Rebekah Bastian, the Co-Founder and CEO of OwnTrail, started off her professional life with a mechanical engineering degree because she wanted to be an inventor. She ended up realizing it wasn’t what she expected, and later got a job with Microsoft as a program manager. After about three years there, she sought something different from a large, corporate environment. That’s how she ended up at a new startup called Zillow, where she worked for the next 15 years, essentially touching every part of the company. Rebekah then wrote a book, which ended up becoming an entire startup—and she left her career to pursue it.

Show Notes

Rebekah Bastian, the Co-Founder and CEO of OwnTrail, started off her professional life with a mechanical engineering degree because she wanted to be an inventor. She ended up realizing it wasn’t what she expected, and later got a job with Microsoft as a program manager. After about three years there, she sought something different from a large, corporate environment. That’s how she ended up at a new startup called Zillow, where she worked for the next 15 years, essentially touching every part of the company. Rebekah then wrote a book, which ended up becoming an entire startup—and she left her career to pursue it. 

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Nonlinear is presented by Teal and hosted by our Founder & CEO, Dave Fano. At Teal, we’re building the first genuinely consumer-first platform to help people grow and manage their careers. Our goal is to empower people to land jobs they love with free tools that guide and automate the process. Learn more at

This podcast is produced by Rainbow Creative with Matthew Jones as Senior Producer and Drew MacPowell as Editor and Associate Producer. Find out more about how to create a podcast for you or your business at

What is Nonlinear?

Everyone's career path is different, built by pivotal moments and choices. We're on a mission to amplify those stories and examine how our decisions shape our careers.

Nonlinear is hosted by Dave Fano, Founder & CEO of Teal—a genuinely consumer-first platform designed to help people grow and manage their careers. Our goal is to empower people to land jobs they love with free tools that guide and automate the process. Learn more at

Rebekah Bastian: [00:00:00] I felt a lot of ownership over Zillow, both in a practical sense that like I had equity in the company. And also just because I'd been helping grow it for a long time and felt like it was my baby and a lot of.

David Fano: Thanks everyone for joining today, where with Rebecca Bastian, who I'm incredibly excited to talk to, because we're both aligned on the same mission we're after and kind of slightly different ways, but we've both become incredibly excited about careers and shining a light to the complexities of navigating careers.

Um, and, uh, I think it's better that, uh, Rebecca described it in her own words. So Rebecca, tell us a little bit about you.

Rebekah Bastian: Hey, Dave, thanks for having me on here. Super excited to talk about it. You're so right. That we're very aligned. I am the CEO and co-founder of own trail, which is a platform where women visualize and navigate our life paths.

So we are all about the [00:01:00] very real nonlinear paths and the way that our personal and professional lives are inherently intertwined as, as we navigate. Um, and in addition to being a startup founder, I'm a writer, an artist, a mom, a community builder. I'm a budding angel investor and startup advisor. So lots of things that I really.

Embrace the multihyphenate, which I think is sometimes not always as obvious in, in our, like the bio that we might traditionally share about ourselves or the titles that we hold.

David Fano: Yeah. And I'm, I'm excited. Thank you for that. I'm excited to talk about that. Cause I think a lot of people struggle with that and, and for, for, for the right reasons.

Cause I'm not sure the world's ready for, for people to do that. And it's folks like you blazing the trail pun intended, uh, making it easier for, uh, for everyone. So. The way I like to kick this off is when was the first time in your life that you really thought [00:02:00] about your actions in the context of career, um, where you were taking like a deliberate choice in a way that you thought it would affect your career?

Not necessarily like what you're doing today, it'd be like, okay, this action I'm taking is for however we define career, but like,

Rebekah Bastian: Right. Yeah. I mean, there's, there's definitely been some points like that, but not as many as you might think. I guess, you know, the third time I went to college filled out the first time that I went to community college and then I transferred into, uh, um, mechanical engineering at university of Washington.

So I'd say around that point, like mechanical engineering was, uh, um, a means to an end career wise kind of, but the career in my head was I want to be an inventor. You know, I guess as an entrepreneur, I am that, but not in the same, like kind of gadget focused way I initially, but that would probably be like the first career driven decision that, oh, I

David Fano: love that.

So when, when did [00:03:00] you, when were you able to put words around this idea of being an inventor? Like what, what helped you arrive at this notion of being an inventor? It's like such a specific word. Um, but like when you hear it. I think of beaker on DuckTales. I think you and I are like similar generation where we probably watched that show.

Um, but that's, that's kind of like, you know, the, the gadget maker, the what, what, like, how did you arrive at that?

Rebekah Bastian: Yeah. Or like penny on inspector gadget. Right. But, um, well, you know, like, like most of the stories where like, it's funny, cause you can look at like my LinkedIn or my resume and be like, wow, she's had a very.

Accomplished career. And a lot of ways, you know, I grew to be a corporate executive and I've started coming. I like most of the things that turned out to be really smart career decisions were not made with a whole lot of like planning or, or being too strategic. So the inventor, why not? I was like sitting around with an ex boyfriend and his brother drinking tequila.

And I was like, what do I really like? I'm like, I like inventing stuff. I [00:04:00] want to be an inventor. And then his brother. Well, I think mechanical engineering is a degree you get for being an adventure. I say, okay, that's going to be what I do. That one went down.

David Fano: We have that in common. You know, I went to my high school, counselor, college counselor, whatever that was.

