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April 27, 2020 66 mins

The 2008 recession was a devastating time for many Americans. But amidst the chaos, it was also the breeding ground for a new creative class: Developers who coded their visions into reality. Uber and Lyft redefined transportation, Airbnb shook up the travel industry, and TaskRabbit helped pave the way for the gig economy. In many ways, the uncertainty we face today mirrors that crisis. TaskRabbit’s founder Leah Solivan joins the show to explain why she believes founding her company in harsh conditions was key to her success, and why the pandemic provides a similar opportunity for innovation.


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Speaker 1 (00:00):
First contact with Lori Siegel is a production of Dot
Dot Dot Media and I Heart Radio. There was this
certain heart back in in two thousand and eight, two
thousand nine, and there were things that got solved that
I think we're really interesting and really changed things. I
don't know if this is just me being nostalgic for

it or if this is real, but I can sense
that same moment happening now because there's a lot more
constraint just in the last couple of months. It's forced
by constraints, right, It's like we were so constrained by
not having outside capital, by not having a team around us,
Like we just had to figure out how to do
everything ourselves. And I think that forces actually some different solutions.

I think we'll see more of that, you know, now
and into the next decade. When I started covering tech
in two thousand and nine, we were coming out of
the recession and there was this new creative class emerging.
Uber and Lift redefined transportation, Airbnb shook up the travel industry,

and task Grabbit helped pave the way for the gig economy.
But everything feels uncertain again. I'll say this. A decade later,
I sensed that same creative spirit in Silicon Valley. It's
this feeling of opportunity that emerges from chaos. I believe
that once again, there will be companies that grow out

of this moment, this moment that's filled with extraordinary pain
and uncertainty. My next guest is someone who knows a
lot about this. Leah Sullivan. She's the founder of task Grabbit,
a company born out of the two thousand and eight recession.
I'm excited to have her on because this isn't an
after school special, so I don't want to sugarcoat it.

What she did was extremely difficult. Building a company that
changes the world is hard, so it is battling your brain.
So it was taking risk. Add all of this to
the backdrop of a global pandemic, and now we're talking.
It's been over a decade since she launched task Rabbit,

and now Leah helps run an early investment fund called
Fuel Capital, and she's not afraid to talk about mental health,
about stress and anxiety, you name it, all while building
a startup. It stems from her own experience doing something
big and not shying away from the chaos and uncertainty.
But before we get to the interview. I just want

to tell you, guys how much I've appreciated your feedback
and your ears during this time. We're nearing the close
of our first season, so I'm a little sentimental and
I'll say this, please stay in touch with me. We're
launching a newsletter this summer and it'll be your best
source to stay in the loop about any extra episodes
virtual town Halls were hosting, and other future projects that

I'm going to be working on. So sign up at
dot dot media dot com backslash newsletter. I promise I
won't spam you. Okay, let's jump in. I'm Laurie Siegel
and this is first contact. I want to kind of
start at the beginning and just give you the simple

what I ask everyone as we start this, which is,
how are you doing? It's such a funny question these days,
isn't it. Um. Usually i'd respond, great, everything's great, Everything's fine,
And I feel like I'm hanging in there. It's just
a lot right now, and UM, I think also having
the perspective about, you know, what's going on in the news,

what's going on in the front lines, what's going on
in hospitals. I mean, certainly gives you perspective on how
grateful I am and fortunate and privileged I feel to
be where I am. I'm at home, I'm safe, I'm
with my children. Everybody is healthy. But you know, between
the home schooling and working full time, and you know,

not having the support system that I used to, it is.
It has been a complete shift, in a complete transition.
So I just feel like I'm hanging in there. We
start out each of these episodes with this idea of
first contact, and this one is near and dear to
me because I was thinking about our first contact and
and tech years. It was a long long time ago.

It was do you remember it? I do. Actually, you
interviewed me on CNN. I was terrified, UM, And I
mean it must have been a decade ago at least.
I went back in preparation for this. I went back
and I found the interview. Um. It was from two
thousand eleven, and it was two and eight when you

started talking of it. Um. And then in two thousand
eleven I interviewed you, and I remember this idea of
the gig economy and all they didn't you know, you
guys made this popular, like this didn't really exist and
so I was on the startup Beat and up create
the startup Beat a CNN and I remember we were
following a task grab It around named Susie, and we're

interviewing you about it and talking about this thing called
the gig economy and this idea of having other people
help out with your errands. And that's when I met
you for the first time. Yes, I remember. I remember
standing outside around the fountain, I think, and you were
interviewing me outside and New York was bustling and it
was a beautiful day. And yeah, that was the first,

the first interview we did together. It's almost um. I
look back at that and it almost feels um. I
don't know what the word is, but it's so nostalgic
to look back at that moment and tech because and
we'll get into this, you found a task grab It
out of a pretty chaotic moment in two thousand and eight,
but there were so many interesting tech companies that did

come out of that moment. But this idea of um,
New York bustling and and you know, people being able
to come into our homes and do things and help
us out, and almost this idea that you had that
gave birth to this whole industry of the gig economy.
It was so special and and now fast forward all

these years later, over a decade later, and we're sitting here,
I'm interviewing you self, isolated in my home, with this
idea of when will we allow people in our homes again?
And what's going to happen. It's just it almost feels
very nostalgic sitting here talking to you, especially given that
I had the opportunity to interview you at the beginning
of that. It does. I mean, it was a different time.

I mean three months ago was a different time. I
think the thing that gets me excited and gives me
comfort about the future is, as you said, when you
think about all of these companies that were innovated out
of that chaos and out of that crazy time. There
were so many I mean it was Lift, it was Uber,
it was Airbnb, it was task grab it there were

just tons of great innovations that happened in the gig
economy and the peer to peer marketplaces. And so I
think now is a time for another step change for consumers,
and we're going to see a lot of behaviors change
and a lot of new innovations come out of you know,
this time and throughout the next decade that we'll be

talking about, you know, in the year. I want to
go back to two and eight. You were at IBM, um,
and you decide right before the recession to quit your job.
Your a rising star at IBM, and I know for
a fact, having covered Silicon Valley for many years that
it is not easy to be the woman in the

room and in many of these places. But you made
the decision to to kind of quit your job. And
I think, and I will say this, I think, especially
in media, sometimes we have the luxury of perspective to
look back and say, and then she quit her job,
and then she created test grab it, and then it's
sold for all this, you know, I think that is
way too simple of a story. So just take me

