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Blazing Your Own Trail With Rebekah Bastian & Kt McBratney

In Episode 66, Melinda is joined by the founders of Own Trail: Rebekah Bastian and Kt McBratney. Rebekah and Kt share their journey on how they’ve blazed their own trail as entrepreneurs building a platform that’s intentionally diverse, builds empathy, encourages authenticity, and creates impact for women globally. They also provide actionable takeaways on how you can increase allyship and incorporate DEI into your own platforms.

Additional Resources

Learn more about Rebekah’s work:

Learn more about Kt’s work:

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Rebekah: “Sometimes being an ally to yourself is empathy for your own journey. It’s not always just empathy for someone else’s journey but it’s understanding, owning, and empathizing with your own journey, and helping yourself. Sometimes helping yourself looks like asking for help from others because it can be scary to ask for help, it can take work to ask for help. Sometimes just asking for help is an act of allyship to yourself.”

Kt: “When she (Rebekah) mentioned this idea of the power and the potential to see the change that women everywhere— regardless of industry, geography, generation, life stage— if we all could let go of this myth of one right path and follow our path, I truthfully believed [and still believe] that that can change the world and the change that so many of us are trying to accelerate in lots of different areas. But from this one place of confidence, clarity, and a sense of belonging of following and blazing your trail, that affects your work life, your relationships, your relationship with yourself; and I think that it’s truly an unstoppable force that could catalyze and mobilize it all together, it could make the world into a lot better shape than it is now.”
Headshot of Kt McBratney, a White nonbinary person with long platinum hair and a pink animal print blouse.
Guest Speaker

Kt McBratney

Co-Founder & Chief Brand Officer of OwnTrail

Kt McBratney is obsessed with disrupting the status bro. She’s the co-founder and chief brand officer at OwnTrail, the platform where women visualize and navigate their paths through life. She’s also a visual artist, borderline book hoarder, and former marketing executive who’s spent her career building communities and brands across industries.

Headshot of Rebekah Bastian, a White woman with long brown hair, dangling turquoise earrings, and leather jacket on top of a white shirt
Guest Speaker

Rebekah Bastian

CEO & Co-Founder of OwnTrail

Rebekah Bastian is an entrepreneur, award-winning writer, artist, tech executive, mentor, wife, mother, and aerial acrobat. She is the CEO & Co-founder of OwnTrail and was previously vice president of product and vice president of community and culture at Zillow. Rebekah is the author of Blaze Your Own Trail, is a contributor to Forbes, and is a frequent speaker on social impact, career navigation, and building AuthenTech companies.

Learn more about the host and creator of Leading With Empathy & Allyship, Melinda Briana Epler.


MELINDA: Welcome to Leading With Empathy & Allyship, where we have deep, real conversations to build empathy for one another and to take action to be more inclusive and to lead the change in our workplaces and communities. 


I’m Melinda Briana Epler, founder and CEO of Change Catalyst and author of How To Be An Ally. I’m a Diversity, Equity, and Inclusion speaker, advocate, and advisor. You can learn more about my work and sign up to join us for a live recording at ally.cc. 


All right, let’s dive in. 


MELINDA: So, hello everyone. Today, we’ll be talking with Rebekah Bastian (she/her) and Kt McBratney (she/they), co-founders of OwnTrail, about how they have blazed their own trail as entrepreneurs building a platform from the ground up that is intentionally diverse, builds empathy, encourages authenticity, and increase impact for women globally. So hello, you two. How are you?


REBEKAH: Hello! Good. Happy to be here. 


Kt: Yes, excited to be here. I’m doing well.


MELINDA: Okay, so let’s jump in. Can you each tell us a bit about you and your background stories? And then, how do you come to do the work that you do together?


REBEKAH: I guess professionally, before doing OwnTrail, I was at Zillow for 15 years. I was one of the early employees there, through product management to vice president of product. And then, in the last couple of years there, I was vice president of community and culture, which is when I first met you, Melinda. We did a couple of tech inclusion events together, which is fun. I was really at that intersection of Product Strategy and training equitable systems, and social impact is really kind of that sweet spot that drives me. 


I wrote a book towards the end of my time at Zillow called Blaze Your Own Trail, which is kind of a choose your own adventure exploration of the different decisions and pathways that women take through our personal and professional lives. Really with a goal of the kind of experientially showing that there is no one right path through life and that there’s solidarity and a lot of the less talked about experiences that we go through. 


