David Novak (Podcast Host and Interviewer) (3:19)

Yeah, well, you just went right into that frying pan with the whole family and learned a lot, you know, and when you did this, you were working at Airbnb and you were the head of operations in North America. Did people think you were crazy doing this? I mean, this could be a career stopper. What gave you the courage to even do it?

Anya Smith (CEO of TaskRabbit) (3:36)

You know, it was before the pandemic. So I would say the good thing now is it's the concept of a gap year is not as big of a deal today, like the five, six short years as it was back then. I did have some people tell me, you know, you're just kind of getting going with your career. This is going to be hard, or maybe hard to explain a year break in your. On your cv. What are you going to say? But I was fairly determined. My husband and I made this decision way prior to the actual execution. So, you know, five years prior, because we didn't have enough money, we had to save money in order to actually be able to not work for a year. And we had to do some planning around what are we going to do with the kids, what are we going to do with our house, and so on and so forth. So it wasn't sort of a rush decision, and I was pretty certain that we'll always be able to find jobs. You know, we're both educated people who have done some things, and hopefully we'll be able to figure out how to do some other things when we return. So even though I was obviously somewhat concerned, I really felt that the learnings and the growth and the adventure and the spirit and the having the time with our family as a unit of five to spend together a little bit more was well worth the effort.

David Novak (Podcast Host and Interviewer) (5:00)

Well, we're going to get into TaskRabbit here in a bit, but I'm curious, Anya, what's a story from your childhood that shaped the kind of leader you are today?

Anya Smith (CEO of TaskRabbit) (5:10)

I think probably one of the biggest stories is the fact that I moved here when I was 12 from Poland. I arrived in Sioux Falls, South Dakota, of all places. I didn't know how to speak English. And neither really did my parents, nor did their degrees transfer over. They had to work really hard to make ends meet. And that meant that I had to work really hard as well to help out because we just didn't have enough money. Very early on, I learned that the opportunity in America was pretty profound. So I got my first job at 12 as I had a paper route and started earning cash. And that was really exciting. And also, as part of the paper route, we needed to sell the paper. And so on weekends, we would go door to door to try to sell subscriptions. And those lessons of sort of being told no over and over and over a thousand times stay with you really a lifetime. So I think understanding how to be accountable, how to be responsible, how to work hard, and then also how to be able to work through adversity are some of the main lessons that I took from those early days of trying to make ends meet when things were not so rosy.

David Novak (Podcast Host and Interviewer) (6:37)

Yeah. Curiously, I actually sold encyclopedias door to door when I was a kid.

Anya Smith (CEO of TaskRabbit) (6:43)

Okay, God bless you.

David Novak (Podcast Host and Interviewer) (6:44)

So you're out there selling newspapers. Did you pick up one thing that helped you make the sale? More than anything else, I would try.

Anya Smith (CEO of TaskRabbit) (6:52)

To ask questions more and listen more than trying to sell. So I would have these questions around the news, and I barely knew what the news was, but I focus particularly on the local news and local sports teams. And I would talk about, did you know that the o' Gorman Knights did this or this? And you can read more stories like this in the Argus Leader, and that seemed to help a little bit.

David Novak (Podcast Host and Interviewer) (7:20)

That's great. My big pitch was, if I could show you a way to give your kid a better education, would you be interested? John and Mary, and then I.

Anya Smith (CEO of TaskRabbit) (7:29)

Who's going to say no to that? Exactly.

David Novak (Podcast Host and Interviewer) (7:32)

Now, as I understand it, Anya, your dad moved to the United States from Poland three years before the rest of the family did. What kind of impact did that have on you?

Anya Smith (CEO of TaskRabbit) (7:44)

I mean, so it was actually two years before, but he had been gone from Poland for three years because he was first in a refugee camp in Austria. I think it's really hard, but I don't know that I really recognized it as a child as much as I do now being a parent. Because now the thought of my kids not seeing their dad for three years seems extremely difficult. And it sort of shows me a lot more appreciation for my mom and really just how tough it is to be a single mom and to actually make things work on your own. I think as a child, I missed my dad, but I was Also very excited at the prospect of reuniting with him again. And so when that news came through, it was very exciting and very gratifying.

David Novak (Podcast Host and Interviewer) (8:32)

You talked about how the opportunities in America are so profound. And, you know, here you come across the pond, you know, and you can't speak the language. Did you find the impressions of America match up with what you thought it would be or did it exceed it, or, I mean, how did it all sync up?

Anya Smith (CEO of TaskRabbit) (8:55)

It's hard to really, I guess, understand what the expectations were. Our expectations were like the movies, you know, the movies in a. In the late 70s and early 80s, and that's what we would kind of see. But really it's when you show up, and I mean, as many immigrants will tell you this story, it's that walk into the grocery store for the very first time that ends up being extremely overwhelming and just almost unbelievable. And that is certainly what happened to us as well. You just, you know, I came from somewhere where at the time there were lines to get into the store and there were lines and food was rationed and you could only get however many kilos of meat and however many kilos of sugar or candy. And the grocery store shelves were in fact empty. And so to walk into a store where there is so much produce and it's being sprayed on with water to look more fresh and it looks beyond perfect, it's pretty crazy.

