00:00:04
Speaker 1: Rube. Working in uncertainty is something that I have to do now every day, and that is definitely very similar in some sense to being dropped off in the middle of bonos aires without speaking the language. I remember it was pouring outside. We had ten big suitcases. Our airbnb was not ready, and I thought, Oh my gosh, what did we do? Like, why did I leave this really amazing life that I had.
00:00:33
Speaker 2: If you took a year off work, would that help or hurt your career? It was a risk that Anya Smith took, and ultimately it was the best decision that prepared her to lead a team as.
00:00:44
Speaker 3: The CEO of Task Rabbit.
00:00:48
Speaker 2: I'm Jessica Chen and this is leading by example. I'm an Emmy Award winning journalist, founder of soul Cast Media, a communication training company, and the author of the book Aren't Not Loud How to get noticed at work.
00:01:03
Speaker 3: For all the right reasons.
00:01:05
Speaker 2: In many industries, taking time off is unthinkable. There's an unspoken fear of falling behind. But for Anya Smith, packing up her bag and moving out of Silicon Valley actually accelerated her career. In her words, it was one of the best things she ever did to become the leader she wanted to be. Before Amya left for Argentina, she was three years in at Airbnb during a time of rapid growth, while her husband Rob was leading operations at Glassdoor. Yes, it was exciting, but they weren't sure if it was the life they truly wanted and frankly, it's tough to lead a team if your heart isn't in it. By taking a year off to focus on anything but her job, Amya started to identify her priorities for her career and family, and she knew what she wanted to do. In twenty twenty, she became CEO of haask Rabbit, an online platform connecting customers with independent taskers who can do everything from shoveling the driveway to mounting a TV. Today, Anya shares how a hard reset might be the key to growth as a leader, and she offers tips on how you can navigate uncertainty in your own career and come back even stronger on the other side.
00:02:34
Speaker 3: Anya, thank you so much for joining us.
00:02:36
Speaker 1: Thank you for having me. I'm excited to be here.
00:02:38
Speaker 2: So I'm just going to dive into this because I have a lot of questions for you, and I really want to start from the beginning. So for me and the work that I do, I find it very interesting in terms of understanding how the way you were raised, how that shapes the way we lead people today. You are the daughter of Eastern European immigrants, and I'm just curious to take us back.
00:02:59
Speaker 3: Well, what was it like growing up in your family?
00:03:03
Speaker 1: Well, thanks, first of all for having me. I was raised by immigrants. I myself am also an immigrant, and so I moved to United States when I was twelve, And really, when I think back to my childhood, so much of it comes down to one world, which is independence. We were just asked to be on our own quite often and had to really figure out how to make things work for ourselves. And so that came with a lot of challenges, but also lots of upsides and wins, and you gain confidence when things go well. And you know, it was a whole different world to live here in the United States and learn the language and understand how the world works. We frankly didn't have a lot of money, and so that meant that we had to figure out on our own how to actually have money and you know, really try to fit in. So very early on, as soon as we moved here. I started by getting a first job fairly quickly, which was a paper route, and then really after that just continued more out of necessity. But I really actually didn't know any other way. That was just what we did in our family.
00:04:18
Speaker 3: So you said the word independence.
00:04:20
Speaker 2: Was that something that your parents were like, Anya, you have to learn to be this way or was it something that you sort of realized yourself as a way to almost survive because perhaps your parents were working a lot, or what was the dynamic there.
00:04:33
Speaker 1: Yeah. No, we didn't have like family meetings and family dinners and family discussions where these big values were being driven into us. That's just not how we operated. We sort of learned by doing, and I think that is still a way that I learned best, which is by trying to roll up my sleeves and actually doing something versus reading about it or trying to understand what it is from some other angles. For our family, we are all really busy working.
00:05:04
Speaker 2: I feel like your story resonates so much with me because my parents immigrated here to the US. I was born here in the US, but I think being raised in a family of immigrants, you see a lot of their sacrifice too, and it almost feels like you as their child as a kid, like you want to make them proud in a way you don't want to disappoint them. And hearing your story of being like I went out, I got a job I wanted, and I needed to be independent.
00:05:27
Speaker 3: I love that so much. Do you feel like that stayed with you in some way?
00:05:31
Speaker 1: Definitely. It's incredible sort of as an adult to understand and recognize how much of who you are has to do with your childhood. And the concept of independence and what that means is really important to me and has always been important. It's also very important to my husband, and so it is one of the key values that we try to ensure that our kids feel as well, because I think what independence really means is being able to get up really almost any time when things don't go well. And I guess the similar concept to resilience, where you just have to keep going and every day is a new day and life is not fair and that's just part of life, but you have to be able to sort of brush us off, and it is all about getting up the next day and knowing how to move forward.
00:06:22
Speaker 2: Moving forward, that's so big, So moving forward into kind of your career. You've had a lot of amazing experience at a lot of the big companies that we hear of in the Bay Area. Now you're, of course here with task Rabbit acquired by Akia. So when you think about when you started this role at task Rabbit, this was I think in the middle of the pandemic. Pandemic might have just started. There were a lot of changes, a lot of uncertainty. Tell me what was going through your mind during that period of time as a new leader in a new company.
00:06:53
Speaker 1: It was actually, I'll say quite hard, and I don't wish it on anyone to start a new job when you can meet people face to face, I think that's really hard. I am definitely a person who likes to connect with people, who likes to build relationship and really values that even day to day casual connection. And so I came from Uber where things were very crazy. I was at Uber Eats and that business actually multiplied multiple times as a pandemic started, and by middle of March and middle of April, it was just really really insane. And then fairly quickly that summer I started speaking with task Rabbit, and then I started a task Rabbit at the end of August, and we were still very much so in a pandemic mode, so we were still all working from home, so I didn't actually have a chance to meet anyone in person, including my team, until November that year. But I think that that was really hard. I think it would have been much different to be able to walk in somewhere and say, hey, everyone, I'm here to learn. It was more difficult.
00:08:01
Speaker 2: So what was something that you had taken from all your prior experience and now that you're in this new role, what was kind of like a leadership skill that you wanted to make sure that you did write.
