Sam talks with Rebekah Bastian, CEO & Co-Founder of OwnTrail, author of “Blaze Your Own Trail,” and leader of the AuthenTech movement. She shares key milestones on her professional and personal journey that led to an entrepreneurial leap, the compassion and depth associated with a re-imagined social platform, and her mantra of “trust the process.” Rebekah reinforces two important reminders that life isn’t a linear path and we’re better together.
Sam Ushio (00:07):
Welcome to Ikigai Stories. I’m Sam Ushio. The goal this podcast is to people who attention working hard to actions with priorities, and ultimately to provide a platform of inspiration for those seeking to live a life rooted in purpose. Rebecca Bastian is the CEO and co-founder of Own Trail, a female focused platform designed to visualize and navigate unique paths in life. The content based network is reimagining the idea of a social network by creating authentic spaces that foster connection on shared experiences, not a friend or follow account. Most important own trail acknowledges and celebrates the fact that our personal and professional lives are intertwined and that life isn’t a linear path that we often perceive in others, and consequently forecast for ourselves. Rebecca’s personal journey underpins the own trail ethos of authenticity as demonstrated by key stops along her trail. A highly successful 15 year career at Zillow, including vice president of product and vice president of Community and culture, started with a Craigslist ad when she asked yourself the question, why not try, what’s the worst that can happen?
She shares that her academic career began by failing out of college, but ended with an undergraduate and master’s degree in mechanical engineering from the University of Washington and the University of California Berkeley respectively. Rebecca’s resume is nothing short of impressive, but what’s most impressive is her mastery of the growth mindset combined with a clear commitment to creating authentic spaces that inspire others to discover their very best. As Rebecca pitched investors for Own Trail’s capital raise, she found difficulty in describing the company’s category. They’re not FinTech or health tech or ed tech. And that insight served as a catalyst to create a new category termed authentic, a movement that prioritizes community over audience intention. Over attention and value over profit. Over 100 companies have joined the authentic movement, including two organizations from prior Ikigai Stories episodes. Pop Smart Kids with CEO Priyanka Raha and Supporti CEO Brigette Granger.
The authentic movement is inspiring and in an era where headlines talk about the negative impacts of tech technology, authentic showcases, companies that are leading a new era of tech aimed at positively impacting society. Before we jump into this amazing conversation with Rebecca, a quick note on an exciting offering coming your way in 2022 from Ikigai Lab, two thirds of Americans are rethinking their purpose in life because of Covid 19. According to McKinsey, people are hungry to reconnect with their true self and forge relationships with others who are seeking to live with greater intention. Experiences by Ikigai Lab are in person events, immersed in nature, intentionally designed to provide participants with time to reflect on their journey, connect with a purpose driven cohort, and create a custom Ikigai Roadmap experiences range from one day retreats to multiple day excursions, all hosted in the natural wonder of the Pacific Northwest.
Each experience integrates the Japanese concept of moai, values-based cohorts designed to provide support and accountability during and beyond the event. Each experience is limited to a maximum of 16 participants and includes one year’s access to the Ikigai Lab community. The first Ikigai Lab retreat will take place on Friday, April 8th at the University of Washington’s Center for Urban Horticulture at Beautiful Oasis immersed in Northeast Seattle on the shores of Lake Washington. More details on experiences by Eki firstname.lastname@example.org. Now, please enjoy this episode of Ikigai Stories with Rebecca Basian, CEO and co-founder of Own Trail, Leader of the Authentic Movement and an inspirational human being teaching us all how to live with more intention and authenticity. Rebecca, thank you for being here on Ikigai Stories.
Rebekah Bastian (04:38):
Happy to be here. Thanks for having me.
Sam Ushio (04:40):
Yeah, absolutely. So I’m really excited to have this conversation with you. I think there’s a, a, a lot of initiatives and efforts that are underway that really bring to life the philosophy of ikigai that you’ve, you’re doing currently you’ve done in the past. so I’m really excited for this conversation, really grateful that you’re spending some time. And would love just to start off with own trail, if you could please just share with the listeners what is Own Trail?
Rebekah Bastian (05:13):
Yeah, So Own Trail is the startup that I’ve been building for the past couple years, and it is a platform for women to visualize and navigate our life paths. So the visualized part of that being the trails that, that we share on own trail. And those are a really authentic view across our personal and professional lives into the milestones that we’ve experienced thus far, and those that we’re working towards in a way that’s like the things that have really made us who we are. So it’s not the picture perfect end results that you might see on social media or LinkedIn, but it’s like, what, what has our journey really looked like in a really vulnerable and authentic way? and so women share and own our stories through those trails and find connection and inspiration from each other’s trails. and then the, the navigating life part of that really comes in as women are supporting each other through those journeys.
So women can ask for help from the community on a milestone that they’re currently navigating or that they’re working towards. And then the community rallies around and helps in the forms of, you know, experience, resources, connections, opportunities. it’s, it’s been really cool to see that unfolding. And so it’s really this platform for both connecting and sharing authentically, but also like getting our aspirations done, like making things happen and lifting each other up in a way that, you know, ultimately can create this kind of ripple effect of of change for how women are able to, to, you know, grow our lives and the belief systems that surround us. So that’s, that’s the big vision there and and it’s been really fun to be working on.
Sam Ushio (07:00):
I love it. I love it. so own trail has been in existence. When did, when did things start?