David Novak (Podcast Host and Interviewer) (10:00)

Yeah. And that was happening in South Dakota and most people have never been there, you know.

Anya Smith (CEO of TaskRabbit) (10:05)

Exactly.

David Novak (Podcast Host and Interviewer) (10:07)

You know, I've heard it said that you can't be what you cannot see. Who did you have as a model to show you what was possible in your life and career?

Anya Smith (CEO of TaskRabbit) (10:17)

Really, actually, growing up in South Dakota, the models that I had were people who were willing to extend a hand and who were very helpful. I didn't necessarily have models of my career. Being somewhere outside it seemed so far fetched and so, you know, frankly, not in a possibility of my life. But I did learn a lot from people who had surrounded me and my family and were really willing to help. I particularly think about teachers who were there very early on who were teaching us English. You know, we landed in February, and by May, as school got out, we could slightly speak a little bit of English, but certainly needed a lot more help. And this one teacher in particular, Ms. Carlson, she took my brother and I and every day we would meet at school and she didn't have to do this just so that she could read to us and that kind of help. And just being so selfless and being able to Give to another human is really profound. And I think those are likely the biggest lessons that I learned in terms of having a career mentor. So early on, once I left and went to college and started going to different competitions and different, you know, doing different things outside of college, I also had the opportunity to intern at usaid, which of course now no longer exists. You know, there were many, many mentors who came around and really taught me the importance of hard work or the importance of building certain skill sets and so forth. But it's those early folks in Sioux Falls that I credit for a lot of really my success.

David Novak (Podcast Host and Interviewer) (12:10)

Great. And you worked at Booz Allen right out of college. What did being a consultant teach you about leadership?

Anya Smith (CEO of TaskRabbit) (12:18)

I think there are a few things, but one is that the problems are very difficult and even people who are very, very smart don't necessarily have all answers. I focused primarily on working for either USAID or World bank, and we were doing a lot of development work internationally. And so we were working with big governments and big institutions trying to think about concepts like the rule of law or competition law and so forth. And that was really exciting. I was just a sponge, willing to do anything and really willing to learn a lot. But what was very clear is that the problems were very complex and people who were way smarter than me, you know, all my colleagues were sort of Ivy League, Harvard, Yale, Princeton educated. And we were all grappling with pretty difficult challenges. And I found the atmosphere very, almost riveting, very exciting. And I really love the people with whom I got to work and some of the problems that I got to solve. But I did feel like I needed to go back to school to gain more technical skills to, to continue going.

David Novak (Podcast Host and Interviewer) (13:36)

And, you know, you work for some great companies on your way to being, you know, CEO. You worked at Walmart and the largest retailer in the world. What did you learn about leadership at Walmart?

Anya Smith (CEO of TaskRabbit) (13:48)

I think what I did learn is that sometimes when a company is so big, as Walmart obviously is, the decision making process can be really slow. And trying to figure out how to stay nimble and how to make decisions really quickly was really important. And one of the ways of doing that is figuring out really early who has the power to make the decision. And knowing that before you put a lot of time and investment and effort trying to influence a set of people who maybe in a given day or time or in this structure, don't actually have the power to make the decision. So understanding who has the power to make that decision, I think is really important. And in A sort of very matrix organization that was very much so focused on the e commerce world here in Silicon Valley, which is why I worked, versus Bentonville, which is sort of the, obviously the home base. There was a lot of tension between the two. And trying to get the clarity of understanding who makes a decision I think was really important in order to make any progress.

David Novak (Podcast Host and Interviewer) (15:00)

You also worked at Airbnb, as we mentioned, and Airbnb is rooted in trust. Opening your home to a stranger and feeling good about it. What's the story from your time there that shaped how you think about building trust with customers that you use in your company today?

Anya Smith (CEO of TaskRabbit) (15:18)

I think first and foremost, you have to listen to your customers, and I do that all the time today at TaskRabbit. But I did that Uber and I did that at Airbnb. Sometimes it may seem maybe not as fruitful because you hear similar stories, but there's been no conversation that I've had with a Tasker or a courier or a host from which I didn't come away thinking about a problem, maybe slightly different. And after a while, you start seeing certain patterns emerge or certain trends that are really hard to do if you only have one off conversation here and there. And so for me, the essence of really building trust is to be able to listen to the customers. They may not always know the answer, but really to understand their problem in a way that can shape your thinking about how to build and how to solve that problem, I think is essential in being able to move forward and to make a difference. And so we spent a lot of time listening to our customers at Airbnb.

David Novak (Podcast Host and Interviewer) (16:26)

And when you're at Uber, I mean, you're here, you're there with a company that sets a standard on, you know, for on demand convenience. That had to play a huge role in how you think about your current job.

Anya Smith (CEO of TaskRabbit) (16:40)

Well, absolutely. I mean, Uber is a. Is a fantastic marketplace and I would say, you know, best in class in terms of being able to really optimize the match between the client and, in this case, the courier or the driver to really provide you with that convenience that is so, so much needed at TaskRabbit. I focus on that a lot as well. But there's a lot of things that come into that. It's not as much of a commodity product. We are trying to really solve problems for people in their homes. And that can be anything from picking up leaves to painting your nursery to mounting a TV to cleaning, you know, cleaning before or after you move or before after you have a party. And so Many things in between, and being able to provide the person who, the right tasker, who's highly skilled, highly dependable, who can do that job and do that job really well for the right price and the right time. It's a really hard problem to solve. And so the lessons from Airbnb and from Uber are very much front and center. All of these companies, we're really trying to think about how to best provide that match between exactly what the client needs and exactly the best Tasker, in our case, who can provide that kind of a service.

