Create Your Own Trail, Invent What's Next with Rebekah Bastian
In this episode of Good Enough for Now, creator and co-founder Rebekah Bastian walks us through how creativity, community, and entrepreneurship have shaped her path and oriented her identity.
After publishing her book, Blaze Your Own Trail, Rebekah decided to leave her corporate executive job at Zillow to co-found OwnTrail, a revolutionary authentic social platform.
Tune in now to hear how the various steps along her winding, non-linear path have led her to achieve authentic connections and empowerment.
LISTEN NOW
three reasons why you should listen to this episode:
Discover another way of telling the story of your life journey
Realize how to unapologetically own every step in your story and path
Empower yourself by witnessing and participating in collective authenticity
Interested in creating your own trail? Good Enough For Now Listeners receive 25% off your first year of OwnTrail membership by using promo code “GEFN” at checkout at www.owntrail.com.
Highlights
We catch up with Rebekah in Seattle, where she lives with her husband and two kids. She’s a digital and aerial artist, creator, and her path has been anything but linear. Two years ago, she left her corporate executive role at Zillow to co-found a social platform start-up, OwnTrail.
I'm really passionate about community and really authentic connections, which is a lot of what we're building with OwnTrail.
Originally, Rebekah went to college for music and then flunked out. When she returned to community college, she realized she loved math and science and decided to complete a Master's in Mechanical Engineering before becoming vice president of product and vice president of community and culture at Zillow. Her book, Blaze Your Own Trail documents this windy road and sets the foundation for OwnTrail, a social platform where people publish and share every step in their life journey.
I've definitely lived the things I'm trying to convey in OwnTrail, which is that there's no such thing as a right path certainly, but usually not a linear path either.
On OwnTrail, users share more than just their career trajectory. They share their whole lives––and not just the good parts.
It is much more real than what you would see on like LinkedIn or social media where it's not just the highlight reels, but it's like all the things you really navigated and the things we're navigating right now and the things you're working towards both in terms of owning that yourself but also for seeing what other people's journeys are and really the solidarity and confidence that comes from seeing everybody's winding path.
Through building a community where the reality of everyone’s path is laid bare, authentic connections that are centered around support and accountability are made possible.
How do you take action on that trail? How do you move to that next milestone and how can we all be supporting each other and how we get there?
Documenting every step in your path and visualizing it forces you to redefine your perspective and pushes you toward embracing it.
It's actually really empowering and kind of freeing in a sense to just really own your story in that way unapologetically. Like, this is all my story, these are the things that happen, I'm proud of the things that I've been able to make it through and that's brought me to who I am and that informs where I'm going and all of that.
A creative and artist at heart, Rebekah created a Venn Diagram of her life. In doing so, she found that community, entrepreneurship, and creativity anchor and orient her toward each step in her journey.
What I was able to visualize with that is that these aren't all like different fragmented things, pulling me in different directions. They're all complimenting each other.
When envisioning her next steps, she leans into these values. Staying true to herself and her path empowers her to keep pushing forward authentically.
When you define your values and you bring people together around them, you kind of find your people and that's kinda a magical thing that can happen.
Rebekah is excited about the future of OwnTrail, as she sees it as a revolutionary response to the hustle culture that has left so many people burnt out and dissatisfied.
I heard someone say once that you wanna build a company around a whole kind of revolution, not just a feature. And I think that's definitely what we're doing here. So we got our work cut out for us.
What Good Enough For Now means to rebekah:
The first thing that popped into my head was the idea of building in public and learning in public. Conversely, if you're building in private, you get to this state of perfection before you lift the drapes and let people see what you've been working on, which I feel is the antithesis.
ABOUT
Rebekah Bastian is a creator. She’s created a startup, a tech movement, a book, multiple written, visual, and aerial art pieces, and two humans. 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, a board member of JPEG Morgan and Bellwether Housing, a contributor to Forbes, and an investor and advisor to AuthenTech and Web3 companies.
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Stephanie (00:04):
Hi and welcome to Good Enough For Now, we are Your Hosts. I'm Stephanie Kruse.
Harper (00:10):
I'm Harper Spero. And our show is for people who wanna make meaning from life's detours so they can find the creative resilience to move forward.
Stephanie (00:18):
We'll explore stories of transition, false starts, unexpected U-turns, and other moments of reinvention that happen as we move through life. Each week we'll bring you a fresh perspective from our own lives and share insights from guests. We bring on the show.