And I was a comic book artist. I like drawing, I like making stuff. And I said, I want to be the person that makes those like really cool car drawings, like the thick black lines and the markers. And she said to me, that's a mechanical and. And I came home and told my dad that, and he goes, that's not that he's like, he didn't know what it was called, industrial design, but he knew it wasn't mechanical engineering and he couldn't get into the word engineering.

And he's like, that's definitely not that. Um, and so he was a builder. I ended up studying architecture, but you know, it was kind of, I was led to led to believe that mechanical engineering. Which is I think a very, you know, we both now know probably a pretty good sense of what mechanical engineering is, and it's not what we were after, as I would say, like both being more like [00:05:00] ideas, people.

Rebekah Bastian: Yeah. I mean, I definitely had a heartbreaking two weeks at the end of undergrad. I told this professor. So I had, I didn't know what to do after undergrad. I still wanted to be an adventure and I had applied to two grad schools. And then I was like, well, if that, if I don't get into one of those, then I'll figure something out.

And that one had already rejected me. And I talked to this professor in my program and I was like, yeah, I don't know. I want to be an inventor. And he's, he's like this really. Old like kind of bitter guy. And he goes, well, you, you pick the wrong degree for that. I was like, oh no. And then like a couple of weeks later, I got into grad school at UC Berkeley for mechanical engineering.

But like the whole master's program, there was all about like new product developments. And while I didn't go on from there to actually didn't accomplish engineering, like I actually, the most important stuff I learned degree wise was there around like, how do you. Come up with ideas that solve problems and you know, which basically is, is inventing.

And then a lot of the [00:06:00] processes around that.

David Fano: So you've got this degree, um, and you've got, I would say you had clarity on what you wanted to do, which was inventing, like how'd you pick your first job? Like what, what were like, how'd you think about.

Rebekah Bastian: Yeah, you're going to keep getting this theme for me with every question I answer.

So I had was doing a long distance relationship with my boyfriend who was still up in Seattle and I was out in Berkeley. He's my husband now. So that worked out basically. I just wanted to get back to him. And, um, in terms of like where I live next and I signed up for an interview on campus with Microsoft and I was like, oh, they built hardware stuff.

I'll go do a hardware interview. And I showed up and the guy. Um, yeah, I don't know how to give a hardware interview. I'll give you a program manager interview and this was something I'd never heard of before, but I, you know, very low pressure since I'm like, oh, pray I'm interviewing for something. I don't even know what it is.

I'll just have fun with it. I ended up paying the job. So I ended up moving back up [00:07:00] here and working at Microsoft for two or three years, um, on outlook and learn what a program manager is and experienced that.

David Fano: Uh, I think the really important thing there for people to take away is the say right. Balance of being open to opportunities, you know, having some might some intentionality, which I think you did, um, right.

And it doesn't always have to be like for work, but, and the kind of distinction between work and life, I think is a false one, right. They're very much integrated. And when people try to kind of like compartmentalize them, Ends up not working out, but you did have an intentionality, you are open to opportunities and you, and you ended up going to work at a really remarkable company, like fresh out of school.

Rebekah Bastian: Yeah. I, everything you're saying like, yes, yes, yes. That's exactly it. Like the way our personal professional lives are intertwined and the way you can like be directionally guided by values or passions or skills or what you want to be working on, but [00:08:00] like staying open to where that can lead. Cause. You know, a lot of like pretty much everything cool I've ever done in my career.

It wasn't something that I could have predicted much ahead of time.

David Fano: And so you're at Microsoft and you're there for around two years working on outlook, which is like a software on everyone's computer at the time. Um, and like,

Rebekah Bastian: That's another favorite software. I got a lot of complaints,

David Fano: but I loved Microsoft and outlook.

I thought obviously, you know, I have a, like a different level of sympathy for software given that I've been trying to make it for so long. Um, and every, every day my sympathy grows bigger. Um, so. So how, what was that like? Cause I think a lot of people in that moment in their life, they think about like, oh, should I go work at a big corporate or a little company?

And they ended up like really getting wrapped around the axle on a topic like that. You know? How were you [00:09:00] able to like make the most out of that? And how did you think about that experience as you were going through it?

Rebekah Bastian: Yeah, I mean, I took it cause I didn't have any other job offers, so there wasn't like a big like decision tree.

Um, I didn't apply to, I just, I didn't know where to, I just didn't really know where else to go. Um, and to be honest, I didn't like it that much. Although, like, I think I got a lot of really good experiences there in terms of like the big corporate experience and just learning like this role program management, which, you know, AKA product management, which is something I've now done for like, pretty much all my career.

Um, but it wasn't that fun. And I was, I was just kind of like, oh, so this is what it's like to have a real job. Kind of a drag, but okay. You know, like, I didn't know, like I've been bartending up until then, and also doing like every other random job in the world. So like, this was my first real job. I was like, okay, well this is what working life is like, you know?

And so, um, it, yeah, it was okay. And I think part of it was like I was working in a very legacy product. So there wasn't a huge opportunity [00:10:00] to like, make a lot of changes or like innovate from scratch that much. I mean, like the big corporate thing probably isn't my jam that much, like there's a lot of layers.

Um, decision-making and less transparency. At least there was at that time in that org. So it was, um, yeah, but the thing that made me leave was the commute. I hated the commute and I was, I live in a neighborhood in the Northwest corner of Seattle Ballard, and Microsoft is in Redmond across that bridge and it's terrible traffic.

And, um, so I went eventually, I just decided I'm like, this is making me crappy. So I decided to look for other jobs. Yeah. It's actually the first employee at Xeloda answered an ad up a Craigslist. Everyone else had kind of known someone there already. And it was super early days, but I literally was like, well, downtown Seattle, that sounds much better.

