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 iHeartRadio. There was this certain heart
back in two thousand and eight, two thousand and nine,
and there were things that got solved that I think
were really interesting and really changed things. I don't know
if this is just me being nostalgic for it or
(00:23):
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 months.
Speaker 2 (00:31):
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 force
is actually some different solutions. I think we'll see more
of that, you know now and into the next decade.
Speaker 1 (00:54):
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 Lyft redefined transportation,
AIRBNBA shook up the travel industry, and task grab. It
helped pave the way for the gig economy. But everything
feels uncertain again. I'll say this a decade later. I
(01:18):
sense 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.
(01:40):
Leah Sullivan. She's the founder of Task Grab It, a
company born out of the two thousand and eight recession.
I'm excited to have her on because this isn't an
afterschool special, so I don't want to sugarcoat it. What
she did was extremely difficult. Building a company that changes
(02:00):
the world is hard, so it is battling your brain,
so it is 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 Grab It,
and now Leah helps run an early investment fund called
Fuel Capital. And she's not afraid to talk about mental health,
(02:21):
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
(02:42):
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 we're hosting, and other future projects that
I'm going to be working on. So sign up at
media dot com backslash newsletter. I promise I won't spam you. Okay,
(03:05):
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.
Speaker 2 (03:23):
It's such a funny question these days, isn't it. 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 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,
(03:44):
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's healthy.
But you know, between the homeschooling and working full time
and you know, not having the support system that I
used to, it is. It has been a complete shift,
(04:06):
in a complete transition. So just feel like I'm hanging
in there.
Speaker 1 (04:09):
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
in ten years. It was a long, long time ago.
It was a do you remember it?
Speaker 2 (04:24):
Yeah? I do. Actually, you interviewed me on CNN. I
was terrified, and I mean it must have been a
decade ago at least.
Speaker 1 (04:34):
I went back in preparation for this. I went back
and I found the interview. It was from twenty eleven,
and it was two thousand and eight when you started to.
Speaker 2 (04:43):
Ask about it.
Speaker 1 (04:44):
Yeah, and then in twenty eleven I interviewed you, and
I remember this idea of the gig economy and all
this this didn't you know, you guys made this popular,
Like this didn't really exist, and so I was on
the startup Beat. It helped create the startup beat up CNN,
and I remember we were following a task grab It
(05:04):
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.
Speaker 2 (05:16):
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.
Speaker 1 (05:29):
It's almost I look back at that and it almost
feels 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
(05:51):
idea of New York bustling, 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 now fast forward all these
years later, over a decade later, and we're sitting here,
(06:13):
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.
Speaker 2 (06:29):
It does. I mean, it was a different time. I
mean three months ago, it was a different time. I
think the thing that though 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 Lyft, it
was Uber, it was Airbnb, it was task grab it
(06:51):
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
(07:12):
decade that we'll be talking about, you know, in the
year twenty thirty.
Speaker 1 (07:15):
I want to go back to two thousand and eight.
You were at IBM, and you decide right before the
recession to quit your job. You're 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.
(07:38):
But you made the decision 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 task, 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,
(08:01):
before all this happened at IBM, and thinking, you know,
something is broken and I want to fix it. What
were you like back then?
Speaker 2 (08:09):
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 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
(08:31):
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,
(08:52):
I got really excited about those emerging technologies, particularly mobile
location based awareness and then social technology. I 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 had listened to me about it. I had gotten
(09:13):
connected with Scott Griffith, who was the CEO of Zipcar
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 zipcar 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
runmi errand dot com. It wasn't even called tats rabbit yet,
(09:35):
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 these people would be laid off.
I ended up leaving my job in June of two
thousand and eight.
Speaker 1 (09:51):
Do you remember the day you left your job.
Speaker 2 (09:53):
I do. It was June twenty fifth. 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 got to meet with
my manager. And then that manager's like, no, no, you
got to 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
(10:13):
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 walk
in that day, quit my job and make the leap.
Speaker 1 (10:36):
I guess I go back to this idea of like,
were you afraid? I mean it's like you look back
at all you were able to do, and of course
you were able to do it, right, you have the
luxury of perspective right now, But in that moment, where
did that confidence come from? 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
(10:58):
all these things, but when you're actually 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 of perspective, you know, what, do you
(11:19):
wish you could go back and tell that girl?
Speaker 2 (11:21):
Well? I mean it's funny because I was hesitant, I
was afraid, but I also sort of had hit my
max of what I felt like I could do at
IBM as far as what would make me happy. There's
plenty more I could do there, but I knew it
wasn't going to make me happy. And so I remember
(11:41):
having this conversation with myself, and 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 queue by yourself, and
you've programmed software. You've never interacted with customers, you've never
raised money from investors, you've never high you've never fired, Like,
you don't know how to do operations. But I think
(12:04):
I realized that. And this sounds kind of silly, but
I told myself, you know what, 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
(12:25):
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 leap
to do it.
Speaker 1 (12:40):
You actually launched task grab It. 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 come out, the app store had launched.
(13:02):
There was just this canvas for creativity for the smart
people who were paying attention, and out of that came
task grab It. So tell me about actually launching task
grab It in this environment. What did you learn?
Speaker 2 (13:15):
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 to outsource? And
how much would you be willing to pay, and so
(13:37):
I wasn't actually even sure if the market was there yet.
And then September two thousand and eight year old 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 months.