00:08:14
Speaker 1: I think the biggest thing is having curiosity. So I already mentioned being able to learn, and so the first thing I did is I went on a listening tour and I met with every single employee of the company. And you know, that was a lot of zoom calls, but it was so valuable to really understand from someone who's maybe a junior code or someone who's running operations, someone who is really thinking about our customer experience, someone who is designing what our app looks like, and really understand what is working, what is not working, And that helped to set the first set of strategies that then we could go forward with.
00:08:54
Speaker 2: So during your listening tour, was there any difficult decision that you had to make as all the information that you've gleaned through the conversations that you had.
00:09:03
Speaker 1: I think one of the biggest of not the biggest responsibility that I have as a CEO of a company's to make decisions. Now, I try to ensure that I make fewer decisions because I really want to empower my team to make majority of the decisions. By the time the decisions come to me, they're kind of I would say, slightly less fun. They're usually two or three not great options. And I think Brian Chesky often talks about this, and I think Jeff Bezos talked about this as well as just this one way door decisions, right, and so these decisions are impactful enough that you can't undo them fairly quickly. So for example, going back to the office that means signing up leases, spending a lot of money to make it work, you know, calling people back and so on, it would be really hard. Of course, it's doable to then say Okay, actually this was a little experiment that didn't quite work. And so these one way door decisions are quite difficult, and I think as leaders and as a leader of task Rabbit, I really try to focus on making those decisions quicker rather than trying to drag on and get more data, because that to me just feels a lot more like excuse to not make the decision. And so I try very much so to focus on understanding what are the biggest trade offs and thinking about the impact and trying to really foresee several steps down the line and how a certain decision will impact whatever it is that we're trying to do, and really what our customers will feel like at the end of the day.
00:10:42
Speaker 3: Right, So, pivoting a little bit.
00:10:44
Speaker 2: I know you're a huge advocate for diversity flexibility. I'm just curious what advice do you have for people who also value that and that is something that they also want to see in their workplace, Because I know this is something that you care about, but perhaps they're working for an organization that might not value it as much.
00:11:03
Speaker 3: But I just want to understand how do you think about that.
00:11:06
Speaker 1: I fundamentally believe that the more different perspectives we have in the room, the better off we are in solving challenging problems, and so at task we really are trying to bring people who we think are the best people for the roles that we have, and we want to ensure that they come from different backgrounds because our customers are very diverse as well, and when I talk about customers, I talk about both taskers and clients, and so it's important to us to ensure that we have that type of environment and that type of culture within task Rabbit, Otherwise I think it becomes very difficult to serve our customers. And I think you mentioned flexibility that is hugely important and for a good chunk of time. Really, the first four plus years I've been here were a remote first company where we would just get together once in a while, usually once a month or something like this, maybe once every quarter for an off site, and then just recently we've started going back to the office, and I do think it is really important for people to come into the office and collaborate and really have the opportunity to chat and to connect on very different issues that are really hard to come by just on Zoom because you can't really have these random conversations. That being said, it's still really important for me that we maintain that level of flexibility, and so we're only asking people to be here two days a week, and we are making sure that our employees and our teams know that. First and foremost, what's important is ensuring that we can do right by our taskers and buy our clients. But we also have to make sure that we as teams are functioning well, are productive, and have that between being in office but also being able to work from home. And I do think it allows you to pull from a larger pool of employees, just because I think it is really important to provide that level of flexibility and autonomy to people.
00:13:15
Speaker 2: As a working mom, I feel like flexibility is everything. I have two young kids as well, and I have a lot of friends who are in the stage where our kids are very young, and a lot of them took breaks in their own career because they felt like they couldn't find a job that offered flexibilities.
00:13:31
Speaker 3: So why is that something that's so important to you?
00:13:34
Speaker 1: So I'm a mom myself. My kids are now a little bit older, they're all teenagers, but earlier in my career I took a year off with each child, or almost a year off, and they are each two years apart, which then meant that really for about five years, three of those five years I was off work completely, and then the two in between. I wouldn't say that they were the most stellar, ambitious years of my career, knowing I was going to leave again, and so I do think, you know, when I was raising my kids, when they were younger, we didn't have the flexibility, but whether it was Airbnb or Walmart or Expedia or Uber, I did negotiate to work from home once a week, and just subtracting the commute time was very helpful.
00:14:26
Speaker 2: I think I read somewhere that you and your husband had a point system that you guys created.
00:14:31
Speaker 3: Can you tell us a little bit about that, Yeah.
00:14:33
Speaker 1: And we do, and we still use it. Very early on, when my first one was born, and as I mentioned, I took a year off, we were contemplating what is life going to look like when I go back to work, And then once I did, we realize, like, there's just a lot of things that need to get done when you have a child, and when I wasn't at home all day, we didn't know who would do those things. And we started talking about the fact that we also don't want to be missing dinners with her, and we want to be there when she goes to bed and put her to bed, and we want to be there when she wakes up. And so we started realizing that some of the jobs that we've had in the past would probably not work for us. But then there was financial trade offs as well, and so we started ranking every role that one could possibly have in a number system, either a one where you work part time or you're not working, a two where you have a quote unquote normal corporate job where you're doing fifty hours a week and maybe some travel. And then there are the sort of threes, which is you're a startup, you're investment banking or consulting, and you're on the road all the time and you're fairly not present. And we made a very conscious decision that between the two of us, we don't want to ever be above four and a half. So that's really hard because both of us were quite and still are ambitious in our careers, and so neither one of us wanted to go down to a one, which therefore then forced both of us to stay at this two level, and it meant that sometimes we would be reaching a five. But as long as it was temporary or we knew that that was not a full way to go forward, we were fine with it. But it would keep us on our toes because we would have a shared language that would say, hey, we're like out of five and we've been out a five for a while now, and we don't see a way out of a five unless one of us changes something. But you know, for some couples, maybe they are fine with a six. They just get more help, and that's totally fine. There's no wrong way. But this just gave us a way to think about the problems and the challenges we were facing while raising a young family.
00:16:48
Speaker 2: We'll be back with more leading by example after a quake break. There was also another story that I read that you spent some time in Argentina. Can you tell me about that period of time in your life and how that kind of shaped even just your perspective on leading today.