Yeah. That was the end of my, my Microsoft years.

David Fano: And w what were you looking for? Were you looking for like program management, product management? [00:11:00] Like that's the roles you were, you were after, and that's what you found on Craigslist.

Rebekah Bastian: Yeah, exactly. And I, this time I interviewed for two jobs and got both of them, but I, I chose this one, which was really funny, cause like they, it was such still startup mode at the time that they wouldn't really tell me what they were working on.

Like I knew that it was, you know, the founders had a great track record. They were the FA the co-founders Expedia. And, um, I knew it was in the real estate space. And the people that I met in the interview loop seemed really awesome. And I was like, you know, what's the worst that can happen. Like it doesn't work out and I take another job.

Startups sounded fun. Um, so yeah, I just kind of leapt into it and it was an incredible decision, like obviously in hindsight.

David Fano: Yeah. I mean, you ended up being there for 15 years and we'll talk about the various roles you had there. Um, today in today's day and age, that's, that's not that common. Um, but to, you said, like what's the worst that can happen.

And I feel like a lot of people don't treat career decisions that way, especially earlier in their life. [00:12:00] Um, And I'm sure you've mentored a lot of people now at this point. And, you know, you've been able to, to be kind of iterative on different parts of your career, even though you had that sort of stability in Zillow for 15 years.

Like how, how, how do you think about that and how do you guide people on this, this mindset that like you can be iterative? Most career decisions are actually not one way doors, uh, two way doors to use another Seattle company reference, um, and Amazon framework. And I kind of believe that, but I think it's hard to convey that to folks, you know, but you kind of, I think the folks with higher risk tolerance are willing to sort of embrace that and take a little bit more like an entrepreneurial approach to their career, even though they're not starting companies like H how'd you think about that then?

And how do you think about that now?

Rebekah Bastian: Um, I think I thought about it more then by not thinking about it that much, you know, like I didn't have nice over this suspicion. I was just like, this sounds [00:13:00] interesting, you know, I mean, you know what I'm trying to think of, like the timing, like. I got married right in between Zillow and on, or right between Microsoft and Ellis.

I guess I wasn't married. I didn't have kids yet. I felt like the, some, you know, like I could always get another job kind of feeling. So I just, I didn't think too deeply the way I think about it now is, is a lot more intentional. And what I've learned is that, you know, like you said, careers can be iterative, but I would even take that a step further and, and say that they're additive, which means that you're never starting over.

You're adding to the experience that you already have. And I think that's something. Learns through the complete fear and identity complex that comes from taking major swings in your career several times that, um, and what I find is that like, oh, that was really scary, but on the other side, it's still me and I'm not starting over.

I still have all the skills and experiences that I already had. And now I'm adding new ones as well. And I think that additive nature is, is kind of reassuring. You know,

David Fano: I think that. [00:14:00] Better adjustment of the language and iterative. Um, they're additive and, and I think that's great because I think all these things, and I think people don't approach their career that way, like, Skills, uh, within teal, sometimes as assets.

It's like, I have this thing. I don't want to use it. I don't want it. I have this ability. I don't want that to be my day job, but also you don't need to resent it. Like you have to recognize it as a thing that you have. It's in, it's an additive component of who you are and you can tap into it when you need to.

Um, oftentimes like people can fleet the content. With the ability. And so it's like, I hated that job. I don't ever want to do that again. It's like, oh, you just didn't like what the situation you were in, but maybe the task wasn't so bad, you know? And like you actually, there's a reason you went into that field in the first place.

Um, all right. So, oh, go ahead.

Rebekah Bastian: Oh, no, it's just, I agree that it's, it's not, it's less about, you know, the skills can be applied to so many different things and takes so many different forms. [00:15:00]

David Fano: All right. So you, you go to Zillow, um, ends up being obviously an incredible company, still a credible company. I check my testaments all the time.

I look at my, I think I look at those emails faster than almost anything where like a new house pops up in my neighborhood. So it's been a really, an incredible company doing some incredible things. And you started there as a, as a very early employee, you know, job tenure these days is two to three years.

You were there for 15, which I think, you know, but you, you were able to move up in the company. You know, and, and explore a lot of different things and I have a bunch of different roles. So once you were there, what was kind of like that next moment you were like, all right, I'm ready to do my next thing.

And you kind of hit one of those career plateaus and made you think about, you know, how, how to get the next thing, you know,

Rebekah Bastian: He needs to be honest, there was only one moment that felt like this might be a plateau. I want to consciously do the next thing. I think the rest of it, like, which I'll talk about.

But, um, for the most part, it was all like [00:16:00] the growth was very organic, you know, like, um, you know, early, early startup days is, are really cool because you can basically just raise your hand for anything. And it's like, there's so much work to be done and, you know, Like, if you say, Hey, can I help with that?

The answer is generally. Yes. You know? And so I did that a lot and, um, got to take, you know, work on most areas of the product over time because of that. Um, you know, like one pretty cool one early on that happens a little bit more intentionally, but, but also like I have another theme in my career is like side projects turning into full-time things, but, um, pretty, pretty early on there when the iPhone first came out.

Some developers. And I were like, Hey, this is really cool. Let's play around with like what a mobile app would look like. And we just did it on the side and it took a really long time because this was before there was like APIs for functionality and stuff. And, um, we, we would just work on it because it was cool and exciting to us for quite a while.