David Novak (Podcast Host and Interviewer) (18:12)

So you were like the perfect match to take on the CEO role, given your past experience, you know, how excited were you to take on that CEO role for the first time?

Anya Smith (CEO of TaskRabbit) (18:23)

I was super excited. You know, I often tell people the story of when I came here, and my parents really, it was hard to make ends meet, and we're all trying to work hard. I do wish that some of these platforms, you know, existed then, but of course, we didn't even have cell phones then, so it's hard to think about how that would work. But I do know that my parents would work double shifts and trying to match shifts and trying to get more hours and so forth. It would have been really great to have these platforms on the side where they could have learned a skill or provided a skill just to supplement their income and just to make things a bit easier. And I, you know, I meet with taskers all the time and there were so many that come here and they come with, you know, I just met a set of Taskers. They're all from Iran and they were all electricians and engineers at home. And it's harder for them to get jobs here, but they provide such great service to our customers. And, you know, I had one come to our house to do some electrical work, and it's just a pleasure because he knew what he was doing. He did it very quickly and really solved the problem that I had in my house. But really, we also gave him an opportunity to earn a meaningful income. So for us, it is all about trying to provide more of these types of opportunities for taskers so that they can continue to earn money that can help them with their families or their schooling or whatever else it is that they need.

David Novak (Podcast Host and Interviewer) (19:57)

I love how you had a tasker come to your house and help you out. You think back, you've been CEO now for six years. What's the most memorable story you have where you personally use the TaskRabbit to, to get something done at your house?

Anya Smith (CEO of TaskRabbit) (20:13)

I don't know I have so many taskers come to our house. You know, as part of working at TaskRabbit, we provide a stipend to everyone so that everyone can constantly be trying out the product. So I have had dozens and dozens of tasker at our taskers at our house, doing all sorts of jobs. I would say, you know, there was one tasker who came and did a lot of work, a lot of painting for us, and he had a great story because he had been doing sales, and then the pandemic hit and his company shut down and he could no longer do sales. And he was trying to find new jobs in sales, but this was really the height of the pandemic, and people were still not hiring before sort of 21 started. And so he said, you know, when I was in college, I painted houses, and I loved doing that. I really found it so satisfying. And I thought, well, I can do this in the meantime until I find my sales job. And, you know, he kept coming back because I had just moved in a pandemic, as everyone else had, and so there was a lot of painting to do. And he said, you know, over time, I realized that this is so much more freeing. I love doing this. I love meeting my customers. I love providing a really good service. Maybe at some point I'll go back to sales, but this is great right now. And this was just. It's such a heartwarming story that we're able to provide some sort of a path for people who are maybe in between jobs or in between careers or maybe, you know, they are working at night or going to school at night, but need some. Some. Some more flexibility during the day. And so I've met so many taskers like that who are really trying different ways to add an incremental income.

Podcast Host (possibly a co-host or producer) (22:01)

Hello, friends. I hope you're loving this conversation between David and Anya. I certainly am inspired. Perhaps I'll move to Argentina. Who knows? I want to remind you, as we do every episode, to stay tuned to the very end so that you don't miss the debrief. David and I are going to be breaking down some of the concepts that Anya talks about so that we give you something really tangible to take away and to apply to your own leadership or to your own life. So stay tuned to the very end of the episode, and I will see you. See you soon.

David Novak (Podcast Host and Interviewer) (22:28)

You know, for someone using TaskRabbit for the first time, there's got to be a little skepticism about whether the person they're hiring is really qualified to do the job. I mean, I even see commercials that kind of make fun of that, you know. You know, how do you overcome that?

Anya Smith (CEO of TaskRabbit) (22:45)

Well, I think that of course I'm slightly biased, but of course we have the best taskers on our platform. And the way you know that is really by checking their reviews. You know, the majority of our taskers have really high ratings and reviews, and you can read about the jobs that they have done. You can read from past clients, you can see photos of some of the work, and you can, through that, you can gain a bit of trust and understanding that they have a lot of experience in whatever it is that you're hiring them for and will come in and, you know, hopefully do a really good job for you. I know that I've had the best of luck with our taskers and it's really helped, really, more than anything, our marriage, but it's been really great.

David Novak (Podcast Host and Interviewer) (23:40)

I'll tell you what, I need a tasker to help me. I can tell you that for sure. Consumer businesses experiment constantly. What's an experiment or a test that you ran that that didn't work, and what did you learn from it?