back to Leah, before the before we entered this recession,
before all this happened at IBM, and thinking, you know,
something is broken and I want to fix it. And
what what were you like back then? Yeah, I mean,
it's a great question. I think I always tell the
story as this moment of inspiration and it was like poof,
I waved a magic wand right and I was off

starting my company. But I think the relevant parts now
um are so much more detailed, and there's so much
more rooted in the economic time and the market that
was emerging. And so it was February of two thousand
and eight when I was working at IBM. I did
have the idea because I was out of dog food
one night and I thought, there's got to be a

way to get this dog food. The iPhone had just
come out, you know, a few months earlier, and so
all of a sudden, we all had these little mobile
devices in our pockets that we weren't really fully utilizing
the technology on yet. And as an engineer myself, I
got really excited about those emerging technologies, particularly mobile location
based awareness and then social technology. Mean Facebook was really

just breaking out of the college scene at that point
and becoming more mainstream. So I spent the next few
months thinking about the idea, talking to anyone who would
listen to me about it. I had gotten connected with
Scott Griffith, who was the CEO of zip Car at
the time in Boston, and he really took me under
his wing. And I was still at IBM then, but
he said, you know, I really think you're onto something.

The way I think about zip car and getting people
to share resources in a neighborhood is very similar to
how you're thinking about At the time, the company was
called run my errand dot com. It wasn't even called
tats grabb it yet, and he really encouraged me to
make the leap. Now, I had no idea that this
recession was coming. I had no idea that the stock
market was going to crash or that all of these

people would be laid off. I ended up leaving my
job in June of two thousand and eight. Do you
remember the day you left your job. I do. It
was June. I remember going in and giving notice to
my manager and and you know, as sort of that
frantic they tried to keep me, and they're like, no, no,
you gotta meet with my manager. And then that managers

like no, no, you gotta meet with my manager. And
I was like, you know, three or four managers up
the chain by the end of the day, right. But
I had made the decision that I wanted to do
something more. I love engineering, I love programming, I love creating,
but I had all these other skills that I wasn't
using at IBM, and I just was really passionate about

the idea and that's sort of what gave me the
confidence to to walk in that day, quit my job
and make the leap. Well, I guess I I go
back to this idea of like are you afraid? I
mean it's like you look back at all you were
able to do, and of course you're able to do it, right,
you have the luxury of perspective right now, But in

that moment, where did that confidence come from? And and
maybe this is kind of one of those like how
do you how do you talk to yourself when you
know you can do all these things? But when you're
actually you going in to do it, it's much more complicated,
you know, and it does take a certain and maybe
what I'm getting at is it takes a certain kind
of person to follow through with that feeling that they

can actually go do it and then and then go
do it? So how did you prepare yourself mentally for it?
I mean? And now having the luxury perspective, you know,
what do you wish you could go back and tell
that girl? Well, I mean it's funny because I I
was hesitant, I was afraid, but I also sort of
had hit my max of what I felt like I

could do it IBM as far as what would make
me happy, There's plenty more I could do there, but
I knew it wasn't gonna make me happy. And so
I remember having this conversation with myself, and it sounds
kind of funny, but I remember this clearly, and I
was saying, you know, how are you going to launch
a company? How are you going to build a product?
Like all you've done is program You've sat in a

cube by yourself and you've programmed software. You've never interacted
with customers, you've never raised money from investors, you've never
high or you've never fired, Like, you don't know how
to do operations. But I think I realized that. And
this sounds kind of silly, but I told myself, you know,
at Leah, it is not rocket science. You're going to
figure it out. And I literally made the decision that

I was going to stop worrying about all the things
I didn't know how to do, and I was just
gonna go figure it out. And I am a constant learner.
I like to learn all the time, and so that
part of it. I decided to look at is very
exciting instead of very terrifying. But it was like this
active mental shift I had to make before I could

get comfortable making the lad to do it. You actually
launched task grabbit, and I think this is it's so
important to talk about, Like so much was happening in
two thousand and eight. You know, there was so much
chaos everyone was talking about, you know, Wall Street was
under fire, and I think this, this moment for me,
is really fascinating for technology because you you know, you

hold up your iPhone and you talk about the iPhone
out come out, the app store had launched. There was
just this canvas for creativity for the smart people who
were paying attention, and out of that came task grabb It.
So tell me about actually launching task grabbit in this environment.
What did you learn? Well, you know, I spent sort
of those June summer months coding the first version of

the site, and I was talking to potential customers, and
I mean I was literally sitting at the local coffee
shop actually coding, and then as customers would come in
and be like, hey, what do you think of this?
Would you use a service like this? What would you
need outsource? And how much would you be willing to pay?
And so I wasn't actually even sure if the market
was there yet. And then September two thousand and eight

rolled around and the stock market crashed and everyone was
being laid off and the world changed overnight, and very
much like the world has dramatically shifted overnight in the
last couple of months. And that was a hard time
because is I was thinking, Oh my god, what did
you just do? You left this cushy job at IBM,

and you've decided to focus on this company that you
don't even know how to build, Like, how are you
going to do this now? Because the company was focused
on putting people to work. It actually, very serendipitously turned
out to be the perfect time to build a company
like task Grab It. And I wish I could say

I had seen that coming and I had the foresight
from you know, February in June like to know that
that's what was going to happen. But I didn't. I
honestly didn't. And part of it was was luck in
some ways that the timing hit for this need and
what I was building was filling a gap, and sometimes

those things just cannot be predicted. When I look at
having covered entrepreneurs and the ones who succeed throughout the years,
I think there's some qualities that a lot of them
have right that I could just see, And I think
the first is probably resilience. Another one is being scrappy.
So I'd be curious to know how back in in
the day that played out. How were you very scrappy

and building out task grab it? Yes, a lot of scrappiness,
and uh, that's just kind of in my d NA anyway,
That's kind of how I'm built. So that was a
good thing because when the recession hit in September, yes,
I had to question everything, But what I didn't have
to question was whether or not I could figure it out,

whether or not I could actually pull it off, whether
or not I could do it. I mean, it was
just a matter of like finding new ways and coming
up with new things and and creative outlets to explore.
And so you know, when I left IBM in June,
I thought I probably had about six months of runway
where I cashed out twenty eight thousand dollars from my