Harper (00:33):
Join us when you need a moment to get out of your head. Feel us alone and maybe a little bit more
Stephanie (00:39):
Together. Together.
Speaker 3 (00:50):
So I've been thinking a lot lately about the different parts of identity, who we are and in particular who I am, who I've been, the places I've lived, the experiences I've had. I recently took my eldest child, my daughter who's a high school junior back to my alma mater for graduate school, which is a big huge public university in the southeast. And I haven't lived in the southeast for 20 years, but when I was there I could definitely access that part of my identity, right? Who I was at that time, the things that I was exposed to, the ideas that I shared with other people and it has such meaning for me and it was so fun to share it with her. I've also lived in California for a long time and that was where a lot of my marriage took place and my kids were born and we raised them up until elementary age.
(01:48):
And I really identify with that, the lifestyle there, the outdoors, the sustainability that pioneer spirit of California. And that's part of me too. And yet when I meet people here where I live now in Connecticut, you know, they may or may not know about those parts of who I am, but I have all that. Um, it might not be the first sentence when I introduce myself, but if you get to know me you start to understand that I have this other background or these other stories. And I think our guests, Rebecca Basian starting Own Trail, which is really about uniquely telling the story of your life journey taps into this idea of identity. And I know Harper for you, you probably have some thoughts about what that means given your recent experiences.
Harper (02:34):
Yeah, I was so fascinated listening to Rebecca because when I think about my own story, number one, my identity was always so tied to being a New Yorker. It was, Hi, I'm Harper, I'm from New York City. I've never lived above 23rd Street <laugh>. It was like my identity, this is it. There's no branching out of this. And in almost a year of living in Tel Aviv, I'm like oh my god, I can be more than that. And the other interesting angle about this and why I think on Trail is so smart and what Rebecca's doing is so smart is that it's not just LinkedIn where you're getting the like highlights of someone's career and professional life, but you're also getting the behind the scenes of health and relationship and travel and volunteer work and the full picture of who the person is. And Rebecca does a phenomenal job with Own Trail at gathering all of that information to show who your identity is in the way that you wanna be represented, whether it's the good or the bad, it's all there. Whereas LinkedIn is like a bit performative and a bit, let me show you the highlights. It serves a purpose, but this can work really collaboratively with LinkedIn or other platforms, even a resume. So let's get into it.
Stephanie (03:51):
Rebecca Basian is a creator. She's created a startup, a tech movement, a book, multiple written visual and aerial art pieces and two humans. She is the CEO and co-founder of Own Trail and was previously vice president of product and community and Culture at Zillow. Rebecca is the author of Blaze Your Own Trail, a board member of JPEG Morgan and Bellweather Housing, a contributor to Forbes and an investor and advisor to Authentic and Web three companies.
Harper (04:22):
Welcome Rebecca. So happy to have you here.
Rebekah (04:25):
So happy to be here. Thanks for having me.
Harper (04:27):
Absolutely. So let's start, can you tell us a little bit about where you are in your life right now,
Rebekah (04:33):
<laugh>? Well, physically I'm in Seattle, Washington in my startup garage. I am the CEO and co-founder of Own Trail, which is my first time being an entrepreneur. I've been building own trail for about the past two and a half years and left a, a corporate executive role to go do this. So first time founder, although I feel like after two and a half years of building a startup, you've survived enough to almost be like a, a second time founder by now. In terms of what you've learned <laugh> Um, I'm a mother of two boys actually today is the nine year old birthday and then I have an 11 year old as well. And I have a husband who has a vintage furniture store. I have a dog and a cat. I have a lot of great communities that I'm part of, both physically here in Seattle and thanks to the internet all around the world as well. And I'm really passionate about community and really authentic connections, which is a lot of what we're building with own trail.
Stephanie (05:31):
That is fabulous. And there are so many things that are in your life clearly that could have taken your time away from building own trail given all that you just described to us. But if we go back a little bit into your journey of sort of what brought you to this place, one of the things in reading the Prep before the interview and your own trail was that you went to quite a few few colleges, <laugh>. Can you just tell us what that experience was like and how that came to be and how it shaped you as you move forward in your life?