(13:58):
And that was a hard time because because 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,
(14:19):
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 and 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
luck in some ways that the timing hit for this
(14:42):
need and what I was building was filling a gap,
and sometimes those things just cannot be predicted.
Speaker 1 (14:49):
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 the day that played out. How
were you very scrappy and building out task grab it?
Speaker 2 (15:11):
Yes, a lot of scrappiness, and that's just kind of
in my DNA 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.
(15:33):
I mean, it was just a matter of like finding
new ways and coming up with new things 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.
(15:55):
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 the mode that I stayed in for the next
(16:16):
eighteen months. It really wasn't until the following year, near
the end of two thousand and nine, that I was
able to raise seed round of funding from investors out
here in the Bay Area and Marico at Floodgate Fund
led a million dollar round of seed funding. But prior
to that, it was maxing out credit cards. It was bootstrapping.
(16:37):
It was just running super super lean. It was just me.
I couldn't hire anyone. So I was the first task
Grabbit ever and I did a ton of ariage.
Speaker 1 (16:47):
You were the first task Gravit.
Speaker 2 (16:48):
Oh yeah, I did a ton of errands, Oliver.
Speaker 1 (16:50):
Ow So we tell me, so you were actually going
if I went on the earliest iteration of task Gravit,
it would have been you, the founder of task Grabbit.
Speaker 2 (16:57):
Doing my errands all the time.
Speaker 1 (17:00):
Yeah, that's incredible.
Speaker 2 (17:01):
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'd
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,
(17:25):
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
(17:46):
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 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.
Speaker 1 (18:08):
God, I remember when even like Dennis the founder of
Force Square, I remember back in the day going to
south By Southwest in like twenty eleven and calling up
FORCEM trying to call their PR person, be 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 they become companies and put in the press
(18:30):
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.
Speaker 2 (18:46):
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
and seven, two thousand and eight as well, And we've
talked about this before. 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
(19:07):
to figure out how to do everything ourselves. And I
think that Force is actually some different solutions, some different
product solutions. I think we'll see more of that you know.
Now 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
(19:28):
ground anymore. They could hire out for that, right, and
they could learn from secondhand 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.
Speaker 1 (19:44):
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 because I sense that
this is another moment of constraint. And I think Silicon
(20:06):
Valley and you you're an investor now, and we'll get
to that, like got very noisy, right, and a lot
of people outsourced, outsourced, outsourced, and there was this certain
heart back in two thousand and eight, two thousand and
nine which made way for companies like Airbnb and Uber,
and you know, there were things that got solved that
I think were really interesting and really changed things. And
(20:27):
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 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
(20:50):
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.
Speaker 2 (21:05):
Yeah, I mean, 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 part
of it. I hope I'm the one funding it, right,
(21:26):
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 be
(21:46):
a part of it.
Speaker 1 (21:51):
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
(22:12):
two thousand and eight two thousand and nine, Like we
saw Airbnb, uber Lyft, task grabbit. 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 are like ripe for some disruption right now.
Speaker 2 (22:31):
Well, back in two thousand and eight, it 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, Uberlyft, task grabbit. Now there's
this whole step function change in how we're working. We're
all working remotely from home. Work will never be the
(22:55):
same again. It's been now almost two months of sheltering
in place, we're 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 going to be so hard, I'm working from home.
And then you know, Zoom just completely took off and
(23:18):
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 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 we'll, you know, as soon as this shelter
(23:39):
in place is 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 they haven't been stress tests the
(24:02):
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 worked 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,
(24:23):
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,
(24:43):
I mean telemedicine. Just the necessity of it has just
blown up. But again, like the tools 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 in telemedicine. And then the third area
I'm really excited about and watching closely is just education.
(25:05):
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 great tools or platforms that have
(25:29):
emerged as the leaders in that space, particularly for elementary education,
and so I think that's a huge opportunity that we'll
see innovations around as well.
Speaker 1 (25:38):
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, it's like you've got to
be all in or you're all at it. There's something
(25:58):
that feels a little bit like it doesn't one hundred
percent mirror the human experience. And this is me putting
on my tech in humanity hat, and I think you're right.
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
(26:19):
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 what you end
up investing in. Do it quick, please, Lea be very interesting.
I want to go back to the early task Gravit days.
Sorry to take you on that tangent. I just think
it's so fascinating and you're such an interesting person for
(26:42):
me to pick your brain on this, because you were
at the beginning of this, 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 og task Rabbit, which I think is just fascinating.
But then I saw that you actually went on Craigslist
to try to find task Grabit people. This is before
(27:03):
you guys have extensive background checks and all this kind
of stuff. And that was even when I interviewed you
in twenty eleven. I remember asking you about that. But
back before that, you went on Craigslist for your earliest
task people of a task Grabbit, and the way you
decided if you would hire people was if they were
(27:24):
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.
Speaker 2 (27:37):
Right. Yeah, Well, I realized that I couldn't actually do
it all if this company was going to scale 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
(27:58):
rabbits in person over 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.
I didn't have kids at the time, or else I
would have, you know, thought about putting them in my house.
(28:19):
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, oh, okay, yes,
I definitely trust this person to, you know, drop groceries
(28:41):
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 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.
Speaker 1 (29:00):
That The thing is, like, I don't think people realize that.
I just want to like set everyone back like eight
ten years. Like 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 carvia and app
(29:20):
or like would you ever hire a stranger to do
a chore for you? Because I remember those were my
lead INSes 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 is a
little insane, and I think that's important for people to understand.