The book is actually what led to OwnTrail. I didn’t think I was starting out to build a company, but I was kind of working on what I thought would be a cool book launch platform and just started having a cascading number of ideas around problems to solve and ways to solve them through ultimately, what is women sharing our authentic journeys through life. 


I met Kt right around that time that I was just starting to work on that. She can tell you a little bit more about that meeting. Sometimes as far as me, it’s like, she asked me out on a friend date because she thought I was delightfully weird or something like that.


Kt: You said that even better than the night I met you. No, yeah, it was right around that time that I had met Rebekah. My background professionally has been almost exclusively in marketing swim lanes, but across lots of different organization types, from nonprofits to the agency world to entertainment. And really, I’ve been in working to build brands and communities and grow early-stage startups for the past eight years or so. 


It was a move to Seattle for my partner’s career that led me to even be in the time and place to meet Rebekah. I was a new parent, and I was having a hard time finding my people in Seattle. I happened to go to an event where Rebekah also went. We both almost skipped it. Thankfully, we did not. 


I remember how she stood out during intros by being unapologetically herself by not recycling the same old 30-second bio leading with what you do for a living. I thought that was really cool and really compelling. And so, I did. I asked her out on a friend date, and it was on this friend date over coffee that she told me not just more about her book but about this idea that is now OwnTrail as we know and love it. I couldn’t get the idea out of my mind. And soon after, she asked me to come on board as an advisor. And even sooner after that, I was all in as a co-founder.


MELINDA: Can you say a bit about what OwnTrail is so everybody has a good understanding before we move deeper?


REBEKAH: OwnTrail is a platform where women visualize and navigate their life paths. The foundation of that is Women’s Trails. So, that’s basically a series of interconnected milestones that span our past, present, and aspirational life across our personal and professional lives that really authentically share who we are. So, not just the highlight reels or the kind of end results that you might see on LinkedIn or social media, but like the authentic journeys behind that. 


And from that foundation of authentically owning and sharing our story, women are connecting with each other, and we have a really vibrant community that’s formed. It’s really catalyzed with women helping each other. So, through our trails, we can ask for help on the different things that we’re navigating, and the community rallies around to help with that. And so, it ends up being a really kind of intimate support system of both being there for each other and connecting in very real ways, but also getting things done and progressing through our lives that defines the purpose and fulfillment that we’re looking for.


MELINDA: Rebekah, we’ve known each other for a few years now. And so, I know that diversity, equity, and inclusion are really important to you. And also, your background in products and kind of combining them together as we’re building this platform, you’re building with diversity, equity, and inclusion in mind. Can you talk about how you did that and what that process was like? Either one of you, both of you.


REBEKAH: I mean, the delightful thing is being able to build a company and build a product with these attributes at its core as opposed to something that’s kind of tacked on to the side, right. I feel so lucky to be able to build with an incredible team something that OwnTrail is inherently an inclusive platform. It’s inherently an intersectional platform the way that we operate internally, the way that we work with our community, which is we do a very community-led kind of development process, and ideation process. But just the values that are really driving us along the way are all centered there. 


And so, we launched about a year and a half ago, and from day negative one, this has been really the core of how and why we’ve been building. It’s just so much, I guess, easier in some ways. It just makes so much more sense to be making decisions inherently based on creating a space where inclusivity and safety are really at the core of it, and that a big part of the power of OwnTrail is in seeing people who look like us in the places that we aspire to. 


And so, diversity has to be core to that because, in order for everybody to be able to see someone that has identities and experiences that resonate with them, you need really inherent diversity across the community. We’ve been growing that since the beginning as well.


Kt: Also, building a platform that is women-centered is also very similar to the sense that that is baked into the core, right? So, by centering experiences and intersectional identities, that for better and mostly for worse, the world hasn’t been designed for. It just fundamentally shifts our building from the features to the security measures to even how we speak to our community. 


We don’t say, users. We don’t use dehumanizing language because we don’t believe that that values the individual, that that creates safety and authenticity. At the end of the day, we’re people building for people. And keeping that human-first mentality is really really core to being able to execute on any diversity, equity, inclusion, belonging, any of those efforts. It really starts from being able to always see people as people and not movable numbers on a spreadsheet.


MELINDA: Can you talk about some practical ways that that plays out? I think in terms of community-centered design and human-centered design, what does that look like at a practical level as people are listening to who may be able to influence product design? What does that look like? 