Rebekah (06:07):
Yeah, definitely. It was, it was a while ago. I'm 44 now, but yeah, I was in college from I think basically eight on and off from 18 to 24 I guess. So yeah, the first one was a liberal arts school in Colorado that I failed out of pretty quickly just for really lack of going to school <laugh>. Actually interestingly I just had a, a weird like anxiety dream last night about like being enrolled in college and not going, Those still happened <laugh>. But yeah, I was just, I was partying a lot of that time and didn't really know what I wanted to be doing and actually went on a music scholarship and like didn't even continue doing music really <laugh>. So after I failed out there I moved to Seattle with an ex-boyfriend, I mean current boyfriend at the time and just you know, worked here for a while and then ended up enrolling in community college here and that's where I discovered I really liked math and science kind of stuff.
(07:00):
And so after brainstorming over drinks one night about what kind of a degree would lead to being an inventor, which I felt like I would like to do <laugh>, I came up with mechanical engineering and decided to pursue that. And so I took some classes to prepare for that and ended up transferring into UDub to do a mechanical engineering degree there. Sorry, UDub is University of Washington here. And then I ended up going to grad school at Berkeley and getting a master's in mechanical engineering there and then proceeded to not do mechanical engineering for career <laugh>. So.
Stephanie (07:34):
Well why I asked you was not so much for you to, I wasn't trying to put you on this spot for your resume, but more just to say like everyone starts out with a windy road. Yeah. Even if you end up in with a graduate degree in mechanical engineering, which sounds like something you would've had to be super focused on to accomplish the way you get there is not a straight line. So I think you come by this own trail idea of yours very naturally.
Rebekah (07:59):
Yeah, I've definitely lived the things I'm trying to convey in own trail, which is that there's no such thing as a right path certainly, but usually not a linear path either. And that, you know, these different twists and turns along the way are what make us who we are and it's the unexpected opportunities that can kind of arise from that that lead to really cool things.
Harper (08:19):
There's so much to your backstory that's really interesting and I wanna make sure we dig into, but I feel like it's really important to acknowledge what own trail is and how you got there because it'll help us go backwards and figure out how you got to your own trail.
Rebekah (08:34):
Yeah, yeah, I love that. That way of looking at it. So what own trail is is a social platform where people achieve their next milestone and the way that we create that is people really sharing authentically what their journey has been but also really where they wanna be going next. And then we have both a tool set that we kind of consider like an OS for your life aspirationally is what we're building here, but also really the support of a community to help people reach those aspirations and work towards what's next for them. Acknowledging that what's next isn't always the next rung on a ladder or the next step in like what society has told us we're supposed to be doing. And I think a lot of the people that end up on own Trail are ones that have maybe been following what they thought was like a right path that they were told they're supposed to be following and are suddenly like, wait a minute, this isn't fulfilling me, this isn't really what I want.
(09:26):
And so it's a lot of people that are like getting more real with where they want to be and where they're going and then really coming together to support each other and help each other along the way. When we first launched it was really the idea of sharing your authentic trail. So this is something that it spans your personal professional life. It is much more real than what you would see on like LinkedIn or social media where it's not just the highlight reels, but it's like all the things you really navigated and the things we're navigating right now and the things you're working towards both in terms of owning that yourself but also for seeing what other people's journeys are and really the solidarity and confidence that comes from seeing everybody's whining path. And particularly, you know, we've really been focused on a diverse community in a really intersectional community because of the importance of seeing people that look like you that are in those places you aspire to or that you're going through right now. And so we really started with like the trail is the foundation there and people just sharing very authentically. And then from there we've really built over time how do you take action on that trail? How do you move to that next milestone and how can we all be supporting each other and how we get there.
Harper (10:36):
I remember when we first connected and you sent us your trail and Steph and I both spent hours <laugh> working on our own to share with you. But because we just got totally into it and realized how much is missing from something like a LinkedIn or a resume and the value that you provide in saying we're gonna acknowledge health challenges and failures and mistakes and all the bumps along the way that people are typically not talking about. Obviously one of the many reasons why we started this podcast. So it really, really resonated with us to go through that process and then start telling people like, this is a great supplement to your resume, to your LinkedIn. Can you talk a little bit about your history now that led you to create this and the jobs that you had before?