(29:41):
I'm sure when you started out people kind of said
no or kind of looked at you a little bit
like this girl's 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.
Speaker 2 (30:00):
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
(30:24):
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 twenty ten, twenty eleven, and liftin 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
(30:45):
going well, and that's the hardest time to make a change.
But behavioral changes come when there's stress on the system.
Speaker 1 (30:53):
Do you remember out of curiosity, just like go back
with me in time, do you remember the biggest know
you got or the most like the most frustrating no,
or because you went to I'm sure a lot of investors,
or you left a job that was cushy, Like, you know,
do you remember any specific interaction that sticks with you
(31:13):
of someone who just did not believe in you or
this idea?
Speaker 2 (31:17):
Absolutely, like just more than one, honestly. 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
and nine. I mean, it's a long time where I
would just meet with investors, angel investors, vcs. Now. At
(31:39):
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 a venture
as well. But you know, I remember talking to, you know,
(32:03):
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, like what 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,
(32:23):
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
(32:46):
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 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
(33:09):
whether that was going to be a long standing trend
or if it was just a fad.
Speaker 1 (33:14):
Wow, that's interesting. I saw something you wrote that I
thought it 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
(33:35):
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 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.
(33:55):
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 love to
where the wild things are. What was your big audacious
goal and then what were the baby steps that you
(34:16):
had to take to achieve them.
Speaker 2 (34:20):
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 Aaron'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
(34:42):
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 they be like, oh, that's a service where I
can you know, get my dry cleaning picked up or
get my groceries to li And yes, that was the
(35:02):
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
(35:24):
harry 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
(35:45):
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 to take baby steps to get there and tie
all the dots together. It was like, you know, putting
(36:06):
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
(36:27):
you know, continues to evolve today. But that wasn't apparent
in two thousand and eight, two thousand and nine, in
twenty ten. 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.
Speaker 1 (36:47):
When you look back and you talk about having these
big goals and you can have the luxury of perspective
and you kind of look at what you were able
to do. You know, no one 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 were the kind of person
(37:07):
who has the ability to have these big, lofty, as
you call them, like hairy 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 grab it that you just felt like that
this was just like a very very dark dark space
(37:29):
for you that you felt like a failure in some capacity.
Speaker 2 (37:35):
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 ask 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 thirty percent of the team, huge failure near
the end of the company, when we were getting acquired,
(37:56):
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 and away from the web. So it's like
(38:18):
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
(38:38):
went down, or you know, really exciting things happened too
our big fundraises that we did and announced. 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
(38:59):
my thought feel great about the highest highs when I
knew that around the corner there was gonna be a
failure or a 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.
Speaker 1 (39:19):
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 the extremes.
Speaker 2 (39:34):
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 it high, you're
kind of like all right, but like remember last week
when you had that big low, And I think over
(39:56):
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 when
you know you're the one staying level. It's like, you know,
sharing that experience in perspective with the team, And yes,
(40:17):
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 a 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
(40:39):
at a time where everything was super super difficult, it
kind of gave us the perspective that, like, even when
things are 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.
Speaker 1 (40:57):
Okay, we've got to take a quick break to hear
from our sponsors more with my guest. After the break,
(41:17):
I want to go back to you talking about having
to lay off folks. 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.
Speaker 2 (41:36):
Yeah, I mean that was the lowest low of the
entire company. Out of everything I experienced, was doing that layoff.
Speaker 1 (41:46):
What was the hardest part of it.
Speaker 2 (41:49):
It's just failing those people. It 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 in business development.
(42:09):
But it's like, whose fault was it that we over
hired in some areas and we underhired 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
(42:33):
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
(42:53):
team or managing the team, it was hard for me.
You know, I felt a lot of empathy with people
that I'd 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, and so
that was hard. But you know, with perspective and with
(43:14):
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
(43:37):
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 going to 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. And so it's it's not easy
(44:00):
and it's very emotional.
Speaker 1 (44:01):
Do you remember what you said that morning?
Speaker 2 (44:04):
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
(44:26):
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 going to be sustainable. And guess
what in most companies, like eighty 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
(44:46):
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
(45:07):
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 team members and their managers to talk
(45:30):
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
(45:50):
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 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,
(46:12):
if not everyone can stay, that is terrible, 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 made this kind of mutual agreement between
the company and the people that stayed that they were
going to be in it. And it may not have
(46:33):
been easy, 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.
Speaker 1 (46:41):
How do you know how to lead like that?
Speaker 2 (46:43):
Right?
Speaker 1 (46:43):
Like it's like 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?
Speaker 2 (47:04):
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 and task grab it 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?
(47:25):
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 got to know who's there and
(47:47):
who really wants to be there. And 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 this same package
and we had two or three people walk.
Speaker 1 (48:03):
I was gonna say, did anyone walk? Yeah? They did.
Speaker 2 (48:06):
Wow, we had two or three people walk.
Speaker 1 (48:08):
And how did that feel it?
Speaker 2 (48:12):
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. So
(48:34):
I think it was relief in the end.
Speaker 1 (48:36):
That's such an interesting story. You know, this is such
a This is such a moment to kind of slow
down a little bit. 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. So what happened? You know what? When you
(48:58):
talk about ending up in the hostelpitle 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 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?
