0:00

from day

0:02

one, the highest volume

0:04

task on the site was

0:07

always IKEA furniture assembly. From

0:10

day one. I mean, I

0:12

was like going to IKEA, getting these flat

0:14

packs with my little Allen wrench, like putting

0:16

IKEA furniture together. So

0:18

it was

0:20

always a popular task, okay?

0:27

And I would always, you know, I'd give

0:29

these talks and be like, can anyone in

0:31

the room guess the most popular task on

0:33

TaskRabbit? No one would ever guess it

0:35

was always IKEA. TaskRabbit

0:39

can help you find someone handy to do

0:41

all sorts of work, like assemble a bookshelf,

0:43

pick up your dry cleaning, or help with

0:45

the yard work. And that's

0:47

Leah Sullivan, who founded the company and

0:50

in the early days especially, often did

0:52

the tasks herself. She

0:54

grew the company to impressive scale and

0:57

then became laser focused on a perhaps

0:59

non-obvious partner, IKEA. They

1:02

were on our dream list for a long time. We want

1:04

to be in store. We want to be part of

1:06

their checkout process, you know? But

1:08

they were really very elusive, very

1:11

difficult to get to. Private company,

1:13

family owned out of Sweden. And

1:16

at that point, we were live

1:18

in London internationally. London was our

1:20

fourth largest market. It happened

1:22

to be IKEA's first largest market in the

1:24

world. Leah convinced IKEA

1:27

to pilot a partnership with TaskRabbit

1:29

in London. You'd buy IKEA

1:31

furniture on checkout, you could sign

1:33

up to have TaskRabbit deliver it and assemble it.

1:36

Drove up average order value immediately for IKEA.

1:39

They were psyched. And

1:43

we were excited we had all these new customers. I mean, it

1:45

was a win-win. It was so obvious. We

1:49

were not thinking acquisition, but

1:52

IKEA started thinking acquisition. That

1:57

led Leah to successfully exit her Boston

1:59

founded Texas. startup to a Swedish

2:01

furniture giant. TaskRabbit's

2:03

scale stories about meeting customers'

2:06

timely needs and Leah's ability

2:08

to leverage transformative technology. You

2:13

got to have incredible talent at every position.

2:17

There are fires burning when you're going out. Can

2:19

you believe it? Such an idiot. And

2:22

then you go back to, this is totally

2:24

going to be amazing. There are so many

2:26

easy ways. I have no idea what

2:28

to do. Sorry, you made a mistake. But you have to

2:30

time it right. Oops. Or can you

2:32

have a free vegetable party? So it just

2:34

seems absolutely nutballed 10 years later. But well,

2:36

that's just how you do it. We haven't

2:38

made just how you do it. This

2:43

is Masters of Scale. I'm

2:51

Jeff Berman, your host. Leah

2:54

Sullivan founded TaskRabbit in 2008 and helped

2:56

lead the company as it expanded to

2:58

more than 40 cities. We'll

3:01

hear more about that impressive scale story later.

3:04

First, I wanted to hear about her second act. She's

3:07

now a general partner of an early stage

3:09

fund called Fuel Capital. Leah,

3:14

welcome to Masters of Scale. Thank you so much for

3:16

having me. I'm thrilled that you're here. Before

3:19

we get to how you

3:21

built a company and sold it to IKEA,

3:23

you've been doing Fuel Capital now for how

3:26

long? Almost eight years. Yeah,

3:29

almost eight years now. And what made

3:31

you decide to stop being an operator and start being

3:33

a VC? It was a

3:35

big decision to go over to the dark

3:37

side, as some would say. I

3:41

really started TaskRabbit out of a place

3:43

of being a technologist.