Rebekah (11:29):
Yeah, definitely. Well, professionally, what I think prepared me for building a company was, was my experience at Zillow before this. Cause I was there for 15 years, so that's the bulk of my professional experience. Started as one of the first employees as a product manager and grew into vice president of product and worked on a lot of different areas of the company there. And then I made a career pivot into vice president of community and culture, which was really focused on creating equitable systems both internally and externally at the company and creating social impact through our business. So kind of that intersection of product strategy and social impact I think is like professionally what prepared me to, you know, as much as you can be prepared to build a startup, which <laugh> nothing truly prepares you. <laugh>. Um, <laugh>.
Stephanie (12:15):
Well said.
Rebekah (12:16):
Yeah. But you know, I think experientially, in addition to clearly my own non-linear <laugh> path with plenty of failures along the way was just getting to know a lot of other people's journeys as well. I'm the person that says yes to a lot of different coffee chats with new people and everyone seemed to have this kind of resounding concern, I guess, of feeling like there was some right path that they were supposed to be on and feeling like they were getting it wrong or like they were supposed to know exactly where they were going and how they were gonna get there. And you know, there's so much kind of uncertainty and anxiety that comes from that really pretty unrealistic thinking around how we're supposed to be navigating our lives that I just found myself wanting to shout from the the rooftops. Like there is no one right path, you can't get it wrong, you know, and be true to yourself here.
(13:05):
So that actually led me to writing a book called Blaze Your Own Trail. I don't know if you know like the Choose your own adventure books, um, the Childhood series. Yeah. But it's that format where you're reading and you make a decision at the end of each chapter and that tells you where to go next and it's exploring the different decisions and pathways that women take through their personal and professional lives. And so that was actually what led specifically to starting on trail was I'd signed with a publisher and was kind of playing around with what I thought would be a cool book launch website and that kind of took on a life of its own I guess. You know, I just started having some really big ideas around the power of seeing the infinite number of different windy, non-linear, imperfect paths that people take and how powerful it is to see those and share your own. And so that's what turned into this idea for Own Trail. I met my co-founder Katie around that time and she really loved the idea and we ended up running with it and we both put executive roles that we were really happy in in order to build this and it was a good move. <laugh>.
Stephanie (14:05):
That's amazing. That's great. No, I think graphically representing a story is so powerful compared to if you will, the traditional resume bullet point, right? Yeah. Even a LinkedIn profile at this point. And it reminds me when I was at Dell years ago, there was a woman who had gone out on maternity leave, taken a career break and was coming back and I was interviewing her, this person that had so much more experience than I had at the time and she had made a PowerPoint of her career trajectory and it was actually very much a squiggly line, but it continued moving mm-hmm. <affirmative>, you know, to the next level. And that really stuck with me because I felt like it was something that so many people don't talk about. Yeah. Or at least haven't talked about before. Now I do think there are more people talking about it now, about the fact that your life has twists and turns, hence your career. That there isn't to paraphrase you, there isn't one Right way. So when you think about setting examples in what you're doing for women in particular, how have you seen own trail or the feedback you've gotten on your writing open more eyes and ideas.
Rebekah (15:24):
Well I think when people see, like I'm sure when you saw that women sharing her career journey, like it sounds like that inspired you to share more of your own in that way, right? Mm-hmm <affirmative>. And I think that's really what we see happening here is that when you see other people sharing really authentically and not just the highlight reels and not just the wins or the end results, but the whole story, then you're like, Oh I can do that too. So it's that kind of like authenticity leads to authenticity thing and then it's this effect of like, it's actually really empowering and kind of freeing in a sense to just really own your story in that way unapologetically. Like, this is all my story, these are the things that happen, I'm proud of the things that I've been able to make it through and that's brought me to who I am and that informs where I'm going and all of that.
(16:11):
And so I think it's both the solidarity that comes from realizing you're not alone in having this kind of wonky path because we, we all do. And being able to say like, Oh, this place that I aspire to, like here's all these different trails that have gone there and they all do it differently. Like there's not one way. So kind of really experiencing that but then also just seeing and being influenced by that level of authenticity, it brings people closer. Like we've heard from a lot of people that they've made really impactful relationships on own trail friendships and like support systems because when you're connecting with people, even if they're coming from, you know, really different backgrounds or physical locations or anything, but you're, you're showing up in this really authentic way, it really, it creates a different dynamic than, you know, trying to get the most likes and the most friends or followers on social media or you know, like it's, it's just a really different kind of dynamic and it, it's affecting people in a powerful way. And I think it's needed right now. You know, I think we're at a time when we're all kind of noticing and feeling the inauthenticity and the way people share and connect and even like the boxes that we're trying to fit ourselves into. And when you see like patterns and even just like what's happening with the workforce right now, there's a lot of people that are making big pivots in their lives and looking for more fulfillment and more realness. And I think that this is a solution that really speaks to that.