Rebekah Bastian (07:06):
We launched in February of 2020, which you might remember from when the pandemic launched as well. <laugh>, so
Sam Ushio (07:12):
Right. You just had a little bit of a head start. Yeah,
Rebekah Bastian (07:16):
<laugh>. Yeah, exactly. So it was, it was interesting timing, but actually from a business standpoint, I think we’ve had some tailwinds just because, you know, it’s about helping women make it through hard things, which there has been no shortage of the past couple years. and it’s and it’s fully online own trail.com. And so, you know, as, as people have been physically from each other, in a lot of cases, it’s been a way to kind of digitally connect more authentically.
Sam Ushio (07:45):
Yeah. So there’s, there’s a a lot to unpack there, both just launching a business right before the stay at home orders, a quarantine orders kicked off, but then also being a very purpose driven, mission driven organization. can you talk about both of those? Just maybe what it was like launching right before the, the world stopped? Yeah. And then also how has the community rallied as a result of just all this transformation that’s happening?
Rebekah Bastian (08:18):
Yeah, absolutely. I mean, I think so, you know, I gave, I had been at Zillow for 15 years before this and had a great career there. And <laugh> gave my notice in January of 2020 that I would be leaving. I didn’t actually get fully out of there until April. There was a, an off ramp period, but I left because of trail and because I was really excited to, to be going all in on this. I think if I had known what was coming, I would’ve been scared to give my notice, you know, cuz there’s so much uncertainty there. but I’m so glad that I did because I think I’ve, I’ve, I’ve had this level of fulfillment and purpose and excitement during, you know, the past year and a half, whatever that’s been that has really kept me going and, and kept me, you know, optimistic in some ways.
And I think the optimism really comes from the own trail community, which has been, you know, just so much passion and authenticity, which is, you know, I keep bringing that up cuz that’s really at the core of what we’re building. But and, and excitement for really building this with us. You know, we see Owen Trails being, you know, we’re providing this space room and to be sharing stories and connecting and supporting each other, but it’s the members of the community that are really like creating that. And and the community’s just been phenomenal. And I, you know, on a personal level, I’ve just gotten to meet some of the most incredible women through this whole process and continue to do so, which is really cool. so I feel like in a lot of ways the, the timing has been right, Like, you know, I think we’re, we’re at a time where more and more people are kind of aware of and rejecting the toxicity that comes from mainstream social media and looking for a place to be more, more authentic, more real you know, less commoditized. Like we will never have an advertising based business model in Agile. We refuse to commoditize the numbers of our community. And I think that that really shows in the, the way that we create the different dynamics on there as well. And so I think the combination of people being digital first in a lot of ways and and really looking for the values driven space to be connecting in real ways has, it’s been the right timing.
Sam Ushio (10:38):
Yeah. So was there a point where on the, like Postlaunch where the community was really galvanized, where it was clear that timing actually was per perfect or very close to right, because this is what the community needed.
Rebekah Bastian (10:55):
I mean, we didn’t have it before to compare it to <laugh> and so Yeah. You know I think so. I dunno, I mean it’s, we’ve been growing so organically we grow through word of mouth of women telling their friends about own trail. And so it’s not like there was like some big step function. I think the biggest step function probably was when we introduced Help Beacons, which was a couple months ago. So cuz what we’ve been hearing from our community was like, Wow, this is really powerful to be able to own my story in this way that I never had before. And to be able to see what other women’s paths have really looked like and now what, you know, cuz it’s kind of like this almost like, kind of, it’s powerful but kind of passive, the experience of sharing and, and connecting in that way.
And so once we introduced Health Beacons, which was like ask for help for the community, from the community for what it is that you’re working through or towards and, and get that help and being able to, to support each other in that way, I think that was really like kind of the, the step function in terms of that aha moment of like, Oh, this is, this can be, you know, this is kind of, you know, it’s the action that I need in my life and it’s the support I need in my life. And so it kind of, I don’t know, I feel like there’s been something that kind of clicked with that release and that continues to happen and there’s a, a new level of vibrancy and just getting done like <laugh> when they’re helping each other achieve their aspirations here in really powerful ways. And so that’s been really cool to see.
Sam Ushio (12:20):
How about authenticity? So, so I, so I had the opportunity to check out your own trail, which is, it’s incredible. I mean, I, I I love how how, you know, you make a a you make the point within own trail that nothing’s linear. Like life just isn’t linear. Like, there’s this photo montage that we see and everyone thinks, well, you know, it was abc. but I, what, what I love that you point out is like, it’s a, and then you jump over to F and then you go over to s and like, there’s this, it’s a, it’s sometimes a bumpy road. so I love how you’re modeling authenticity by putting yourself out there and saying, here are the different paths along the journey, which I’d love to, to kind of break down here in a minute. But in terms of fostering authenticity within a community mm-hmm. <affirmative> how do you do that and how does that, you know, it, how does, it’s easy to say it’s sometimes hard to execute. Yeah. So how, how do you execute on bringing that to life?
Rebekah Bastian (13:22):
Yeah, I mean, step one is safety, right? So creating a space where, like I mentioned, you’re not being commoditized. That’s like, you know, <laugh>, that’s table stakes right there, right? Like, what I share isn’t being used to then sell me to advertisers or whatever, right? because I think that those dynamics, like, that’s just prohibitive. you know, the fact that we’re centered on women and very intersectional in terms of the multiple identities that women hold. but having that centered space, I think creates an extra level of safety and, and space for kind of the shared experiences that that span a lot of different women’s lives. and we, I mean, we have a lot of like safety tools built in, Although to be honest, we haven’t really had to <laugh> to do much with them yet. It’s been organically free trusting kind of space.