Anya Smith (CEO of TaskRabbit) (23:56)

Well, there are many. And honestly, if we're running experiments that do not fail, then we're probably not being bold enough. One of our key core values is to be bold. And so we talk a lot about as a company, as a culture, how important is to be testing and experimenting things that may fail. So sometimes you think something will work and then you put it on. And even though you may do, some user groups and consumers kind of tell, yeah, this would be great when you actually test it out, it turns out that people actually don't do what they thought they were going to do if that was live. So as an example, we are testing different ways that we allow customers to choose, or perhaps not choose taskers, depending on the type of category and the type of program. So we have found that in some instances, customers really do prefer to choose a tasker. They like seeing a list and they want to read all about them and they want to see who they're going to choose. But in other instances, we have found that actually when we tell them this is what it's going to, this is what it's going to cost you, and someone's going to show up at your house and assemble this piece of furniture, they like that, too. And so understanding in which instance, which type of paradigm works better has been very complex, and I would venture to say more complex than we had anticipated. But I think that that's okay. It's really great to test with customers and understand that in some instances we did not think through the second or third effects of the changes that we're making.

David Novak (Podcast Host and Interviewer) (25:42)

Speaking of complexity, when you face a complex decision without a lot of data, without necessarily precedent to lean on, what's the first question you ask yourself?

Anya Smith (CEO of TaskRabbit) (25:54)

Am I doing the right thing? What is the right thing to do? At the end of the day you can kind of peel it down and often you can go back to what's the right thing to do. I think as you sort of move further up, there isn't just necessarily data. If there is data and it clearly tells you do A, not B, of course you're going to do A because that's what the data says. Data often sort of doesn't tell you the why behind things. And then often it just, the data is very unclear and that's when the decisions kind of go up further and you're trying to make a choice with very limited information, with very limited data, and you kind of have to come back and say, okay, well, what's the right thing? And what does your gut say? And really your gut to me is just the experience of having been in that situation before, making a similar decision before or seeing some similar trends or recognizing a pattern. And it doesn't mean that I'm always right. I'm wrong more often than I'd like to admit, but that's okay. I think making a decision first and foremost is more important than just trying to continually to get more data in order to be more certain. Making a decision, especially if the decision is reversible quicker, I think is more important than waiting for more data that may or may not provide more certainty.

David Novak (Podcast Host and Interviewer) (27:20)

Now, you mentioned earlier that one of your core values is being bold. And you just, I would imagine doing the right thing for your customers is right up there. Maybe the wording isn't exactly it. What's something that you're trying to build into the culture that's, that's, that's relatively new that you think is going to be a requirement for, for you taking the taskers to a whole different level.

Anya Smith (CEO of TaskRabbit) (27:42)

So I think it is about being bold. It is about feeling safe enough to really try a lot of things that may or may not work and knowing that it's okay because that's the only way you can learn and actually try and do better next time. And I have a lot of work to do on that as well. Right. Often I don't want to let go of something. We try something and the experiment didn't do what we thought it was going to do. And if I still believe that it's the right thing, then maybe I'll try to influence it and say, well, what if we tried it this way or that way? And that's not really always the best answer. Sometimes just letting go and moving on and trying something new is the right answer. And so understanding what it means to be bold and how to take risks and how to be okay when they fail, I think it's. It is something that we're really trying to build into the culture because this concept of speed is really important. As we get bigger, and we did over 3 million jobs last year, which is a lot of jobs, it's easy to sort of get a little bit stuck in this analysis paralysis as opposed to making decisions quicker.

David Novak (Podcast Host and Interviewer) (28:53)

So you're becoming a bigger and bigger company every day. How do you keep a big company small? I mean, how do you wipe out big company itis?

Anya Smith (CEO of TaskRabbit) (29:01)

I think you take the best from some of the big company stuff and you kind of forget the rest. I think not all big companies are bad companies. There are many things that are really good, but we still have to be nimble. There's always a spectrum, and so there are processes and systems and so on. And it's very easy to kind of get very sort of suckered into those as we become bigger. But I keep reminding the team that we still have a lot of flexibility. We can make exceptions, don't have to have a process or a rule or something for every single thing we do. We still need to be very nimble in how we make decisions and how we execute and learn quicker and quicker. And I think that's sort of the core thing of trying to figure out how we. How to keep learning at a faster pace than, you know, your next competitor.

David Novak (Podcast Host and Interviewer) (29:54)

And one of the things I know every leader now is trying to get up to speed on and lead in the area is the sole area of. Of artificial intelligence. How are you personally using AI to make you a better leader, of course?

Anya Smith (CEO of TaskRabbit) (30:08)

Well, I think like most folks, I am there on chat and on Gemini constantly. Not just. I think I originally started with, you know, help me rewrite this in a simpler, clearer way. I'm more likely to use it now as a bit of a tool to let me think strategically a little bit more. I also use it to prep for big calls. I use it to prep for these types of interviews. I use it to prep for a lot of bigger events. I can have a conversation and say, hey, I am coming on David's podcast. Tell me, what do you think are some of the key themes that I should be thinking about and so forth. And I can have a live conversation, which is really helpful. But that's my individual productivity, being able to build gems and being able to simplify the more mundane tasks that we all have to do. But what I'm really thinking a lot about is not just individual productivity being increased. I'm also thinking about just some functional work that we can do. Of course, CS is a perfect example or customer service. And this is where we're seeing a lot of benefits engineering. Other functionalities have a lot of things going for them from AI. But where I'm starting to spend a lot more time and thinking about is how do we use the large language models and really even small language models to help us drive revenue more? So. And what that really means is to help the customer have a better experience. So to provide, you know, more seamless experience, to provide more information that is needed for them so that they're much more likely to find someone who they need to help them. And so that's the more exciting part of AI.