IBM pension and I thought, okay, twenty eight thousand dollars
I can make that last six months, I can you know,
invest a little in the company and I can live
off of this. And when, of course September hit, it
was an awful time to be raising money. There was
no way I was going to be able to raise
any money before the end of the year, and so

bootstrapping became sort of a necessity, and and the mode
that I stayed in for the next eighteen months. It
really wasn't until the following year, near the end of
two thousand nine, that I was able to raise a
seed round of funding from investors out here in the
Bay Area and Maraco at Floodgate Fund led a million

dollar round of seed funding. But prior to that, it
was maxing out credit cards. It was bootstrapping, It was
just running super super lean. It was just me. I
couldn't hire anyone. So I was the first task grab
it ever, and I did a ton of You were
the first task grab it. Oh yeah, I did a
ton of errands, Oliver. So we tell me that you

were actually going If I went on the earliest generation
of task Gravit, it would have been you, the founder
of task Grabbit, doing my errands all the time. Yet
what was awesome about that. So I had this little
Honda Metropolitan scooter that I would just ride around the
city and I'd pick up people's dry cleaning, and I
deliver groceries. I do all kinds of things. What was

great about that time, as I look back, is that
it really really taught me what the customer needs were,
not just from the standpoint of clients who needed tasks done,
but what the actual taskers needed to be successful. And
so I became sort of obsessed with the supply side

platform and the supply side marketplace and really focused in
on what are the tools I need to build to
make sure that they can be successful and build out
their own businesses like entrepreneurs on this platform. That is
an insight I wouldn't have gotten unless I had been
actually a task grab at doing the jobs myself as well.
So I think in times of scrappiness, in times where

you're really forced to bootstrap and be lean, I think
it can actually be very beneficial because you get really
really close to the customer, and I think you think
and you build differently. God, I remember when even like
Dennis the founder of four Square, I remember back in
the day going to south By Southwest and like two
thousand and eleven and calling up forced from trying to
call their PR person, like who's going to be the

big company? Just Dennis answers the phone because he's the
PR people. I don't think people understand, especially as people
get bigger and as we we glorify companies as as
they become companies and put in the press like how
involved the best founders are in a very scrappy way,
to the point where you are probably going and getting
the groceries on your scooter to try to understand the product.

I don't know if people fully understand that that is
how some of the best businesses are built. I think
that some of that is forced as well. It's forced
by constraints, right. It's like Dennis started around the same
time that I did. He was two thousand seven, two
thousand eight as well, And we've talked about this. For
Dennis and I, it's like we were so constrained by

not having outside capital, by not having a team around us,
like we just had to figure out how to do
everything ourselves. And I think that forces actually some different solutions,
some different products solutions. I think we'll see more of that,
you know now and into the next decade. I think
as the market improved and more capital, you know, came

into the market, people founders didn't need to be the
ones on the ground anymore. They could hire out for that, right,
and they could learn from second hand from those people.
But things get lost in translation. So I think it's
actually kind of interesting to be super scrappy and super
bootstrapped in the beginning and really understand the market. There's

something really interesting about this moment. Having covered your story
back in the day, Dennis's story, and having gotten my
early start in my career watching entrepreneurs make something out
of the recession and make something out of this moment
of constraint. I think part of why I'm excited to
be here with you is is because I sense that
this is another moment of constraint, and I think Silicon

Valley and you, you're an investor now, will get to that,
like got very noisy, right, and a lot of people outsourced, outsourced, outsourced,
and there was this certain heart back in in two
thousand and eight, two thousand nine which made way for
companies like Airbnb and Uber and you know, we're there
are things that got solved that I think We're really
interesting and really changed things. And I think, I don't

know if this is just me being nostalgic for it,
or if this is real, but I can sense that
same moment happening now because there's a lot more constraint
just in the last couple of months, you know, I
I hear Silicon Valley chatter again. I'm beginning to see
the same entrepreneurs who have been kind of distant for
a while beginning to kind of come back and solve
some real problems. And I'm assuming you as an investor,

i'd be curious to know, like what are you sensing,
Like what's the feel you invest in early stage companies?
What is the feel now sitting in Silicon Valley as
at another moment of constraint. Yeah, I mean I think
I think it is real. This is a real moment
of inflection, I think for technology companies for consumers. So

as an investor, I'm incredibly excited. I'm really excited. I
can't wait to see what is born out of this moment.
And I just hope I'm I'm part of it. I
hope I'm the one funding it, right, Like that's the job,
it is the dream job. This actually, as an investor,
could be seen as a dream moment. And so I
think the opportunity is there to really drive innovation, to

find founders that are resilient, that are scrappy, that are innovating,
you know, in a different way, on a new level,
and to really support them and and be a part
of it. Okay, we've got to take a quick break
to hear from our sponsors more with my guest after
the break. You know, we saw what kind of came

out of two thousand and eight two nine, Like we
saw Airbnb, Uber, lift, task grabb it. You know, we
saw the sharing economy. This is very near and dear
to me because this is where I got my start
covering technology. What kind of industries do you think are now?
We're kind of seeing our like right for some disruption
right now. Well, back in two thousand and eight was

really driven by technology around location, around mobile, around social
right and like, so people were thinking about different ways
to mash up those technologies Airbnb, Uber, Lift, task grabbit.
Now there's this whole step function change and how we're working,
we're all working remotely from home. Work will never be

the same again. It's been now almost two months of
sheltering in place of working from home. I mean, there's
no better way to shift consumer behavior than to actually
put constraints around it. And I think at first people
were like, oh, this is gonna be so hard, I'm
working from home, and then you know, Zoom just completely

took off and blew up. It's like Zoom is the
next Facebook. Now Zoom is the next platform. Like what
does that mean for for remote work? Um and for collaboration?
And then I think, you know, people are going to
figure out new ways of balancing working from home working
in person. Do I think that, well, you know, as

soon as this sheltering places over, do you think we'll
all go back to the normal in office, face to
face nine to five. I don't think so. I don't think,
you know, unless you really have to be there in person.
People now have been sort of trained to utilize these
remote tools, and they're okay. I mean, I think at
best they're kind of mediocre because is they haven't been

stress tests the way that we have stress tests them
over the last two months, and so it's in times
of stress, right that entrepreneurs and innovators are going to say, like, okay,
this work to a certain extent, but like, here's the
next level of it, here's the next iteration, here's the
next phase. So remote work is definitely an area I'm
really excited about. You know, in two thousand and eight,

it was all about how the future of work was
changing and how jobs were becoming more flexible and the
gig economy was emerging. And now it's like, Okay, we've
seen what the future of work is, like, how does
that now evolve into the next phase, into the next decade.
I think another area that's super exciting is around digital health,

