Money Rehab with Nicole Lapin - How To Take a "Gap Year" as an Adult Without Falling Behind with Taskrabbit CEO Ania Smith
Episode Date: August 21, 2024Is it possible to take a "gap year" without falling behind in your career? Ania Smith says with careful planning, it is. In fact, Ania says the gap year she took with her family helped deepen a skills...et that has benefitted her in her job as the CEO of Taskrabbit. Today, she tells Nicole how she and her husband prepped and budgeted for their gap year and the incredible point system they use to make sure that family comes first; and then, Ania and Nicole dive into all things Taskrabbit, including how the company is tackling the supply and demand questions that are stumping other gig employers, and the oddest jobs– literally— people post on Taskrabbit For more on Ania, follow her on LinkedIn: https://www.linkedin.com/in/aniasmith All investment strategies involve risk of loss. The information shared in this podcast is for informational and entertainment purposes only. Listeners should do their own research and consult a financial advisor before making any investment decisions. See terms for additional details: https://moneynewsnetwork.com/terms/Â
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One of the most stressful periods of my life was when I was in credit card debt.
I got to a point where I just knew that I had to get it under control for my financial future
and also for my mental health. We've all hit a point where we've realized it was time to make
some serious money moves. So take control of your finances by using a Chime checking account with
features like no maintenance fees, fee-free overdraft up to $200, or getting paid up to
two days early with direct deposit.
Learn more at Chime.com slash MNN.
When you check out Chime, you'll see that you can overdraft up to $200 with no fees.
If you're an OG listener, you know about my infamous $35 overdraft fee that I got from
buying a $7 latte and how I am still very fired up about it.
If I had Chime back then, that wouldn't even be a story.
Make your fall finances a little greener by working toward your financial goals with Chime.
Open your account in just two minutes at Chime.com slash MNN. That's Chime.com slash MNN.
Chime. Feels like progress.
Banking services and debit card provided by the Bank Corp. Bank N.A. or Stride Bank N.A.
Members FDIC. SpotMe eligibility requirements and overdraft
limits apply. Boosts are available to eligible Chime members enrolled in SpotMe and are subject
to monthly limits. Terms and conditions apply. Go to Chime.com slash disclosures for details.
I love hosting on Airbnb. It's a great way to bring in some extra cash.
But I totally get it that it might sound overwhelming to start or even too
complicated if, say, you want to put your summer home in Maine on Airbnb, but you live full time
in San Francisco and you can't go to Maine every time you need to change sheets for your guests
or something like that. If thoughts like these have been holding you back, I have great news for
you. Airbnb has launched a co-host network, which is a network of high quality local co-hosts with
Airbnb experience that can take care
of your home and your guests. Co-hosts can do what you don't have time for, like managing your
reservations, messaging your guests, giving support at the property, or even create your
listing for you. I always want to line up a reservation for my house when I'm traveling for
work, but sometimes I just don't get around to it because getting ready to travel always feels like
a scramble, so I don't end up making time to make my house look guest-friendly. I guess that's the best way to put it. But I'm
matching with a co-host so I can still make that extra cash while also making it easy on myself.
Find a co-host at Airbnb.com slash host. I'm Nicole Lappin, the only financial expert you
don't need a dictionary to understand. It's time for some money rehab.
Can you close your eyes for a second and think about what it felt like to be 18?
There were probably a lot of feelings. I mean, we all had a lot of feelings at 18.
But I want you to remember one in particular, that you could do anything. That you had a sense that you had some commitment coming, whether it was a job or going to college or starting a family, but that maybe
you didn't have to start that commitment just yet. That maybe you could take a gap year. You could
move to the other side of the world if you wanted to. You could try a weird out there job that you
knew you would never want to do for the rest of your life, but you could take a chance. 18 feels like the one time you can step out of the stream
of your life without risking forward momentum. But Anya Smith would tell you with careful planning,
you can recreate this moment in your life again without risking a career setback.
Anya and her husband Rob were both in high-powered jobs. She
was at Airbnb. He was at Glassdoor when they decided to take their three kids on a gap year
to Argentina. You might think that taking a year off work would have stopped Anya and Rob's careers
in their tracks. But he now has a big finance job in Silicon Valley, and she is the CEO of
TaskRabbit. So clearly, they are crushing it. And today,
Anya explains how they pulled all of this off. In our conversation, we talk about how she and
her husband budgeted and prepped for their gap year, what lessons they learned from taking a
step back from their demanding jobs, and the point system they use to make sure their family comes
first. And then, of course, Anya and I dive into everything TaskRabbit, including how they're tackling the supply and demand questions that are stumping other gig
employers and the oddest jobs that people post on TaskRabbit. Anya Smith, welcome to Money Rehab.