Speaker 2 (49:21):
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 COO, and a couple of other
execs on the team what was going on. But it
was a three million dollar raise. Now, we had raised
like forty five million dollars to date, we were close
(49:43):
to profitability, the business was doing well, and we were
short this three million to get to profitability. And so
I was like, this is going to 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 rays. I mean, way harder than what
I did even in two thousand and eight. And there's
(50:05):
a lot of different reasons for that and different dynamics
for that. Some of them I understand more now as
an investor, but at the time it was just 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
(50:26):
of stumble Upon, and we were walking and you know,
we're like, oh, this is so stressful. And he was
going through a raise and 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 my stomach
(50:46):
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
(51:10):
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
(51:31):
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, this goes stress ahead.
Speaker 1 (51:39):
When you're sitting there and you have like a stress
in 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?
Speaker 2 (51:48):
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 going to 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. I actually stayed in the
hospital for five days. They pumped me full of antibiotics.
(52:11):
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.
Speaker 1 (52:28):
Oh my you still let it greenish.
Speaker 2 (52:32):
I mean, I don't know. 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 his COVID time, it is
(52:53):
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,
(53:14):
just really taking care of your physical, mental, and emotional
health as well, because I've been at points where I've
hit the wall, where it hasn't been sustainable. It's just
not a good place for anyone to be.
Speaker 1 (53:28):
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, and there were lots of
good moments, and I like that you included our CNN
interview in one of them.
Speaker 2 (53:38):
I'll take that.
Speaker 1 (53:40):
But was there a moment that you felt in all
of this that you had made it.
Speaker 2 (53:47):
Here's the moments that I look back on the most
and think that made it all worth it. And we
were lucky because at task grab It, we had these
little interactions in these little story every single day of
amazing things that would happen on the platform, just matches
that were made or you know, interesting stories that happened,
(54:08):
and those were the moments that we really held on
to 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. We're
open in Boston and San Francisco. And at the time,
there was this woman in San Francisco who posted on
task grabbit and that she had a twenty year old
(54:29):
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 grabbit to find someone to
go to the hospital to bring them a healthy meal
from Whole Foods and a cozy blanket from her and
(54:51):
sit with him every day for a week during his
treatments and then call her afterwards to tell her how
her son was doing. E scare 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, just two markets
open very early days. It was like twenty ten. I
(55:13):
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 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.
Speaker 1 (55:34):
And you guys eventually sold to Ikea. Did you feel
like you could breathe because you talk about that rollercoaster?
What was the feeling after the papers were signed?
Speaker 2 (55:45):
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
(56:06):
years it's going to be gone. And so I was
the last one to vote. We were a bored of
I think seven at the time. I was the last
one to vote. We all went around very dramatically. We
were like, yes, I approve, 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
(56:27):
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, that helped shift
me out of the day to day and shift me
(56:48):
out of the business because I had now this newborn
at home, and so it was like a lot of
personal life changes as well that sort of were 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.
Speaker 1 (57:09):
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.
Speaker 2 (57:20):
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, my very normal,
very normal day. Yeah, but I definitely remember that moment
in feeling like whoo. I felt like I was standing
like on the edge of a cliff and it was like,
I've got a jump. This is it.
Speaker 1 (57:43):
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?
Speaker 2 (57:55):
So you know, for me, I've told the story that
I found a task Grabit 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,
(58:18):
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 ar 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
(58:39):
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
(58:59):
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
(59:20):
great move for me.
Speaker 1 (59:22):
Yeah, and I read something that 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
(59:44):
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
(01:00:07):
of a global pandemic. What advice do you give them?
Speaker 2 (01:00:12):
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
(01:00:34):
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
(01:00:55):
were carving out time and space for yourself as far
as as 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
(01:01:16):
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 Fuels Portfolio is we're
holding weekly meditation sessions for our founders over zoom. You know,
we're trying to connect founders with resources around healthy eating
(01:01:40):
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, even if it's just
like ten minutes a day to just like sit quietly
and make your mind stop, you know, wish that I
(01:02:00):
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
(01:02:22):
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
mental health standpoint.
Speaker 1 (01:02:37):
And if you could go back and you know, tell
two thousand and eight Leah building out Task Grab It
Anything as you now having kind of just gone through
this huge journey and being on the other side of it,
and even now at this crazy moment, what would you
tell her.
Speaker 2 (01:02:57):
I've been just recognizing 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
(01:03:19):
a time that's really chaotic and really hard, it's going
to make you operate differently. It's going to 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 their behavior along with
you is you know, it's like no other time, and
(01:03:42):
so I'm glad I went for it, even though it
was just a crazy, crazy journey, and so I encourage,
you know, other people to go for it.
Speaker 1 (01:03:50):
To 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
(01:04:11):
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 for us 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
(01:04:35):
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,
(01:04:56):
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 you're interested in.
My number is nine one seven five four zero three
four one zero. Also, a lot of you been texting
(01:05:17):
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 shout outs. The first is Frontline Foods. It's five
hundred 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
(01:05:38):
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
(01:05:59):
to our show notes. Follow along on our social media.
I'm at Lori 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 Lori Siegel
and Derek Dodge. This episode was produced and edited by
Sabine Jansen and Jack Reagan. The original theme music is
(01:06:22):
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 Lori Siegel and this is first contact. First contact
(01:06:48):
with Lori Siegel is a production of Dot dot Dot
Media and iHeartRadio
First contact with Lori Siegel is a production of Dot
Dot Dot Media and iHeartRadio. There was this certain heart
back in two thousand and eight, two thousand and nine,
and there were things that got solved that I think
were really interesting and really changed things. I don't know
if this is just me being nostalgic for it or
(00:23):
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 months.