I mean telemedicine. Just the necessity of it has just
blown up. But again, like the tools have have not
been stress tests the way that they have in the
last two months, and so there'll be new innovations and
digital health and wellness and telemedicine. And in the third
area I'm really excited about and watching closely is just education,

I mean online learning. It's like, again with all the
schools closed, my kindergartener is on Zoom and she's on Duo,
and she's you know, she can barely spell, but she's
like on I Message texting with her teacher and her friends,
and it's like a whole new world of learning, and
there haven't really been um great tools or platforms that

have emerged as the leaders in that space, particularly for
elementary education. And so I think that's a huge opportunity
that will see innovations around as well. Yeah, I mean,
it certainly feels like all of a sudden overnight, the
only means towards humans connection we have is through this screen, right,
I'm zooming with you right now in order to do
this interview. But it seems like a lot is lost

in context. If we wanted to have a moment to
kind of go off on our own or come back,
or there's there's it's like you've got to be all
in or you're all out of it. There's something that
that feels a little bit it like it does mirror
the human experience. And this is me putting on my
tech and humanity hat um And I think you're right.
I I can sense that there's got to be something else, right,

like zoom is okay, but all of us are getting exhausted.
I think by this one way experience that leaves no
room to have kind of the serendipity of the human
experience and the lightness that comes along with just being
around a room and having that casual element. So I'd
be curious to let me know you end up investing
in Do It Quick please, leiah um be very interesting.

I want to go back to to the early task
Grabbit days. Sorry to take you on that tangent. I
just think it's so fascinating and you're such an interesting
person for for me to pick your brain on this,
because you were at the beginning of this um and
I think you very much represent you know, innovation out
of constraint, and so I go back. I didn't realize
that you were the initial the o G Task Grabbit,

which I think is it's just fascinating. But then I
saw that you actually went on Craigslist to try to
find task grab people. This is before you guys have
extensive background checks and all this kind of stuff. And
that was even when I interviewed you in two thousand
and eleven, I remember asking you about that. But back
before that, you went on Craigslist for your earliest task

grab people of task grab It, and the way you
decided if you would hire people was if they were
people that you would trust to go into your grandmother's home.
Was that it. Can you just take us to that.
What was the thinking behind the next iteration of we
go beyond Leah as task grab at number one and
into Craigslist phase two? Right? Yeah, Well, I realized that

I couldn't actually do it all if this company was
going to scanal and be successful, And so I put
the ad on Craigslist, and I wanted to see just
who would respond. I mean, I was actually very curious,
you know what types of people would respond to the ad.
I met thirty task grabbits in person over a coffee

at the local coffee shop where I was spending my
days coding away, and I met with him for about
thirty minutes at a time, and I just sort of assessed, like,
is this someone I would feel comfortable sending over to
my grandmother's house. Um, I didn't have kids at the time,
or else I would have, you know, a fact about
putting them in my house. But the point was is like,

can I trust this person with my loved ones, with
someone that I care for and really love and that
you know is vulnerable, you know is going to be
maybe a little more vulnerable than the rest. And so
those early days I had to sort of make that
gut check and say like, Okay, yes, I definitely trust
this person to you know, drop groceries over at my

grandmother's house. I knew though, that I needed to build
in some background checking and some automation and the application
process and and some protections. I mean, remember this is
a time where jumping into a stranger's car was unheard of,
like you would not do it. That The thing is, like,
I don't think people realize that. I just want to

like set everyone back, like like I because maybe it's
because I remember going on camera and doing kind of
a bit of a cheesy stand up and being like,
imagine going into a stranger's home. Can you imagine going
into a stranger's carvea and app or like would you
ever hire a stranger to do a chore for you?

Because I remember those were my lead in's um because
at the time it was just unimaginable, and then everything
changed so quickly, and I think people forget that you
could have been looked at it's a little insane, and
I think that's important for people to understand. I'm sure
when you started out, people kind of said no or

kind of looked at you a little bit like this
girl is just kind of crazy. She's you know, just
too ambitious whatever. I think that's really important for people
to understand that all of this seemed insane until you
came along, and until it wasn't until it wasn't, and
that that's kind of the point. Like I actually think
that because of the economic crisis that we went into

in two thousand and eight, and because of the stress
put on the market and the stress put on the
labor market, I mean, that really helped shift consumer behavior
into making that step function change, into being okay with
you know, inviting a stranger into your home to do
a chore or eventually jumping into a stranger's car, which

didn't come that much later, you know, it was two
thousand and ten, two thousand and eleven and Lift and
Uber took off. So it is in times like these
that the consumer is actually open to change. And it's
really hard to force that change when everything is sort
of normal and going well, and that's the hardest time
to make a change. But behavioral changes come when there's

stress on the system. Do you remember out of curiosity,
just like go back with me in time, Do you
remember that the biggest know you got are the most
like the most frustrating. No, or because you went to
I'm sure a lot of investors, or you you left
a job that was cushy, like you know, did do
you remember any specific interaction that sticks with you of

someone who just did not believe in you or this idea? Absolutely?
Like I just more than one, honestly, Um. I mean
I talked to every investor I could get introduced to
in the Boston area between I don't know, September of
two thousand and eight and maybe the summer of two
thousand nine. I mean, it's a long time where I

would just meet with investors, angel investors, vcs. Now at
that time, it was also not a time where there
are a ton of seed investors set up quite yet,
particularly on the East Coast, particularly in the Boston area,
so Founder Collective hadn't even started yet. I actually met
those guys, you know, right when they were raising their
first fund. So it's a different time for venture as well.