Thank you so much for having me.
I'm so excited to talk specifically about this gap year that you and your family took. It was
about six years ago, right? In Buenos Aires. At the time, I'm fascinated because you and your husband are
both at the height of your careers. Why did you do that? So we had been planning for quite some time.
Really, it goes back to when I was pregnant with my youngest son. And I knew then that our lives
are going to just about, they were already crazy and they were going to about to get worse. And so I remember having a conversation one day with my husband saying,
is this sort of it for the foreseeable future? Or can we start thinking about taking some time
off at some point? And then I've always thought that when your youngest one is five,
when you're a little
bit more free.
And so we started saying, hey, how about five years from now when he's five?
Let's see if we can make that work.
And then actually when he turned five, we were not ready.
I had only been at Airbnb for a couple of years.
My husband had been at Glassdoor for a couple of years and it just didn't quite seem like
the right time, especially for me at Airbnb.
But we also knew that there would never be the right time. So we promised ourselves that we're
going to reevaluate this every year. And so a year went by. And as it happened, there is all sorts of
stuff glass door got purchased. So there is some possibility of taking a break from my husband. And
then I thought, yes, I should wait
for four years. But then when I wait, he starts something, it'll never work. And so we decided
to pull the trigger and say, okay, we are ready. And we got ourselves together to do it quite
quickly. But it had been in our minds for quite some time. And we had been saving money for quite
some time in order to make it happen, because really it meant
no income for a year. And then of course, spending money on top of it and a double whammy. Of course,
the cost of living in Argentina was much lower than it was in a Bay Area. I think it still is.
Yes. And so you decided to do it quickly, but six years in the making, it sounds like. Your kids
were what, six, eight, and ten.
How did you even talk to them about the idea of a gap year?
Oh, wow. It's such a great question. I remember just being scared. And so we had dinner together every night. And my husband and I practiced and said, okay, tonight we're going to say it. We
didn't want to tell them too early because then we thought it's just going to prolong the pain.
But we also wanted them to have some warning and not say, hey,
tomorrow we're moving. So probably around April timeframe, we sat down with them and said, hey,
this summer we have all this travel planned where we're still going to do the travel, but then
we're going to continue that on and we're going to actually not come back for this next school year.
It was definitely not an easy conversation, even at their young ages,
especially the oldest one was not pleased.
And did you tell them how they were going to fill their time?
Did you guys even know how you were going to fill your time?
Like how much planning went into this?
I'm assuming you said you saved, you made a budget,
maybe a family P&L or something like that. Yes, but there was so much planning. I left my job in April and until we left
for, we first went to Asia that summer. And so until we left in June, I was working all day,
every day on the planning, literally. So it just takes a lot to take yourself out
of your day-to-day life, right? We knew for them, what we wanted to do is make sure that they
continue going to school. And it was really important for us to make sure that they learned
Spanish. And so that's really what we focused on is trying to find a school for them. I didn't speak any Spanish. And
what I wanted to do is find a school that isn't the expat American school or British school for
a couple of reasons. Most of those types of schools are actually located on the outskirts
of towns or in the suburbs. And we really wanted to live in the center of Buenos Aires. And then
secondly, many of those schools teach
in English and our whole goal was to ensure that our kids learned Spanish. And so that meant getting
some help and getting some friends to make phone calls for us and interview schools and try to do
this long distance until we had a chance to get down to ourselves. So we knew that kids would be
going to school. And then we started thinking a lot about what we were going to do with our time. So first and
foremost, we're going to spend a lot more time with our kids, right? They would be down to school
at three or something. So that meant that we still had some time in the morning and midday
to give ourselves back. And so we started thinking about what are we going to do? Like,
which hobbies we're going to pursue? And what are we going to do, like which hobbies we're going to pursue
and what are we going to do with our time?
And that was really fun.
What did you do?
So we both did different types of things.
We studied Spanish.
We did that for a couple of hours every morning.
And then we went and did long workouts every day.
And then we had long lunches every day, which is really nice.