00:17:16
Speaker 1: Yeah, so this happened before the pandemic, so at the time, it was not that common to take a year off, especially at the height of your career. When you know, we were both in our late thirties or early forties, in the middle of raising our very young family and both working in these Silicon Valley startups or big companies that were doing big, fun things. But we kind of knew that we weren't married to that lifestyle and we weren't sure that that's what we wanted to do. And my husband and I have traveled together extensively before we had children, and so we always knew that this is something that we've wanted to do and also expose our kids to. You know, I can't replicate my child for my kids, and I obviously I'm very thankful for even all the hardships during my childhood because they shape me and who I am as a leader. But I can try to put them in a different new environment and have them learn to adapt and learn to be resilient. And so it was very exciting for me to be able to provide that kind of experience for my kids.
00:18:23
Speaker 3: That must have been so nerve wracking, you know.
00:18:25
Speaker 2: I feel like for a lot of people, and perhaps a lot of our listeners who are very ambitious, who are very career oriented, they could never imagine taking that one year, that gap year off, right, because what's going to happen? They're going to fall behind? Right? Did it? Make you feel like you fell behind. Did it make you feel like you stalled in your career in any way?
00:18:44
Speaker 1: No, it made me accelerate in my career. I came back more confident in who I am and what I wanted to do, what I didn't want to do, and I was able to find work quite quickly. I mean, it was a very different market, to be fair, but working in uncertainty is something that I have to do now every day, and that is definitely very similar in some sense being dropped off in the middle of Buenos Aires without speaking the language, you know. I remember it was pouring outside, We had ten big suitcases, our airbnb was not ready, and it was dark and cold, and I thought, oh my gosh, what did we do? Like, why did I leave this really amazing life that I had. But obviously it worked out and it was definitely worth every minute.
00:19:32
Speaker 3: So you said it made you feel more confident, how.
00:19:35
Speaker 1: So, because I felt like, if I can do this, if I could rent out my house, pull my kids out of school, leave our jobs, sell our cars and just kind of leave our lives and go somewhere where we had never been to Argentina, and we didn't know anyone there either, and to know that I can show up and set up my life there and set up school for the kids and do the thing things that we were doing here while still learning new hobbies and learning new skills and really taking the time to take a step back and think about what we want out of life, what do we want for our family, for our careers, And having that gift and that break was amazing. For the first time in my life, I felt extremely content with the choices that we've made because we had a year to decide to do something else and we didn't.
00:20:27
Speaker 2: Because I feel like the opposite of contentment is always wondering. Yeah, always kind of chasing, but not really knowing what you're chasing. Would you say that's what it is?
00:20:37
Speaker 1: Absolutely? There's always you know what if we could do something differently. I mean, life in a Bay Area can be crazy, and so it was very refreshing to take a step back and say, is this what we want? And by the time we made that decision to move back to the Bay Area, we were really confident that that is what we wanted to do for a variety of reasons, and it felt really good.
00:20:59
Speaker 3: How do you feel like that then? Made you the leader you are now a task rabbit.
00:21:04
Speaker 1: I talk a lot about leadership in terms of curiosity, as we talked about already, but another big attribute or skill is having the courage to take some risks and to do something that may or may not work out. So that happens every day here, and a lot of the decisions that I make do not go the way I had hoped, but that's okay. I think it's better to make those decisions and then learn if things are not working, then just do not make decisions at all. And I think having the courage and becoming a little bit less risk averse and knowing that in most decisions that I make, there's just not enough information to be certain ever about anything exactly, and so in a case when we moved to Argentina, there was so much uncertainty, But actually being able to jump off the cliff sometimes, I think is really helpful for all of us.
00:22:00
Speaker 2: And do you feel like this is something that you sometimes can see yourself communicating to your team internally as well.
00:22:06
Speaker 1: My goal is to make sure that everyone feels that this is the best job that they've had, that they are being encouraged to really be bold and I think that people are motivated by many different things, and so understanding what everyone's motivations are and why they come to work every day and why they come and join us at test Rabbit is really important. So while this type of inexperience is very encouraging and motivating to me, it may not be to everyone. So for me, it is understanding motivations so that you can try to, as a leader, build the environment that allows every individual to really thrive based on who they are and what motivates them specifically.
00:22:52
Speaker 2: So as we wrap up here, I actually have a few spitfire questions to kind of get you thinking about leadership and just kind of your philosophy. So the first one is, what's one decision that you made in the first six months a task Rabbit that you would never want to make again.
00:23:10
Speaker 1: I think I made some poor choices in terms of how we communicated certain decisions to the company. They're so clear to me, some of these decisions, and I don't think I understood how important it was to get that message across to the team multiple times over and over in different ways, just given the importance of whatever the decision is, and so learning the communication piece and the art of communication to the team is really critical and it's taken me some time to get there.
00:23:46
Speaker 3: Oh I love that.
00:23:47
Speaker 2: By the way, what I teach is communications. So when you say communications, instantly had this like, oh my gosh, was it more you just communicated versus kind of like explaining the process or what was it that you learned and how you should.
00:23:59
Speaker 1: Maybe just not consistent enough and often enough we made a decision of some sorts and then we had a bullet on a slide at all hands and then we moved on. And that's just not enough for some of the decisions that we're making. And so I think we're much more careful today.
00:24:16
Speaker 3: Here's another question.
00:24:17
Speaker 2: What's the worst leadership advice you had ever received, and what's one piece of advice you would give to a new CEO.
00:24:26
Speaker 1: I think early on in my career, when I was raising my kids, one of the pieces of advice that I received about this life work balance was probably not quite right for me. I was definitely struggling and trying to think about how to make it work, and someone in a leadership team said, hey, you just need to hire more people, and that was not actually something that would have worked for me or my family. But I came home thinking that this is what I should do, and it took a lot of time in thinking to be like, no, actually, this is not who we are. And I guess I wish that that advice would have had more curiosity in it. And I think when I think about what are the best piece of advice is always to be curious and take a step back before you judge, which is really hard for me to do. I'm often too quick to jump into conclusions and so having a curiosity to ask the right questions I think is really important for anyone, especially a first time CEO.
00:25:28
Speaker 2: So the name of this podcast is leading by example. What does that mean to you? And how do you exemplify this in your own work?
00:25:36
Speaker 1: I think what we do is way more important than what we say. So while I talked about communication, I think the why and explaining the why behind decisions is really critical. But I think showing people how we live our values is really important as well. And so you know what happens in a room when I'm in a room, what types of processes or ways of war do we have that exemplify who we are? As task Rabbit and the teams here a task rabbit, and so I think it is really important to think about how we show up day to day versus how we talk about how we show up. How do you show up is really what people mostly see and what they mostly remember.