And then when it finally came [00:17:00] out, It was huge. And we were like, you know, Steve jobs is sharing it on stage and, you know, we're featured. And like next thing, you know, like two thirds of our usage is on, on mobile. And so I got to like be the first, um, product leader on, on the mobile app scene and stuff. So that was like a pivot and it really cool experiencing to lead in that phase.

But it wasn't, it wasn't waiting for like, Hey, we're looking for somebody to do this. It was like seeing an opportunity and taking it. And that's something that like, Got onto and freights every chance I get since then, too, because that's, um, you know, when you talk about like, where do you apply your skills?

It's kind of like, you know, where you're needed and what you're passionate about. And sometimes you have to, to create those things,

David Fano: creating. Is something that I think feels super foreign to people where it's like, well, that's not the J D I'm worried I'm gonna get in trouble. Uh, you know, no one asked me to do that.

And it seems like you've done that a few times. And so I'd be curious, like what advice you'd have for someone who's, you know, maybe feeling stuck. A lot of people think their choices to like leave, [00:18:00] uh, you know, leave the company, but they actually want to stay at the company. And that's what. A whole lot of heartache to do that, but you feel like there's no growth potential.

I feel like you've been able to find ways to keep the growth loops going. Um, so can you talk a little bit about that one? And that's a huge shift to go from a VP of product, which is, you know, pretty up there in the product org to then like making almost like a whole functional pivot within the.

Rebekah Bastian: Yeah. I mean that one that's where, when I mentioned the identity complex and that's where that one came, I was like, which is the funny thing was that like, you know, like I mentioned, I've been, I've been spending years doing side projects around like, you know, creating social impact for our products, getting more diversity in our tech or like cultural events.

To really take what was a very positive cultural organically, and turn it into more like intentionally positive culture and, um, all those things. And then like I had that aha moment of like, this is where my real passion lies. Like when friends would ask me how's work going and start like excitedly talking about all the side projects, you know?

[00:19:00] And so, um, so I basically pitched this idea for this new division of the company. And I started with my boss. Um, and then went over to my future boss or chief people officer, and then, you know, our CMO and our CEO. And basically like, it was a very iterative proposal where each person, they talked to kind of like, you know, ripped a little bit and adding to it to the point where everyone's signed off on this idea.

And I was able to convince them that like, yes, even though like at that time, my, my product or was everything driving revenue for the company. So I had to make a pretty compelling pitch that. Yeah, this thing that is literally the bottom line of the company, isn't going to falter if I step away from it, but there's so much upside for this new area that we haven't fully invested in yet.

And so, but then the wild thing was then I freaked out after everyone said, yes, that's when I was like, wait a minute, I'm a product person. I'm a woman in product. I'm a woman in engineering. Like all these titles that I'd always kind of rolled my eyes at, that had been given. Suddenly I'm like, wait, that's [00:20:00] who I am.

I can't go over. I'm not like I'm going to go work in HR. Like that's, that's nuts. And so like, I actually went so far as to send the Friday night email to everyone saying, nevermind, I don't think this is a good idea. Unfortunately, they were like, um, Hey, let's talk about it on Monday. Kind of talk me off the ledge, but it was really scary.

And, um, so it's both, I guess I mentioned that because. How do you create the opportunity to get buy off? Which, you know, I think also a big part of that equation is working at a company that's open to that. It's that kind of thing. And not all companies are, unfortunately, but, um, but then there's also like, you're, there's an eco piece that you have to grapple with too.

And that's like, that's probably the biggest example of what I mentioned earlier of like learning that our careers are additive and not, you're not starting over because like once I finally. Took the plunge and got my bearings and started building in this new space. I realized like, wow, I'm using all of the skills that I already have all the experiences I already have.

I'm learning a [00:21:00] ton of new stuff too. And that's really awesome. And so that was that, that real kind of additive conclusion. And

David Fano: how, how did you think about that time on side projects? So, you know, going back to this, this tension between like my time and where I put my time. And, you know, every hour over 40 I'm like diluting my hourly rate, you know, company doesn't own that time.

And, you know, I'm a big believer that we all actually work for ourselves, whether we run the company or, or an employee. Um, but how did you think about how you were investing that time and, and, you know, cause you could've been doing something outside, you know, in today's parlance, that would be a side hustle, you know?

Um, but you were choosing to focus on. Corporate extracurriculars. Um, how how'd you think about that?

Rebekah Bastian: Yeah, I mean, I'll say for one, it's a great question. If you want a attention for one thing, like I have gotten to this point and I've been at this for a while, I think [00:22:00] where like, I pay attention to what gives me energy and what drains my energy.

And when it seems like it gives me energy, I have a huge capacity for doing them. And it doesn't feel like a compromise on my time. Like if these were like things around like. The slaps when I should be doing it, that would be a really different story. You know? So these were things I was excited about that were energizing to me.

Um, I felt a lot of ownership over Zillow, both in a practical sense that like I had equity in the company. And also just because I had been helping grow it for a long time and, you know, it felt like it was my baby in a lot of ways, you know? And so I didn't, I didn't have that, um, feeling of like, this is my time, not their time kind of.

Um, and so I think that's, I mean, which I think is super important is to give employees that sense of ownership both financially and emotionally. Right. Because that really, that, that drives a lot of that. And, but also I actually kind of thought about it in a flip sense, which was. Wow. I feel so lucky that I get to be working on this stuff.