Speaker 2 (00:31):
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 force
is actually some different solutions. I think we'll see more
of that, you know now and into the next decade.
Speaker 1 (00:54):
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 Lyft redefined transportation,
AIRBNBA shook up the travel industry, and task grab. It
helped pave the way for the gig economy. But everything
feels uncertain again. I'll say this a decade later. I
(01:18):
sense 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.
(01:40):
Leah Sullivan. She's the founder of Task Grab It, a
company born out of the two thousand and eight recession.
I'm excited to have her on because this isn't an
afterschool special, so I don't want to sugarcoat it. What
she did was extremely difficult. Building a company that changes
(02:00):
the world is hard, so it is battling your brain,
so it is 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 Grab It,
and now Leah helps run an early investment fund called
Fuel Capital. And she's not afraid to talk about mental health,
(02:21):
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
(02:42):
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 we're hosting, and other future projects that
I'm going to be working on. So sign up at
media dot com backslash newsletter. I promise I won't spam you. Okay,
(03:05):
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.
Speaker 2 (03:23):
It's such a funny question these days, isn't it. 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 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,
(03:44):
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's healthy.
But you know, between the homeschooling and working full time
and you know, not having the support system that I
used to, it is. It has been a complete shift,
(04:06):
in a complete transition. So just feel like I'm hanging
in there.
Speaker 1 (04:09):
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
in ten years. It was a long, long time ago.
It was a do you remember it?
Speaker 2 (04:24):
Yeah? I do. Actually, you interviewed me on CNN. I
was terrified, and I mean it must have been a
decade ago at least.
Speaker 1 (04:34):
I went back in preparation for this. I went back
and I found the interview. It was from twenty eleven,
and it was two thousand and eight when you started to.
Speaker 2 (04:43):
Ask about it.
Speaker 1 (04:44):
Yeah, and then in twenty eleven I interviewed you, and
I remember this idea of the gig economy and all
this this didn't you know, you guys made this popular,
Like this didn't really exist, and so I was on
the startup Beat. It helped create the startup beat up CNN,
and I remember we were following a task grab It
(05:04):
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.
Speaker 2 (05:16):
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.
Speaker 1 (05:29):
It's almost I look back at that and it almost
feels 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
(05:51):
idea of New York bustling, 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 now fast forward all these
years later, over a decade later, and we're sitting here,
(06:13):
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.
Speaker 2 (06:29):
It does. I mean, it was a different time. I
mean three months ago, it was a different time. I
think the thing that though 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 Lyft, it
was Uber, it was Airbnb, it was task grab it
(06:51):
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
(07:12):
decade that we'll be talking about, you know, in the
year twenty thirty.
Speaker 1 (07:15):
I want to go back to two thousand and eight.
You were at IBM, and you decide right before the
recession to quit your job. You're 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.
(07:38):
But you made the decision 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 task, 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,
(08:01):
before all this happened at IBM, and thinking, you know,
something is broken and I want to fix it. What
were you like back then?
Speaker 2 (08:09):
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 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
(08:31):
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,
(08:52):
I got really excited about those emerging technologies, particularly mobile
location based awareness and then social technology. I 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 had listened to me about it. I had gotten
(09:13):
connected with Scott Griffith, who was the CEO of Zipcar
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 zipcar 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
runmi errand dot com. It wasn't even called tats rabbit yet,
(09:35):
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 these people would be laid off.
I ended up leaving my job in June of two
thousand and eight.
Speaker 1 (09:51):
Do you remember the day you left your job.
Speaker 2 (09:53):
I do. It was June twenty fifth. 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 got to meet with
my manager. And then that manager's like, no, no, you
got to 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
(10:13):
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 walk
in that day, quit my job and make the leap.
Speaker 1 (10:36):
I guess I go back to this idea of like,
were you afraid? I mean it's like you look back
at all you were able to do, and of course
you were able to do it, right, you have the
luxury of perspective right now, But in that moment, where
did that confidence come from? 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
(10:58):
all these things, but when you're actually 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 of perspective, you know, what, do you
(11:19):
wish you could go back and tell that girl?
Speaker 2 (11:21):
Well? I mean it's funny because I was hesitant, I
was afraid, but I also sort of had hit my
max of what I felt like I could do at
IBM as far as what would make me happy. There's
plenty more I could do there, but I knew it
wasn't going to make me happy. And so I remember
(11:41):
having this conversation with myself, and 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 queue by yourself, and
you've programmed software. You've never interacted with customers, you've never
raised money from investors, you've never high you've never fired, Like,
you don't know how to do operations. But I think
(12:04):
I realized that. And this sounds kind of silly, but
I told myself, you know what, 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
(12:25):
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 leap
to do it.
Speaker 1 (12:40):
You actually launched task grab It. 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 come out, the app store had launched.
(13:02):
There was just this canvas for creativity for the smart
people who were paying attention, and out of that came
task grab It. So tell me about actually launching task
grab It in this environment. What did you learn?
Speaker 2 (13:15):
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 to outsource? And
how much would you be willing to pay, and so
(13:37):
I wasn't actually even sure if the market was there yet.
And then September two thousand and eight year old 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 months.