00:26:22
Speaker 3: I love that.
00:26:23
Speaker 2: It's like the action and can you communicate the action, because that's really what people want to hear, right, Like, it's not just saying it, it's being able to articulate it in many ways.
00:26:32
Speaker 1: That's right.
00:26:33
Speaker 3: This is a fun one.
00:26:34
Speaker 2: What's the most unusual thing that you have ever heard of someone booking a task rabbit for?
00:26:41
Speaker 1: Oh? I mean there are so many things. I mean the things that we always have really fun time learning about is just waiting in line for the craziest things. So you know, there's some like muffins or donuts or whatever in some hot bakery in New York City, or there's some tickets. There's still a lot of like weight in line type of occasions, and very often taskers get hired for that.
00:27:06
Speaker 3: I love that, and honestly, that's a good one. I mean, waiting in line is hard sometimes.
00:27:10
Speaker 1: Well, and it just takes so much time, right.
00:27:13
Speaker 2: Exactly, Anya, I want to say thank you so much. Is there anything else that you wanted to share that I didn't get to ask, just in the essence of the topic of leading by example today.
00:27:25
Speaker 1: Yeah, I think it is really important to lead by example, and I try to think about how I can do that with my team. One of the things is I always ask for feedback, and you know, it's not always the most complimentary feedback. Let's say, and I have it all summarized, and then I put it up on a board so that my entire team can see exactly what I'm doing well and what I'm not doing well. And I think it's really important to show up and say, hey, I am very far from perfect. Here are things that I do well and I will continue to lean into those, and then here are some things are one thing that I'm going to work on this here because it's really important for me to get better.
00:28:07
Speaker 2: Anya, I think that's amazing. You know, most people would want to hide a performance review that isn't only positive news, but you're like, no, this is what it is.
00:28:16
Speaker 1: Unfortunately, if you have a performance review with only positive news, it's really kind of unhelpful. Yeah, and so I would much rather understand and you know, at this point in my career, there's generally no surprises, and so it is about thinking about, well, which part do I really want to prioritize and get better at.
00:28:36
Speaker 2: But I love that you're very transparent about it. I think to me, that really does show leading by example. So that's amazing. Thank you, Anya, Well, thank you for having me.
00:28:46
Speaker 1: This is great.
00:28:49
Speaker 2: That was such an amazing conversation with Anya. I don't know about you, but I walked away feeling super inspired, particularly because there are three main things that she talked about that resonated with me and I want to talk to you about it. The first one was when she talked about how leadership is actually something that begins when we're really young. The second was when she talked about how the best decisions really only work when people believe in them. And the third one is sometimes you just got to stop chasing the chase. Let's start with the first one, you know, she talked about how leadership is actually shaped long before we even go into these leadership roles. Anya talked about how growing up as an immigrant, she learned how important it was for her to be independent. She took on a paper route, she earned her own money, and she didn't have to rely on her parents and ask for money, and through that experience, she says, she learned that you know, you don't sit back and wait, You take action, and when things don't go as plan, you get up, you keep going, you figure it out. Hearing her story made me reflect on how we can build that same mindset for our team too. So maybe the real question isn't about how we manage people, it's about how do we empower them. It's not about control, but it's about trusting. How do we create an environment where people feel safe to try, safe to fail, and support it enough so that they can find their own way forward even though they might not have all the answers, because so much of building resilience doesn't come from just sitting around and waiting for things to come together. A lot of it comes from doing and having the freedom to try. The second thing that Anya said that really stuck with me was this the best decisions only work when people believe in them. This was when she talked about how when she first stepped into her role, it was really clear to her the decisions she had to make for the company, and she says she communicated this new direction to her company, and even though it felt right to her, it didn't exactly land the same way with her team. This was so honest of her to admit this. It reminds me how we cannot overestimate the level of buy in we get from people, and as a leader, we sometimes have to explain the why we have to build that excitement and get people to see the vision that we are excited about. This is where I believe storytelling becomes really important, and this is what I talk about a lot in my communications classes because it's easy for us as leaders to dive into the logistics the operations of things. We know what needs to happen, but if there's big change going on, we can't assume that just saying it once people understand a lot of times we have to come at it in multiple ways, especially if this is such an important thing that everybody needs to get on board with now. The third one was one that really stayed with me, and this was all about stop chasing to chase. This is when she talked about how she took a year off, packed up all her things, and moved her entire family to just hang out and live in Argentina. This was not pre kids she did this with her kids, and it made me think about how I think for a lot of us, in our mind, we might be thinking, well, I can't take a year off. That's scary, that's going to hold me back. I'm such a career oriented person. But she said, and this meant so much to me, that doing this was actually one of the best things that she did for her career.
00:32:38
Speaker 3: You know, she was working in.
00:32:39
Speaker 2: Silicon Valley at the time, where a lot of times there is that culture you go, go, go, But it allowed her to stop and reevaluate what was important for her and her life and most importantly, what was the life she wanted to build for herself and for her family. And it was because of that time she spent that's when she went, wait, I do want to come back. I do want to work. I do want to do this kind of work. In her words, that experience made her feel even more confident coming back. But it's amazing to hear her talk about this because that year it also made her realize how important flexibility is to people who.
00:33:20
Speaker 3: Work as well.
00:33:21
Speaker 2: Now as a working mom, I definitely know how important flexibility is for people who work, and I imagine that is exactly how she leads her company today. So a big thank you to Anya. Thank you so much for joining us. This was such a great conversation, and to all of you for listening. If you enjoyed this episode or have feedback on what you want to hear and guess you'd like to hear from, please rate and review Leading by Example.
00:33:48
Speaker 3: Every review, every rating.
00:33:50
Speaker 2: It really does help us reach more people and make this show the best it can be. I'm Jessica Chen, the author of Smart Not Loud, How to Get Noticed at Work for All the Right Reasons, and the CEO of Soulcast Media, a communications training company. So for more information about me and what I do, you can head over to Solcastmedia dot com or add me on LinkedIn and Instagram. A huge thank you to our production team at Ruby Studio, especially Matt Stillo and Sierra Spreen. We will be back in two weeks with another episode of Leading by Example.
00:34:24
Speaker 3: I'll see you then.