3:45

My background is engineering. I love

3:47

technology. And I sort of

3:49

accidentally started this company and it

3:52

took up 10 years of my life and

3:54

had a great outcome and it was an incredible

3:56

journey and that was all good, but

3:59

at the end of it. that I had felt

4:01

like I had missed out on

4:03

other emerging technologies that were forming

4:05

and I was excited to kind

4:07

of be able to dig in

4:09

and learn and I wanted

4:11

to do something next that stayed

4:14

within the realm of entrepreneurship

4:17

but allowed me to kind of continue

4:19

to expand my learning and work with

4:21

more founders. So I'm curious when

4:23

you're either vetting entrepreneurs or

4:26

you're coaching your portfolio leaders,

4:28

what are you drawing on from your own

4:30

experience that is surprising to you? What do you

4:33

find yourself going to with them? I mean,

4:35

a lot of PTSD. Yeah. I

4:38

mean, honestly, it's just, I have so much

4:40

empathy for the journey and

4:42

the process. And

4:44

I had a very complicated

4:46

board dynamic at different points

4:48

in my TaskRabbit journey and

4:51

I was always super sensitive to

4:53

the imposition that an investor

4:55

can have on a founder. And

4:58

I always wanted to be that investor that

5:00

was gonna be really helpful and

5:02

was kind of the back channel

5:05

call or the back channel reference.

5:07

And I've been very careful to

5:09

not be in imposition. So I

5:11

think it's really about having sort

5:13

of that personality, that low ego,

5:15

that sense of humbleness that you

5:17

can bring to a board

5:19

meeting that allows you to ask good

5:21

strategic questions and not just asking questions

5:23

for the sake of asking but

5:26

to really understand deeply the business

5:29

and how you can be helpful. As we sit here, if

5:31

my math is right, we're about 16 years after you

5:34

found a TaskRabbit. Sounds crazy to me. What

5:36

is different that is not

5:38

obvious starting a company

5:40

today than when you

5:43

started TaskRabbit? I mean, I

5:45

think a lot of things are very

5:47

different. I mean, let's start with the

5:49

technology stack first. I

5:52

left my job as an engineer at IBM where

5:55

I was programming in C++ and Java. We

5:57

were burning CDs and we were shipping them

5:59

around. the world on an 18 month cycle.

6:02

For some of our audience, we're going to have to explain what that

6:04

is. But yeah, go ahead. Okay. Now

6:06

I'm working with a couple startups and

6:08

advising that are building AI products. Okay.

6:12

This is a different game. We're

6:15

talking GPUs. We're talking very expensive.

6:17

We're talking one server, one

6:19

GPU can run one thing at a time.

6:22

And I'm like, how do you launch this to the

6:24

masses? I don't

6:27

understand. And so I

6:29

think that technologies like AI, it's

6:31

a big game changing technology, but

6:33

the costs are still so high

6:35

to launch something. I think startups

6:37

need to raise a lot more

6:39

money to get started right now

6:41

today than I did. I

6:44

mean, I started with 250K from angel investors,

6:46

right? And that got me pretty far. Is

6:52

the cost of especially an AI driven startup

6:54

right now, is that making you

6:56

hesitate more about making investments? Is that changing

6:58

how you invest? It absolutely is

7:01

changing where I think

7:03

it makes sense for

7:05

early stage, small

7:07

funds to invest. I

7:10

mean, it's almost like when we used to

7:12

look at hardware companies and we're like, whoa,

7:14

this is going to take way too much

7:16

capital, like ROI on our investment. The math just

7:18

doesn't work for our fund. I

7:21

mean, I think to some extent to

7:23

some of the big AI companies, you see the

7:25

same thing. And so you see the big players

7:27

like Andreessen, or you see Microsoft investing in open

7:30

AI. You need really, really

7:32

deep pockets to be successful. I think it's

7:34

harder for the small funds to play here.

7:37

Yeah. Okay. I'm

7:39

going to take you back to winter 2008.

7:42

It's a snowy night in Boston.

7:45

It was a dark, snowy night. It was

7:47

literally, right? It really was actually. It was a

7:49

big snowstorm. And so what

7:51

happened that night that gave birth to what

7:54

became TaskRipping? So

7:57

I was getting ready to go out to dinner. called

8:00

a taxi to come pick me up.

8:03

We were meeting friends, and we

8:05

realized we were out of dog food.

8:08

And we had this 100-pound yellow lab

8:10

named Kobe at the time. Amazing, amazing

8:12

dog. And I thought,

8:14

you know what? How

8:17

are we gonna get this dog food? This is such

8:20

a stupid problem. We're gonna be late for a reservation.