And then in the afternoons, we spent a lot of time really trying to learn new hobbies.
So we danced.
I went horseback riding a ton.
My husband learned how to drum.
I took a photography class.
So we did lots of those types of things.
We also, actually, I was just talking about this to someone today.
It's really hard when you're generally quite ambitious, which both of us
are to let go. So this concept, for example, of seeing a movie in a movie theater at 11am on a
Tuesday, it was really hard to say that's okay, that we will go back and work again, that we have
to give ourselves the space to relax as well and really think about what we want to do with the
rest of our lives. Where do we want to live? What types of careers do we want to pursue? Do we want
to keep working in tech or not? And what is that going to look like? And so we spent a lot of time
focused on that. Yeah, the planning alone, it sounds like the type A ambitious you really snapped into high gear for this.
It sounds like even that part was exhausting, even though it was supposed to be a relaxing
experience. It took some lead up. And also, I'm assuming you guys had a lot of discussions about
being able to find an on-ramp again when you did decide to rejoin the workforce at such high levels
that you guys were at.
That's right. And that spring before we left, I was just focused on making sure we find renters for our house, making sure we can pack up, making sure we can sell our cars, all of those types of
things, speaking with the school so that they could give us some guidance as to what our kids
should be learning the next year, because we knew that we would pull them off for a year
and then they'd come back and not go back a year.
They would keep going.
And so what did that mean?
So it was a lot of planning, but it was exciting as well.
And then we promised ourselves
that for the first six to eight months,
we're really not going to focus onto what's next.
We're gonna first decompress and relax
and focus on ourselves really and our family. And we won't start working on what's next, we're going to first decompress and relax and focus on ourselves really and our family.
And we won't start working on what's next until the spring. And we stayed pretty true to that,
I would say. And you, it sounds like you saved, you had a budget, how detailed was like a P&L
or a financial plan? And did this gap year change the way you guys looked at money?
Certainly it changed. When you have no income, we don't have infinite funding in any case.
So we had to be quite strict.
So yeah, we knew how much we would spend obviously on rent and food.
And then our expenses after that were quite low because we have car payments or many other
things.
We were making some money on the rent from our house in Marin.
And so that also helped to set up or help to offset some of the costs. And then we knew that
we would want to travel quite extensively. Obviously, winter in Argentina is the opposite
timing. And so therefore, summer is the opposite timing. So we knew middle of the year around
Christmas time, we're going to have some time to take
off.
And we really wanted to travel in Patagonia.
And that's just expensive, whether you come from here or from there or really anywhere.
The cost of a hotel room is the same.
Yeah.
And I think one of the most valuable skills that any executive or CEO can have is this
ability to adapt to change really quickly.
It sounds like this gap year was a crash course in that.
Of course. And we really wanted our kids to be able to do that. It's really hard to
show up at a new school with all new friends, with a totally different layout, different ways
of learning. And then most importantly, not knowing the language. It forces you to really try to
figure out how to navigate that. And for us, it was really important that it helped our kids to
build independence and to build resilience. I think resilience in particular is really important
to grasp that skill quite early on and continue to push yourself into new learnings and new territories. And honestly,
to feel uncomfortable because that is the easiest way to learn. And so it was important for me to
give my kids the opportunity to take them out of their comfort zone in Marin and their kind of very
nice life and somewhat of a bubble and make them figure out how to navigate something totally new
and different. It's super cool that you did that.
And as the year came to a close, it sounds like for the first six months, you didn't
do any thinking about what's next.
And then what happened?
You guys thought maybe you would move back to Park City or even South Dakota.
Fascinating choice.
You ended up back in the Valley.
I grew up in South Dakota.
So then that was easy to think
about. We had a lot of conversations. And when you think about it, we had a lot of time, right?
We would take, drop off our kids at school sometimes and then just say, okay, let's skip
the Spanish lessons today. And they're working out, but let's go and have a really long breakfast
through lunch and just talk about different options and what we want our lives to be.
And it's really nice to have that space because normally, especially when you have kids, you're
just constantly busy.
And honestly, at least for me, I'm just trying to survive.
There's a lot going on when you have a two, four and a six year old, especially trying
to still maintain a career outside the home for both of us.