Speaker 1: Rube. Working in uncertainty is something that I have to do now every day, and that is definitely very similar in some sense to being dropped off in the middle of bonos aires without speaking the language. I remember it was pouring outside. We had ten big suitcases. Our airbnb was not ready, and I thought, Oh my gosh, what did we do? Like, why did I leave this really amazing life that I had.
00:00:33
Speaker 2: If you took a year off work, would that help or hurt your career? It was a risk that Anya Smith took, and ultimately it was the best decision that prepared her to lead a team as.
00:00:44
Speaker 3: The CEO of Task Rabbit.
00:00:48
Speaker 2: I'm Jessica Chen and this is leading by example. I'm an Emmy Award winning journalist, founder of soul Cast Media, a communication training company, and the author of the book Aren't Not Loud How to get noticed at work.
00:01:03
Speaker 3: For all the right reasons.
00:01:05
Speaker 2: In many industries, taking time off is unthinkable. There's an unspoken fear of falling behind. But for Anya Smith, packing up her bag and moving out of Silicon Valley actually accelerated her career. In her words, it was one of the best things she ever did to become the leader she wanted to be. Before Amya left for Argentina, she was three years in at Airbnb during a time of rapid growth, while her husband Rob was leading operations at Glassdoor. Yes, it was exciting, but they weren't sure if it was the life they truly wanted and frankly, it's tough to lead a team if your heart isn't in it. By taking a year off to focus on anything but her job, Amya started to identify her priorities for her career and family, and she knew what she wanted to do. In twenty twenty, she became CEO of haask Rabbit, an online platform connecting customers with independent taskers who can do everything from shoveling the driveway to mounting a TV. Today, Anya shares how a hard reset might be the key to growth as a leader, and she offers tips on how you can navigate uncertainty in your own career and come back even stronger on the other side.
00:02:34
Speaker 3: Anya, thank you so much for joining us.
00:02:36
Speaker 1: Thank you for having me. I'm excited to be here.
00:02:38
Speaker 2: So I'm just going to dive into this because I have a lot of questions for you, and I really want to start from the beginning. So for me and the work that I do, I find it very interesting in terms of understanding how the way you were raised, how that shapes the way we lead people today. You are the daughter of Eastern European immigrants, and I'm just curious to take us back.
00:02:59
Speaker 3: Well, what was it like growing up in your family?
00:03:03
Speaker 1: Well, thanks, first of all for having me. I was raised by immigrants. I myself am also an immigrant, and so I moved to United States when I was twelve, And really, when I think back to my childhood, so much of it comes down to one world, which is independence. We were just asked to be on our own quite often and had to really figure out how to make things work for ourselves. And so that came with a lot of challenges, but also lots of upsides and wins, and you gain confidence when things go well. And you know, it was a whole different world to live here in the United States and learn the language and understand how the world works. We frankly didn't have a lot of money, and so that meant that we had to figure out on our own how to actually have money and you know, really try to fit in. So very early on, as soon as we moved here. I started by getting a first job fairly quickly, which was a paper route, and then really after that just continued more out of necessity. But I really actually didn't know any other way. That was just what we did in our family.
00:04:18
Speaker 3: So you said the word independence.
00:04:20
Speaker 2: Was that something that your parents were like, Anya, you have to learn to be this way or was it something that you sort of realized yourself as a way to almost survive because perhaps your parents were working a lot, or what was the dynamic there.
00:04:33
Speaker 1: Yeah. No, we didn't have like family meetings and family dinners and family discussions where these big values were being driven into us. That's just not how we operated. We sort of learned by doing, and I think that is still a way that I learned best, which is by trying to roll up my sleeves and actually doing something versus reading about it or trying to understand what it is from some other angles. For our family, we are all really busy working.
00:05:04
Speaker 2: I feel like your story resonates so much with me because my parents immigrated here to the US. I was born here in the US, but I think being raised in a family of immigrants, you see a lot of their sacrifice too, and it almost feels like you as their child as a kid, like you want to make them proud in a way you don't want to disappoint them. And hearing your story of being like I went out, I got a job I wanted, and I needed to be independent.
00:05:27
Speaker 3: I love that so much. Do you feel like that stayed with you in some way?
00:05:31
Speaker 1: Definitely. It's incredible sort of as an adult to understand and recognize how much of who you are has to do with your childhood. And the concept of independence and what that means is really important to me and has always been important. It's also very important to my husband, and so it is one of the key values that we try to ensure that our kids feel as well, because I think what independence really means is being able to get up really almost any time when things don't go well. And I guess the similar concept to resilience, where you just have to keep going and every day is a new day and life is not fair and that's just part of life, but you have to be able to sort of brush us off, and it is all about getting up the next day and knowing how to move forward.
00:06:22
Speaker 2: Moving forward, that's so big, So moving forward into kind of your career. You've had a lot of amazing experience at a lot of the big companies that we hear of in the Bay Area. Now you're, of course here with task Rabbit acquired by Akia. So when you think about when you started this role at task Rabbit, this was I think in the middle of the pandemic. Pandemic might have just started. There were a lot of changes, a lot of uncertainty. Tell me what was going through your mind during that period of time as a new leader in a new company.
00:06:53
Speaker 1: It was actually, I'll say quite hard, and I don't wish it on anyone to start a new job when you can meet people face to face, I think that's really hard. I am definitely a person who likes to connect with people, who likes to build relationship and really values that even day to day casual connection. And so I came from Uber where things were very crazy. I was at Uber Eats and that business actually multiplied multiple times as a pandemic started, and by middle of March and middle of April, it was just really really insane. And then fairly quickly that summer I started speaking with task Rabbit, and then I started a task Rabbit at the end of August, and we were still very much so in a pandemic mode, so we were still all working from home, so I didn't actually have a chance to meet anyone in person, including my team, until November that year. But I think that that was really hard. I think it would have been much different to be able to walk in somewhere and say, hey, everyone, I'm here to learn. It was more difficult.
00:08:01
Speaker 2: So what was something that you had taken from all your prior experience and now that you're in this new role, what was kind of like a leadership skill that you wanted to make sure that you did write.