(13:58):
And that was a hard time because because 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,
(14:19):
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 and 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
luck in some ways that the timing hit for this
(14:42):
need and what I was building was filling a gap,
and sometimes those things just cannot be predicted.
Speaker 1 (14:49):
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 the day that played out. How
were you very scrappy and building out task grab it?
Speaker 2 (15:11):
Yes, a lot of scrappiness, and that's just kind of
in my DNA 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.
(15:33):
I mean, it was just a matter of like finding
new ways and coming up with new things 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.
(15:55):
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 the mode that I stayed in for the next
(16:16):
eighteen months. It really wasn't until the following year, near
the end of two thousand and nine, that I was
able to raise seed round of funding from investors out
here in the Bay Area and Marico at Floodgate Fund
led a million dollar round of seed funding. But prior
to that, it was maxing out credit cards. It was bootstrapping.
(16:37):
It was just running super super lean. It was just me.
I couldn't hire anyone. So I was the first task
Grabbit ever and I did a ton of ariage.
Speaker 1 (16:47):
You were the first task Gravit.
Speaker 2 (16:48):
Oh yeah, I did a ton of errands, Oliver.
Speaker 1 (16:50):
Ow So we tell me, so you were actually going
if I went on the earliest iteration of task Gravit,
it would have been you, the founder of task Grabbit.
Speaker 2 (16:57):
Doing my errands all the time.
Speaker 1 (17:00):
Yeah, that's incredible.
Speaker 2 (17:01):
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'd
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,
(17:25):
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
(17:46):
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 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.
Speaker 1 (18:08):
God, I remember when even like Dennis the founder of
Force Square, I remember back in the day going to
south By Southwest in like twenty eleven and calling up
FORCEM trying to call their PR person, be 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 they become companies and put in the press
(18:30):
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.
Speaker 2 (18:46):
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
and seven, two thousand and eight as well, And we've
talked about this before. 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
(19:07):
to figure out how to do everything ourselves. And I
think that Force is actually some different solutions, some different
product solutions. I think we'll see more of that you know.
Now 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
(19:28):
ground anymore. They could hire out for that, right, and
they could learn from secondhand 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.
Speaker 1 (19:44):
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 because I sense that
this is another moment of constraint. And I think Silicon
(20:06):
Valley and you you're an investor now, and we'll get
to that, like got very noisy, right, and a lot
of people outsourced, outsourced, outsourced, and there was this certain
heart back in two thousand and eight, two thousand and
nine which made way for companies like Airbnb and Uber,
and you know, there were things that got solved that
I think were really interesting and really changed things. And
(20:27):
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 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
(20:50):
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.
Speaker 2 (21:05):
Yeah, I mean, 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 part
of it. I hope I'm the one funding it, right,
(21:26):
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 be
(21:46):
a part of it.
Speaker 1 (21:51):
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
(22:12):
two thousand and eight two thousand and nine, Like we
saw Airbnb, uber Lyft, task grabbit. 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 are like ripe for some disruption right now.
Speaker 2 (22:31):
Well, back in two thousand and eight, it 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, Uberlyft, task grabbit. Now there's
this whole step function change in how we're working. We're
all working remotely from home. Work will never be the
(22:55):
same again. It's been now almost two months of sheltering
in place, we're 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 going to be so hard, I'm working from home.
And then you know, Zoom just completely took off and
(23:18):
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 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 we'll, you know, as soon as this shelter
(23:39):
in place is 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 they haven't been stress tests the
(24:02):
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 worked 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,
(24:23):
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,
(24:43):
I mean telemedicine. Just the necessity of it has just
blown up. But again, like the tools 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 in telemedicine. And then the third area
I'm really excited about and watching closely is just education.
(25:05):
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 great tools or platforms that have
(25:29):
emerged as the leaders in that space, particularly for elementary education,
and so I think that's a huge opportunity that we'll
see innovations around as well.
Speaker 1 (25:38):
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, it's like you've got to
be all in or you're all at it. There's something
(25:58):
that feels a little bit like it doesn't one hundred
percent mirror the human experience. And this is me putting
on my tech in humanity hat, and I think you're right.
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
(26:19):
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 what you end
up investing in. Do it quick, please, Lea be very interesting.
I want to go back to the early task Gravit days.
Sorry to take you on that tangent. I just think
it's so fascinating and you're such an interesting person for
(26:42):
me to pick your brain on this, because you were
at the beginning of this, 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 og task Rabbit, which I think is just fascinating.
But then I saw that you actually went on Craigslist
to try to find task Grabit people. This is before
(27:03):
you guys have extensive background checks and all this kind
of stuff. And that was even when I interviewed you
in twenty eleven. I remember asking you about that. But
back before that, you went on Craigslist for your earliest
task people of a task Grabbit, and the way you
decided if you would hire people was if they were
(27:24):
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.
Speaker 2 (27:37):
Right. Yeah, Well, I realized that I couldn't actually do
it all if this company was going to scale 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
(27:58):
rabbits in person over 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.
I didn't have kids at the time, or else I
would have, you know, thought about putting them in my house.
(28:19):
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, oh, okay, yes,
I definitely trust this person to, you know, drop groceries
(28:41):
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 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.
Speaker 1 (29:00):
That The thing is, like, I don't think people realize that.