8:22

Are we really gonna stop on the way home while the stores

8:25

will be closed? The iPhone had

8:27

just come out four months earlier. And

8:29

I grabbed my iPhone, and I thought, why can't

8:32

I use this device to connect

8:34

with someone right now in real time

8:36

and get the dog food? You know,

8:39

at that time, no one was using location-based

8:41

awareness in their tech stacks to pinpoint where

8:43

people were, right? Because the iPhone had just

8:45

come out. Facebook was just

8:47

sort of breaking out of the college scene,

8:49

becoming more mainstream, but no one was really

8:51

leveraging the social graph to build trust between

8:53

users. But for me

8:55

as an engineer, I saw these three

8:58

technologies, social, location, and mobile, and I

9:00

thought, there's a lot here. There's

9:02

a lot that we can do. And

9:04

so that was really where the idea for

9:07

TaskRabbit was born. I used my iPhone at

9:09

that moment, and I thought, okay, if such

9:11

a site existed, what would it be called?

9:13

And I typed in the domain name runmyaron.com,

9:16

and it was available on GoDaddy for $6.99, so I bought

9:18

it. And then

9:20

for the first 18 months that we existed, we ran

9:22

under that name. But at the

9:25

time you had this idea, and the

9:27

URL's available, and you're putting these new

9:29

things together, you've got a

9:31

pretty good job at IBM. I have a

9:33

great job at IBM. So did

9:35

you decide to jump right away, or did you take

9:37

your time? How'd you play it? It took me a

9:39

little while, and really thinking back to that time, I

9:42

realized that a couple things. One,

9:44

I started out

9:46

as a quality engineer at IBM, not

9:48

as a programmer. And

9:51

I had a background in computer science, but

9:53

I got my first job as a QA

9:55

engineer. And so I was looking for bugs

9:57

in the code, them

10:00

and then I'd pass it to the engineers to fix.

10:02

It took me a really long time for them to

10:04

move me into an engineering role. I had to really

10:06

fight for it. I actually had to get a job

10:08

somewhere else and come to them with an offer and

10:10

say, this person's willing to hire me as an engineer.

10:13

And do you think that was misogyny? Do you think

10:15

that was... At that time,

10:17

honestly, probably

10:19

a little bit. And I was

10:22

also pretty young. I was

10:24

in my early twenties at the time. I

10:26

was young, female. I

10:28

saw young men come out of

10:30

college and get the engineering job and that

10:32

always bothered me. But

10:34

it was also a track at IBM in

10:37

a big company where you had to pick

10:39

if you wanted to be a technical track

10:41

or a managerial track. I loved

10:43

being on the technical side. I think they thought I'd

10:45

be better on the managerial side. Again, I'm not sure

10:47

if it was because I was a young woman. I

10:50

mean, honestly, you can ask anyone about my

10:52

people management skills. I think my

10:54

technical skills are better. I'm

10:56

guessing you're pretty good at both. Yeah, I mean,

10:58

but you know. So

11:01

I was a little bit frustrated, to be honest

11:03

there. I had spent eight years there. And

11:06

did you have a mindset of like, hey,

11:08

30 years in a Goldwatch is still a

11:11

career choice? That is the model I had

11:13

seen in my life. My father spent 30 years

11:15

in the Air Force. No one

11:17

in my family was an entrepreneur. No

11:19

one had started their own business or company or even

11:22

worked for a small company. My parents

11:24

were extremely proud of me getting the job at

11:26

IBM. Sure. But there was always

11:28

this nagging, you can do more, you can do more,

11:30

you can do more. And

11:34

so I think I started to kind of

11:36

follow that curiosity. And

11:39

when I saw these new technologies

11:41

develop and emerge, I just started

11:43

playing around with them, nights and

11:45

weekends. And

11:47

I think that's what sort of started

11:49

to pull me away and drive me towards,

11:52

if you have a great idea, maybe you could

11:55

actually go build it, you could go start it.