00:08:14
Speaker 1: I think the biggest thing is having curiosity. So I already mentioned being able to learn, and so the first thing I did is I went on a listening tour and I met with every single employee of the company. And you know, that was a lot of zoom calls, but it was so valuable to really understand from someone who's maybe a junior code or someone who's running operations, someone who is really thinking about our customer experience, someone who is designing what our app looks like, and really understand what is working, what is not working, And that helped to set the first set of strategies that then we could go forward with.
00:08:54
Speaker 2: So during your listening tour, was there any difficult decision that you had to make as all the information that you've gleaned through the conversations that you had.
00:09:03
Speaker 1: I think one of the biggest of not the biggest responsibility that I have as a CEO of a company's to make decisions. Now, I try to ensure that I make fewer decisions because I really want to empower my team to make majority of the decisions. By the time the decisions come to me, they're kind of I would say, slightly less fun. They're usually two or three not great options. And I think Brian Chesky often talks about this, and I think Jeff Bezos talked about this as well as just this one way door decisions, right, and so these decisions are impactful enough that you can't undo them fairly quickly. So for example, going back to the office that means signing up leases, spending a lot of money to make it work, you know, calling people back and so on, it would be really hard. Of course, it's doable to then say Okay, actually this was a little experiment that didn't quite work. And so these one way door decisions are quite difficult, and I think as leaders and as a leader of task Rabbit, I really try to focus on making those decisions quicker rather than trying to drag on and get more data, because that to me just feels a lot more like excuse to not make the decision. And so I try very much so to focus on understanding what are the biggest trade offs and thinking about the impact and trying to really foresee several steps down the line and how a certain decision will impact whatever it is that we're trying to do, and really what our customers will feel like at the end of the day.
00:10:42
Speaker 3: Right, So, pivoting a little bit.
00:10:44
Speaker 2: I know you're a huge advocate for diversity flexibility. I'm just curious what advice do you have for people who also value that and that is something that they also want to see in their workplace, Because I know this is something that you care about, but perhaps they're working for an organization that might not value it as much.
00:11:03
Speaker 3: But I just want to understand how do you think about that.
00:11:06
Speaker 1: I fundamentally believe that the more different perspectives we have in the room, the better off we are in solving challenging problems, and so at task we really are trying to bring people who we think are the best people for the roles that we have, and we want to ensure that they come from different backgrounds because our customers are very diverse as well, and when I talk about customers, I talk about both taskers and clients, and so it's important to us to ensure that we have that type of environment and that type of culture within task Rabbit, Otherwise I think it becomes very difficult to serve our customers. And I think you mentioned flexibility that is hugely important and for a good chunk of time. Really, the first four plus years I've been here were a remote first company where we would just get together once in a while, usually once a month or something like this, maybe once every quarter for an off site, and then just recently we've started going back to the office, and I do think it is really important for people to come into the office and collaborate and really have the opportunity to chat and to connect on very different issues that are really hard to come by just on Zoom because you can't really have these random conversations. That being said, it's still really important for me that we maintain that level of flexibility, and so we're only asking people to be here two days a week, and we are making sure that our employees and our teams know that. First and foremost, what's important is ensuring that we can do right by our taskers and buy our clients. But we also have to make sure that we as teams are functioning well, are productive, and have that between being in office but also being able to work from home. And I do think it allows you to pull from a larger pool of employees, just because I think it is really important to provide that level of flexibility and autonomy to people.
00:13:15
Speaker 2: As a working mom, I feel like flexibility is everything. I have two young kids as well, and I have a lot of friends who are in the stage where our kids are very young, and a lot of them took breaks in their own career because they felt like they couldn't find a job that offered flexibilities.
00:13:31
Speaker 3: So why is that something that's so important to you?
00:13:34
Speaker 1: So I'm a mom myself. My kids are now a little bit older, they're all teenagers, but earlier in my career I took a year off with each child, or almost a year off, and they are each two years apart, which then meant that really for about five years, three of those five years I was off work completely, and then the two in between. I wouldn't say that they were the most stellar, ambitious years of my career, knowing I was going to leave again, and so I do think, you know, when I was raising my kids, when they were younger, we didn't have the flexibility, but whether it was Airbnb or Walmart or Expedia or Uber, I did negotiate to work from home once a week, and just subtracting the commute time was very helpful.
00:14:26
Speaker 2: I think I read somewhere that you and your husband had a point system that you guys created.
00:14:31
Speaker 3: Can you tell us a little bit about that, Yeah.
00:14:33
Speaker 1: And we do, and we still use it. Very early on, when my first one was born, and as I mentioned, I took a year off, we were contemplating what is life going to look like when I go back to work, And then once I did, we realize, like, there's just a lot of things that need to get done when you have a child, and when I wasn't at home all day, we didn't know who would do those things. And we started talking about the fact that we also don't want to be missing dinners with her, and we want to be there when she goes to bed and put her to bed, and we want to be there when she wakes up. And so we started realizing that some of the jobs that we've had in the past would probably not work for us. But then there was financial trade offs as well, and so we started ranking every role that one could possibly have in a number system, either a one where you work part time or you're not working, a two where you have a quote unquote normal corporate job where you're doing fifty hours a week and maybe some travel. And then there are the sort of threes, which is you're a startup, you're investment banking or consulting, and you're on the road all the time and you're fairly not present. And we made a very conscious decision that between the two of us, we don't want to ever be above four and a half. So that's really hard because both of us were quite and still are ambitious in our careers, and so neither one of us wanted to go down to a one, which therefore then forced both of us to stay at this two level, and it meant that sometimes we would be reaching a five. But as long as it was temporary or we knew that that was not a full way to go forward, we were fine with it. But it would keep us on our toes because we would have a shared language that would say, hey, we're like out of five and we've been out a five for a while now, and we don't see a way out of a five unless one of us changes something. But you know, for some couples, maybe they are fine with a six. They just get more help, and that's totally fine. There's no wrong way. But this just gave us a way to think about the problems and the challenges we were facing while raising a young family.
00:16:48
Speaker 2: We'll be back with more leading by example after a quake break. There was also another story that I read that you spent some time in Argentina. Can you tell me about that period of time in your life and how that kind of shaped even just your perspective on leading today.