But you know, I remember talking to um, you know,
potential advisors that I wanted to bring on, or potential
angel investors and telling them about the idea, and they
were so skeptical, so skeptical what did they say. Well,
one thing in two thousand and eight that wasn't quite apparent,

at least on the East Coast honestly at the time,
was that social networking was going to be a thing.
I remember Facebook was started in Boston and Mark went
to the West Coast to get funding, you know, Boston.
In that the East Coast area didn't feel like they
had missed or lost that yet, right, because it wasn't

big enough yet to be a miss or a loss,
and so everyone was still very skeptical that, oh, this
other entrepreneur Mark, you know, he's out on the West
Coast now and he raised all this money and like,
but we don't really believe in it still. So there's
a little bit of that. I literally had um a
pitch deck that I would show investors for East Coast
investors and then a different pitch deck for West Coast investors,

because the conversations were so different, specifically around social and
whether that was going to be a long standing trend
or if it was just a fat Wow. That's interesting.
I saw something you wrote that I thought was was
great when you talk about having a founding story and
you gave a commencement speech and I think you spoke

about this. You talk about having a founding story has
three parts, a personal backdrop and moment of inspiration, and
an innovated path forward. And I think we talked a
little bit about your personal backdrop of you know, the
problem that led you to do task grab it. And
oftentimes we oversimplify these stories, but I do think it's
really important to have these, you know, because they are
rooted in something and and even as founders, like there's

a reason why you become obsessed with something and why
you drive towards something, and you had your moment of
inspiration and then there's something else you wrote. You said,
a big lesson you have is to have big, harry
audacious goals, but take baby steps. And you even went
on to compare it, which I absolutely loved to where
the wild Things are. Um, what was your big audacious

goal and then what were the baby steps that you
had to take to achieve them? Well, it became a
parent in September of two thousand and eight that the
world was changing. And then I had started this company
as an Errand's business, but that what I was building
actually fit into the market in a much bigger way

and so the vision very early on became we're going
to change the future of work. We're going to change
the labor markets, we're going to change the way people work,
and we're going to make them successful working in a
new and flexible way. That was the big, hairy, audacious goal.
And it's funny because you know, investors, customers would look

at task, grab it and then be like, oh, that's
a service where I can you know, get my dry
cleaning picked up or get my groceries to word. And yes,
that was the easiest way to explain it to someone
who needed to understand it quickly. But my vision was way, way,
way bigger than that, and it was very ambitious, right,
And so if you shared that very ambitious vision with

an investor in the beginning, chances are you would be
laughed out of the room. And that's the type of big, hairy,
audacious goal I think is the most interesting. Come up
with something where you will be laughed out of the
room because it's so big and so ambitious and everyone's
just kind of like, I don't even understand where you're

going with this. And so that was the goal at
the time. I think what I realized is I had
to break it down into these little pieces. I had
to tell customers and investors that, yes, you can get
your groceries delivered, Yes you can find someone to help
you pick up your dry cleaning, because you know, feeding
them that whole big vision was too much at once,

and I had to take baby steps to get there,
um and tie all the dots together. It was like,
you know, putting all these points on the board along
the way that would lead us to the overarching goal,
which in the end, as I look back, you know,
a decade later, I can say like, yeah, we did
a lot to change the way the labor market worked

over the last decade, and yes this is a new
phase of work, and yes the gig economy stayed and
it's here and it's you know, continues to evolve today.
But that wasn't apparent in two thousand and eight, two
thousand nine, and two thousand and ten. And so it
was about kind of having that overarching vision, but making
sure that what you were doing on a daily basis

actually was going to push the business forward and closer
to that vision in some way. When you look back
and you talk about having these big goals and you
can have the luxury perspective, and you kind of look
at what you were able to do. You know, no,
when I know who's ever been able to do anything big,
hasn't had big failure or hasn't had to just just

get it knocked out of them. Because if you're the
kind of person who has the ability to have these big, lofty,
as you call them, like Harry goals right like from
where the wild Things are, then I think that probably
comes with the ability to fail pretty spectacularly. So was
there a moment that you could go to in this
journey of task Grabbit that you just felt like that

this was just like a very very dark dark space
for you, that that you felt like a failure in
some capacity. I mean, I honestly had a lot of
those moments. There were three major ones. I like, just
hit me when I'm hearing you asked the question, and
I think you know the one that I'll tell you about. Well,
I'll tell you the three quickly and then I'll dive

into one. I mean it was when I had to
lay off of the team huge failure um near the
end of the company, when we were getting acquired. I
was three million dollars short of profitability. That three million
dollar raise literally almost killed me, put me in the hospital,
you know. And then it was like early on, just
like the product was not performing and we had to

make this huge product shift into a more mobile centric
product in a way from the web. So it's like
fundraising failures, it's people failures, it's product failures that were
really really difficult. And I think every day was sort
of this roller coaster ride of ups and downs. And
there were some really exciting things like being on CNN

with you, or you know, we were on Good Morning
America one morning and we had so much traffic that
the servers went down, or you know, really exciting things
happened to our big fundraises that we did and announced
um And I think what I realized as a founder
is that the highs versus the lows were so dramatic

that I couldn't let myself ride that roller coaster fully.
I couldn't let my feel great about the highest highs
when I knew that around the corner there was going
to be a failure or the lowest low, because it
was just it was too jolting. It was like just
too emotionally draining, and so I kind of learned how

to stay level throughout the whole thing. But yeah, you
hear a lot of founders talk about that roller coaster
where the highs are high and the lows are low.
How do you find that middle ground? Like what did
you what did you do specifically that that helped you
balance a little bit of of the extremes. You know,
in the beginning, it was hard because I just didn't

have the experience, and so I'd get really really excited
or really really depressed. And I think after you go
through that a few times, you're just your body just
physically and emotionally can't handle it. And then I think
the next time you hit a high, you're kind of like,
all right, but like remember last week when you have
that big low, And I think over time you just
kind of learned to manage it. I think keeping things

in perspective experience helps with that over time, keeping your
team sort of on that same wavelength, because you don't
want them riding the highs and lows um when you
know you're the one staying level. It's like, you know,
sharing that experienced in perspective with the team, and yes,
you want the team to celebrate when great things happen,
but you also want to keep it in perspective and

kind of keep a reality check on things, particularly when
you're building a company out of recession and sort of
you've had that like scrappy DNA where it was really
really hard to raise capital, Like everything was really hard
in the beginning. And I think because we started at
a time where everything was super super difficult, it kind
of gave us the perspective that, like, even when things

were going great, the reality is is that it may
not always go great, right, and so it's kind of
like just learning how to stay somewhere in the middle. Okay,
we've got to take a quick break to hear from
our sponsors more with my guest. After the break, I