David Novak (Podcast Host and Interviewer) (31:56)

You light up when you start talking about AI. How do you create that kind of enthusiasm across the organization?

Anya Smith (CEO of TaskRabbit) (32:03)

You know, it's like a change. It's going through a change curve, and it's different for everyone. And, you know, like I coming back to my kids, I have some who are just very eager and curious. Some I make it sound like I have hundreds of kids, I only have three. But then I have one of my children who any change seems to cause just a lot of stress. And I think it's similar for everyone in the organization. Some people are very open and excited and they want to try and they want to learn. And we have AI Power Hour. We have all these tools and we have all these learning opportunities to learn more. And then there are people who are more sort of reserved, and it's going to take a little bit of time for them to adapt to these new technologies. And that's okay, but we are all heading in that direction. So it's not as if, you know, at some point we'll say, well, that was kind of fun, but we're no longer going to do that. It is about how do we get ourselves thinking in this mindset and how are we more and more likely to start using these tools to become more productive, to work smarter, and then again, most importantly, to provide a better experience to our customers.

David Novak (Podcast Host and Interviewer) (33:21)

I've heard you say that TaskRabbit feels like the place you were meant to be. Explain.

Anya Smith (CEO of TaskRabbit) (33:28)

It feels like such a right home for me, such a great role, because it takes into account sort of everything from the experiences I've had in marketplaces, especially working with people. Right. We're connecting a person to a person. But then I also have some of the retail experience from Walmart. And then, of course, we're owned by Ikea, which is company based in Europe. I grew up in Europe. I've also worked and lived in Europe since then, in my adulthood. And so all of these things mashed up together, I think make this the right role for me. But I think more than that, if you kind of peel the layers, it is about just having the passion to help people like our taskers. And that's when I come back to my childhood. It is really exciting to feel like this past year there were millions of tasks that we completed by thousands and thousands of taskers who got to earn this incremental income. And that is really motivating to me and hopefully my team as well. I think it's a great place to be, and I feel great every week when we look at our tasker earnings and how much have they earned this week, and is it more or less than week before? And it's exciting to understand that we're making a difference in people's lives. Our, our mission is to transform lives one task at a time. And I feel that every day we get to live that mission.

David Novak (Podcast Host and Interviewer) (34:58)

And now, you know, you're. You're an experienced CEO, you know, but when you look back, you know, what was the, what was the biggest challenge or maybe the most difficult tasks, no, no pun intended, that you had to. Had to really step up the learning curve on.

Anya Smith (CEO of TaskRabbit) (35:16)

Oh, it's, it's. I. I'm still learning, and there's so much more to learn. I would say that probably one of the biggest things was making some decisions too slow and then making others too fast and not understanding the difference between the two and why I should slow down on some decisions and actually go faster than others. And so definitely that. That's been a learning. Really my job as a CEO is to do few things and to do them really well. Right. The first one is to set the vision. Like, I really have to have a plan. I would say that in the first few years, the plan was very single, which was to do certain work with, to integrate us more with ikea because it was our partner and our parent. But I think over the time, we've developed a much more strategic plan, which I'm very Very excited about. The next thing is really being able to execute and execute really well. And so that's all about setting the right culture and really making sure that we have the right team in place to build on the plan that we have set out and then finally having to be able to communicate all of that really well to our teams. I think communication is really important, and I don't know that we've done very. That I've done very well on that every time. So still a lot of learnings there as well.

David Novak (Podcast Host and Interviewer) (36:38)

You know, you mentioned the importance of team and people. What's the time when you didn't have all the answers and your team taught you what great leadership is all about?

Anya Smith (CEO of TaskRabbit) (36:50)

Oh, that's like every day. Every day I learn from my team, and every day it's not necessarily the same lessons is different. People bring in something different to the table. Right. I've got someone on my team who's fantastic, super smart, but he is a bit of a disruptor. Ideas are always sort of can be a little bit disrupting, but they make me think more than normally. So it's great to have that kind of person on your team because it just helps you think about problems a bit differently. I've got people on my team who are very strong and able to give me feedback, which is really, really needed. It's a gift. And it's great that so many of them choose to sort of pull me aside afterwards and say, maybe you can do that better next time. And that's okay because that is really the only way I'm going to learn. And so there are many lessons from my teammates every day, and I really cherish that.

David Novak (Podcast Host and Interviewer) (37:53)

You know, has there been something that you've learned about human motivation that a lot of leaders consistently get wrong?

Anya Smith (CEO of TaskRabbit) (38:02)

I'm not sure that a lot of leaders get wrong, but I think it is really important to understand that everyone on your team is likely motivated by very different things and to understand what it is that motivates them, then helps you, I think, be a better leader to them. Because for me, you know, the best, the best reward is really seeing people on my team grow and develop. And it is really the best part of my job. But in order to do that, I have to understand what motivates people. And some people get motivated by titles, Some people buy money, some people by the scope of their work, some people buy the flexibility of their job or, you know, there's so many things that motivate people and understanding what it is and what makes them tick and being able to provide them with the opportunities that allow them to shine best and in the things that motivate them to do their best work. It's really hard, but it's by far the most rewarding part of my job.