But I think the biggest dynamic that we’ve seen happening is that the level of authenticity and thus the implied trust in sharing authentically has gone up over time. And and I think what’s really happening there is that authenticity leads to more authenticity. Like if you look at my trail and you see that I’m sharing really vulnerable moments in my life, then you feel like, Oh, this is, and then you look at, you know, a hundred, a thousand whatever, more trails and see the same thing, then you’re like, Oh, this is a space where people are sharing this way. I feel like I can do that too. yeah. And then also, you know, know, I guess there’s other kind of mechanisms like women can use their real names or anonymous screen names depending on what, if they’re comfortable having what they’re sharing tied back to their, their identity because it’s, we think of it as a content based network as opposed to a profile based network.
It’s not about like having the most friends or even needing to like know what your friend’s name is, whatever, because it’s like we’re connected based on shared experience, not on our, our friend or follower account. and along those lines, like when you show appreciation on someone’s trail, that’s a private not of appreciation. It’s not a public like, so like all of the popularity contest dynamics and the winner take all kind of dynamics that happen on social media, like we’ve intentionally tried to build different dynamics in those because we know that those are things that really squash authenticity. And so we look at, the way we measure this is we look at the number of, the percentage of trails that have what we consider to be vulnerable milestones on them. And that’s gone up every time. And we look at the percentage of trails that have both personal and professional milestones intertwined because you know, in a world where we’re asked to compartmentalize the two, showing them all together is also an active authenticity.
and that is really high and gone up over time as well. And then just the, the number of milestones for trail, so like the amount of information that you’re sharing has also gone up over time. So those are kind of our indicators for for that. And, you know, our belief is that like we can, you know, achieve all the kind of traditional startup milestones in terms of, you know, like traffic and engagement and all those things. But if we don’t have trust and authenticity high and remaining high throughout, then we’re not doing it right. And so that’s really kind of at the core of, of how we’re looking at success.
Sam Ushio (16:34):
I love it. I love it. Yeah. So you’ve got, you’ve got clearer metrics that you’re focused on in terms of just measuring authenticity and vulnerability. those, those, Well, and there’s, there’s a couple things that you said there that really resonate. So the, you know, the interconnection between personal and professional and those worlds, we historically, I think we’ve tried to keep those worlds separate. And I put on my personal hat when I’m home and then I take that off and put on my professional hat. And realistically that’s just not the case. That’s never been the case. so honoring that and depicting that on a journey, love is outstanding. The, the, the vulnerable milestones. Do you call ’em milestones? Yes. The vulnerable milestones. Do the users know that those are, I mean, they probably know like, okay, this is something that’s very vulnerable, but is it identified that they know that this ist a vulnerable category?
Rebekah Bastian (17:34):
No. Like we had, so each milestone has, you can you select, there’s a category and then there’s subcategories for those. So we’ve just kind of like, this is more like how we view internally. So like, for example, Yeah. a milestone around harassment or discrimination or a milestone around infertility or you know, relationship issues like those, we’d consider those to be vulnerable milestones. And those are the categories. So they know what category they’re selecting and then we kind of know that which ones tend to be more kind of vulnerable sharing. Yeah. Yeah.
Sam Ushio (18:06):
Okay. Okay. so I think the catalyst to move into own trail was the book that you authored. Yeah. can you talk about that, that book, cuz you wrote that book while you were working at Zillow, you were working in, in corporate. Yeah. can you just talk about that book and how that was a springboard into own trail?
Rebekah Bastian (18:28):
Yeah. Yeah. So my book is called Bla Your Own Trail. And it is I don’t know, for, for you or your listeners if you know that choose your own adventure books. It’s like a childhood book. Oh
Sam Ushio (18:39):
Yeah. Love those <laugh> love those.
Rebekah Bastian (18:41):
So it’s that format. It’s you know, you’re reading it in the second person, you’re the one going through the experience, and then 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 this big decision tree. There’s 19 different endings. and it’s exploring the different decisions and pathways that women take through our personal and professional lives with the idea that there is no one right path. So, you know, my, I guess the inspiration for the book really came from years of conversations that I’ve had with, with women that, you know, as I’ve been in different leadership and mentorship and friendship roles that there there’s this kind of common thread of feeling like we need to know where we’re going and how we’re gonna get there and we’re scared we’re gonna get it wrong, you know?
And so and my message is always like, you can’t get it wrong. There’s no right, right. <laugh>, there’s no right path. And so, Right. the book was really trying to kind of experientially bring that home. and I weave a lot of data into it as well that trying to create like a sense of solidarity. Cuz another thing I’ve observed is that oftentimes we’re going through things that don’t get talked about as much. Maybe they’re taboo or like they haven’t been normalized. And so we feel like we’re the only ones that are experiencing that when in reality there’s, there’s so many different people that are experiencing that same thing. So through data I’m able to be like, Okay, this is happening to you right now in the story and FYI, X percent of women go through this in real life. You know, so like kind of making you feel less alone in some of those things.
so yeah, that was the book and it was really fun to write and definitely had no intention of turning it into a company or leaving my job <laugh>. But what happened was I had signed with a publisher Barrett Kohler, who was great. And there’s like, you know, a year period from when you signed the contract to when the book comes out. And so I was playing around with what I thought was gonna be a really cool book launch website. I’m like, Oh, we could do something cool where women kind of share the trails they’ve blazed or whatever. And as I started thinking more about it, I just realized there was, there’s a, there, there, you know, in terms of the power of seeing people who look like us and the places that we aspire to and the power of really owning our stories authentically.