Kt: I think there’s one. I know, Rebekah, you got a ton from the product side because we are a product-led company. One thing that’s different from a marketing standpoint in terms, especially in the startup world, is not forcing people through a funnel against their will and kind of badgering them to share their authentic stories. 


As we put ourselves out there and share some things that are vulnerable, or maybe process some of the milestones in our life, we want to hold space versus push people through to a conversion goal. And while we are growing rapidly, and we want to encourage as much growth and create a diverse, robust environment and collection of trails, we also know that we can’t be successful in that if we push people through marketing funnels. 


So, part of that is having a very intentional and yet still growth-oriented mindset where we, again, treat people like people, and we respect their choice to share their information, to share their story, and to tell it in their own words, which is also part of how even people create their trails.


REBEKAH: Yeah. So, what Kt’s saying is making sure that everyone has agency over how and what they’re sharing is really important for safety and just respect, right? So, we have different settings for that. Women can choose to use their real names or anonymous screen names. You can mark different milestones on your trail as being private that only your explicit connections can see them. 


I think even taking a step back in terms of the “how.” One thing that we’ve done from the beginning is just building strong relationships with the members of our community and talking with them all the time. I think there’s this kind of archaic version of building a company, which is that, like, “We are the company. We know what you need. This is how you’re going to use it. You’re going to like it.” and kind of shoving it down people’s throats in that way. 


And, you know, kind of what Kt, you’re saying in terms of not having a formulaic funnel that you’re pushing people through, it’s also just like, not being arrogant enough to think that we know exactly how people want to use what we’re building or what they need. We have some really big visions that are guiding us. But like, we’ve made big decisions too along the way in terms of how we execute on those visions based on what the community has shared with us. And having that kind of two-way communication. 


We always say that we’re building this with the community, not for the community. I think that that’s a really big differentiator. I won’t go up totally on a tangent, but I think when you look at a lot of what’s happening with this new web free space, like, yes, there’s technology, and there are new models around that, but inherently, it’s really that it’s like more community-based. 


I think in a lot of ways, even though we’re not building on the blockchain right now, we have a lot of that kind of ethos in terms of how we’re approaching the entire process of building up this company. 


Kt: Yeah, and I think that there are some practical tactics around research interviews, user testing, those kinds of things along the way, but also having lots of organic, passive, and active feedback loops throughout everything, and not only aligned to our goals as a business, but very much being responsive and receptive to hearing what other goals our community has that we might serve. I think it’s that service mentality that is part of that. We are building with, not for. You can feel the difference when a company is talking at you versus with you, and we must certainly always want to be talking with you. It helps us build better. It helps us to have the impact that we want rather than thinking that we know it all. We’re very aware that we don’t know what we don’t know. And there’s a whole amazing world of women out there that know a lot.


REBEKAH: Also, it’s just kind of fun this way. Like, this is the most fun in our careers. You know, we’re just making new friends all the time. It’s very invigorating.


MELINDA: Nice. Nice. Yeah. As a result of doing this, we’ll talk about a few things. One is the diversity of the platform and kind of the way you’re thinking about intersectionality. Do you want to talk a little bit about that? Both as White founders building a platform but intentionally thinking about intersectionality in that and what has led to a diverse group of a diverse community.


REBEKAH: Yeah, definitely. Everything from kind of tactically, which is that we do ask about the identities that people hold, which I think, you know, it’s all optional, but we asked about a lot of different identities, which lets us be able to sit here and tell you accurately also like who is on our platform, which is more than 50% women of color. We have women from, I think, about 50 different countries now, ages from 18 to 75. I think we indexed kind of higher than US averages for LGBTQIA and disability, different abilities. 


And so, the result is that we’re both plucking out information, which I think a lot of times people are just like, you know, there’s this whole kind of not comfortable asking those things. Like, there’s not that many words out there that even ask that or create space for those identities. It’s kind of, I think, people kind of find comfort in that, kind of colorblind mentality of we just don’t talk about it. 


I think recognizing that the identities that we hold are such an important part of our experience as we navigate our lives and embrace that. We’re not displaying those identities on people’s profiles or anything like that. But it’s used to be able to, like, you know, that scenario talks about, like, what are the trails that people that hold my same identities or same experiences and finding solidarity and inspiration in that. Who’s someone who I really identify with who’s in this place that I might be working towards in my own life? 