David Novak (Podcast Host and Interviewer) (39:02)

You know, looking back, what do you think is the most meaningful recognition you personally ever received, and what did it teach you about how people want to be seen?

Anya Smith (CEO of TaskRabbit) (39:12)

You know, it was early on in my career, and we were in a big meeting, and I was by far the most junior person in that meeting, like, by leaps and bounds. And, you know, it was some big meeting, talking about. I don't even remember what it was, but at one point, the most senior person in the room who was a CEO at the time, looked at me and said, anya, what do you think? And I was kind of shocked that he would even care. I didn't even know he knew I was there, let alone that he knew my name, let alone that he asked me what it is that I thought. And I felt very heard at that moment. And it's a great lesson that I need to keep repeating to myself, because I think at the end of the day, everyone wants to belong, and they want to feel heard. They want to feel like their contributions matter. And I think showing that to people by being this leader who can listen and allow people to be their best selves is the hardest part. And so that was a great lesson very early on in my career and a great story.

David Novak (Podcast Host and Interviewer) (40:22)

I love that story. What's the most powerful recognition that you've ever given to someone else?

Anya Smith (CEO of TaskRabbit) (40:28)

You know, we were working on a project at Airbnb, and it wasn't going very well, but we had a great breakthrough because this person decided to be very creative and could have actually gotten in trouble for their creativity. But I pulled him aside and said, well, I love that you thought about this so differently than the rest of us, and who cares? You know what? We'll just do this, and then we'll ask for forgiveness later. And I love that you did this. And this person was quite junior, and he got so excited. Like, I could see it in his eyes, because I think he was a little bit worried because it was kind of going out on a limb. And I knew that this had given him the momentum to keep going. And so it's really, again, the most rewarding part of my job.

David Novak (Podcast Host and Interviewer) (41:16)

Awesome. That's great. This has been so much fun, and I want to have some more with my lightning round of questions. So are you ready for this?

Anya Smith (CEO of TaskRabbit) (41:23)

I am.

David Novak (Podcast Host and Interviewer) (41:24)

The three words that best describe you.

Anya Smith (CEO of TaskRabbit) (41:27)

Lively, curious and ambitious.

David Novak (Podcast Host and Interviewer) (41:30)

If you could be one person for a day besides yourself, who would it be?

Anya Smith (CEO of TaskRabbit) (41:35)

I would love to be like a dancer performer on stage somewhere.

David Novak (Podcast Host and Interviewer) (41:42)

Your biggest pet peeve.

Anya Smith (CEO of TaskRabbit) (41:43)

When someone on my team comes to complain to me about someone else on our team, and then I ask, have you spoken to that person? And they hadn't yet. I don't like that.

David Novak (Podcast Host and Interviewer) (41:55)

Me either. What's something you'd only know about Poland if you're from there?

Anya Smith (CEO of TaskRabbit) (41:59)

You know, on Monday after Christmas. Oh, after Easter, it's this day called Schmingus Dingus, which is essentially like. It comes from this tradition, I think, of baptism around Easter. But what you do is you dump water on people and, like, buckets of water. And so kids play with, like, toys of water, but as you get older, you do buckets of water and people get soaked. And it's a very fun tradition. It's usually still cold in April, but it's a fun, fun day. It's a celebration.

David Novak (Podcast Host and Interviewer) (42:29)

You've lived in South Dakota, Poland, Arizona, China, London, San Francisco. What place taught you, shaped your leadership the most?

Anya Smith (CEO of TaskRabbit) (42:38)

You know, I lived in Kenya for a little bit of time, and I ran a cashew processing plant, and I spent a lot of time teaching people there how to use Excel. And I think one of the things about leadership that is really important is having the patience and the grace to be able to really listen to people. And I think just there was just such a big gap of learning, and yet having the patience to do that, I think was really important. And it definitely taught me huge lessons.

David Novak (Podcast Host and Interviewer) (43:18)

What's the most creative TaskRabbit job you've ever seen someone post?

Anya Smith (CEO of TaskRabbit) (43:23)

I don't know. But the very fun jobs are always waiting in line. So for crazy things like I just read in the New York Times how there's sample sales and these people line up all night in tents and wait for to go have a chance to buy a sweater or a dress. And a lot of taskers get hired for this in order to wait in line for hours and hours and hours on end.

David Novak (Podcast Host and Interviewer) (43:48)

I love it. What's something you've been curious about lately that has absolutely nothing to do with work?

Anya Smith (CEO of TaskRabbit) (43:54)

I spend a lot of time thinking about affordable housing and the NIMBY and NIMBY movements and what we're seeing in our governments. And really especially a lot of it has to do with local governments. And we're seeing a lot of change in mayors across the country. And I think a lot about this concept of abundance by Ezra Klein in his book and There's a lot of work that we need to do as a country in order to, I think, make more chairs. Because we kind of have this musical chairs game and there's just not enough chairs at the end for everyone to have a place to live.