11:58

But it was a big decision. And

12:00

it wasn't an easy decision to leave. I

12:03

ended up cashing out to start the

12:05

company, my pension from IBM. Wow. That's

12:08

a big decision. How did you get to the point

12:10

of saying, I'm maybe not

12:12

going to burn the boat, but like I'm

12:15

going to go and do this and give

12:17

up a very safe, very secure, prestigious career

12:19

track? I'm not sure exactly

12:21

what gave me the confidence to do it in

12:23

that moment. But I think I remember being eight

12:25

years old and asking my father what the highest

12:27

position in a company was. And

12:30

he told me it was being a CEO. And

12:32

I remember asking him that question when I

12:34

was eight and then creating my first startup,

12:36

which was this recycling program in my elementary

12:39

school. Wow. I liked being the boss. Yeah.

12:41

And I think, so I had the personality

12:43

that was like, I have the ideas, I

12:45

like being the boss, I like organizing things

12:48

and people. And then I think

12:50

as I built up the skill sets, I sort of realized,

12:52

you know what? Maybe I could do this. I

12:54

think a key person, though, a key mentor

12:56

that really got me over that hump was Scott

12:58

Griffith, who at the time was the CEO

13:00

of Zipcar. How'd you get to him? It was

13:03

complete serendipity. I was out to dinner one

13:05

night with friends, telling them about the idea. And

13:08

this one woman said, oh, you know who would love

13:10

this? My friend Scott. You should email him. Here's his

13:12

email, scott at zipcar.com. You know, just go shoot him

13:14

an email. This was on a Saturday night. I was

13:16

like, okay. I didn't know he was the CEO. And

13:19

so I emailed him, cold email. I said, oh,

13:22

your friend said I should email you about this

13:24

idea. He writes back Sunday

13:26

morning and he's like, why don't you

13:28

come by my office this week? And I see that

13:30

he's the CEO of Zipcar. And I'm like, OK, I

13:33

should prepare for this meeting, you know. And

13:35

so I got lucky. And then Scott and

13:37

I just really hit it off. I'm curious,

13:40

because so many of

13:42

the entrepreneurs who we talk with on Masters

13:44

of Scale have a similar story where they

13:46

were at a company, they had a job

13:48

and they didn't leave right away. They spent some

13:50

time working on nights, weekends, whatever. When entrepreneurs are

13:53

coming to you and they're in that position, they

13:55

work at Meta or Microsoft or whatever it is,

13:57

but they have this thing. What

14:00

advice do you give them about when to make

14:02

the jump and actually go to it full time?

14:04

It's really hard to be all in on something

14:06

if you have a day job. So

14:09

I do believe that you have to give it

14:11

your all. You have to dedicate your all one

14:13

way or another. I'm also

14:16

very sensitive that not everyone has

14:18

the access, the opportunity, the privilege,

14:22

just to be able to do that without a safety

14:24

net. So I'm very sensitive to that

14:27

fact as well. But

14:29

I sort of look back on my journey and it was

14:31

like the $27,000 pension plan, any

14:35

little thing. It was the credit cards

14:37

that took me time to pay off,

14:39

whatever it was. And so

14:41

my advice is if you

14:44

really have conviction around something, you are

14:46

gonna find a way. You're

14:48

gonna find a way to go for

14:50

it. And

14:55

so many startups fail too. So

14:57

many ideas are just not good

14:59

or the timing's not right or

15:01

the market's not right. And

15:03

so I'm always digging in with entrepreneurs

15:05

too that aren't sure. Like

15:08

is this the idea? Is this the

15:10

thing? Is this the thing? Cause it's

15:12

a lot to sacrifice if it's not

15:14

the thing. If it is the thing,

15:16

it's a lot to sacrifice. Yeah and you have to

15:18

sign up, be ready for it to be a 10

15:20

year plus journey and to your point, it's seven people

15:22

in a room and if the trash needs taking out.

15:25

You're taking it out. Absolutely,

15:27

yeah. And I

15:30

leave my job at IBM, I wake up the next

15:33

morning and I just start coding.