And so, kind of from an implementation standpoint there that’s been a big one. But I also think, you know, we’ve talked about just the fact that OwnTrail is the framework for people’s stories. It’s creating space, right? We’re not filling in those stories. The stories belong to each of the women that share her trail on OwnTrail. 


And so, by thinking intersectionally in terms of how we spread the word about OwnTrail, which has been growing organically so far, and I think it helps that we started with some pretty diverse networks to begin with, and that kind of helped propel some of those network effects. But, you know, also just like whose stories are amplifying and highlighting. 


I’m able to leverage my Force column to do different interviews of trailblazers, and those are really primarily focused on the stories that you don’t normally hear and that people are not usually seeing in the news and trying to do more both on our platform and on our platforms outside of OwnTrail to really create space and amplify a really diverse range of voices and experiences.


Kt: Yeah. And I think as White founders, it’s our responsibility to be aware of and acknowledge the privilege that we have. We do have it. And to use that to create space to amplify others, to hold space for others, to pass the mic and all of those other acts of allyships. And also, to check our privilege when that’s appropriate. 


Rebekah and I often have very authentic conversations with each other. I feel fortunate that we have chosen to partner together where we can have those conversations about identities and privileges that we hold or that might be different between the two of us. Because as both White founders, we, of course, have intersectional different identities and experiences that form our perspectives and any even implicit biases that we have. 


So, being able to create a culture where we can discuss that, especially founder to founder, I think, is really valuable in how we build and how we lead and creating space to have a team that isn’t centered around us. I think that that’s a very important thing about how we’re building OwnTrail. And that’s personally really important to both of us, is that it isn’t and it has never been around the two of us. 


Whenever we can use our platforms to lift up OwnTrail and the people on it, that’s amazing. And we are grateful for that. But at the same time, this is not the Rebekah and Kt show. It’s OwnTrail, and there’s an entire world out there of trailblazing women that we think and truly believe that deserve space and the spotlight. 


MELINDA: I spent a little time using the platform in creating my OwnTrail last night. And because you’re creating a past path and then the future ideally, and you can send up beacons to ask for help and guidance. As folks that are pivoting in their career, or they’re pivoting in life, like major transitional moments, so it requires being vulnerable and requires some real authenticity to really plan that out and to ask for that help. 


And so, there’s a, I think, something to be learned here, both for people who are developing platforms and for anybody who’s working to create psychological safety so that people can be vulnerable and authentic. How are you thinking about that? How are you building that? What is that? What are the components there?


Kt: Oh, I love this question. I love this idea about building fundamentally differently, right? It’s not just a technical paradigm or a narrative paradigm shift of how we tell our stories, but it’s fundamentally building a company that kind of is an antidote to how social media as we know it exists. It gamifies our attention. It monetizes our experiences instead of prioritizing them. We’re very intentional about not engineering in FOMO, about creating psychological safety that really has those agency mechanisms built-in. And that’s really fundamental, I think, to all of how we’re building that. What were you going to say, Rebekah? 


REBEKAH: Yeah, I mean, I completely agree with what you said. I was actually going to dive into a kind of a, like, what are the ingredients part of it. I think the core, like we’ve talked about, is safety and agency, right? Without that, nothing else really matters. And kind of like Kt was getting at, we have network effects like social media, essentially. But that’s really where this stops. We will never be advertising-based. We will never sell people’s data. 


I think when you’re making that decision, it really opens you up to create different dynamics in terms of how people interact with the platform. We don’t have to create the FOMO, or the doom scrolling, or the popularity contests that are kind of inherent to social media dynamics. And so, a lot of that. But also, what we’ve seen, which is really cool, is that by creating the basis of safety and agency and not commoditizing humans, then that opens up people to be authentic. But then what ends up happening is that authenticity leads to more authenticity. 


So, we actually measure the percentage of what we consider to be vulnerable milestones on a trail and the percentage of trails that have both personal and professional milestones, which even that in itself, like in a world where we’re asked to compartmentalize our personal, professional lives, aggregating it to is an act of authenticity as well. And so, when we look at that, they’ve been going up steadily over time. And, you know, what we believe is happening there is that when women see other people sharing such vulnerable and authentic experiences, and we’ve heard people say this too, is that like, “Oh, that’s okay to do here. This is a space where that’s okay.” A lot of it is like, “Well, you never asked. You never gave me this face.” It’s not that I don’t want to share that, but it’s just like LinkedIn. That’s not okay to share there. Like, I go on social media, and I see everyone’s picture-perfect family photos, you know. Like, this is where I can be wrong. 