And just, you know, kind of questioning some of these norms around the ways that we kind of compartmentalize and filter ourselves out, you know. And so I met my co-founder Katie around that time and also brought on our VP of engineering, Carolyn, around that time, and she was an old friend of mine. And the three of us ended up quitting our jobs that we loved and to, to fill this out <laugh>. So it was kind of that accidental entrepreneurship thing. But we, we definitely felt like we can’t not do this. Like we, we’d gotten far enough into kind of visualizing what this could be that we’re like, no, I mean, like for me personally, I was like, this is literally the thing I was meant to do. Like everything I’ve experienced so far has led to this and just can’t not do it. And and zero regrets. It’s been a, a really fun experience so far.
Sam Ushio (21:44):
Yeah. So can you unpack that point right there? Just that, or the, the point about you know, it, it was calling you, it was pulling you, it was, and eventually you had to answer that call and say, Okay, I’m gonna take this step and I’m, I’m gonna do it. cause I think especially right now in, you know, where we’re at in the world, I think a lot of people are recalibrating just their path. and putting a lot more thought into what am I doing and why am I doing it? Mm-hmm. <affirmative>. so can you just unpack that a bit? Like, you, you, you were getting cues from the book and from you know, readers in the audience and everything and the universe and, but what was, what was, at what point did you take that step? Like what was that catalyst for the step? Yeah,
Rebekah Bastian (22:33):
I mean, so I’ve actually, I have many stories like this in my life where I’m doing things on the side for a while and taking more and more steps of growing them. And then there’s just kind of this like moment where like the thing on the side can’t just be on the side where I’m like, this is a thing. But I think, you know, sometimes it gets referred to as like the side hustle, which I have mixed feelings about just that phrasing. Cause I’m not a fan of like hustle culture, but I do think that there’s something about, like, you don’t always have to be like, Oh, I have this idea and I’m gonna a hundred percent pivot into it right now. You know, like, I think by working on things on the side, you can prove to yourself that it’s something that you wanna be doing.
You can prove to others that it’s something that can work, right? yeah. And you can get enough experience and traction that when you do decide to make that full pivot, like you’re not just blindly jumping off of a cliff. And, you know, I did that, you know, I think early on at Zillow I did that with building our first mobile apps on the side with, with some really incredible developers. I did that at Zillow, creating the community and culture team where I’d been doing years of kind of side work in that space and then decided to go from VP of product into creating this new org. and I definitely did that when launching own trail where I’d just been, you know, working on this incrementally on the side. And, you know, there was for a while in my head kind of thinking like, this could be on the side forever, this could be like a cool project I’m doing on the side.
And then I definitely did have a kind of an epiphany moment, I guess, where I realized that like there’s kind of this self-fulfilling prophecy where if this did stay a site project, then it has a lot less likelihood of really ticking off and being impactful than if I went all in. And so and by the time I had that realization, I’d already kind of we’re already building it and we already had like a team formed around it and it was, and, and the team felt the same way that I did, you know, <laugh>. So Yeah.
Sam Ushio (24:21):
Rebekah Bastian (24:21):
Helps. Yeah, totally.
Sam Ushio (24:24):
Yeah. so, so a so maybe if we shift gears a bit cause it’s, I’m kind of going and jumping all over the place, not in, not in a linear order by any means. I’m here for it. So blaze your own, right? It’s your jam, right? Yeah. Blaze your own trail and led to own trail. And then now can you talk about authentic, the the authentic effort and, and what that is and what that looks like today?
Rebekah Bastian (24:53):
Yeah, definitely. So, yeah, another side thing <laugh>, there’s a, there’s a theme which is so okay with own trail, I guess this, this largely came up for me from a fundraising perspective, which was that you know, as we were raising our oury round with Own trail and you know, which is totally a numbers game, and you end up reaching out to a lot of different investors and stuff, and there there’s kind of these check boxes of like, what type of company are you? And I didn’t really feel like I fit into any of the check boxes. Like, I think probably the closest one that, that, that you, that I might pick would be social media. But like we see ourselves as the antithesis to social media. Like I don’t wanna be in that check box, you know? Yeah. And so I started talking about this idea of, I just, I’m, I loved puns, so I came up with this name Authentic, which I’m like, it’s a new kind of tech company that is like community driven, right?
And it’s about like, you know, kind of network effects of community, like social media, but it doesn’t commoditize people and it’s really values driven. And yes, it’s profitable companies, but also we’re not compromising people’s mental health or like, so society’s ability to function in order to to, to reach those points. And so, anyway, I was talking about it kind of on Twitter, and then I wrote an article I write in Forbes. So I wrote an article in Forbes about authentic. And and what happened was like all these different founders started reaching out and being like, Hey, I didn’t feel like I had a name for what I’m building either. And this is totally it. Like, can I be authentic? And I’m like, Sure. It’s, you know, I just made up a word, you know, So, but but there was some really good energy there and really, really cool founders and companies.
And so I created a Slack channel. There’s about 150 founders on there now and really innovative, like you all different like industries and verticals and, and business models, but they all really share this kind of value driven, people centered kind of approach to building tech companies. And and so that’s really cool. Like we, we, it’s a very supportive community. We ta we message them and Slack, we do kind of regular meetups online. and then I started thinking about like, okay, well what could I be doing with this community where there’s all this like energy and, and stuff here and still figuring that out. But so far what I’ve been doing is because like one of the common threads of like where this community could use support is finding the right investors. Because similar to my experience, which I’m very lucky that so far we have found incredible investors that are very value aligned with us.