And it was really nice to have the
space. And we wanted to let ourselves know that, hey, maybe, and this is obviously pre-pandemic,
and the way we work has really shifted, obviously, in the last four years. Before then, most of us
couldn't quite imagine where we would be today. And we spent a lot of time talking about what
would it be like if we left the Bay Area and
moved to a small town? What would we like? What wouldn't we like? What do we want out of our
lives? What do we want for the next decade where our kids are still at home? How present do we want
to be? What do we want out of our careers? What will we want after the kids leave? And so there's just a lot of questions and meandering and letting things simmer and then talking again and again. And then to the point where I started interviewing, as did my husband, in different parts of the country, even while we were still living in Argentina.
I flew out to Washington, D.C. I used to live there and really love that area and thought maybe it's time to move back to the East Coast. And then after all of that, it became fairly clear to us
that no, we actually still want to stay in tech. And this is why and this is the impact that we
want to have. And this is what we want to do. And so that clarity and knowing that we're making that decision in a very deliberate way was really freeing.
Oftentimes, figuring out what you don't want to do is just as important as figuring out what you do want to do.
And so getting back to that choice sounds like it wasn't an easy one.
It took a lot of discussions.
How did you ultimately get the job as CEO?
Was it toward the end of your gap time?
No. So I first came back and started
working at Uber. So I looked at many different opportunities in the Bay Area and I obviously
had already made some connections prior to my departure. And so I started having long
conversations. I flew up a couple of times and I really believed in what Uber was doing,
particularly on the Eats side. It was very complimentary to my skillset and I really believed in what Uber was doing, particularly on the Eats side. It was very complementary to my skill set.
And I really loved the team.
And I was very excited about the new opportunity at Uber.
And then did TaskRabbit reach out to you directly?
Did an executive search firm?
Like, how did it work?
Sometimes I think people think getting a job as the CEO is a confusing black box.
It can be.
And I think there is no one path. I think that there's
multiple different ways. It also depends on what the company is, the size of the company, all the
things. But for me and in my, in this instance, it was an executive recruiter that reached out and
said, Hey, we are running a search for this role. And they're looking for someone who has marketplace
experience. And would you be interested? And that was that.
And you and your husband have a point system that I really love in and it surrounds career.
Can you share what that is? Both my husband and I come back, come from a background of investment
banking and consulting. And unfortunately that's not always a good thing. And there are a lot of
spreadsheets in your household. There are like way more than there need to be, honestly. And so when we first started having children,
there was a lot of talk about, wow, what does this mean for our careers? And my first child
was born in London. And so in the UK, the actual benefits are quite better than they are here. And
so as a new mom, you're guaranteed a year off work,
which is really, truly spectacular. And so I took the year, which is very nice. But then we started
thinking about when I go back, what does that mean? And how is that going to work? And I want
to work less because I can't work the way I did before I had the baby. And we started having these
conversations where what does it mean? And what will it mean in the long term? And then we came up with a system where we
essentially said, okay, there are some principles for us as a family that are important. One of
which is, we don't want to be weekend only parents. So we wanted both of us wanted to spend time in
the mornings and the evenings with our children,
not just on weekends. We knew lots of people who often had, for example, two nannies, right? There was someone who would come in and start from set and work from seven to four. And then another
person would show up and work from four to 10, which would give the parents a lot of flexibility
to work late or do work dinners and so on. And I totally understand that. I think that everyone
should do what works for them because it's, this is a really rough road overall. And so you need
to know what works for you and what makes you happy. For us, for us, it was very clear that we
wanted to spend time with our kids. And so we started waiting, what does that mean for our careers? And we decided that any sort of part-time role or almost no job would equate to a very busy and demanding role, like a consultant
or banker would be a three. Often those roles would require 70, 80, 60 hour weeks that make
it very difficult. And so what we decided is that between the two of us, we don't want to
really ever go above four and a half. And because neither one of us wanted to let go of our career,
it automatically meant neither one of us could also have this high demanding job,
because that would indicate that we would be closer to a five. And so we both started thinking
about how do we succeed in more quote unquoteunquote jobs that allow a bit more flexibility
and allow us to manage our house in a way that give us that space with our family that we felt
was very much so needed. But then you said that there was a time when your husband Rob's company
was going through a capital raise and then there were big initiatives for you at TaskRabbit, which I'm assuming is a very
solid three or three plus.
I don't know.
So collectively, you said you guys were at a five.
In those moments where the points are too high, which I love this point system and coming
up with a system and a process for something that feels squishy.