want to go back to you talking about having to
lay off folks. UM, this isn't something you prepare for
as like a first time founder. Can you tell us
the day that you realized you had to lay off folks,
the hardest part of it, and what you would go
back and kind of tell yourself now about it. Yeah,
I mean that that was the lowest low of the

entire company out of everything I experienced, UM was was
doing that layoff? What was the hardest part of it, Um,
it's just familing those people. I just it felt like
a true failure of my team. And you know, the
reasons behind it were, Okay, the product wasn't performing, we

need to reorganize the team and hire more engineers, and
we needed to cut from marketing and operations and business development.
But it's like, whose fault was it that we over
hired in some areas and we under hired in others?
It was mine, right, And so it was it was
awful to have to really admit to myself that I

had failed in managing the way that the company was scaling.
And so you know, going in, you know, that morning
and talking to the team that I couldn't keep there anymore,
it was it was my worst nightmare come true. And
as bad as it was for me, I knew it
was a hundred times worse for them, which is like,

you know, it's so so hard for everyone. I think
anything that had to do with people or failing the
team or managing the team, it was hard for me. Um.
You know, I felt a lot of empathy with people
that I had brought on board who really believed in
the company and the mission and believed in me, and
then I felt like I was failing them personally. Um.

And so that was hard, but you know, with perspective
and with looking back, I realized that it is what
saved the business. It's really what made the business thrive
in that next phase and afterwards, and as hard as
it was, it had to be done if I wanted
the company to be successful. And so, you know, I

talked to entrepreneurs today that are looking at their runways
and their cash flows and they're looking at the market
and they're having to make these tough decisions and it's
like PTSD all over again. But I tell them, listen,
you're gonna do this, and it's gonna be hard, but
you're gonna look back three years from now when the
market improves, and you're going to realize this is the

decision you made to save your company. Um. And so
it's it's not easy and it's very emotional. Do you
remember what you said that morning? Yeah? I mean it
wasn't a huge surprise in that one of the things
we really valued at Task Grab it was transparency. And
so people had seen the projections. People saw that our revenue,

you know, was not tracking to where our monthly cash
burn was and I remember saying three months before the layoffs, like, guys, listen,
we've got to like we've got to increase revenue. We've
got to increase demand, like otherwise our cash burn it
doesn't match up. It's not gonna be sustainable. And guess
what in most companies, like eight percent of cash burn

is headcount is people, right, so if you have to
decrease burn, it's like you've got to decrease people. And
so that was ninety days out. Then it was like
sixty days out. Then it was thirty days out, and
I remember thirty days out being like you guys seriously,
like we've got to do something big this month. And
if we don't do something big this month, like I'm
not sure what's going to happen. So then that next

month came and you know, we went in as a
team and I just said, listen, we've been talking about
this now for a quarter and we're just not running
in a sustainable way, and you know, today's the day
that we have to reorganize and we have to rethink
about how the company is going to move forward, and

not everybody can stay. And so we then kind of
broke off with UM team members and their managers to
talk in more detail. And you know, I think one
of the things that I did that was hard but
I think was good to do was that after I
talked to the team about what was happening and that
not everyone was going to be able to stay, I

also gave the option to the remaining team if they
wanted to walk, If they wanted to leave that day,
no questions asked, they could take the same package that
everyone else got. Because I felt like, you know, I
had chosen where I needed to cut, where the company
needed to cut, but that doesn't mean that those people

staying had chosen me or had chosen the company. And
I kind of wanted this like mutual agreement moving forward
that it's like, if not everyone can stay, that is
terrible UM, but the people that are here, they actually
also want to be here too, And I think that
actually helped with that transition because it it made this

kind of mutual agreement between the company and the people
that stay that they were going to be in it.
And it may not have been easy UM, but they
still really believed in the business and they believed that
they wanted to be a part of our mission, and
I think that helped moving forward. How do you know
how to lead like that? Right? Like it's like, what
what an interesting decision like that little decision to say like,

you know, okay, we've got to let people go, but
I also want people to choose me. Well, that's a
leadership moment too, you know, And that's you as a
leader doing something extra that's a little bit different. Where
do you think that comes from? I got it from
an advisor, honestly, I remember sitting. I was having brunch

with Gina Bianchini, who runs Mighty Bell. She's the founder
of ning very successful exit and she's been an advisor
to me in task Rabbit for years and I was
meeting with advisors leading up to this. I was like,
oh my god, like how do I do this? How
do I do this in the best way? Like there's
no perfect way, Like, how do I do this in
the best way? And I was just getting feedback from

as many people as I could, and it was Gina
who said, you know what and then do this. And
when she said it, I was like, really like what
if people leave? What if everybody leaves? You know? And
she's like, you gotta know who's there and who really
wants to be there, And it was it was hard

actually to say that and to share that with the
team and to give people that option to say, like
you can walk to you and get the same package.
And we had two or three people walk. I was
gonna say, did anyone walk? They did? We had two
to three people walk. And how did that feel it?
Um well, I mean none of it felt good. I

mean it was just but you know, it was actually
a relief in the end, because I felt relieved that
I knew that the team that did stay actually really
wanted to be there. And if I hadn't done that,
and if I hadn't kind of gone through that really
hard extra piece, it would have always been a question.
Um So, I think it was relief in the end.

That's such such an interesting story. You know, this is
such a This is such a moment to kind of
slow down a little bit. And and one of the
things you said when you're talking, we're taking through like
the hard moments of the company. As you mentioned, you
ended up in the hospital at one point during fundraising.
So I just feel like the human in me cannot
just brush over that. Um So, what happened. You know what,

when you talk about ending up in the hospit bittle
during a fundraising round. Like, I just also feel like
it is really important for people to hear what actually
happens behind the scenes with successful companies. And I appreciate
the fact that you'll go there, uh and talk about it,
and I think that's important for building successful companies in
the future. So you ended up in the hospital during

a fundraising round. What what happened? At the time, I
didn't tell anyone. My board didn't know, my current investors
didn't know. The only person that really knew was Stacy,
my CEO, and a couple of other exacts on the
team what was going on. But it was a three
million dollar raise. Now, we had raised like forty million

dollars to date, we were close to profitability. The business
was doing wow, and we were short this three million
to get to profitability. And so I was like, this
is gonna be easy. We'll go out, we'll talk to
some investors, we'll get three million dollars, and then we'll
be self sustainable. And it was the hardest raise. I mean,

way harder than what I did even in two thousand
and eight and there's a lot of different reasons for that,
in different dynamics for that. Some of them I understand
more now as an investor, But at the time, it
was just so so stressful and stressful to the point
where I was out with another entrepreneur one Monday afternoon

and I was taking a walk and at the time,
he was the CEO stumble Upon, and we were walking
and you know, we're like, oh, this is so stressful.
And he was going through a raise that I was
going through this raise, and we were swapping notes, and
after the walk, I drove home and he later tells
me that I looked a little green during the walk,
but he didn't say anything. And so I drive home

and I my stomach starts to hurt. And I get
to the house and at this point, I have one child.
I have an eighteen month old daughter. So I put
her to bed. It's like seven o'clock. I put her
to bed. I sit on the couch and it's just
getting worse and worse and worse, to the point where
I can't get off the couch, and so I call
an uber to take me to the emergency room. And