David Novak (Podcast Host and Interviewer) (44:38)

What's the one thing you do just for you?

Anya Smith (CEO of TaskRabbit) (44:40)

I read a lot of news every morning and then I follow certain writers and really enjoy reading some of the long form pieces that they put out. And it's one of my favorite pastimes.

David Novak (Podcast Host and Interviewer) (44:57)

If I turned on the radio in your car, what would I hear?

Anya Smith (CEO of TaskRabbit) (45:00)

Npr.

David Novak (Podcast Host and Interviewer) (45:00)

What's something about you that few people.

Anya Smith (CEO of TaskRabbit) (45:02)

Would know that I know very little about pop culture.

David Novak (Podcast Host and Interviewer) (45:07)

What's one of your daily rituals, something that you never miss?

Anya Smith (CEO of TaskRabbit) (45:11)

I think working out. I generally try to get a little bit of a workout in almost daily as I'm getting very old. It feels like it's something very necessary.

David Novak (Podcast Host and Interviewer) (45:22)

All right, we're out of the lightning round. Great job. I got a few more questions. I'll let you go here. You know, I understand you and your husband have a point system used to balance your career and home life. Tell us about it.

Anya Smith (CEO of TaskRabbit) (45:36)

We do. And it was just kind of serendipitous how it came about. But then again, when you are talking to an ex consultant and an ex banker, maybe this is what happens. But when our first child was born, we, you know, I took a bunch of time off. My husband did just a little bit of time. And then we kind of started talking about how whether or not we can continue to afford to live in London because it was so expensive. And we decided that the only way we can do that is if one of us goes back to these professional services, consulting or banking. And we kind of looked at each other and decided that neither one of us wanted to do that. And then we started talking about why that is. And then we decided that really generally what does that mean for our family and how much time we spent with our family. And so we rated every job to be either a 1, 2 or 3, meaning a 1 you're kind of barely working or maybe part time working. A two is quote unquote normal job. You're working nine to five. Some travel, sometimes you have a big project, but generally you're home at 5 and you can fix dinner for your kids. And then a three is sort of a crazy job where you're on the road all the time, where you're working 60, 70, 80 hour weeks and so forth. And we decided that between the two of us, we really should never Go above four and a half, you know, maybe sometimes temporal, temporarily hit a five, but it shouldn't be a permanent state. And if we are getting close to a 5, then one of us probably needs to make a change. And so we've tried to live by that. And it's definitely been a way for us to think about when, you know, there's a lot of work that comes with raising a family and a lot of fun times that we don't want to miss. And so in order to do that, we kind of have this framework.

David Novak (Podcast Host and Interviewer) (47:26)

You walk the talk. I mean, not many people take that gap year. And you took it. You know, that's a great example. You know, last question here. What's one piece of advice you'd give to anyone who wants to be a better leader?

Anya Smith (CEO of TaskRabbit) (47:38)

Be curious and learn to listen.

David Novak (Podcast Host and Interviewer) (47:40)

Anya, thanks so much for being on the show. I appreciate it.

Anya Smith (CEO of TaskRabbit) (47:43)

Thank you for having me. It's been great.

Podcast Host (possibly a co-host or producer) (47:50)

David, what an inspiring conversation. I also would like to be friends with. I want to be friends with everyone we interview. But she is a lady who just has such an interesting, interesting story. I can't believe that she moved to the US when she was 12. She's now worked at Walmart, Airbnb, and she's the CEO of TaskRabbit. Her story is just fascinating.

David Novak (Podcast Host and Interviewer) (48:07)

Yeah, she came here as an immigrant from Poland, moves to South Dakota when she's 12, doesn't, doesn't have the language, knows nothing about the United States of America, and started to adapt. And, you know, I think this is a great example of how we all, as people and leaders, can learn from going into new environments. You know, I related to her very much. Not because, you know, I couldn't speak English here in the United States, but I relate to her because I lived in many different places when I grew up. I lived in 23 states by the time I was in seventh grade. And, you know, when you have to go into new situations, you learn how to work through anxiety that we all have. So, you know, we all go into rooms that we don't know. Everybody. We. We go into situations where we don't necessarily have the answer. All these things create anxiety. And when you put yourself in new environments and force yourself to do new and different things and meet new and different people, you're just up in your game as a leader and a person. And obviously, she learned a lot by doing that. And it's great to see a great leader and especially a female leader rise the ranks. Coming. Coming in in a manner that she did I was very impressed with that.

Podcast Host (possibly a co-host or producer) (49:25)

I love that as a key takeaway from that conversation, put yourself in new environments because you learn a lot about what you're capable of and it also forces you to, to dig deep and really understand who you are and what you stand for. Because if you walk into a new environment and don't know anybody and perhaps you don't even know the language, you really do have to fall back on who you are and what you know that you're good at. So I love that as a key takeaway, put yourself in new environments and, and learn more about yourself and how you want to show up.

Anya Smith (CEO of TaskRabbit) (49:51)

Up. Yeah.