And so, that just, I think it creates a feeling of safety that then is kind of a cycle that keeps going. The reason we’re measuring those things is because we know that if we don’t keep trust and authenticity high and growing, nothing else matters. We could do all the growth and engagement and everything in the world, but we’re not going to be fulfilling our mission without keeping that really high level of authenticity on the platform.


Kt: Yeah, and I think fundamentally, right, the reward of posting your social media perfect is the algorithm gives you a little pat on the back. It gives you more access. It gives you more followers. It gives you that like counter that makes you feel like you’re winning. We believe that by sharing your trail in connecting with others, that’s winning. Right? There’s no way to win at OwnTrail. You can’t be the most popular because we aren’t building in those binary winner-take-all mentalities. We don’t have likes on OwnTrail. The closest thing we have is an appreciation button. 


First of all, you might see someone’s vulnerable milestone, and you don’t like that they had a miscarriage, but you appreciate that they are sharing that experience. And so, appreciation is a much richer form of letting someone know that you see them and that you’re grateful, or that all of the multitude of meanings that it could have. 


And it’s also a private notification. So, if I appreciate Rebekah’s trail, it’s just me. She gets the notification saying that I did it. It doesn’t need the world to know. The world doesn’t need to know how many times Rebekah’s trail was appreciated because it’s about her feeling seen and that other person letting someone know. Especially in a world where our likes and our interests and our experiences, even the vulnerable ones, and sometimes, especially the vulnerable ones, are being counted and monetized against, we believe that there’s a lot of power in the action of connecting with other people being the reward itself and not us as a platform giving you a cookie for doing what we want you to do.


MELINDA: Yeah. So, going into that a little bit. Kt, you mentioned acts of allyship and those beacons that people send out that are a call for help or support. When people answer that, that is allyship, right. So, how are you designing to increase allyship on the platform? I think that’s something that a lot of people would want to know


Kt: Yeah, we were just talking about this earlier in a meeting. Rebekah, you’ve had some great thoughts around how we’ve built, but also how we’re building towards it. 


REBEKAH: First of all, I think one of the first steps for its allyship is just being able to really hear other people’s experiences, right. And so, I think just the ability to understand someone’s journey from their trail is step one, right? Because I don’t think you can fully be an ally until you understand what the person has been through. 


And, of course, this is more individual allyship when you look at an individual person’s trail. But there are also things that can be deduced, and we’re actually filling in a lot of the gaps in data that is understood about an intersectional perspective on what women experience in their lives too. So that kind of leads to greater identity-based allyship too.


MELINDA: Yeah. And building empathy, I think, when you see people’s trail and how they’ve come to where they are, the ups and downs along the way, that does build empathy too. Yeah.


REBEKAH: And then from there, I think also, sometimes misguided allyship can look like trying to do something for someone that they don’t actually want you to be doing, that they haven’t asked for. So, that’s why it can be so powerful to ask for help. And sometimes the help is really tactical, like, I’m looking to get this specific job, can you introduce me to the hiring manager for XYZ company, right, like very specific things. But sometimes the help is even just like, I needed advice on this situation from someone who’s been in it before. 


The powerful thing about the ladder actually is that non-consensual advice can be damaging, right. But sometimes, people who want to be acting as an ally or want to be a supportive offer that because they don’t know where to be helping out. And so, being able to know this is what someone wants help on and this is how they want help, and this is from what type of person they might want it from, and really kind of takes away a lot of the assumptions there and gives really concrete steps to be an ally, a supporter, a friend, an accomplice, and any of the things that fit in there.


Kt: Yes! And because a help beacon is connected directly to a milestone, that’s a part of a whole trail. You have context. It’s harder to fall into the trap of defining someone by a single experience or request or things like that. You have more context and can see them as a more real person. So, kind of going back to step one. In case people try or think that it’s easy just to skip past that, there’s always a connection back to see that person as a whole person, and not only for that one element of who they are. So, I think that those two things work really well and interplay together. 


REBEKAH: I guess the other part of that that we’re riffing on earlier was what does it mean to be an ally to yourself? Right? Because we give so much to others often, especially, I think women inherently are givers, right? And so, sometimes being an ally to yourself is empathy for your own journey, right? It’s not always just empathy for someone else’s journey, but it’s understanding, owning, and empathizing with your own journey and helping yourself. 