Harper (17:28):
What's really interesting is that you acknowledge that you quit your job while still enjoying what you are doing. And I think so often people leave jobs and go to other jobs or start businesses because they're miserable and they wanna get out and you're saying this was a good situation, but I had another agenda which I love so much.
Rebekah (17:48):
I mean I was really lucky to have the privilege of leaving because there was something I was running towards instead of something that I was running away from. You know, I think that's not always the case. So I definitely feel lucky for that. But I also think that when things aren't terrible, people can often get in a RU and get stuck and not have as much of a reason to leave. And so for me, I've made some big transitions certainly within Zillow and before <laugh>. But then obviously the transition of leaving to start a company oftentimes comes from side projects for me. Which I think it gives you the ability to try out a path without completely changing course. You know? So like for example, when I took the pivot from being, you know, a product leader to a community and culture leader, that was scary.
(18:29):
But I'd been doing a lot of those projects for years, like as side projects before I made the switch and had kind of proven to myself that that was what I was most passionate about at the time and proven to the company that I could be really effective in doing those things. And so then I was able to make the case both internally and externally for making that pivot. And I think the same thing with Own Trail, like it started off as a side project of a book launch website and then I realized there was a there and I started pulling a team together. But it definitely could have gone on indefinitely as a side project too, right? Like mm-hmm <affirmative> after long enough of realizing we had an incredible team coming together, realizing we had a really big idea we were working on and realizing that like there was no way I could not do this <laugh> then I kind of was able to have that conversation with myself and my family and my co-founder and all the right people about like, you know, if we keep doing this as a side project indefinitely, then it has a lot less likelihood of really being successful than if we go all in.
(19:24):
But by that time it wasn't like this rash decision, it was something that we'd already been kind of investing it. And I'll mention that there's been plenty of side projects and plenty of ideas that I haven't gone all in on too, right? The ones that really end up sticking and that end up being right for me are the ones that then force kind of a bigger pivot. But it's a nice way to prove that to yourself first.
Harper (19:45):
I think about how we often lead with our accomplishments and our resume and our bios and everything's like, here's everything that I've done that I'm so proud of. And for so long it used to be like hush hush that I'd say I had eight jobs in 10 years before I started my business. And when we started working on our bios for this business, that is the first sentence in my bio and I've pivoted the way that I approach that because for me there's a level of accomplishment of where I've gotten cause of those eight jobs and how I've become who I am. And I wonder what your take is, given what you do with own trail and your own story, why you think people are now leaning towards sharing these moments in their lives that could have been looked at as mistakes or failures back in the day. And now it's like the more vulnerable you are, the more people connect with you.
Rebekah (20:44):
Yeah, I mean I will say that it's not for everyone, right? <laugh> like there's some people that really wanna still hide behind the highlight reels and that's okay for them. Cause the people that are on own trail, it's an incredibly diverse community in terms of geographies, ages, ethnicities, sexual orientation, just backgrounds, types of careers or non careers and all, all the different things there. But there is this kind of psychographic thing that I think everyone has in common, which is really looking for realness, looking to kind of break out of the status quo and stop fitting into these molds or you know, stop hiding behind the highlight reels. And I think that's what really brings these people together. And I will say that I think we're in a a time where more and more people are starting to feel that way. You know, like just mm-hmm <affirmative>, screw it, I'm tired of being what you want me to be and ready to be who I am. And so I think that's kind of the commonality there. So for people who have reached that point, which can take, you know, lots of unpacking to get there, this is really the, the antidote to a lot of the com compartmentalization that we've been forced into.
Stephanie (21:44):
Yeah, that's such a great frame of the compartmentalization. I think it has been, you know, silos in our lives the way we have lived them and through the pandemic and working from home, everyone's work was forced into home and home forced into work, right? It broke apart those walls. So now it's what's next, right? Mm-hmm <affirmative>, speaking of new models, there's some conventions around entrepreneurship we've been hearing about for years, right? Hustle culture and I know that we've been debunking girl bosses, but how have you taken your own individualistic approach even into the entrepreneurship space?