I get to the er. You know, you go through triage.
I wait like five or six hours. Sort of long
story short. By that point, it was my colon that
had gotten infected and it was the stressed induced colitis,
and the surgeon came in. I was admitted to the hospital.
I was put on antibiotics. The surgeon came in the

next day and was like, have you been under a
lot of stress lately? And I was like, you have
no idea, and he was like, yeah, go through your
head when you're sitting there and you have like a
stress and like you're in a hospital bed and they say,
have you been under a lot of stress? Like, what
do you even think to yourself? This is what I'm thinking.
I say out loud, my company is going to fail

because my body has failed. And that is exactly what
I was thinking. And I was like, I'm not even
gonna get this three million dollar raised done. I was
very close with some investors and I'm like, because I'm now,
I'm in the hospital and I'm gonna have to have
this surgery. And luckily I avoided the surgery. Actually stayed
in the hospital for five days. They pumped me full
of antibiotics. I was on the phone with investors in

London at the time, closing this three million dollar deal
and got it done. But literally was that was a Monday.
I left the hospital on Friday afternoon and went straight
to a pitch meeting. I could barely walk. Um well,
I mean I don't now, I remember. My poor stomach

was like so distended. It was awful. It was awful,
but it was like, what are you gonna do? I
was like, I have to get this money closed. And
it's like I meet with founders today and they're like
trying to get like a little bit of a bridge
raised right now, right in this COVID time. It is
like the same thing. I'm like, oh my god, I

feel their pain. Like it's so stressful because you just
feel like everything is going to fall apart if this
doesn't happen, and your body can only take so much.
And so that's why, now having gone through all of that,
I am such a proponent of, you know, as a founder,
just really taking care of your physical, mental, and emotional

health as well, because I've I've been at points where
I've hit the wall where it hasn't been sustainable. Um,
it's just not a good place for anyone to be. Yeah,
was there a moment that you felt because I just
kind of put you through the ringer and talking about
all the bad moments, um, And there were lots of
good moments, and I like that you included our seeing
an interview in one of them. I'll take that, um.

But was there a moment that you felt in all
of this like that that you had made it. Here's
the moments that I look back on the most and
think that made it all worth it. And and we
were lucky because a task grab It, we had these
little interactions in these little story as every single day

of amazing things that would happen on the platform, just
matches that were made or you know, interesting stories that happened,
and those were the moments that we really held onto
as a team and said, like, this makes it all
worth it. I'll tell my favorite story real quick, which
was we were only open in two markets, were open
in Boston and San Francisco. And at the time, there

is this woman in San Francisco who posted on task
grab It and that she had a twenty year old
son living in Boston. She couldn't fly out there to
be with him, and unfortunately he was going through chemotherapy
treatment at mass General Hospital. He's twenty years old, and
so she posted on task grab it to find someone
to go to the hospital to bring them a health

female from Whole Foods and a cozy blanket from her
and sit with him every day for a week during
his treatments and then call her afterwards to tell her
how her son was doing. And that Oscar that picked
up the job in Boston was actually another mom. And
so the bomb that these two moms formed across the
country was just incredible. And I think, you know, with

just two markets open very early days, it was like
two I realized what we were building was successful. Like
it didn't matter the amount of revenue I drove or
what sort of acquisition offer I got in the end,
but just the the opportunity to change and improve people's
lives like that is what kept us going through the

whole thing. And we had tons of stories like that
on an ongoing basis. And you guys eventually sold to Ikea.
Did you feel like you could breathe because you talk
about that roller coaster? What was the feeling after the
papers were signed? Oh my gosh, it was such a
weird day. I remember being on the board call where
we voted to approve the acquisition, and it was so exciting,

but at the same time, it was this dramatic moment
of my baby. My baby is gone. You know, this
thing that I've worked on and raised for the last eight, nine,
ten years, it's it's going to be gone. And so
I was the last one to vote. We were a
board of I think seven at the time. I was
the last one to vote. We all went around very dramatically,

We're like, yes, I approved, Yes, I approve, and everyone
said yes, and it got to me and I was
so choked up in that moment, and of course I
approved the deal. I was very exciting, but it was
just such a huge transition. I knew it was going
to be a life transition and a huge transition for
the company, for the business, and for me. At the
same time, I was pregnant with my second child, and

so I think actually for me personally, and that helped
shift me out of the day to day and shift
me out of the business because I had now this
new born at home, and so it was like a
lot of personal life changes as well. That sort of
we're good for me and helped me move forward maybe
in a way that was really healthy. Whereas if I

didn't have those sort of distractions and new joys and
things in my life, it probably would have been a
lot harder. Would you do the day you voted? What
was like the first thing you did after you you
gave your approval and you kind of set your kid
off to college in a metaphorical sense, yes, yeah, Well
I was at home. I was at my house, and

I think I just remember just going downstairs and just
playing with my own children, like very normal, very normal day. Yeah,
but I definitely remember that moment and feeling like I
felt like I was standing like on the edge of
a cliff and it was like I've got a jump,
this is this is it? And and you're now investing.