How did you decide who needs to take lower points? And there are so many different ways and it comes down to really
communication. Five for two months is okay. Five for a year, probably not. And we needed to
understand what it really means and which one of us is willing to give in or offer more flexibility,
right? There was a time when we were both really busy and we asked my parents to move in for a
little bit of time because that felt like we would get the extra support for our kids, but it also
felt very temporary, right? We're both going through a lot of work. It's not going to be
permanent, but we wanted
some extra support right then. So we're very fortunate to have that kind of flexibility
and very fortunate to have those types of choices. And it doesn't always perfectly work out because
again, we're both quite ambitious. And obviously my job is quite demanding. My husband is also
building a career. It takes a lot of give and take. It means sometimes I can't go on a business trip
when I thought I could,
or I have to say no to a dinner
and same goes for my husband.
And that's sometimes very difficult.
How often do you guys check in on this number?
And what's your number right now?
We check in whenever it feels like it's not working.
So if it's working,
we're not even having the conversations.
If things are not working, we're like, having the conversations. If things are not working,
we're like, this isn't quite a four and a half. This is looking closer to five for extended period
of time. And again, it's quite personal how we manage it. Sometimes for me, the way I structure
it is having the flexibility, right? As an example, my daughter is at a camp this summer and she has a big performance and
I want to surprise her and I didn't think I was going to do this but I just decided this and
I have the flexibility to say okay let me take the second half of the afternoon off
and clear out my calendar so I can run to the airport camp light and then show up in Michigan and watch her perform. And I think so while my job is very
demanding, the flexibility and the autonomy that I have really helps to offset some of the
long and grueling hours. Hold on to your wallets. Money Rehab will be right back.
One of the most stressful periods of my life was when I was in credit card debt. I got to a point Hold on to your wallets. Money Rehab will be right back. So take control of your finances by using a Chime checking account with features like no maintenance fees, fee-free overdraft up to $200, or getting paid up to two days early with direct deposit.
Learn more at Chime.com slash MNN.
When you check out Chime, you'll see that you can overdraft up to $200 with no fees.
If you're an OG listener, you know about my infamous $35 overdraft fee that I got from buying a $7 latte and how I am still very fired up about
it. If I had Chime back then, that wouldn't even be a story. Make your fall finances a little
greener by working toward your financial goals with Chime. Open your account in just two minutes
at Chime.com slash MNN. That's Chime.com slash MNN. Chime feels like progress.
Banking services and debit card provided by the B Corp. Bank NA or Stride Bank NA.
Members FDIC. SpotMe eligibility requirements and overdraft limits apply.
Boosts are available to eligible Chime members enrolled in SpotMe and are subject to monthly limits.
Terms and conditions apply. Go to Chime.com slash disclosures for details.
I love hosting on Airbnb. It's a great way to bring in some extra
cash, but I totally get it that it might sound overwhelming to start or even too complicated if,
say, you want to put your summer home in Maine on Airbnb, but you live full time in San Francisco
and you can't go to Maine every time you need to change sheets for your guests or something like
that. If thoughts like these have been holding you back, I have great news for you. Airbnb has
launched a co-host network,
which is a network of high quality local co-hosts with Airbnb experience that can take care of your
home and your guests. Co-hosts can do what you don't have time for, like managing your
reservations, messaging your guests, giving support at the property, or even create your
listing for you. I always want to line up a reservation for my house when I'm traveling
for work, but sometimes I just don't get around to it because getting ready to travel always feels
like a scramble, so I don't end up making time to make my house look guest-friendly. I guess
that's the best way to put it. But I'm matching with a co-host, so I can still make that extra
cash while also making it easy on myself. Find a co-host at Airbnb.com slash host.
And now for some more money rehab.
And now for some more money rehab.
Let's talk business. Now, you have worked at public and private companies. Which do you prefer? There is really no preference, honestly. For me, it just really depends on the mission of the company and what the overall vision is. I really spend a lot of time thinking
about the team and thinking about what are the goals and what the company's trying to accomplish.
It really doesn't matter how many zeros there are. I think it matters more whether the company has
the type of culture that I want to be a part of or that I want to help to set, whether there is an opportunity
for continued growth and how fast the company's growing. So there's a lot of other factors. I
haven't really spent time thinking about how different it is, whether it's public or private.