00:17:16
Speaker 1: Yeah, so this happened before the pandemic, so at the time, it was not that common to take a year off, especially at the height of your career. When you know, we were both in our late thirties or early forties, in the middle of raising our very young family and both working in these Silicon Valley startups or big companies that were doing big, fun things. But we kind of knew that we weren't married to that lifestyle and we weren't sure that that's what we wanted to do. And my husband and I have traveled together extensively before we had children, and so we always knew that this is something that we've wanted to do and also expose our kids to. You know, I can't replicate my child for my kids, and I obviously I'm very thankful for even all the hardships during my childhood because they shape me and who I am as a leader. But I can try to put them in a different new environment and have them learn to adapt and learn to be resilient. And so it was very exciting for me to be able to provide that kind of experience for my kids.
00:18:23
Speaker 3: That must have been so nerve wracking, you know.
00:18:25
Speaker 2: I feel like for a lot of people, and perhaps a lot of our listeners who are very ambitious, who are very career oriented, they could never imagine taking that one year, that gap year off, right, because what's going to happen? They're going to fall behind? Right? Did it? Make you feel like you fell behind. Did it make you feel like you stalled in your career in any way?
00:18:44
Speaker 1: No, it made me accelerate in my career. I came back more confident in who I am and what I wanted to do, what I didn't want to do, and I was able to find work quite quickly. I mean, it was a very different market, to be fair, but working in uncertainty is something that I have to do now every day, and that is definitely very similar in some sense being dropped off in the middle of Buenos Aires without speaking the language, you know. I remember it was pouring outside, We had ten big suitcases, our airbnb was not ready, and it was dark and cold, and I thought, oh my gosh, what did we do? Like, why did I leave this really amazing life that I had. But obviously it worked out and it was definitely worth every minute.
00:19:32
Speaker 3: So you said it made you feel more confident, how.
00:19:35
Speaker 1: So, because I felt like, if I can do this, if I could rent out my house, pull my kids out of school, leave our jobs, sell our cars and just kind of leave our lives and go somewhere where we had never been to Argentina, and we didn't know anyone there either, and to know that I can show up and set up my life there and set up school for the kids and do the thing things that we were doing here while still learning new hobbies and learning new skills and really taking the time to take a step back and think about what we want out of life, what do we want for our family, for our careers, And having that gift and that break was amazing. For the first time in my life, I felt extremely content with the choices that we've made because we had a year to decide to do something else and we didn't.
00:20:27
Speaker 2: Because I feel like the opposite of contentment is always wondering. Yeah, always kind of chasing, but not really knowing what you're chasing. Would you say that's what it is?
00:20:37
Speaker 1: Absolutely? There's always you know what if we could do something differently. I mean, life in a Bay Area can be crazy, and so it was very refreshing to take a step back and say, is this what we want? And by the time we made that decision to move back to the Bay Area, we were really confident that that is what we wanted to do for a variety of reasons, and it felt really good.
00:20:59
Speaker 3: How do you feel like that then? Made you the leader you are now a task rabbit.
00:21:04
Speaker 1: I talk a lot about leadership in terms of curiosity, as we talked about already, but another big attribute or skill is having the courage to take some risks and to do something that may or may not work out. So that happens every day here, and a lot of the decisions that I make do not go the way I had hoped, but that's okay. I think it's better to make those decisions and then learn if things are not working, then just do not make decisions at all. And I think having the courage and becoming a little bit less risk averse and knowing that in most decisions that I make, there's just not enough information to be certain ever about anything exactly, and so in a case when we moved to Argentina, there was so much uncertainty, But actually being able to jump off the cliff sometimes, I think is really helpful for all of us.
00:22:00
Speaker 2: And do you feel like this is something that you sometimes can see yourself communicating to your team internally as well.
00:22:06
Speaker 1: My goal is to make sure that everyone feels that this is the best job that they've had, that they are being encouraged to really be bold and I think that people are motivated by many different things, and so understanding what everyone's motivations are and why they come to work every day and why they come and join us at test Rabbit is really important. So while this type of inexperience is very encouraging and motivating to me, it may not be to everyone. So for me, it is understanding motivations so that you can try to, as a leader, build the environment that allows every individual to really thrive based on who they are and what motivates them specifically.
00:22:52
Speaker 2: So as we wrap up here, I actually have a few spitfire questions to kind of get you thinking about leadership and just kind of your philosophy. So the first one is, what's one decision that you made in the first six months a task Rabbit that you would never want to make again.
00:23:10
Speaker 1: I think I made some poor choices in terms of how we communicated certain decisions to the company. They're so clear to me, some of these decisions, and I don't think I understood how important it was to get that message across to the team multiple times over and over in different ways, just given the importance of whatever the decision is, and so learning the communication piece and the art of communication to the team is really critical and it's taken me some time to get there.
00:23:46
Speaker 3: Oh I love that.
00:23:47
Speaker 2: By the way, what I teach is communications. So when you say communications, instantly had this like, oh my gosh, was it more you just communicated versus kind of like explaining the process or what was it that you learned and how you should.
00:23:59
Speaker 1: Maybe just not consistent enough and often enough we made a decision of some sorts and then we had a bullet on a slide at all hands and then we moved on. And that's just not enough for some of the decisions that we're making. And so I think we're much more careful today.
00:24:16
Speaker 3: Here's another question.
00:24:17
Speaker 2: What's the worst leadership advice you had ever received, and what's one piece of advice you would give to a new CEO.
00:24:26
Speaker 1: I think early on in my career, when I was raising my kids, one of the pieces of advice that I received about this life work balance was probably not quite right for me. I was definitely struggling and trying to think about how to make it work, and someone in a leadership team said, hey, you just need to hire more people, and that was not actually something that would have worked for me or my family. But I came home thinking that this is what I should do, and it took a lot of time in thinking to be like, no, actually, this is not who we are. And I guess I wish that that advice would have had more curiosity in it. And I think when I think about what are the best piece of advice is always to be curious and take a step back before you judge, which is really hard for me to do. I'm often too quick to jump into conclusions and so having a curiosity to ask the right questions I think is really important for anyone, especially a first time CEO.
00:25:28
Speaker 2: So the name of this podcast is leading by example. What does that mean to you? And how do you exemplify this in your own work?
00:25:36
Speaker 1: I think what we do is way more important than what we say. So while I talked about communication, I think the why and explaining the why behind decisions is really critical. But I think showing people how we live our values is really important as well. And so you know what happens in a room when I'm in a room, what types of processes or ways of war do we have that exemplify who we are? As task Rabbit and the teams here a task rabbit, and so I think it is really important to think about how we show up day to day versus how we talk about how we show up. How do you show up is really what people mostly see and what they mostly remember.