But it took a lot of work to, to find them. And so I was thinking, well, if there’s investors out there who are excited about this type of company, then I could just like, you know, we could create our own little ecosystem in ways. So I have a list of, I think about 75 investors right now that are excited about authentic companies. And so every month I send out a deal flow email to them of all the companies that are currently raising from this community and make connections. And it’s just, you know, it’s, it’s low overhead, but it’s been a really cool way to support that community, learn more about the investment space myself, cuz I have an aspiration of investing in underestimated founders that are building a onset companies myself someday. And have started writing some small angel checks around that as well.
So it all feels like it’s it’s, it doesn’t feel distracting from what I’m doing with Unroll. It feels very additive because like having, like anyone who is building a company knows that having a supportive community of founders that are also going through it at the same time as you is crucial for both mental health but also just like networking and idea generation and stuff. So that’s been really helpful and and I think, I mean, I’m meeting really incredible investors that, you know, hopefully will end up working with us when, when we’re raising next as well. And so it’s all felt very aligned with, with what we’re doing.
Sam Ushio (28:46):
Yeah. I, in, in many ways it’s the blazer your own trail you know, ethos kind of carries on through authentic. Yeah,
Rebekah Bastian (28:55):
I feel like
Sam Ushio (28:56):
It. yeah. yeah, so there are two previous guests, podcast guests whose companies are in authentic raha and particular ranger from, from pop smart kids and supporting. Yeah. so that’s part of the reason why it hit my radar. yeah, I love everything that you’re doing there. and I believe there’s a hundred and over a hundred companies that are part of it currently. Yeah.
Rebekah Bastian (29:22):
Over a hundred companies and about 150 founders cuz of like co-founder stuff. Yeah.
Sam Ushio (29:27):
Okay. Okay. Yeah. Very cool. Very cool.
Rebekah Bastian (29:30):
Yeah, it’s been, I’m excited to see where it goes, which I’m just kind of, you know, letting it happen kind of organically, but who knows, maybe I’ll, or maybe someone will step up and <laugh> want to do something a little, I’ve definitely had a lot of ideas for like how to structure it more, but I, I like that, you know, I just feel like there’s enough gatekeepers in the world, you know, so the more you can kind of create spaces that don’t require them, that’s pretty cool too. Yeah.
Sam Ushio (29:53):
okay. So if we shift gears a bit, we kind of touched on this a little bit when we were talking about, well just every stop actually, but, so if we kind of go back to the beginning, I always say to the beginning, you can define where the beginning is <laugh>, you know, can you, can you provide some context on your journey to writing a book own trail launching own trail, launching a movement called Authentic? Can you just kind of start there and, and work your way up to the present?
Rebekah Bastian (30:22):
Yeah, yeah. It’s interesting cuz like, this is kind of the premise is like, well yeah, you can, you can tell a lot of really cohesive, clean stories when you’re looking in arrears, right? It doesn’t always feel so, so clear when you’re in it. But yeah, I mean, let me start by saying that, like, I didn’t realize I liked writing until I started writing blog posts at like, I think I was 35 when I got asked to write my first blog post. And then I ended up like, you know, being a contributor and having a post and then Forbes and writing a book and all this stuff. So, and I, I don’t know, like I’m, I’m kind of thinking backwards, but I’m like, it’s not also clean, right? It’s not like I can say like ever since I was a kid I went to start a company and be writing all this stuff, you know, like, so I don’t know, I’m not exactly sure where to start, but like, I’ll say that I failed out of college the first time I went and then ended up going to community college and then ended up getting a couple degrees in mechanical engineering from UDub for undergrad and then Berkeley from Master’s.
So like, there’s one little non-linear path that that ended up Okay. I, I started as a program manager at Microsoft right after grad school without knowing what a program manager was like. I literally showed up to the wrong interview and <laugh> not a program manager job and took the job because I wanted to move back to Seattle to be with my boyfriend, who is now my husband. So that one worked out, but like, that was not a very intentional decision. But that, you know, I was at Microsoft for, for years and then ended up being one of the first employees at Zillow as a very early stage product manager there. And and it was dumb luck. Like I was literally the first employee to answer a Craigslist ad there and didn’t even totally know what they were building cuz they were in such stealth mode at the time.
But took the job and that ended up being like this incredible 15 year career where I grew from like entry level product manager to VP of product, worked on all these different areas, started our community and culture org. Like incredible, incredible growth there that like, started with a kind of like, why not, why not try? What’s the worst that could happen? You know? So I mentioned this because it’s like, you know, I think a lot of people have this conception that it’s, you’re supposed to like have a plan and know what the next steps are and take these really intentional steps towards your plan. And I think like the, the coolest things that have happened to, to me have not been that planned out or that intentional, but but I follow my gut, you know? And I think that’s, that’s served me well and also luck, you know, <laugh> yeah.
So yeah, so basically that like the 15 years of Zillow, I could, you know, we could talk for another hour just about that, but just really incredible opportunities to learn and grow and try new challenges, which, you know, and then ultimately writing a book on the side and then that turning into a company. But I think that like everything I learned, you know, around product strategy and culture and social impact and creating equitable systems and like all those things that I had the opportunity to learn while I was at Zillow were all things that like, made, made me, you know, if I talked about like I was meant to do this. Like those are the things that kind of, those are part of the pieces of preparing me to be meant to do this next step in, in terms of starting this company.