We just generally had CEOs on who find being a public company a pain in the ass or like really stressful to keep tracking stock?
There's no doubt that running a public company would be much more stressful, right? You have
to continually answer to the street. I sit on a board of a public company and that is a lot of
responsibility and certainly a lot less than what the CEO has to be thinking through every day and day and day out.
There's pros and cons on both sides, right? Working as part of the Inca or IKEA family,
there are some amazing, amazing benefits. And then it also means that we're not beholden to
the street in the same way. But that can also mean that the pressure maybe is not always what it needs to be. And
it is really fascinating to understand the trade-offs. I would argue that it's very easy
to always say the grass is always greener. I think that it just, it really depends on so many
factors. You have really leaned into this gig economy too. Leadership positions, you mentioned
Airbnb, and then you came back from Buenos Aires, went to Uber. What about the gig economy to leadership positions, you mentioned Airbnb, and then you
came back from Buenos Aires, went to Uber. What about the gig economy is so fascinating to you?
There's so many things. First thing though, and foremost is just the way that I grew up. And I
think I talked about this, or you mentioned it, that I was in South Dakota. I moved to United
States when I was 12. And we moved from Poland
into South Dakota. And it was really hard, just like it is for many immigrants to try to find
your footing and try to find a way to make an income and to make ends meet. And so my parents,
both of whom had to work really, really hard. And so they would have double shifts at factories.
Eventually they opened up a restaurant,
but their hours were so high and there was no flexibility.
So my parents couldn't come and see our performance
and they couldn't come and do the things
that I get to do for my children.
And so I think having some flexibility
and being able to fill in the hours, especially
some weeks or some months were particularly tough. And so trying to make ends meet, having that
flexibility to add a meaningful income, I think is really important. And so I can't help to think
that had these types of platforms existed 30, 40 years ago, when we moved here, it would
have really provided a lot of, a lot of help to families like our family. And this is why I have
such a soft spot on the supply side of the business. So at Airbnb, I worked with hosts at
Uber, I worked with couriers, and then a task driver, I obviously oversee the entire company,
but I certainly spend a lot of more of my time with taskers and really trying to understand what their needs are and really feeling quite good about the fact that we do provide a lot of opportunity to earn a meaningful income.
And so that is what drives me to work in these platforms.
I think that there is another component, though.
They're really hard
and there's the challenges are still really fun to solve. And these platforms have only been around
for 15 years or so. So the problems still seem new and people are getting better and better.
It's super analytical and it's really exciting to see and to keep learning about how to better
optimize a match between in our case, a client and a tasker.
And so that's really fun.
And I like that.
Yeah, I have a little bit of experience in both of those areas that you discussed.
I'm first generation American, too.
I actually worked in South Dakota at the CBS station, KELOLAND.
And I remember how far apart everything was.
I remember how far apart everything was. And so I'm sure in a place like South Dakota, Sioux Falls,
where I was, something like this would have really helped just the geography of something so spread apart. And so, yeah, having a soft spot for the worker side is totally understandable.
Have you seen, though, this sort of catch-22 of a ton of workers trying to come onto the platforms, but then with more
workers flooding the platforms, the price of the gigs has to go lower because of supply and demand.
Well, TaskRabbit is a little bit different, and this is what makes TaskRabbit very special as
well. Taskers get to set their own rate, right? And so that's a little bit different than Uber,
Right. And so that's a little bit different than Uber, where Uber helps to set the rate for the drivers or the couriers.
In this case, a tasker can come onto our platform and say, hey, this is what I'm really good at.
Let's say I'm really good at mounting a TV or I'm really good at assembling furniture. And so they can understand what types of hourly rates exist on the platform for those services and
price accordingly. And they always have a choice in when they work, where they work,
whether or not they accept the types of jobs that are coming through. And I think our average
hourly rate is much higher than what you get elsewhere. Often it's in the forties and in a $50 range and in the big
cities. And so I think I'm proud to work at a platform that really gives taskers the opportunity
to earn on their, on, on their basis and what they want to achieve. I'm a huge TaskRabbit person,
like huge look into my account or whatever. You'll'll see I have a TaskRabbit problem.
I might need an intervention. I've used it for so many things. It's wild. Anytime I need something,
I'm just like, can I just type this into search and will it come up with it? And sometimes very
weird stuff that I've needed from odd wallpaper to event help and stuff like that, I found on
TaskRabbit. So I'm a big fan.