And sometimes helping yourself looks like asking for help from others, right? It can be scary to ask for help. It can take work to ask for help. And sometimes, just asking for help is an act of allyship to yourself. And so, I think that when we think about the power of the OwnTrail community, it’s how we are helping each other and ourselves, right. And it’s that combination that makes it so powerful. 


Kt: Somebody once described help beacons as opportunity generators. I love that because it is bi-directional. It isn’t a hierarchy. It isn’t imposing assumptions or power dynamics over it. It’s very much a community-based collective-minded thing. Help doesn’t have to imply weakness or deficit or a lack. It’s creating. It’s generating opportunities for people that are wanting to help but to help in the right way. And to be an ally to others and to yourself, I think, is really important when you think about generating opportunity overall and how that can really be an ultimate form of allyship.


MELINDA: We had a conversation with Kelly Hoey about networking and how women network differently, and how successful women network differently in Episode 60. I would say there’s a lot of things that you’re building in the platform that she was talking about in terms of just having different concentric networks that women need to really advance in their careers and ask for help. Having that ask beacon, sending that beacon out, and asking for help. So, there’s a lot of commonalities there. A lot of synergy between this conversation and the one we had a few weeks ago. So, what does that look like? Can you give us some examples of how women are being allies for each other? You kind of say it a little bit, but if you could say a little bit more.


Kt: Yeah. This is actually one of our favorite things to talk about. There are so many examples, and they’re all-powerful in their own way. I think a lot of times, we feel like we need to reserve our ask for help or our ability to help. We have this scarcity mindset like, “Oh, this is going to be my one ask.” What we’re seeing on OwnTrail is very much indicative of the abundance mindset, where you can put out lots of different asks. They can be big. They can be small. They can be life-changing or just helpful. They’re all great. 


One of them has been women who have stepped into the accountability buddies for writing for wellness goals and to create and really forge this relationship that exists on OwnTrail but also off-platform, right? There have been women connecting each other to coaches, making introductions to hiring managers, to doing resume reviews. There was one woman who actually posted a milestone of getting a thousand beta users for her tech company and was wowed by the number of women who were like, “I’ll sign up.” “Who else can I invite?” and was just overwhelmed with the people that were just like, “Sure, absolutely. We’ll step in.” 


And then, some of them are also more personal, where someone is healing or going through maybe a medical issue and just really wants people to have some solidarity and accountability for, and that’s been really amazing. One help beacon I love, and I personally didn’t know I needed to learn from, was about building the best ergonomic at-home workstation. What I think is really powerful, especially about some of these public beacons, are they’re evergreen in their helpfulness, right. I didn’t know I needed to improve my work-from-home setup, but my body is already thanking me from two other people having that conversation and helping each other out. Rebekah, do you have a favorite? I mean, they’re not favorites, but a shining example that I haven’t thought of?


REBEKAH: A lot of the solidarity and advice lens is very moving to me. Kind of like you said, some of those personal things where it’s not that there’s an absolute solution here, but it’s like, I need to know I’m not alone in this. I need to know it’s going to get better. I need to hear from other people that have been through a similar situation. Everything from internal things like self-doubt or things of anxiety or just how you view yourself kind of things to relationships and, like you said, health things. All sorts of just the vulnerability that gets shared in some of those help beacons as someone like, “I’m here to help you. I’ve been there.” Those ones really warmed my heart. There’s so much power in that too. you know, and I think


Kt: I think that those are really good examples of why we chose the name beacon. We want it to be very intentional from the beginning of not falling into transactional nature because it’s really hard to have that psychological safety, that equity, and that inclusion when it feels like there’s a tip for the top, there’s a hierarchy, there’s a give and take. Those solidarity ones, I feel, are examples of people putting up their beacon. It’s like a personal bat signal. They want to be seen. And they want to hear from people who maybe see themselves a little in that, whether it’s currently, past, present, future. That’s really valuable. 


What we’ve found, and I think it was our gut instinct from even when this was the seed of an idea, is that while tech companies tend to measure things in quantitative clicks, that doesn’t necessarily indicate the power of those actions. So like, for example, putting out a help beacon to hear that you’re not alone in grieving the loss of a relationship. It might be a few dozen keystrokes, but the power that the action has can be absolutely life-changing. And that’s really what we’re building for. 