Sam Ushio (33:28):
Right? Like building blocks that led like that gave you the the foundation to, to take that big step. Yeah. You know, there’s some hiccups, right? There are some hiccups. And so you’re saying like you, it wasn’t intentional but it turned out the right way. is there a a philosophy or a mantra or a mindset or is there something that, like a consistent thread so that when you hit those really challenging points where when you dropped out of college mm-hmm. <affirmative>, but still ended up engineering at UDub and a and a master’s from Berkeley, you know, I think there’s these points where oftentimes that some people think that’s a dead end mm-hmm. <affirmative>. So I’m just curious about philosophy philosophically. Is there a Rebecca philosophy that’s kind of carried you through maybe with the benefit of hindsight? Not at the time, but can you reflect back and is there a perspective there? Yeah,
Rebekah Bastian (34:22):
I mean, I won’t claim to have had this philosophy the whole time. It’s definitely grown over time. Like, I think when I fail out of college, I then was hit by a series of panic attacks and moved to Seattle with an ex-boyfriend. Cause I didn’t know what else to do. And so like, I won’t say that I was like guided by a philosophy or a mantra at that time. I just like, I just kind of pushed through. but I have evolved <laugh> to like having kind a philosophy that I would recommend in terms of like this idea that, well, if there’s no one right path, if there’s all these different possibilities, like how do I even directionally decide where to go and what I believe to be kind of a helpful framework for that is triangulating the answer to three questions, which is what am I passionate about?
So that’s like, what are the things that give me energy instead of sucking my energy when I do them mm-hmm. <affirmative>, what am I good at? And that’s not just like, you know, the degrees you hold or the titles you’ve had, but like what are the skills that that, that you are really good at? And that can be a huge range of things, right? and then the third one is where am I needed? And you know, sometimes that’s as simple as like, oh, there’s a job description and I’m gonna apply to that job. But sometimes it’s like, oh, I see this opportunity for innovation or, or change or where I could help out and I’m going to make that happen. But like, basically passion skills and, and opportunity when you kind of triangulate those three, I think can at least directionally point you towards something that is worth pursuing, you know? mm-hmm. <affirmative>, and you asked about a mantra and I, I have one right now that <laugh>, it’s definitely been my mantra through entrepreneurship, but I have also kind of like, I give it to my kids when I get stuck on their homework too and stuff. So it’s, I’m trust the process
Sam Ushio (36:03):
Rebekah Bastian (36:04):
And I really believe that trust the process and, you know, that can mean a lot of different things, but like for me, the process is usually something about like, let myself think really big and really creatively and not be held back by like, you know, exact like exactly knowing what to do and bring really incredible people together to work through those things creatively and then just keep taking steps forward. And that for me is my process. And really cool things keep happening from that. And you know, you can have different processes, but you know, kind of figure out what works for you and then trust it and you’re not always gonna like, know what’s gonna happen today or know how this is gonna resolve itself or whatever, but keep keep going forward and, and it will.
Sam Ushio (36:47):
Yeah. Yeah. Are, are there core values that you, and maybe those are the core values you’re kind of pulling them through, but are there specific core values that you anchor on that you use as a the North Star? Yeah,
Rebekah Bastian (37:01):
I mean, so we have core values at own trail and I actually think, you know, own trail is so like inherently a part of me that I actually think that <laugh> probably my core values too. I mean, my co-founder Katie and I have been, have been working on them, but like, I feel them deeply in my soul, you know, so our core values, which I guess my core values also are authenticity, inclusion, safety, curiosity and trust. And that, you know, I think that those can apply both to like how you’re operating internally or as a team, right? Like it applies internally for our company. It implies internally to me inside of myself. And it implies to how, you know, with own trail, how we’re building for our community, the ways, like the kind of environment that we’re creating for our community and for me, like the way that I want to create relationships and interactions in my life.
So I think that those are, are, those are really the kind of grounding values or I guess North Star kind of values also, where it’s like there’s, you know, we’re faced with decisions constantly in business, in our lives. sometimes they’re explicit decisions where we know we’re making a decision and sometimes they’re implicit. Like we made a decision without necessarily realizing it. But like, if you can have those kinds of values that are that are guiding your decision making, then I just, you know, like whatever happens with intro and I actually think it’s gonna be really successful. Like I’m very blunted on the future, but whatever happens, like we’ve been, every decision we’ve made and we’ll continue to make has been value driven. And so I just can’t imagine regretting this no matter how it turns out. You know,
Sam Ushio (38:38):
Viewers can’t see what I’m, or listeners can’t view what I’m viewing, they can’t see you, but your background is incredible. So I, I’d love to talk a little bit about creativity. Yeah. And just having a background in engineering and creativity are two worlds that often don’t collide as much as they, they they should, at least from an outsider’s perspective, maybe they do all the time. And I’m just casting it in the wrong view. But can you just talk about, so your, your, your background is amazing. you mentioned that you love puns, and I gotta laugh out of serial entrepreneur <laugh> on your Twitter handle, right? <laugh> but can you just talk about creativity, how, how, and you do stitching I mean, and you do
Rebekah Bastian (39:27):
Sam Ushio (39:28):
Is it a amatic? Yeah. So is that always been a part of you or where does this, where does this come from and how do you, how do you nurture it?