I'm excited about with the [00:23:00] resources of a large company, because if I was doing this on my own, I wouldn't have those resources. You know, like this was like, I was working on like products that, that tapped into like the homelessness space and housing stability and stuff. And that was something I was really passionate about.

Like I'm on some boards in that space or anything. How cool is this that I get to leverage the resources of a huge brand and a huge company to be building in this space. I'm really excited about because I see all these people trying to do it on this side with no resources. And it's a really hard thing to tackle, you know?

So I actually felt lucky for being able to do that under the umbrella of a larger company.

David Fano: W what I'm seeing is that you were able to like, understand value, like beyond pure comp, right. Which is, I think. One of the tricky things in today's like discourse around careers is because it's the most measurable.

Everything goes back to comp and I think it's done us a bit of a disservice. We have a ton of work to do on comp in general and equality and diversity across all layers. So it's important that we [00:24:00] measure it, but I also think it's somewhat like muddied the way people are able to think about other forms of value.

Beyond doll. I think you, you gave a great example of like being able to use resources to learn that I may not have had otherwise.

Rebekah Bastian: Yeah. Well, I mean, I know that's traditionally true. That comp is like the deciding factor, but when you look at what's happening right now with the great resignation and people with.

High-paying jobs to do lower paying jobs, or like I've, you know, like we're paying startup salaries here at own trail and we ha you know, includes equity and includes like, you know, what we were definitely. Um, and we're very transparent about all of that, but also. I've had way more amazing applicants for these jobs than a lot of the like much higher paying jobs I've had to hire for in the past.

Like, I think people, especially right now are leading with more than just, um, base salary in terms of their decision making, which is really cool.

David Fano: Yeah. I agree. And I think that's why like, mission and what the company is [00:25:00] after is, is so key. Um, I completely agree with you. Um, and I think that there's folks who are like really looking for mission driven companies, um, and I think comp isn't the main thing, right?

People want to be close to family. And so I think the great resignation reshuffle, realignment, you know, all these different, but I think you're, I think you're absolutely right. Right. I think the reason we've had six months in a row of like record voluntary resignations is for exactly the.

Rebekah Bastian: But I think what you said is straight to, which is that I think it's for people who have made job decisions based primarily on comp, there, they're tying a lot more monetary value to every decision within their work than people that are doing it for more passion-based reasons.

David Fano: Right? Yeah. And that's kind of what I see. It's like what, because we don't have mechanisms to quantify the value beyond the dollar. It narrows the scope for folks. And they can't think about these intangibles, um, in other ways, uh, [00:26:00] which, you know, I think we're, we're starting to see it, which I think is great.

Um, But I think folks, like you kind of understood it a long time ago and well, long time ago, neither you or I are that old, but you know what I mean? Not today. Um, but value is beyond the dollars, right? It was experiencial. It was like the, you know, these boards that you got to be a part of. The other thing that I've seen as, as a pattern in folks that operate this way is a little less than.

Longer time horizon and the decision-making maybe not explicitly, like, I know that in five years I'll be able to do this, but this kind of belief that these actions I'm taking today will have value in the future. And I don't need like immediate returns. Like, do you feel like that's something you were conscious of as you were doing it?

Rebekah Bastian: I mean, kind of, you know, I'll do, I mean, that's basically what. Being responsible is right. Like, [00:27:00] you know, like I do things I don't want to do today because future Rebecca will appreciate it, you know? So in some sense, but, um, but also like, and I think this is a big part of the reason that like I started eligible that I wrote a book called blazer in Israel and it's our own child was like the number of people I ended up having conversations with.

Um, really, and I'm one of those people that says yes to every coffee meeting. So I talked to a lot of people. Um, I just felt like so many people and especially women were like, felt like they needed to know where they were going way out here and exactly how they're going to get there and feeling like they're going to get it wrong.

And like both, like you've mentioned the missed opportunities that can come from that, but also just the stress that comes from that, you know, and. And it's not a surprising feeling because we live in this world where you see what appears to be these picture perfect linear paths and these wins. And so when you're struggling and when you don't know exactly where you're going, or when your path is, is much less linear, you can feel like you're getting it wrong.

And really like bath. The goal behind own trail is like, [00:28:00] let's see what the pads really look. And let's own our story on our own terms, because like what you're seeing on LinkedIn or on social media or on resumes is a very small part of the picture. And, um, and it can lead a lot to a lot of those feelings of being not enough and feeling like you need to like have that, that exact plan.

I'd be curious how,

David Fano: how you guide people on it. Because I wholeheartedly agree with embracing the non-linearity of. Um, careers, the kind of expansive additive nature of our careers. But then on the flip side, I would say that the market wants linear careers, right? Like I want a person who's like done product their whole career.

I want to see that you're super, super focused. That you're a specialist that maybe in some context, right. Maybe startups want generalists, but I feel like generally right in the hiring process, I want to de-risk it. And I want to know someone who's like done this exact job [00:29:00] before and like, this is what they want to do.

And like, my dream state would be this like ultra linear. Perfect. This is who I want. How do you, when people are like managing that tension and you can say, look, I disagree. The market wants generalist, happy to have that conversation, but like, how do you think about this like market versus what what's real and how I navigate.

Rebekah Bastian: Yeah. I mean, I like, I think I like to zoom in more to the micro level where it's not just the market, but it's like, who is that hiring manager? Who's that recruiter. And I think that what they want, like, yes, a shortcut is a very clean, linear, obvious set of titles and big companies and degrees or whatever it is.