I just want to like set everyone back like eight
ten years. Like 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 carvia and app
(29:20):
or like would you ever hire a stranger to do
a chore for you? Because I remember those were my
lead INSes 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 is a
little insane, and I think that's important for people to understand.
(29:41):
I'm sure when you started out people kind of said
no or kind of looked at you a little bit
like this girl's 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.
Speaker 2 (30:00):
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
(30:24):
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 twenty ten, twenty eleven, and liftin 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
(30:45):
going well, and that's the hardest time to make a change.
But behavioral changes come when there's stress on the system.
Speaker 1 (30:53):
Do you remember out of curiosity, just like go back
with me in time, do you remember the biggest know
you got or the most like the most frustrating no,
or because you went to I'm sure a lot of investors,
or you left a job that was cushy, Like, you know,
do you remember any specific interaction that sticks with you
(31:13):
of someone who just did not believe in you or
this idea?
Speaker 2 (31:17):
Absolutely, like just more than one, honestly. 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
and nine. I mean, it's a long time where I
would just meet with investors, angel investors, vcs. Now. At
(31:39):
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 a venture
as well. But you know, I remember talking to, you know,
(32:03):
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, like what 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,
(32:23):
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
(32:46):
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 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
(33:09):
whether that was going to be a long standing trend
or if it was just a fad.
Speaker 1 (33:14):
Wow, that's interesting. I saw something you wrote that I
thought it 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
(33:35):
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 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.
(33:55):
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 love to
where the wild things are. What was your big audacious
goal and then what were the baby steps that you
(34:16):
had to take to achieve them.
Speaker 2 (34:20):
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 Aaron'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
(34:42):
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 they be like, oh, that's a service where I
can you know, get my dry cleaning picked up or
get my groceries to li And yes, that was the
(35:02):
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
(35:24):
harry 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
(35:45):
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 to take baby steps to get there and tie
all the dots together. It was like, you know, putting
(36:06):
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
(36:27):
you know, continues to evolve today. But that wasn't apparent
in two thousand and eight, two thousand and nine, in
twenty ten. 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.
Speaker 1 (36:47):
When you look back and you talk about having these
big goals and you can have the luxury of perspective
and you kind of look at what you were able
to do. You know, no one 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 were the kind of person
(37:07):
who has the ability to have these big, lofty, as
you call them, like hairy 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 grab it that you just felt like that
this was just like a very very dark dark space
(37:29):
for you that you felt like a failure in some capacity.
Speaker 2 (37:35):
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 ask 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 thirty percent of the team, huge failure near
the end of the company, when we were getting acquired,
(37:56):
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 and away from the web. So it's like
(38:18):
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
(38:38):
went down, or you know, really exciting things happened too
our big fundraises that we did and announced. 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
(38:59):
my thought feel great about the highest highs when I
knew that around the corner there was gonna be a
failure or a 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.
Speaker 1 (39:19):
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 the extremes.
Speaker 2 (39:34):
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 it high, you're
kind of like all right, but like remember last week
when you had that big low, And I think over
(39:56):
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 when
you know you're the one staying level. It's like, you know,
sharing that experience in perspective with the team, And yes,
(40:17):
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 a 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
(40:39):
at a time where everything was super super difficult, it
kind of gave us the perspective that, like, even when
things are 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.
Speaker 1 (40:57):
Okay, we've got to take a quick break to hear
from our sponsors more with my guest. After the break,
(41:17):
I want to go back to you talking about having
to lay off folks. 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.
Speaker 2 (41:36):
Yeah, I mean that was the lowest low of the
entire company. Out of everything I experienced, was doing that layoff.
Speaker 1 (41:46):
What was the hardest part of it.
Speaker 2 (41:49):
It's just failing those people. It 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 in business development.
(42:09):
But it's like, whose fault was it that we over
hired in some areas and we underhired 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
(42:33):
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
(42:53):
team or managing the team, it was hard for me.
You know, I felt a lot of empathy with people
that I'd 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, and so
that was hard. But you know, with perspective and with
(43:14):
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
(43:37):
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 going to 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. And so it's it's not easy
(44:00):
and it's very emotional.
Speaker 1 (44:01):
Do you remember what you said that morning?
Speaker 2 (44:04):
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
(44:26):
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 going to be sustainable. And guess
what in most companies, like eighty 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
(44:46):
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
(45:07):
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 team members and their managers to talk
(45:30):
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
(45:50):
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 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,
(46:12):
if not everyone can stay, that is terrible, 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 made this kind of mutual agreement between
the company and the people that stayed that they were
going to be in it. And it may not have
(46:33):
been easy, 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.
Speaker 1 (46:41):
How do you know how to lead like that?
Speaker 2 (46:43):
Right?
Speaker 1 (46:43):
Like it's like 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?
Speaker 2 (47:04):
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 and task grab it 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?
(47:25):
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 got to know who's there and
(47:47):
who really wants to be there. And 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 this same package
and we had two or three people walk.
Speaker 1 (48:03):
I was gonna say, did anyone walk? Yeah? They did.
Speaker 2 (48:06):
Wow, we had two or three people walk.
Speaker 1 (48:08):
And how did that feel it?
Speaker 2 (48:12):
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. So
(48:34):
I think it was relief in the end.
Speaker 1 (48:36):
That's such an interesting story. You know, this is such
a This is such a moment to kind of slow
down a little bit. 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. So what happened? You know what? When you
(48:58):
talk about ending up in the hostelpitle 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 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?