Rebekah Bastian (39:38):
I think I’ve always been creative and I’ve nurtured it more in the past, you know, decade or so, probably. my mom’s an a really amazing artist, so I definitely come from, and my dad’s a astrophysicist and you know, inventor. So I definitely have both sides of those <laugh> of those in my teams.
Sam Ushio (39:59):
So some of, some of it’s nature, right?
Rebekah Bastian (40:01):
Yeah. It’s hard to tell which, Yeah. my background for those that can’t see it is it’s my garage, which we’ve turned into our startup headquarters, and I have it’s very colorful and I have a wall of women behind me, which is all art that is of, and by women for little, little <inaudible> inspiration. but yeah, I mean, I, well for me, first of all, I think engineering and creative outlets can be very intertwined. You’re right, that they’re not always though, right? but like, for example, I designed an aerial rig that’s in my yard here. And it was definitely probably one of the, the biggest uses of my mechanical engineering degrees to date of, of designing it in a structurally sound way. And it’s also I use it for my, for Ariel, I hang, it’s 15 feet and I hang my silks from there, but I also designed it to be a place structure and a, a soccer goal for my kids.
So it was very creative and engineer. So there’s <laugh>, there’s one example of it. But yeah, I, I find that I need creative outlets, like it’s a mental health thing. but it also opens up my creativity in other ways. So like, by flexing creative muscles, or even like, it’s almost less of flexing and more un flexing, like letting go. Like I think that, you know, we all start out pretty creative as kids, and then there’s so much that the world does to us to like, make us doubt those, those creative urges and, and filter ourselves and feel embarrassed by them or whatever. And so, like, it’s almost like a letting go more than a strengthening sometimes to, to really get back in touch with that creativity. yeah. But yeah, I do visual arts, I do physical arts through Ariel. I do writing, which is a very creative kind of outlet for me. all all sorts of things. And and I just find that it really opens me up to thinking through big ideas, you know, in my work life as well. And it’s very cathartic for me. And yeah, just a really big part of my life.
Sam Ushio (42:05):
You do a lot of stuff at a data tactical level. How do you manage just all these different elements? like the, the creativity, Like I totally agree and subscribe to, you know, this, the creativity doesn’t always, it’s not like I put one unit in and I get one unit out in terms of like innovation or productivity or any of these types of things. But it’s, it’s oftentimes like surfaces in other ways. But <laugh>, you write, you run a company, you’re, you’re leading a movement. you, you are doing you’re, you’re a mother of two children you’re a spouse, you’ve got all these elements and like, how, how do you, so there’s a philosophical, but then there’s also a tactical, How do you just manage that? And then at a tactical level, like what do days look like? Is every day different or how do, how does, how do you do that at a tactical level?
Rebekah Bastian (43:11):
Yeah, I guess starting with philosophically like, and and recognizing the, the privilege of being able to do this, but like, all the things that I’m filling my life with are things that energize me. And that’s so lucky to, to <laugh> be able to do that, to like, you know, including my job. Like, you know, but every single one of these things that you’ve named gives me energy and gets me excited to do it. And I think just in, in general, like we have so much more capacity when we’re doing things that energize us versus things that suck the energy out of us. You know, like if I’m, if I’m bored or doing something that like, you know, that I really don’t wanna be doing, then I have a lot less capacity <laugh>, you know? Yeah. So I think that’s, that’s the biggest thing for me.
And then just like, I think it’s just embracing the fact that like, it will never all be done. So like, I just kind of time box my day sometimes very intentionally through like, you know, calendar blocks and sometimes just kind of by, by shifting context as needed. but like I can say honestly, like, I don’t feel overwhelmed or stressed. and I really don’t feel that very often. Like sometimes like fundraising is kind of stressful. Like I’ll go through periods of something that, that feels stressful, but like which by the way, that’s something that probably doesn’t energize me as much as well. but yeah, I mean, I just kind of am like in the moment with the things I’m doing and and shift context and know that like, there’s always more to do. And, you know, those prioritizing like own trail from a professional standpoint, own trail is my priority, and I need to make sure that I’m not blocking anything there and that I’m supporting my, my team in all the ways I need to.
But there’s just, there, there’s a lot of space for it. You know, my kids are eight and 10 now, so they’re not, you know, they like to be around me, but they’re not always needing me to be doing, you know, specific things for them. Every moment. They’re still pretty needy, but, you know, there’s, there’s just a little bit more. But even like, like when I wrote my book, for example my younger kid was five at the time, and he was going through a phase where he wouldn’t go to sleep at night unless I was sitting in a chair in the corner of his room. And so, you know, I, I shifted from like sitting there kind of scrolling Instagram or whatever to like writing a book on my phone. Like I had this idea for the book and I’m like, Oh, I, I seem to have like an hour every night where I’m just sitting here and I literally written most of the book on my phone while sitting in the corner of his room, sometimes have like a glass of wine next to me or whatever. And like, you know, so we, we actually a lot of time in our day and it’s not like I was like, Oh my God, I have to get this writing done. I need to squeeze it in here. But I was like, Oh, this is actually an enjoyable way for me to be spending my time. Cause I’m excited about writing this thing, you know? And so I think we, we have space to fit in things that we want to be doing oftentimes, or we can, we can find own space. Yeah.
Sam Ushio (46:00):
All right. How do you, what kind of mechanisms or just the general awareness that you have in terms of, I dry energy from this versus I don’t, Is that mm-hmm. <affirmative> something that you’ve honed over time, something that you just know? Are there things that you do to, to acknowledge and recognize?