Like that's a really. Shortcut or bias, but like, I think what these humans want is a story that convinces them, that this is the person that can do the job the best. Right. And sometimes that story is very linear and a lot of people tell it that way on their resume. That, like, I think that's a lot of the power of like, you know, creating your trail on own [00:30:00] trail or, you know, going through a lot of the steps that you recommend on teal.

Is that like, how do you own your story and share it? And you're the one that creates the narrative. So your, your narrative, it doesn't get to be creative. Some recruiter, who's looking at 500 resumes today and patches together. What your story is, your narrative is like, you know, what, what are the things that you wouldn't even see on your resume that make you good at your job?

Because for me, I think the things that make me best at what I do, aren't the things that would necessarily be on a resume and or there, you know, it's definitely just a piece of the picture. And so, um, you know, I, I, the things that I would like to see are people owning their stories more. And more fully and authentically and holistically, I would like to see hiring managers and recruiters like learning how to look beyond those shortcuts, which I think there's initiatives at play there.

Um, you know, I'll say anecdotally, cause I've been a people manager for over a decade now and I've hired countless employees. [00:31:00] The best people I've ever worked with have been the people that have had like non-traditional backgrounds in terms of how they learned or the job experience that they got. And that have had winding paths, like hands down.

Like, I feel like I have enough data to say that in this statistically significant way. So like, how do we kind of help people understand that and rethink, you know, some of those biases that they're looking for.

David Fano: Yeah. I love that. I think the idea of the story and owning your story is key. What. What I've seen be effective, like in the context of a job search as a person who like wants to do a lot of different things and has done a lot of different things is that you don't necessarily need to tell the person everything you've done.

I think a lot of people think that they need to like throw the kitchen sink and say, they're going to pick out the 10 things that are relevant. And that's where I think like the onus is on the person growing their career to tailor their story. Like for the interaction. It's like, it's great to have documented.

It all feel incredibly accomplished about. But I don't need to [00:32:00] tell everyone about all of it. Right. And it's like being selective of when I reveal it. And when I tell a particular version of the story, or like a vignette of the story, then everything in the book.

Rebekah Bastian: Yeah. Yeah. I, I, I do a free service for friends over the years.

I've edited a lot of resumes also, and it's definitely like, there's a lot of oversharing on there sometimes that you need to kind of participate. Um, and I think this is something that, uh, I'm sure you, you help people with a lot too, but it's like, it's the two way decision too, right? Where, like, I think it's important to like own the story of where you've been, but it's also really important to look at that and recognize, like, what are the things that you've experienced so far in your life that you want to keep doing or bring forward with you?

And what are the things that aren't serving you that you want to move away from? And then being really intentional about identifying your aspirations based on that and looking for that in the companies that you're interviewing with or the [00:33:00] opportunities that you're assessing and really, you know, I think it's just the power dynamic to where it's a two-way decision and you, you know, you feel confident both in who you are and what you bring, but also what you're looking for,

David Fano: what was there was that kind of like that next big moment from the product to transition and into being part of the, like the HR.

Rebekah Bastian: Um, well, I mean, it was taking the leap and they'll see the team and because it was a new area for me, I mean, I've been doing it on the side, but there's experts in this space. So I think the best thing I did was just hiring a really incredible team to learn from, and to really lead in different areas of that vision, um, which I was so lucky to do.

And again, that. You ended up being able to have really incredible people to choose from when you're hiring for something that has a lot of impact behind it. Like people really liked to apply their skills to making a difference. And so, um, yeah, I mean, I, I grew that team and we did a lot of really innovative work for just over two years before, [00:34:00] uh, two and a half years before I left to start our own trail, which also wasn't like a conscious decision.

Like I never woke up in. I want to go start a company. You know, I, I actually did literally wake up with an idea for the book that I wrote, um, laser own trail, which is, um, it's this like, choose your own adventure exploration of the different decisions and pathways that women take through their personal and professional lives.

And like literally woke up at four in the morning with idea for that, and then just started running with it. And about five months later had signed with a publisher. Um, there's about a year window from when you signed with the publisher. So when the book actually comes out and so I was like, oh, I could do some really cool, like kind of product based things in a book launch website.

And I started playing with that. And then that's really when I started to have these kinds of like really big aha moments around problems to solve and ways of solving them really. How do you embrace nonlinear journeys and how do you own your story and how do [00:35:00] we see people who look like us in the places we aspire to?

When we don't always have to certainly have that in our direct purview and, um, own troll was born from that. And so that was the next, like, when you talk about like huge things, I think obviously leaving a 15 year corporate career and it's very comfortable corporate executive job to start a startup is.

One of, you know, kind of as big of a swing as it can get. So that, that happens actually a couple of days ago. It was our two year birthday. So we we've been doing this for a couple of years now.

David Fano: Congratulations. Um, yeah. Well, we have that in common. Um, well to go back for a second, you said something that I don't want to get glossed over, um, because I think it's a sign of a really amazing leader.

Should be more common. He's like I got to hire people that I could learn from. And I think a lot of people don't, don't recognize that opportunity that comes in hiring and leading. [00:36:00] And that oftentimes we get to like hire people that fill in our gaps. And if we really embrace that, you know, there's so much opportunity, but this pressure that like, I need to know everything.

All my direct reports know, I need to be able to do everything that they can do. And, and, and I don't. I just, I want to call attention to that. And because I feel like you really embody that in a lot of the things you do and the people you work with and collaborate with that hire people that I could learn from.

So can you talk about that a little bit? A little bit?