David Novak (Podcast Host and Interviewer) (49:52)

And speaking of self development, you really got to know yourself to grow yourself. And I think that's another major key takeaway from our discussion with Anya is that she, she actually took a gap year when she was, I think she was running operations at Airbnb. I mean, she was a, she was a very, very top leader. I'm sure she was in position where she could potentially become the CEO there. But she knew somehow in her DNA that it was time for her to step back and, you know, take some time with her family. And they went to Argentina. She took her three kids with her. You know, she, she learned how her three kids are so different, needed to be motivated in, in different ways. But most importantly, she, she got to spend time with her family and get, I'm sure her work life balanced back in order and, and you know, it's something that she, she, she talks about with such, such pride because she, she grew herself by doing it. You know, I'm sure she had time to self reflect and figure out what she wanted to do, how she could raise her game. And you know, I, I think that's just incredibly powerful and, and it, it's self motivating. So she was very much into her self development. She wasn't, she wasn't backing off when she went on that gap year. She was digging in. She was digging into herself and figuring out how she could really, really take it to the next level. And she did it and got closer and closer to her family, which she treasures and, you know, just really exciting to see.

Podcast Host (possibly a co-host or producer) (51:24)

She talks about how she and her husband had to save money before they went because they had the intention to go to Argentina and not work. And you ask her in the episode, you know, you say that's a pretty significant gap in your resume. You know, what do you think about that? And I'm curious, David, where you sit today, if you were reviewing a resume for. Let's say a CEO job and you saw that there was a one year gap where this person went to Argentina or another country with their family. How would you evaluate that as you are evaluating a potential new candidate?

David Novak (Podcast Host and Interviewer) (51:55)

Yeah, well, it wouldn't matter if they're a CEO or someone interviewing for a product manager job. That would stand out to me. And I'd ask them, tell me about that gap. You, why'd you take it? What'd you learn? Would you do it over again? You know, what'd you learn about the place that you went to? Is there anything you do over? You know, I just, you know, I think I would have really had a lot of fun, you know, digging into that question. I'd learn a lot about the person, the way how they answered those questions.

Podcast Host (possibly a co-host or producer) (52:24)

Well, great news, David. I'm going to Argentina for a year. I'm just kidding.

David Novak (Podcast Host and Interviewer) (52:30)

You can't go. You're irreplaceable. You know, you can't do that.

Podcast Host (possibly a co-host or producer) (52:35)

I'm just kidding. I'm not going to Argentina. But I do want to hit on one other big theme from the conversation between you and Anya. She talks a lot about how frequently she hires taskers from their platform to come to their house to complete tasks and how much she really enjoys getting to meet her taskers. One of their main goals as a company is to provide a way for these taskers to create supplemental income and, and live the life that they always wanted to live. And I'm curious, David, from your perspective, what does that say about her leadership style and her commitment to her product that she actually uses her product quite frequently?

David Novak (Podcast Host and Interviewer) (53:13)

I don't know how you can be a good leader if you don't know your product inside and out. And so how would she know what the whole process is without having her taskers, you know, help her at her house? And so she, that's, that's basically what she did. And you know, the closer you get to the customer, the, the better you are. And in this particular case, she's the customer. Yeah, sure, she's the CEO and people are going to want give her the best. But if they, if, you know what, if you can't give the CEO the best, you can't give. Just think what it's going to be like for everybody else. I remember when I used to go on market tours and people would know I was coming me, if I walked into a restaurant and that restaurant was not being run well, which happened unfortunately more than I would have liked. It said I would go, holy crap, what's it like when I'm not, you know, when the CEO isn't there, you know, if they can't do it, well, when I'm walking in, there's a big problem. And so I think, you know, in this particular case, she got close to the customer by being a customer and having the taskers come in. In my case, you know, I got close to the customer by going into stores, you know, seeing our. How our operations were and talking to customers firsthand. And, you know, I think the way how she makes decisions is also something that's very, very important for every leader. She. She makes decisions based on what she's hearing from customers. You know, you, you know, listen and respond to the voice of the customer. Customer. That's a major takeaway that, you know, it's very simple, but people often overlook it. If you want to understand the customer, be a customer. That's a major takeaway. So, you know, she's. She's just a leader that. That understands the importance of doing the basics really well and then pushing her organization to take it to the next level. She's really trying to go for bold thinking and, you know, figure out the next steps on. On AI. Get better at that or herself. But she. She knows how to know herself and grow herself, and I think as a result, you know, she's growing her business absolutely.

Podcast Host (possibly a co-host or producer) (55:33)

Well, I'm so thrilled to. To stay close to TaskRabbit. And I actually hired a Tasker last weekend to install a new chandelier in my house. And Anya, if you're listening, had a great experience. Experience. So excellent work. I loved my Tasker. Eduardo was his name. He did a great job. There was no mess in my house. He was super respectful and kind. So they really know how to. How to set the standard. And. And I'm excited to continue to watch where Anya takes it.

David Novak (Podcast Host and Interviewer) (56:01)

Well, let me tell you, if there's one person in the world that needs a handyman or handy woman, I am. So I'm gonna have to. I'm gonna have to give him a call.

Podcast Host (possibly a co-host or producer) (56:09)

TaskRabbit.com David TaskRabbit.com There we go. Thank you so much for tuning in to another episode of How Leaders Lead with David Noback. We'll see you next.

Anya Smith (CEO of TaskRabbit) (56:28)

Time.