Rebekah (22:24):
Yeah, I mean thank you for naming the kind of stigma of entrepreneurship equals hustle culture because it's very real. I mean I actually for a long time thought, which is you know, in hindsight kinda a ridiculous thought. But I felt like I would love to start a company someday, but I don't think I want to because I can't handle that kind of hustle culture. You know, I'd been an early employee at Zillow at a time when I had a lot of freedom in my life. No kids yet, you know, less obligations in the early days it was pretty around the clock and I loved it. It was really exciting and all consuming <laugh>. But then I was like, oh, I'm not in that state in my life anymore so I don't think I could start a company cuz I can't go through that again. Which the ridiculous part is that in realizing finally that, well if I'm the one starting the company then I can set the culture is like I don't have to follow that playbook.
(23:09):
And we've really prioritized, you know, healthy work life balance and just generally mental health and all of the things that also lead to that like transparency and communication and you know, being able to really show up fully and take time we need when we need it. And the things that are kind of like known best practices now. Although for some reason a lot of companies don't, don't do them yet. We've even been piloting a four day work week, which has been really cool. And what I've seen is that we're both attracting some of the best people I've ever worked with in my career. And from what I hear from them and from what it seems like they're doing the best work of their careers. And I think that, you know, creating that culture that's not going to create burnout and you know, other unhealthy habits really does bring out the best in people and brings the best people to the team. And so I'm really proud of the way that we've been able to do that and break through some of those stigmas of what it looks like to be working at a startup.
Harper (24:07):
That's huge. I love that you're doing the four day work week. I have a friend who works for a company that's doing it and it's going super, super well and they've already extended it through the end of the year because people are enjoying it and being so productive and it's not about more, more, more. I think that is so much of a myth of like it has to be so aggressive and soly that is that a wordy?
Rebekah (24:32):
It's
Harper(24:32):
And that's the way to be. So you talked about the importance of, and you have two sons and a husband and you also have a passion for aerial ACRs. Can you talk us through a little bit about your side hustle, your passion projects and how you spend your time outside of own trail?
Rebekah (24:53):
So yeah, a lot of different creative outlets. Aerial aros being one of them, I do um, visual art, both digital and physical. Um, I write a lot in addition to my book that I wrote, I write regularly for Forbes and some other bylines as well. And then I'm also really into a lot of things in web three. So I'm part of a couple dows and doing a lot in that space, collecting art and stuff. And then yeah of course the family and the friends pieces of it. Recently I actually made a Venn diagram of my life <laugh> and very visual. And so I woke up one Saturday morning and I'm like, I wanna map this out. And what I was able to visualize with that is that these aren't all like different fragmented things, pulling me in different directions. They're all complimenting each other. So the three kind of circles in my Venn diagram are community entrepreneurship and creativity.
(25:42):
And the cool thing about my life right now is that it's full of things in all those circles but own trails really smack in the middle of those three. Hmm. And that's really great. Like it means that everything I'm doing in all these different parts of my life are all enhancing each other and adding to the net sum which is, you know, obviously going into own trail but it's not this like push pull, trying to squeeze it in, pulled in different directions, chaotic thing. It fills me up from different ways and I can feel when I don't have some of those, right? Like if I'm don't have enough time for creative outlets one week I feel myself craving creativity cause I need to be filling up that part, you know? Or if I'm too busy and not having enough time with my family or my friends, like I can feel that need.
(26:22):
And so being intentional obviously about my time, but I think the way that these things compliment each other, but also the fact that I've also, I feel like created a life that's full of things that energize me. And I think, you know, we've all been in places where the things we're doing don't energize us, where they drain us and you have a lot less capacity for doing things right. It just, just, it really sucks your energy and so when you fill your life up with things that energize you, you just end up having a lot more capacity for all those things as well.
Stephanie (26:51):
You mentioned the word intentional and I do think there has to be the intention to choose how you're spending your energy, right? As you just described in your circles of your Venn diagram and where they overlap, which is lovely and amazing that it's within the passion of your work. I wonder though, what have you let go of or had to figure out how not to do in order to have space for the things you do that you are intentional about?