MELINDA: So, can you talk a little bit about the why? Why did you decide to build this platform? Why is it important to you that women are raising their OwnTrails? What started this inside of you?


REBEKAH: Well, I guess the initial “why” was very observation-based, which is that myself as I’ve been in more kind of leadership and mentorship and friendship positions in my life. I just keep talking with more and more women from across the board that there seems to be this consistent idea of like, “I need to know where I’m going and how I’m going to get there. I’m worried I’m going to get it wrong. I need to compartmentalize my life in these ways.” There’s the right way of doing it and then missing it. 


I guess maybe it’s the benefit of having a very nonlinear and life with plenty of failures mixed into it myself. And I’m like, “No, there isn’t. There isn’t a right.” And I think that was really what drove me both to write the book and start OwnTrail was this idea of like when you open yourself up to the idea that there is no one right path and that some of the most fulfillment and satisfaction and success can come from really just being yourself and staying open to possibilities and lifting up others as you lift yourself up. That really kind of abundance mindset comes from a community. Those, I think, are the keys to success and happiness. 


I really just wanted to kind of find ways to experientially discover that for more people because I think that we live in a world where everything from just kind of society overall to familial influences, and suddenly, like employment, influences are all over the place. We’re being told how to be, what boxes to fit into, and how to do it. It’s no wonder that people feel like they’re supposed to be getting it right. Like, we’re told to get it right. And so, I just really want to push back on that idea. 


It’s amazing to see as more and more women that hold so many different identities around the world are sharing their journeys, both the beauty and like all the differences and what we experienced, but there are so many commonalities, too. And a lot of those commonalities are that we’ve been held back by different systems and different expectations that aren’t serving us. 


And so, the way that we’re able to come together to push back against those and essentially blaze our trails through life together is already we’re seeing so much power in that, and really, we’re just getting started. We talk about the ripple effects a lot and what happens when women start really kind of pushing back against those systems and working together to move forward in the way that serves us. The ripple effects are both systemic and personal and incredibly powerful. 


Kt: Yeah, it was that ripple effect that led me to be where I am today talking to you and being on this OwnTrail journey. Because when I met Rebekah, I wasn’t looking to co-found a company. I hadn’t thought of anything like this idea before. I knew my next career move would be to do something on my own, but I had no idea what it was, and I wasn’t looking at it. But when she mentioned this idea of the power and the potential that the sea change, that women everywhere regardless of industry, geography, generation, life stage. 


If we all could let go of this myth of one right path and follow our path, I truly believed and still believe that that can change the world and the change that so many of us are trying to accelerate in lots of different arenas, but from this one place of confidence and clarity and a sense of belonging of following and blazing your trail that affects your work life, your relationships, your relationship with yourself. I think that that’s a truly unstoppable force that if we catalyze and mobilize it all together, we could make the world into a lot better shape than it is now.


MELINDA: Yeah, agreed, agreed. Well, to that end, actually, what would you say to people who are just starting to build a platform, whether that is an entrepreneur or product designer, and product developer, UX designer? What would you say to them as they’re just starting to build so that they really are thinking about diversity, equity, and inclusion and also empathy and allyship and building those into the core?


REBEKAH: Yeah. I think the community is the short answer there, which is both like, you know, look at the community, who you’re building for. Really name the identities that you want to be serving, and hopefully, they’re a lot bigger than the ones that you hold yourself, right. And then building relationships with that community. 


And so, having a diverse community of people that you’re building the platform for and with and making it with, right, building with them and building those relationships. But then I also highly recommend having a diverse community of people that are doing similar things to what you’re doing, right. In our case, we have some really powerful founder communities that we were part of. 


I think that being able to share notes with people, and you know, like, we don’t all have to be on an island thinking we’re the only ones doing this. Anything worth doing is probably worth doing in a lot of different ways at the same time, right. And so, for us, we’ve become friends with a lot of people who are building platforms and communities for women in different ways. And we find ways to collaborate with them. We share notes, and we support each other. 


And then also just founders, in general. Founding a startup is such a unique experience that having other people that are going through it at the same time to commiserate with and celebrate with and all the things in between. So, I think across the board, having communities that you’re in it with, and making sure that those communities are incredibly inclusive and have really diverse representation across the different experiences that are going to be valuable to learning and growing and making sure that you’re building for everybody.