15:35

Like I like roll out of bed. You're a

15:37

one woman band. And I just code for

15:39

like, I don't know, six weeks straight. And

15:43

it's all in my head and I gotta get it

15:45

out of my head. And so I got

15:47

a first version built. And

15:50

sort of what was very helpful in

15:52

that time was I spent

15:54

a lot of time locked away in a room

15:57

coding but I also spent a good

15:59

portion of time. at a little coffee shop

16:01

surrounded by people. And I would

16:03

pull people over. I'd grab them and be like,

16:05

hey, let me tell you about this product. I'm

16:07

like, would you use this? And like, how does

16:10

this interaction feel to you? I mean, I would

16:12

get people in real time and the little coffee

16:14

house, Zumi's coffee shop in Charlestown was super nice

16:16

to me and let me hang out there and

16:18

talk to their customers all the time. Free wifi,

16:21

free refills, you get to go. Yeah, it was

16:23

a lot. And it

16:25

took six to eight weeks to get something

16:27

built that I felt like was ready for

16:29

people to use. And then

16:32

I said, okay, I need to find people

16:34

that are gonna do the jobs. So I

16:36

went on Craigslist, put out an

16:38

ad for someone to run errands and

16:41

I was completely overwhelmed by

16:43

the number of people. Deloshed. Oh

16:45

my gosh. I mean, it was September

16:48

of 2008. The

16:51

stock market had crashed. Everyone was being

16:53

laid off. I had lawyers coming to

16:55

me, teachers looking for work. I mean,

16:58

talk about timing. And I didn't plan

17:00

the timing like that, but it turned

17:02

out to be the perfect time to

17:04

launch a company like TaskRabbit. And so

17:06

the supply side, the taskers or the

17:08

people running errands, it

17:12

was overwhelming. And so

17:14

I hand interviewed every single person

17:16

because I was

17:18

very worried from the beginning around trust and safety.

17:21

And again, this was long before you jump into

17:23

a stranger's car, feel okay about that. I

17:26

started with 30 taskers that I handpicked.

17:28

That's a big number. It was a

17:30

lot, but I felt like for

17:32

what I wanted to do for the launch,

17:35

I found this mother's group in Boston. It

17:37

was 900 moms in one square mile, but

17:39

they were very concerned about trust and safety,

17:41

right? And so I was like, okay, if

17:43

I launch a closed beta just for them,

17:45

I just built it for them. And I

17:48

found 30 taskers that I

17:50

hand selected. Wow. And

17:52

then that's how it started. Still

17:56

ahead, Helia scaled TaskRabbit from a

17:58

single neighborhood in Boston. Austin to

18:02

a global business. Our

18:16

10-year anniversary as a company was coming

18:18

up and I said,

18:20

you know, I really want to do something big.