You're a general partner and an investment fund, you're looking
at companies early on. Why did you decide to become
an investor? So you know, for me, I've told the
story that I found a task grab it because I
was really excited about these three emerging technologies, social, location,
and mobile. And I'm an engineer, that is my background,

and so I love technology. And then I founded the company.
I kind of put my head down in this one
space and this one technology in this one business for
almost a decade. And when I sold Task grab It,
I kind of picked my head up and I thought, Wow,
there's a lot of new emerging technologies that have happened
that I haven't been a part of. There's been bitcoin

and blockchain and a R and all kinds of really
interesting technologies that I haven't had a chance to dig into.
So I knew that whatever I did next, I didn't
want to put my head down in one business and
one technology again for a long time. That I wanted
to find a role that I could really dig into
a lot of different areas at once. And so because

I had great relationships with investors over the years, you know,
a lot of people reached out and kind of introduced
me to the idea of investing full time, and I
spent out a year thinking about it and getting to
know different investors before I decided to finally join Fuel
and it's been a great fit. I get to work
with entrepreneurs every day on their businesses. I get to

learn new technologies every day, and my partner, Chris Howard,
who's the founder of the firm, is just fantastic and
it's just the two of us. So it's been a
really really great move for me. Yeah, and and I
read something that you, you know, you've kind of said
that founders who care for themselves can better care for
their businesses. So, and even in this interview, some of

the things you've said about the conversations you've had with
founders who are trying to make sure to get a
bridge during this time and all this, you've spoken a
lot about how they are doing emotionally. I can see
that that's very much in the DNA of how you're
of your investment strategy. So what do you tell founders
who are in this moment, who are looking at the landscape,

who are dealing with the normal stress and anxiety of
being a founder, which you know better than most is
very stressful, and now have the backdrop of a global pandemic.
What advice do you give them? Well, you know, my
advice is one, you know, think about what your business

needs to survive over the next eighteen twenty four plus months,
and that usually means what is your cash runway. So
we're advising all of our founders to just make sure
they have enough cash in the bank to kind of
ride this out. You know, when I started in two
thousand and eight, it really wasn't until eighteen months later
that I was able to get a seed round together.
And it may take eighteen months or longer for really

the markets to improve and for investors to really re
engage and put capital back into the markets in the
same way they were. And so that's one thing. I think.
The second thing is like, once you've got that figured out,
make sure that you're carving out time and space for
yourself as far a sort of a mental emotional health

and wellness standpoint. And it is so so hard. I mean,
we're all juggling so much. We've got kids running around,
we're homeschooling, you know, we're taking care of all kinds
of things beyond just our businesses. And now work in
life is so integrated because we're all working from home.
So it's sometimes really hard and sometimes impossible to find
the time and space that you need mentally. But one

of the things we're doing as part of Fuel's portfolio
is we're holding weekly meditation sessions for our founders um
over Zoom. You know, we're trying to connect founders with
resources around healthy eating and healthy sleeping that can help
them through this time. I think sometimes it's just you're

in such a frantic panic mode. It's so easy to
stay in that mode. But you can break that cycle
if even if it's just like ten minutes a day
to just like sit quietly and make your mind stop.
You know, I wish that I had done more of
that when I was running Task grab It. And certainly,
you know at the end when I tell the story
about going into the hospital, like I pushed my body

to a place where it couldn't operate anymore, and that
wasn't good for the business either. If I had just
taken some measures to act more sustainably, then I think
it would have been a lot easier for me, and
you know, the business in the end would have reached
the same success in the same story. So I think

it's just having that perspective that it's okay to just
take a pause for yourself from a from a mental
health standpoint, and if you could go back and you know,
tell two thousand and eight Leah building out Task grabb
It anything as you now having kind of just gone
through this huge journey um and being on the other

side of it and even now in this crazy moment um,
what would you tell her. I've been just recognizing, Um,
it's gonna be hard. It's hard for everyone, but I
think actually that was the best time for me to
start a business. Now is the best time for a
lot of entrepreneurs to be starting their businesses. It's going

to be so so hard in the beginning, but because
you're you're innovating something out of a time that's really
chaotic and really hard, it's going to make you operate differently.
It's gonna make you build in a more sustainable way.
And I think the opportunity to achieve a bigger vision,

sort of this game changing vision where customers will change
for the behavior along with you is you know, it's
like no other time, and so I'm glad I went
for it, um, even though it's just a crazy, crazy journey,
and so I encouraged, you know, other people to go
for it too. Okay, guys, that's it for this week's show.

Quick update for you. This is one of the last
episodes of the season. It's been so much fun bringing you,
guys stories of founder journeys, the highs and the lows,
some weird stories like that time I had a relationship
with a bot My quarantine diaries, the one time we
talked about hacking your brain. Thank you, guys for playing

ball with me. This season has been a blast. We
hope to bring you more first contact later this summer. Now,
there's never been a more important time to explore technology
and its impact on us human beings. My favorite part
of doing this show is hearing from you, So don't
be a stranger. Let's stay in touch. The best way
to do that is to sign up for our newsletter

at dot dot dot media dot com backslash Newsletter. We're
launching it this summer and it's going to be your
best source to stay in the loop on any upcoming
episodes that we happen to drop. And we're also doing
these virtual town halls, so we'll let you know about those,
and we're working on a ton of projects that will
keep you in the loop on. So sign up at
dot dot dot media dot com backslash Newsletter. I promise

not to spam you and reach out to me. Tell
me what you're up to and what stories are interested in.
My number is five four zero three four one zero. Also,
a lot of you've been texting me about new initiatives
during this crisis, and I know a lot of folks
in Silicon Valley working on quite a few of them,
so I want to give a couple of shoutouts. The

first is Frontline Food. It's five volunteers and since they've started,
they've delivered more than fifty thousand meals to hospitals and
forty cities. The next is Code Academy. They're working on
more than ten thousand scholarships to Code Academy pro for
students and teachers affected by COVID nineteen school closures. And lastly,
an app called COVID Coach. It's an app designed to

help folks stay sane, stay connected, cope with stress, manage anxiety,
and navigate parenting and caretaking during this pandemic. If you
want to learn more or get involved with any of
these organizations, go to our show notes. Follow along on
our social media. I'm at Laurie Siegel on Twitter and Instagram,
and the show is at First Contact podcast on Instagram,

on Twitter, We're at First Contact Pod. First Contact is
a production of Dot Dot Dot Media executive produced by
Laurie Siegel and Derek Dodge. This episode was produced and
edited by Sabine Jansen and Jack Reagan. The original theme
music is by Xander Singh. And as always, I'm sending
my thoughts to each and every one of you guys,
and so is our whole First Contact crew. During this time,

I hope that everybody is staying home, staying healthy, and
staying human. I'm Laurie Siegel and this is First Contact.
First Contact with Lorie Siegel is a production of Dot
Dot Dot Media and I Heart Radio.
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