Rebekah Bastian: Yeah. I mean, I think I had a fortunate entry into people management in that my first several direct reports, like I was asked to lead this new team. In 2011, which I know because I was eight months pregnant at the time. So I basically started the team and then went on maternity leave.

Um, I was asked to lead this new team that was focused on, um, revenue and tools for, for real estate agents and stuff. And my first several reports were software. [00:37:00] And I am not a software developer, I'm a product. And so I actually think it was a really good entryway into people management, where I had to be humble enough to ask questions and be, you know, be there to clear roadblocks and help prioritize and ask the questions and find people that could give answers that I can give.

And I think that, like, it sets you up to not feel like as a manager, you need to be. You know, no everything or, or micromanaging or whatever. And so, and then obviously over the years, I've also managed plenty of people that share my same experience and background. But I think that that's what set me up to do that.

And I think like the humility of, um, knowing that you don't have to know it all. And, you know, I was, I was lucky to get positive feedback from direct reports who enjoyed me as a manager, even though I wasn't in their like same skillset. And so, um, Yeah, I think that's probably what, what set me up for that.

And then over the years, it's just, it's a, um, it gets reinforced every time you do hire someone smarter than you. And it goes really well, you know? And, um, you [00:38:00] know, I, I certainly, as an, as a manager of managers, I always really try to encourage and appreciate people who are doing the same and, you know, like you're never overshadowed by your employees doing amazing work, like that reflects really well on you as a manager as well.

So, yeah, it's, it's important. And I think, you know, just the employee experience of feeling like. You're coming in because you're bringing something new to the table and not just to filling gaps. It's a really different experience to, you know? Yeah.

David Fano: I think that's a fantastic leadership point as, and you can never look bad for your employees.

Can you say that again? Because I thought that wasn't.

Rebekah Bastian: Oh,

David Fano: you can never look bad by like your employees being amazing. Oh,

Rebekah Bastian: yay. Yeah. Yeah. Like if I'm looking at, you know, a manager that reports to me and their employees are killing it and they're giving recognition to their employees for that, I see them as being a better manager than like, it's very obvious when someone's trying to take credit for someone else's work under them or, you know, it's like, uh, you're not, you're not really [00:39:00] fooling anyone with that for too long.

But it's also comes out in like employee surveys or employee feedback about like, people are happier working for someone who recognizes and appreciates and, um, and gives them the autonomy to do the best work that they can.

David Fano: All right. So you wake up at four or five in the morning to write this book. Um, you know, that even an of itself is a daunting.

The idea of like writing a book makes my head spin because I struggled like write a tweet, but, um, you. You write this book and you sort of, you get it going and you, you know, um, no holding you back. And so talk us through a little bit about that process and like how that became a company. And it, it sounds like you kind of got compelled by it so much.

You're like, all right, I gotta do this. Like, full-time like, I just gotta make it.

Rebekah Bastian: Yeah. So, um, what you in the book process first or the, the company?

David Fano: Yeah, high level, you know, just kind of like your, your thought process, more so than the [00:40:00] tactics, like your emotional journey of like going, you know, identifying this thing that really intrigued you, identifying how, um, how much it could help people.

Then the process of saying, well, actually there's like tooling around this. Oh, wait, that's actually a company. I need to find a co-founder and they're like, you know, now you're two years in and you're doing great and it's awesome. And it's an incredible community, helping a lot of people, but kind of the, the, the, the mental leaps you needed to take to get here.

Rebekah Bastian: Yeah. Okay. So the book was, uh, a process of just like, well, first of all, I really enjoyed writing it. Which I would definitely recommend for anyone thinking about a writer, writing a book. I definitely recommend doing it because you enjoy the process, not just as a means to an end, because otherwise that sounds really painful.

Um, but it was a creative outlet for me. And also I set like daily goals in terms of writing and stuff to keep myself going. Um, and then. Yeah, I could go into a whole different conversation about like the rejection and finally finding a publisher and everything cause like that, the process [00:41:00] in and of itself.

Um, and then, yeah, like when I started so first I was like, like I said, playing around with this book launch website and you know, that feeling when you have like an idea on the tip of your brain, almost like a sneeze that's waiting to come out and you're like, what is it? And I just kept talking to people about like, what is this idea?

Like trying to like, you know, just having more and more conversations, trying to trigger this needs to come out and. And then it finally, like, it just kind of all came together. Like, yes, we need to be able to see what these real journeys look like and be able to share them. Like that was the kind of thing.

And so I started, um, you know, well, first I called my friend, Rebecca who's, who was our first adviser Rebecca level. And she has, she's a huge player in the Seattle startup ecosystem. And so I was like, I have this idea for a startup. Can you advise me on like how to start a startup? I mean, I'd advise other startups before.

So I had some insight into that, but I was. So she, you kind of started helping me think through it. And Carolyn, our VP of engineering is an old friend that I actually used to commute to Microsoft with. And so I, um, [00:42:00] grabbed lunch with her and it was funny. Cause when I had first, um, signed my book and we were hanging out and she's like, oh, well, if you ever want a book launch website, let me know.

I'm happy to help with it. And I called her. I'm like, you know, that website you offer to help me with. And so. Then I'm actually, I just kind of accidentally met my co-founder Katie around that time at an event that we both almost didn't go to. And we connected, and she asked me out on a friend date after that, um, she was kind of new to the area and so looking to meet her people and we totally hit it off.

I started telling her about this thing that I was working on on the side and like, she just got it and was really excited and yeah. That basically started the thing that now happens just constantly every day, which is both of us, like getting these other more excited about different ideas building on that.

