that that you might be going through right now and we're we're stronger together, and I would definitely love for your listeners and. All the listeners that identifies women to share their trails on trail.com and for everybody to you know reach out to the women that inspire you and encourage them to share their trails because it there's there's just so much inspiration that comes from seeing those really authentic journeys.

Corinna Bellizzi: Well that's a lovely way to close, I have a few words i'd like to share and then i'd like to invite you to stick around for a little bit, so we can connect.

Now listeners today we invited you to forge your own trail and actively pursue your best life part of that is taking action for things that you care about. As i've often said it doesn't have to be huge it could be as simple as building your own trail on own trail calm and offering your support to another woman who wants a little encouragement or to hear from your experience. Really it’s just getting started, you could share this podcast with people in your community and who you think might be other do getters that just need a little encouragement of their own. To find suggestions for actions you can take you can visit care more be better calm there you'll find an action page where i've dedicated a section to causes and companies that are worthy. I invite you to join the conversation and be a part of this Community, you can follow us on social spaces at care more be better or just send an email to Hello at caremorebebetter.com. Now this podcast is not backed by any company, if you like, what we're doing and can afford it, you can support the show by donating directly on our site or by subscribing as a patron on patreon just visit care more be better calm and click the donate button Thank you listeners for being a part of this pot in this Community because, together, we really can do so much more.