Rebekah (27:23):
I mean I've gotten a lot better at saying no to things just based on time constraints, you know, <laugh>. So I don't say yes to every social engagement or every like speaking opportunity or every opportunity to write a guest article. And I definitely time box my time because the thing is like most of the things that I do, you could do forever. There's no like end state, which is great, but when there's no end, you just really have to create artificial end points within your day in order to, to fit things in. And so I'm pretty good I think at, at doing that. I mean, not necessarily like all perfectly mapped out on my calendar or anything, but just kind of in my mind I know this is why I'm focusing on at this moment until roughly this point in time and I'm transitioning and, but yeah, I couldn't say that I, there's like a huge part of my life I've said no to. I think it's more like on a opportunity by opportunity basis that you know, just like saying no to enough things that I don't and cause I know how it feels if I have too many things in my day and that doesn't feel great either. So yeah. Yeah.
Harper (28:22):
You created community for other people. So I'm curious what community looks like for you. You mentioned you have things locally in Seattle and obviously virtually, but what role does it play for you in your life these days as an entrepreneur, as a mom, as an artist?
Rebekah (28:40):
Oh my gosh, community is just so important to me everywhere. Like I have all these different kinds of communities, some that I create, some that I join. I started a community called Authentic, um, coined this term authentic when I was kind of talking about and thinking about like, so they're a different category of tech startup that's not the existing check boxes, right? Like, you know, when I was fundraising for Own Trail, I felt like there were literally a lot of check boxes to check about what type of company are you. And I didn't feel like we really fit into any of them. So I started talking about this idea of authentic, which is like, you know, community driven companies that really center people but they're not exploiting or commoditizing people and really leading with values and still, you know, venture skill profitable companies but are really values driven in terms of how they're, they're serving their communities.
(29:26):
And so I wrote a Forbes article about that and was kind of talking about it and all of a sudden all these different founders started raising their hands and being like, hey, I resonate with this. Like I felt like I didn't have a word for what I was building either and this is it. And so a community around that kind of naturally formed, that's a pretty important one in my life now there's I think 150, 200 founders in a slot group there. And um, we do different virtual meetups and I send out deal flow of those companies that are fundraising to investors that are interested in, in being part of that. So that's been one that I think basically is serving the native like other founders that are in similar stages and are building values driven companies that are going through a lot of the same things I'm going through.
(30:09):
And having that community is really huge. You know, I mentioned I'm really into Web three and there's a few communities that I'm part of there. JPEG Morgan is kind of an alpha group for NFTs and then OG Collective is artists and art collectors that come together. And then there's actually uh, an all woman dow that I've been helping Bill called Joan Dow that um, is about making money for women. And so some different communities in that space that are prevalent in my life. And then, yeah, local communities of friends and you know, you mentioned aerial arts, there's a strong circus community here that I adore. And so yeah, just really different facets of my life. That was kinda rambling. But I think the point here in all these examples of my communities is that like there's not one that serves all my needs or all the different experiences and identities that I hold, right?
(30:57):
And so, mm-hmm <affirmative>, um, any given day or any given time, there's probably one community that's the most relevant to what I need. Like right now I need to be talking to other founders and bounce this idea off of them. Or right now I need to commiserate with other parents who are going through this school strike that we're going through, you know, so we're really kinda, we're taking that and modeling that within an own trail too, kind of as we think of what's next for own trail, we're really trying to see how can we emulate some of the fluidity of the micro communities that really stabilize and help you through your life, knowing that there's not just one circle that you're meant to be part of, but like how do you move through those different circles of support systems and friends as you're navigating different parts of your life.
Stephanie (31:36):
I know you've written some Forbes articles about women in business, which makes me think about expectations. Yeah. In terms of how we operate within these communities. From what you've experienced through your career and personal journey now, how do you think about setting expectations for how you show up or what expectations you have for yourself as a leader in your own company? How has that shifted for you?
Rebekah (32:06):
I think modeling authenticity like we talked about earlier, right? Where like I show up vulnerably and and authentically and I think that that brings out some of those dynamics and others with Rill we have our core values and they really help define internally how we operate, but also like what we're building externally. And so I think when you define your values and you bring people together around them, you kind of find your people and that's kinda a magical thing that can happen.
Stephanie (32:33):
See you've ended up inventing something, <laugh> your own system for how to be authentic and intentional and creating your community. You've done it anyway.