What have you used TaskRabbit for? For everything. I have to say I'm becoming
lazier and lazier, but also I talk about communicating with my husband. Before I was
ever at TaskRabbit, I would use TaskRabbit as well. When we bought our first house ever,
my husband said, I'm going to be like the fixer upper guy. And I'm going to fix everything, at least in my case. And I hope this isn't the case for most people. He had big ideas.
And let's say that the execution was not quite as big, not as big, and then it would turn into
a nagging situation. And then that's never like good for a marriage. And after a while, I realized
that I could just do something else
altogether. My husband's attention to detail is pretty minimal. So let's say something was
slightly broken. It's not that he would notice. And then I would just, I would work from home
on Wednesdays. And so on Wednesdays, I would have a tasker come and fix it. He would never notice
that something was broken, nor therefore know that was fixed. And then like life just got better that
way. And now I mean, saving marriages, saving marriages, right? Like a new tagline. Yeah.
It's funny that you say this, because the whole marriage concept has been top of mind for us
lately, because we actually had someone email us and say, Hey, TaskRabbit, big fan, and so on. But
I had a tasker come to my house and like the one hour task turned into a
five hour conversation. And two years later, we're getting married. And we love TaskRabbit,
can you come and officiate our wedding? And so we did. And so we've been talking, we've been having
a lot of fun internally about how important it is that we at the end of the day, we still connect
people, right? It's a little
bit different connection than maybe what you think historically, but we do connect people in our
intimate spaces in our homes. And it was a very, very warm story. We've been having a lot of fun
and our general counsel flew out to Wisconsin, I believe, and, and spend a weekend with a couple.
And it was lovely. So cool. On the flip side, if you were to be a tasker, would you have
a gig? You learn so many things in Buenos Aires. Like I'm assuming tango lessons, like photography.
I don't know. We did salsa, not tango, even though of course it's much more known for tango, but
oh my gosh, lessons are what I would do. I like, it's very sad because I don't actually think that I have the level of skills that our taskers have.
Our taskers are so skilled.
I just bought an Ikea, a whole wardrobe.
It's called a pack system.
So it has three closets.
This is much more popular in Europe.
But I wanted to put this system in my daughter's bedroom.
And there's no way I could have done that.
But a tasker can come in and build the whole thing in record time. And so I sometimes think about what would I be doing? I can
lift and shift. I can help people pack. I can organize. I can definitely clean. So there are
some skills that I have that I would be willing to bet that 98% of our taskers on our platform would be able to do those tasks, let's say in a much more improved way.
Proficient. You figured out any harder things in life than putting together an IKEA closet system. I'm sure you could do it.
I definitely could do it.
But you know what? It would likely take me hours and hours and hours and lots of frustrations and potentially
having to go back and change things.
Yeah, not quite the experience that we want our clients to have, I would say.
I love TaskRabbit because it helps you buy back your most valuable asset, which is time.
And so that's why I'm a huge fan.
What are some of the weird gigs that you've seen people book on
TaskRabbit? I've heard one tasker delivering birthday fish, another one picking up someone's
belongings after a breakup, which I recently talked to a girlfriend about because she was
dealing with this problem. When I was at Bloomberg, we hired a TaskRabbit to stand in line
for the new iPhone and did a story about it. Yeah. So there, there is always those kind of fun and unique
tasks, but really 99% of our business is in our core categories, which is assembly and mounting
and moving and cleaning and so on. And, and really that's what we want to continue to elevate.
That doesn't mean that we don't have some fun tasks. Like the other day, I was talking to one of my girlfriends and she said she had a wedding in Napa and she drove to
Napa and realized she did not have her dress. And so a tasker came, went to her house, picked up her
dress and drove it up to Napa. So there's all sorts of unique ways to really hire people on a platform to help you out. But by and large, majority of our tasks
are really around helping people every day around their home,
which is your day-to-day things
that you have to do around the home.
For anyone thinking about becoming one,
what are some of the highest paying gigs?