So it hasn't stopped since then, but, um, yeah, I mean, we work on it on the side for a few months and then, um, I think we just kind of collectively had this realization that like, if [00:43:00] this is really going to go somewhere, we need to do it. Full-time. And so yeah, we meet and Katie and Carolyn all quit jobs that we love to dive in and do this.

David Fano: And so that, that moment, like if we, if this is really going to happen, we have to do this. Full-time I feel like a lot of people really wrestle with that. And I think it's one of those things. People just think like, oh, they just quit their job. But I think it's far more intentional and thoughtful, especially, you know, you got a family, you had a lot going on.

And I think people do manage that risk and manage that transition, like way more than like the headlines would, would lead us to believe. So again, how did you plan that out and, and like, ultimately make that decision and I'm sure there was a night when you're like, oh, all right. I got to tell people I'm doing this.

This is really overwhelming. And I'm doing it. Like, what was that?

Rebekah Bastian: Yeah, well, so, okay. The first thing I did, which was smart was like, from the beginning of the second, I felt like this could be anything. I like wrote a whole [00:44:00] email to my legal department and said, I'm working on this on the side. First. I ordered myself a computer, but I've been using my work computer forever.

I ordered myself a computer. Started doing everything on there. So it wasn't on like a machine owned by Zillow. And I wrote a letter to, um, you know, the, the, um, in-house counsel that I worked with on stuff. And I was like, this is a project I'm working on. It's I'm doing it only outside of working hours on my own machine.

And I don't know what's going to happen with it. I just wanted to like, fully disclose that. So that was smart to do. Um, not, they think they were going to come after me, but you know, just cover your bases. And then, yeah, I guess we had kind of talked about like, okay, we're going to launch in February because own Trello launched February of 2020, which was the same on the same day that my book came out, we kind plan for the launches to be together for amplification and stuff.

Um, and we were like, yeah, let's like, we'll launch it. Let's see how it goes for several months. And then we can decide if we want to do it full time. But, um, it was actually, I was on vacation in Mexico in December of 29. [00:45:00] Um, and you know, just having some reflective, staring at the ocean kind of moments. And I was like, he was like, this is a self fulfilling prophecy.

Like if we keep doing it on the side to see if it takes off before we make a decision, then has a lot less likelihood of taking off than if we just like, make a leap and go all in. And at this point, like, as Rebecca went to, one of my advisors said to me, at one point she was like, well, the toothpaste is out of the tube now.

Like there's no way at that point, I could've gone back and be like, nevermind. I think I won't do this. I'll just go back to my job. Like, it was just. This thing where I was like, everything I've learned and done in my entire life has led to this moment and I can't not do this, you know? So we talked about it when I got, got back from vacation and we all decided to, we all, um, I gave my notice, I think on January 2nd when I got back from vacation and then it didn't end up leaving until the middle of April, because like, you know, I wanted to do a really very slow off ramp to make sure I was setting the company up with, you know, cause I had started this team and they were so supportive and.

The whole thing was very like good and supportive and [00:46:00] wonderful vibes all around. So, um, it was a lot, there was some months there that I almost can't remember because I was still a VP. It's a low was CEO of own trailer and we were live. And as you know, once you, once you launch, there's no part-time CEO anymore.

Um, and spool to just shut down with the pandemic and my kids were at home and I literally, like, I was just in like the most survival mode ever, mostly blacked it out, but. But yeah, that, that was the most intense few months. And then I think,

David Fano: yeah, it's a, you know, it's amazing how these things come in waves like this, right?

It's like I've got friends like their Mo they decide to move, have a kid, like all the same year. I'm like, they, somehow it just happens like these things cluster, but you came through it on the other end, I think more successful, more resilient. Um, it's really incredible. We could probably do a whole nother episode on own trail, but our goal here is to kind of like talk through the path, um, which I think you gave us an incredible view [00:47:00] into.

Um, so thank you so, so much for that. How can everyone find out about all the cool things you're doing? Your book, your site, your trail, give it to us. We'll link it all in the show notes, but love to have people hear it from you.

Rebekah Bastian: Yeah. Well, if listening to this, you probably find life paths to be interesting.

So please check out on trail and trail that home and, um, anyone can check it out. Anyone that feels comfortable in a space that's centered on women, you are welcome to share your trail there. We would love it. We're growing through word of mouth still. So share it with every inspiring trailblazer that you know, um, and connect with me on there.

I love to, I read every trail and love connecting and following along on people's. Um, both me and own trill are very find-able on Twitter and Instagram and LinkedIn as well. So follow us there. And, um, yeah, I just, I love to, to connect and learn more about the journeys of all your listeners and your book.

Oh yeah. [00:48:00] And, and that's you? Yeah, it's called blaze your own trail. Noble anywhere that books are I, if you go to own and there's a link in this letter for read the book and, um, you can find links to some of my favorite small booksellers there. If you want to go that route. In fact, if you order from my local bookstore secret garden books, and you put in the notes field that you want to sign will call me.

I'll run over and find coffee, please. Yeah.

David Fano: Amazing. That's awesome. Well, Rebecca, thank you so so much. And, uh, we'll get people sharing more of their trip.

Rebekah Bastian: Thank you so much.

David Fano: And that's it for this episode of Non Linear. If you enjoyed today's conversation, make sure to subscribe, share, and rate us wherever you listen to podcasts.|

You can learn more about Teal in our website, or follow us on social media @teal_hq. Thanks again, and please join us again to keep hearing about how we make decisions that shape our careers.