Rebekah Bastian (46:17):
Yeah, I think it’s just like observed it over time. Like, cuz once you start paying attention to that, it’s actually pretty obvious, right? Like, what’s something that, like the second you have a minute to do it, you wanna be doing it or what’s something Yeah. Where you’re like, you keep looking at the clock or wishing it was done already, you know, like there’s, Yeah. It’s, if <laugh> it’s not too hard to Yeah.
Sam Ushio (46:36):
Or not even doing it
Rebekah Bastian (46:37):
How you feel about something or not doing it or putting it off or whatever. Yeah, totally. Right. Yeah, exactly. <laugh>.
Sam Ushio (46:42):
Yeah. so, so how about with with own trails in terms of, of males, men being allies, being advocates for, for the movement how can men support the own trail movement and philosophy?
Rebekah Bastian (47:00):
Yeah, so Own trail is a space that’s centered on women. And so anyone that’s comfortable in that space is welcome there. so we do have some men that create trails. It’s, you know, it it’s just, you know, it’s about having a centered space, but that definitely includes allies. you know, men have, we have men that are investors and advisors that have been so incredibly helpful to us. and, you know, I think just one of the biggest ways anyone can be helpful to own trail is just helping spread the word about what we’re doing. And I think, you know, for ev everybody can reach out to the women in their lives that that could benefit from owning their stories and connecting with each other in this way. And so helping, helping share our vision and what we’re doing there as well.
Sam Ushio (47:47):
We touched on this a little bit, but there are a lot of people that are rethinking purpose. I think the most recent stat that I saw was that two thirds of us employees are rethinking purpose in life because of Covid 19. And that in many ways has a connection point to what they’re doing at work. so they’re connecting purpose to work, but I like the way that you described it a according to those, those three questions. but for someone that’s in that space that is just rethinking purpose you know, based on the different checkpoints, the different milestones that you’ve, you’ve had on your journey, just what, what type of guidance would you give to, to that person who is ready to make a move, but kind of stuck as well and can’t figure out what to do?
Rebekah Bastian (48:41):
Yeah, I mean, I think putting it out there is a big first step, right? I think oftentimes we end up kind of circulating in our own minds about like, what should I be doing or should I take this step or whatever. And so I think just, you know, putting, putting our intentions out there can be a really powerful first step, right? You know, so back to own trail, but we, you know, you can add aspirational milestones in terms of things that you’re working towards and you can add present tense milestones in terms of things that you’re thinking here right now. And I think just putting those out there, like you could put a precedent tense milestone that says like, I’m trying to figure out what I want next and I’m not sure what it is. and you can put out an aspirational milestone that says like, this is the thing that I’m working towards, so I’m not sure how to get there.
Right? And you can ask for help on those and say like, you know, has anyone else been in this situation where you’ve been trying to navigate you know, what might be next or where these are the, the things you wanna be doing, but you’re not sure how. And, you know, get advice from the community that way. But I think like, you know, it’s kind of that like no one, no one’s a mind reader, and so there no one will be able to support you or open up opportunities or give you their perspective unless you put it out there and ask for that. And, and so I think just like sharing transparently is a, is a really crucial next step. And it doesn’t have to, you don’t have to wait till you have it all figured out to share it, right? You can share the fact that you don’t have it figured out, and that’s still a, a step forward.
Sam Ushio (50:05):
Yeah. It pulls back to the authenticity, right? The authenticity and the support communities. those are powerful agents of change. Yeah. so where can people find you? So let’s talk about where people can find you and learn more about what you’re doing and own trail and authentic and everything else. Can you please?
Rebekah Bastian (50:23):
Yeah. Well trail.com I’m very much on there all the time, <laugh>. And so, you know, if you’re, if you’re going to own trail and creating your trail, definitely connect with me on there. and you can message me on there. I’m on Twitter a fair amount at Rebecca underscore Bastion, so find me and, and send, send dms there as well. authentic, we have a website that’s building authentic.com, so if you, you might wanna just put all these in the show notes, <laugh> to make it easy too, but yeah. but yeah, that’s, that’s a great way to learn more about authentic and if you have a company that you identify as being authentic, you can sign up there to join the community. and yeah, and people that wanna invest in authentic companies can reach out to me as well to get on that email list. I’m pretty findable, honestly. I have a website, a personal website, rebecca baston.com that has all the, all the stuff on it too. So yeah, I’m, I’m a findable person and I love connecting with people, so definitely reach out <laugh>.
Sam Ushio (51:23):
I, I will definitely put a plug in for the personal website because you have the creative stuff on there and the holiday cards are amazing.
Rebekah Bastian (51:34):
Thank you. Amazing. Yeah, it’s, it’s a, it’s a good use case for having children dress them up in ridiculous costumes every year for holiday cards. <laugh>,
Sam Ushio (51:41):
Are there any final closing remarks before we wrap up here?
Rebekah Bastian (51:48):
I mean, this is, this is a great conversation. I love talking with you. And I guess the, the closing statement I always want to share is just this idea that there is no right and right path. So, you know, if you’re listening to this, you’ve got it. You know, you, you can’t possibly be doing it wrong. And so keep going. And I’m excited to, to see more people’s trails on your own trail and learn about all those non-linear journeys.
Sam Ushio (52:10):
Well, thank you for your time, Rebecca. Really appreciate you sharing your story. you’ve got a fan over here on everything that you’re doing. Thank you for giving me energy in this conversation. Ahh, thank you, it’s been really fun.