Kt: I would only add that to kind of little, I don’t know, things that I’ve jotted on post-it notes and stuff to my desk before, but one is, be human first. Be a human always. And letting that guide you, especially when you’re at a fork in the road, or when there’s maybe internal misalignment or friction, it’s like, be a human first. Who are you serving? How are you feeling? 


I think that that can really recenter you into building and developing something for people. And then, the other one is to know and work by your values. I think a lot of times, company or personal values get talked about in a hypothetical, and not in terms of practice. And if your values aren’t apparent in the work that you’re doing and how you bring yourself to that work, then they’re just like nice things on a poster or an about page. And those need to be the constellation that is always guiding you. 


Those two things in combination really can support each other and give you the freedom to have strong opinions loosely held to build with the community to ask questions to show your notes when we’ve been taught to hide our work and roll away knowledge. Those can be just like very helpful pillars to cling to when other systems, capitalism, and all of that come knocking at the door and pull your attention and focus away.


MELINDA: Yeah, absolutely. Two more quick questions. One is, where can people learn more and get involved?


REBEKAH: Yeah, it’s OwnTrail.com. I’m sure you will put it in the show notes too. 


MELINDA: We will.


REBEKAH: I would love for anyone that feels comfortable in a woman-centered space to show their trail on OwnTrail. And please recommend it to other people that you think would both benefit from having to authentically share who they are and connect with others in that way. But also, like, who you’re curious about their stories, right? Like, I love this. I use it as a way to reach out. I’m really fascinated by what you’ve been sharing or by what I’ve been watching you from afar. I’d love for you to share your trail on OwnTrails to learn more. A lot of times, people will. Sometimes you just need to be asked.


Kt: I think a lot of times, we think of trailblazers as like Serena Williams, which like, obviously, of course, but if you ask me personally who has been a trailblazer in their life, or someone who they think, whose journey has been exceptional and fascinating and super interesting, it’s usually somebody who’s a lot more “approachable.” They are a teacher. They are a colleague. It’s their sister. It’s their friend. Inviting them to share their trail is actually a nice little sign that you see them and you respect them. And when you’re on OwnTrail, you can connect with Rebekah and I, and of course, learn more about our journeys because, as Rebekah said, they have been nonlinear. There have been hits and misses and a lot of stuff in between. So yeah, we’d love for you to join us there and sit and connect with us individually there as well.


MELINDA: Awesome. Awesome. Usually, I ask people at the end of the session to take one action, to make one action, whether that is an act of empathy or an act of allyship. What is that one action? So, I want to ask you both if you have one action that you would recommend based on what we’ve talked about today?


REBEKAH: I think, stepping aside and giving space for people to show up and to share who they are in the way that they want to, and being there to hear that and to amplify that in the ways that they want, I think is a really powerful action. OwnTrail is a great place to do that, but you can also just do that through your daily life as you’re interacting with people. 


Kt: I would add to treat yourself with the grace that you extend to others. Oftentimes we’re very focused on being empathetic and having external allyship, and also, sometimes the doctor needs to heal by itself.


MELINDA: Absolutely. Absolutely. Well, thank you both so much for this conversation. I want to also just mention, there’s a couple of episodes that if you’re interested in this topic and learning more about this topic, and you haven’t listened to them or watched them yet, I mentioned the episode with Kelly Hoey on Episode #60, where we talk about how women network. And then also on Episode #13, we spoke with Brenda Darden Wilkerson about women championing women as well. So, take a look at both of those episodes, 13 and 60. Yeah, thank you, Rebekah and Kt. I really appreciate this conversation and all the work you do.


Kt: Thank you. It was great chatting with you. I love all of the storytelling you’re doing around this area. 


MELINDA: All right, everyone. This is our last episode of the season. We will be taking a little bit of time off, and we’ll see you in 2022. And so, if you’re missing us in that time away, please take a listen to our past episodes and do leave us a review on iTunes or wherever you are listening. That would mean a lot to us. Thank you. 


MELINDA: To learn more about this episode’s topic, visit ally.cc. 


Allyship is a journey. It’s a journey of self-exploration, learning, unlearning, healing, and taking consistent action. And the more we take action, the more we grow as leaders and transform our communities. So, what action will you take today? 


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Leading With Empathy & Allyship is an original show by Change Catalyst where we build inclusive innovation through training, consulting, and events. We appreciate you listening to our show and taking action as an ally. See you next week.