00:26:22
Speaker 3: I love that.
00:26:23
Speaker 2: It's like the action and can you communicate the action, because that's really what people want to hear, right, Like, it's not just saying it, it's being able to articulate it in many ways.
00:26:32
Speaker 1: That's right.
00:26:33
Speaker 3: This is a fun one.
00:26:34
Speaker 2: What's the most unusual thing that you have ever heard of someone booking a task rabbit for?
00:26:41
Speaker 1: Oh? I mean there are so many things. I mean the things that we always have really fun time learning about is just waiting in line for the craziest things. So you know, there's some like muffins or donuts or whatever in some hot bakery in New York City, or there's some tickets. There's still a lot of like weight in line type of occasions, and very often taskers get hired for that.
00:27:06
Speaker 3: I love that, and honestly, that's a good one. I mean, waiting in line is hard sometimes.
00:27:10
Speaker 1: Well, and it just takes so much time, right.
00:27:13
Speaker 2: Exactly, Anya, I want to say thank you so much. Is there anything else that you wanted to share that I didn't get to ask, just in the essence of the topic of leading by example today.
00:27:25
Speaker 1: Yeah, I think it is really important to lead by example, and I try to think about how I can do that with my team. One of the things is I always ask for feedback, and you know, it's not always the most complimentary feedback. Let's say, and I have it all summarized, and then I put it up on a board so that my entire team can see exactly what I'm doing well and what I'm not doing well. And I think it's really important to show up and say, hey, I am very far from perfect. Here are things that I do well and I will continue to lean into those, and then here are some things are one thing that I'm going to work on this here because it's really important for me to get better.
00:28:07
Speaker 2: Anya, I think that's amazing. You know, most people would want to hide a performance review that isn't only positive news, but you're like, no, this is what it is.
00:28:16
Speaker 1: Unfortunately, if you have a performance review with only positive news, it's really kind of unhelpful. Yeah, and so I would much rather understand and you know, at this point in my career, there's generally no surprises, and so it is about thinking about, well, which part do I really want to prioritize and get better at.
00:28:36
Speaker 2: But I love that you're very transparent about it. I think to me, that really does show leading by example. So that's amazing. Thank you, Anya, Well, thank you for having me.
00:28:46
Speaker 1: This is great.
00:28:49
Speaker 2: That was such an amazing conversation with Anya. I don't know about you, but I walked away feeling super inspired, particularly because there are three main things that she talked about that resonated with me and I want to talk to you about it. The first one was when she talked about how leadership is actually something that begins when we're really young. The second was when she talked about how the best decisions really only work when people believe in them. And the third one is sometimes you just got to stop chasing the chase. Let's start with the first one, you know, she talked about how leadership is actually shaped long before we even go into these leadership roles. Anya talked about how growing up as an immigrant, she learned how important it was for her to be independent. She took on a paper route, she earned her own money, and she didn't have to rely on her parents and ask for money, and through that experience, she says, she learned that you know, you don't sit back and wait, You take action, and when things don't go as plan, you get up, you keep going, you figure it out. Hearing her story made me reflect on how we can build that same mindset for our team too. So maybe the real question isn't about how we manage people, it's about how do we empower them. It's not about control, but it's about trusting. How do we create an environment where people feel safe to try, safe to fail, and support it enough so that they can find their own way forward even though they might not have all the answers, because so much of building resilience doesn't come from just sitting around and waiting for things to come together. A lot of it comes from doing and having the freedom to try. The second thing that Anya said that really stuck with me was this the best decisions only work when people believe in them. This was when she talked about how when she first stepped into her role, it was really clear to her the decisions she had to make for the company, and she says she communicated this new direction to her company, and even though it felt right to her, it didn't exactly land the same way with her team. This was so honest of her to admit this. It reminds me how we cannot overestimate the level of buy in we get from people, and as a leader, we sometimes have to explain the why we have to build that excitement and get people to see the vision that we are excited about. This is where I believe storytelling becomes really important, and this is what I talk about a lot in my communications classes because it's easy for us as leaders to dive into the logistics the operations of things. We know what needs to happen, but if there's big change going on, we can't assume that just saying it once people understand a lot of times we have to come at it in multiple ways, especially if this is such an important thing that everybody needs to get on board with now. The third one was one that really stayed with me, and this was all about stop chasing to chase. This is when she talked about how she took a year off, packed up all her things, and moved her entire family to just hang out and live in Argentina. This was not pre kids she did this with her kids, and it made me think about how I think for a lot of us, in our mind, we might be thinking, well, I can't take a year off. That's scary, that's going to hold me back. I'm such a career oriented person. But she said, and this meant so much to me, that doing this was actually one of the best things that she did for her career.
00:32:38
Speaker 3: You know, she was working in.
00:32:39
Speaker 2: Silicon Valley at the time, where a lot of times there is that culture you go, go, go, But it allowed her to stop and reevaluate what was important for her and her life and most importantly, what was the life she wanted to build for herself and for her family. And it was because of that time she spent that's when she went, wait, I do want to come back. I do want to work. I do want to do this kind of work. In her words, that experience made her feel even more confident coming back. But it's amazing to hear her talk about this because that year it also made her realize how important flexibility is to people who.
00:33:20
Speaker 3: Work as well.
00:33:21
Speaker 2: Now as a working mom, I definitely know how important flexibility is for people who work, and I imagine that is exactly how she leads her company today. So a big thank you to Anya. Thank you so much for joining us. This was such a great conversation, and to all of you for listening. If you enjoyed this episode or have feedback on what you want to hear and guess you'd like to hear from, please rate and review Leading by Example.
00:33:48
Speaker 3: Every review, every rating.
00:33:50
Speaker 2: It really does help us reach more people and make this show the best it can be. I'm Jessica Chen, the author of Smart Not Loud, How to Get Noticed at Work for All the Right Reasons, and the CEO of Soulcast Media, a communications training company. So for more information about me and what I do, you can head over to Solcastmedia dot com or add me on LinkedIn and Instagram. A huge thank you to our production team at Ruby Studio, especially Matt Stillo and Sierra Spreen. We will be back in two weeks with another episode of Leading by Example.
00:34:24
Speaker 3: I'll see you then.