Rebekah (32:44):
Yeah. It's funny you mentioned that the only like physical invention that I've made so far is a pretty cool multi-purpose aerial rig in my yard that I designed and had built, which is like a kid's place structure and an aerial rig. But <laugh>,
Stephanie (32:56):
I love
Rebekah (32:57):
That. That's my one like mechanical engineering related invention. But you're right, I have ended up spending the whatever, 20 years since I graduated with those degrees, inventing all sorts of things and most of them aren't gadgets <laugh>.
Harper (33:12):
So what's next for Own Trail?
Rebekah (33:14):
Well, we're just kind of getting started, you know, I think we've spent the first couple years really creating a foundation of, you know, like I said, how do we kind of manifest these values in a tech product? And that takes very in intentional trying things, building with the community, not just for them. And so we've gotten to a really powerful foundation in terms of people being able to share, to see other people's journeys and to really work together to achieve their next milestones. And now it's about like how do we scale that? And so, you know, we're really working on scaling it through reaching all new people. You know, we've been growing totally through word of mouth so far. So finding ways to reach a larger audience and really impact their lives in this way. I kind of envision this neural network of life paths where they're all intersecting implicitly and explicitly in terms of like the people that you're actually connected to that impact your journey, but also the people that are living these parallel journeys in different areas and how you can be helping each other along. So we got a lot to do still and I'm really excited about it. It's, you know, I heard someone say once that you wanna build a company around a, a whole kind of revolution, not just a feature. And I think that's definitely what we're doing here. Mm-hmm <affirmative>. So we got our work cut out for us. <laugh>,
Stephanie (34:29):
No small task,
Rebekah (34:30):
No <laugh>, but it's exciting.
Stephanie (34:33):
That's amazing. So speaking about having an idea for something, our title for the podcast is the idea around what's good enough for now. Mm. When you hear that phrase good enough for now, what does that evoke for you?
Rebekah (34:50):
The first thing that popped into my head was this idea of like building in public and learning in public. Conversely, if you're building in private, you get to this like state of perfection before you lift the drapes and let people see what you've been working on or whatever. Which I feel like that's kind of like the antithesis. So good enough for now is like wait til it's good enough forever, right? If you're building in public, if you're learning in public, you're sharing along the way, you can put things out there, you can build with your community, you can share openly what you're learning and thinking. And what that means is sometimes you're gonna put something out there that doesn't work or sometimes you're gonna share something you're learning that's wrong, <laugh>. And so it requires a sense of humility and removing the ego enough to be able to be wrong in public or fail in public, right? Because if it's just good enough, it might not always make it, but I love that. Like that's the way I like to operate because you can do so much more when you're not just like waiting in the shadows for perfection and you know, and when you do that you have a whole community along with you too. So I really like that idea of good enough for now knowing that it's almost like a contract with your community that we're doing this together and it's not gonna be perfect, but it's gonna keep getting better together.
Harper (36:04):
Love it. Amazing. Thank you so, so much. Rebecca, can you tell our listeners how they can find you, how they can get your book and join own trail?
Rebekah (36:14):
Yes, well Own Trail's, definitely the best place to find me, it's own trail.com and connect with me on there. So to Rebecca we can post my trail on the show notes. I love to connect with people there. I'm also on Twitter and LinkedIn, Instagram, so like you know the usual platforms, I'm quite findable. My book is available in any bookstore, Blaze Your Own Trail. But in the footer of own trail.com, there's a link about the book and I have some links to some local bookstores there if you wanna order it from them. Kind of pro tip. If you order it from Secret Garden Books, which is a few blocks away from me and put in the notes that you want it signed, they'll call me up and I'll run over and sign it for you. So <laugh>, that's an option if you wanna sign copy. Fabulous. Yes,
Harper (36:57):
So fun. <laugh>, thank you so much Rebecca.
Rebekah (37:01):
Yeah, thank you so much for having me. This is really fun.
Harper (37:03):
Rebecca is offering our listeners 25% off your first year of own trail membership. Head to own trail.com and use promo code Geffen, G e n, just like the first letters of good enough for now to get 25% off. It's your journey, Own it.
Stephanie (37:27):
If you'd like the show, please follow us on Apple Podcasts, Spotify, or wherever you listen and give us a five star rating and review
Harper (37:35):
For show notes and more information, head to good enough for now pod.com
Stephanie (37:40):
And follow us on Instagram at good enough for now Pod. See you next week.