Speaker 2 (49:21):
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 COO, and a couple of other
execs on the team what was going on. But it
was a three million dollar raise. Now, we had raised
like forty five million dollars to date, we were close
(49:43):
to profitability, the business was doing well, and we were
short this three million to get to profitability. And so
I was like, this is going to 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 rays. I mean, way harder than what
I did even in two thousand and eight. And there's
(50:05):
a lot of different reasons for that and different dynamics
for that. Some of them I understand more now as
an investor, but at the time it was just 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
(50:26):
of stumble Upon, and we were walking and you know,
we're like, oh, this is so stressful. And he was
going through a raise and 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 my stomach
(50:46):
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
(51:10):
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
(51:31):
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, this goes stress ahead.
Speaker 1 (51:39):
When you're sitting there and you have like a stress
in 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?
Speaker 2 (51:48):
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 going to 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. I actually stayed in the
hospital for five days. They pumped me full of antibiotics.
(52:11):
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.
Speaker 1 (52:28):
Oh my you still let it greenish.
Speaker 2 (52:32):
I mean, I don't know. 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 his COVID time, it is
(52:53):
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,
(53:14):
just really taking care of your physical, mental, and emotional
health as well, because I've been at points where I've
hit the wall, where it hasn't been sustainable. It's just
not a good place for anyone to be.
Speaker 1 (53:28):
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, and there were lots of
good moments, and I like that you included our CNN
interview in one of them.
Speaker 2 (53:38):
I'll take that.
Speaker 1 (53:40):
But was there a moment that you felt in all
of this that you had made it.
Speaker 2 (53:47):
Here's the moments that I look back on the most
and think that made it all worth it. And we
were lucky because at task grab It, we had these
little interactions in these little story every single day of
amazing things that would happen on the platform, just matches
that were made or you know, interesting stories that happened,
(54:08):
and those were the moments that we really held on
to 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. We're
open in Boston and San Francisco. And at the time,
there was this woman in San Francisco who posted on
task grabbit and that she had a twenty year old
(54:29):
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 grabbit to find someone to
go to the hospital to bring them a healthy meal
from Whole Foods and a cozy blanket from her and
(54:51):
sit with him every day for a week during his
treatments and then call her afterwards to tell her how
her son was doing. E scare 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, just two markets
open very early days. It was like twenty ten. I
(55:13):
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 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.
Speaker 1 (55:34):
And you guys eventually sold to Ikea. Did you feel
like you could breathe because you talk about that rollercoaster?
What was the feeling after the papers were signed?
Speaker 2 (55:45):
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
(56:06):
years it's going to be gone. And so I was
the last one to vote. We were a bored of
I think seven at the time. I was the last
one to vote. We all went around very dramatically. We
were like, yes, I approve, 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
(56:27):
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, that helped shift
me out of the day to day and shift me
(56:48):
out of the business because I had now this newborn
at home, and so it was like a lot of
personal life changes as well that sort of were 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.
Speaker 1 (57:09):
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.
Speaker 2 (57:20):
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, my very normal,
very normal day. Yeah, but I definitely remember that moment
in feeling like whoo. I felt like I was standing
like on the edge of a cliff and it was like,
I've got a jump. This is it.
Speaker 1 (57:43):
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?
Speaker 2 (57:55):
So you know, for me, I've told the story that
I found a task Grabit 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,
(58:18):
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 ar 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
(58:39):
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
(58:59):
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
(59:20):
great move for me.
Speaker 1 (59:22):
Yeah, and I read something that 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
(59:44):
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
(01:00:07):
of a global pandemic. What advice do you give them?
Speaker 2 (01:00:12):
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
(01:00:34):
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
(01:00:55):
were carving out time and space for yourself as far
as as 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
(01:01:16):
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 Fuels Portfolio is we're
holding weekly meditation sessions for our founders over zoom. You know,
we're trying to connect founders with resources around healthy eating
(01:01:40):
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, even if it's just
like ten minutes a day to just like sit quietly
and make your mind stop, you know, wish that I
(01:02:00):
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
(01:02:22):
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
mental health standpoint.
Speaker 1 (01:02:37):
And if you could go back and you know, tell
two thousand and eight Leah building out Task Grab It
Anything as you now having kind of just gone through
this huge journey and being on the other side of it,
and even now at this crazy moment, what would you
tell her.
Speaker 2 (01:02:57):
I've been just recognizing 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
(01:03:19):
a time that's really chaotic and really hard, it's going
to make you operate differently. It's going to 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 their behavior along with
you is you know, it's like no other time, and
(01:03:42):
so I'm glad I went for it, even though it
was just a crazy, crazy journey, and so I encourage,
you know, other people to go for it.
Speaker 1 (01:03:50):
To 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
(01:04:11):
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 for us 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
(01:04:35):
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,
(01:04:56):
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 you're interested in.
My number is nine one seven five four zero three
four one zero. Also, a lot of you been texting
(01:05:17):
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 shout outs. The first is Frontline Foods. It's five
hundred 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
(01:05:38):
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
(01:05:59):
to our show notes. Follow along on our social media.
I'm at Lori 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 Lori Siegel
and Derek Dodge. This episode was produced and edited by
Sabine Jansen and Jack Reagan. The original theme music is
(01:06:22):
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 Lori Siegel and this is first contact. First contact
(01:06:48):
with Lori Siegel is a production of Dot dot Dot
Media and iHeartRadio
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