So that really depends on which metro you're in, right? And then how much skill is needed. Someone who's doing TV mounting, it's actually quite a skill. I don't think I would be able to do it. But I tell you what, there are people who definitely just learn how to do it and learn to do it really, really, really well. And they just go from home to home, just mounting TVs.
from home to home just mounting TVs. And it's a really great opportunity because there is,
you'd think that there aren't that many people who want to mount TVs, but it turns out that it's not just TVs. Then you have to understand how to mount photos and posters and curtains and so on. And
some people are really good at that. And so I would say that's one of our highest paying
categories, but I think it
really matters which city and which Metro, what time of the year, is it a Friday evening? Is it
a Tuesday morning? So there's all sorts of components that go into how taskers price their
jobs. AI is a big topic of discussion. The explosion in the last year has a lot of people
worried about job security. At TaskRabbit, it seems like taskers are AI proof, like you physically have to go and mount the TV.
How much do you think? I still believe that, that you still physically will have to go and move your
boxes out of your house into a truck, into a new house, that you will have to come mow your lawn.
And we don't see that changing in this space that much.
Of course, over time, people talk about robots and all sorts of things, but that still seems
quite far away. And we don't hear concerns from taskers at all.
I know some companies in the gig economy are struggling with too many workers on the platform,
as we mentioned, that sometimes, you know, on other platforms that don't have this dynamic pricing, too many workers
means they might not get paid. So you see other companies like DoorDash putting applicants on the
waitlist. Do you have to deal with that at TaskRabbit or is everybody welcome to post?
So everyone is welcome to sign up, but it may be more challenging in some cities with
some categories, right? Because there may be already an established set of taskers. All that
said though, we keep, we continue to grow. So our job as TaskRabbit is to continue to think about
the health of the platform. And that means growing both sides of the marketplace at similar pace. Because what you don't want is to have too many people who want
a cleaner on a Friday night before a Saturday brunch. And we just don't have that many because
all our cleaners end up five. So there's always opportunities to continue getting new tasks
at a different price in a different geography. Our job is to make sure
that we continually provide opportunities to our taskers and also that our clients feel like
they are able to get their jobs fulfilled when they need them at the price that they need them
in the location that they are. So there's a lot of variability and a lot of opportunity as a result
of that. And you know, we end our episodes
by asking our guests for a tip that listeners can take straight to the bank. Do you have one for us?
It can be anything tips on saving money, taking a gap year, investing, using business tools. I don't
know if you and your husband do like at home for home stuff, Asana, we've seen other couples,
power couples do stuff like that, but anything.
Yeah. So I think we're crazy. We're not yet at Asana stage, but I totally get that. And I totally support that. I think a lot about just tips or thinking about your career growth. Cause
a lot of times people ask me, what can I do to grow my career? Or how do I get ahead? Or how do I get promoted?
And my number one answer to that is always do a really good job at your current job.
And that sounds so simple, but it really, when you take a step back, what does that mean?
That means doing things on time. It means thinking ahead about what your manager may need and being
proactive about suggesting that. That means not only coming what your manager may need and being proactive about
suggesting that. That means not only coming up with the problems, and there is always infinite
number, but thinking about owning solutions. Overall, thinking about ownership. It means
teamwork. It means that people love to work with you. It means having empathy. It means so many
things. Do a really, really good job. Think about what your strengths are, lean into those,
and the rest will happen. And I think people get so excited about, I'm doing my job. I've been here
for two years. I need to get promoted. People are constantly looking for talent to grow their
organizations. And so if you are doing a really good job that comes through.
Yeah. I always say, would you promote yourself? Be really honest.
Great question. If you weren't the CEO of TaskRabbit, what would you be doing?
Oh my gosh. So my husband and I have been talking about this. I usually talk about the fact that I'd love to be a journalist because I think it's really fun to ask questions.
Let's do a job swap for a day.
We should do that. And sometimes my husband's like, oh my God, can you please stop asking
questions? Because I start like, it feels a little bit like I'm interrogating, but I'm honestly just
very curious about people's stories and their lives and what motivates them. So I think that's
really fun. But on a more fun side, I've started dreaming lately about opening up an ice cream store,
an ice cream shop, like gelato, but really nice and fun, like an anchor in a neighborhood.
It's like a fun dream to have when I'm going to bed if I can't fall asleep.
Yes, I love that.
I love ice cream dreams.
I'm very bullish.
Money Rehab is a production of Money News Network. I'm very bullish. rehab at moneynewsnetwork.com to potentially have your questions answered on the show or even have a one-on-one intervention with me. And follow us on Instagram at moneynews and TikTok at
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Thank you for listening and for investing in yourself,
which is the most important investment you can make.