18:24

And we settled on the idea that we were going

18:26

to take a grand vacation

18:28

together. That's Capital

18:30

One business customer and Pinnacle Companies founder,

18:33

Chris Renner. At the

18:35

time, we had about 23

18:37

employees and we

18:40

chose to invite them and

18:42

their significant others to

18:45

a tropical vacation to

18:47

Mexico. Everyone honestly

18:50

thought we were crazy. It

18:52

was 10 years and it was time to

18:55

celebrate as a team. We had survived

18:57

the first few years of

19:00

every small business, the uncertainty of are you

19:02

going to make it or not. So

19:05

we planned this amazing trip

19:08

and we ended up at the

19:10

little beachside restaurant with

19:14

margaritas in hand and

19:16

toes in sand and

19:18

the sun was setting. It

19:21

was magical just to be there

19:23

together. Using his Capital

19:25

One Venture X business card, Chris was

19:27

able to apply his travel rewards to

19:29

fund his first company trip, which has

19:32

become an annual tradition. To

19:34

learn more, go to capitalone.com/business

19:36

card benefits. Welcome

19:38

back to Masters of Scale. You

19:41

can find this episode and more on the Masters

19:43

of Scale YouTube channel. And

19:48

so you do this closed beta, 30 taskers,

19:50

900 moms. What

19:54

do you learn from that? One of the main

19:56

learnings was I needed to be

19:58

the first tasker, the task rabbit. it as

20:00

well. And so I had this little

20:02

Vespa scooter I rode all over Boston

20:04

running people's errands. Wow. That

20:08

was the best learnings that I could get

20:10

about building this company. And

20:13

that's another thing I'll tell founders when they're

20:15

building their business, can you be a part

20:17

of the process? That is how you learn

20:19

about what customers want. Because taskers are customers

20:22

too. And so I needed

20:24

to understand how they were getting jobs,

20:26

finding jobs, how much money they were

20:28

making. Did that make sense for them

20:31

economically? What types of jobs, what types of

20:33

skills did I need to recruit? I mean,

20:35

it was so much learning. I learned very

20:37

quickly that by offering a

20:40

service where you could get anything done,

20:43

one, people had no idea what to post. Right.

20:46

It's unconstrained. You actually needed

20:48

constraints. Exactly. It was like blank space. No

20:51

one knew what to use the service for. And

20:54

then two, on the tasker side, I needed

20:56

people that could do a lot of

20:59

different things that weren't just specialized

21:01

in one or two things. Picking up

21:03

dog food is one thing, but fixing a leaky

21:05

pipe is another. Exactly. Leah

21:08

kept tweaking her Boston model, but was eager

21:10

to expand. A path towards

21:12

scale emerged when she learned about

21:14

something called the Facebook Fund for

21:16

early stage founders. It came with

21:18

significant strings attached. If she

21:20

accepted, she'd get just $15,000 and she'd have

21:24

to give Facebook 2% of her company.

21:28

People, everyone's like, no, that's crazy. And

21:30

I was like, it does seem crazy,

21:32

but it also feels like an

21:34

opportunity and a way for me to open

21:36

doors that I didn't have access to. Growing

21:40

up on the East Coast, not involved

21:42

in any sort of entrepreneurship, no network

21:44

in the startup world. And

21:47

so I was like, I know that everybody

21:49

thinks this is a bad idea, but I think there's

21:51

something here that I'm just going to make

21:53

it into something that's worth it. And so I

21:55

ended up doing it. So that

21:57

15K basically paid for all my flights back

21:59

in the West Coast. because I was running

22:02

the market in Boston. Boston was up and

22:04

running live. I have all these taskers and

22:06

moms and everyone using the service. And

22:09

then I spent a summer going back

22:11

and forth to Palo Alto to do

22:13

this incubator program at Facebook. The

22:16

program came, I assume, with other benefits

22:18

that an accelerator would come with. It

22:20

did. It did. Lots of

22:22

incredible opportunities to network. This is where I

22:25

met Tim Ferriss, who became an advisor. Right,

22:27

pretty good one. He introduced me to Ann

22:29

at Floodgate. He introduced me to Steve Anderson

22:31

at Baseline. I mean, they led my seed

22:34

round. So it really was turning that 15K

22:37

into the million dollar seed round I was able to

22:39

raise at the end. But from the

22:41

beginning, I was like, if it's

22:43

just about this 15K, this is not

22:46

a good idea. But if I can

22:48

turn this into something else, then

22:50

I'll be happy. Okay, so let's jump

22:52

forward a little bit. The company is

22:54

scaling. Things are starting to work. And

22:57

at some point you decide maybe you're not

22:59

the CEO of the company? Yep. What

23:02

happened there? I was an accidental solo founder,

23:04

and I always wanted that business partner. I think

23:07

it was after the Series A. I

23:09

said, you know, this is a real

23:11

company, and it's scaling, and it's turning

23:13

into something really incredible. I

23:15

really want to focus on product and technology. I

23:17

really want to find that business person. I said,

23:20

I'm open to a COO, and I'm

23:22

open to a CEO. I think

23:24

my mistake there was that the company

23:26

was still so young, it was still

23:28

so early, to remove the

23:30

founder as the leader. A

23:33

COO would have been fine. And in fact,

23:35

the second time around, we brought in an

23:37

incredible COO that's been on this podcast before,

23:39

Stacey Brown-Philpott. She really helped

23:41

me take the company fully to scale and

23:43

to exit. But at this point,

23:46

the company still needed the founder to be

23:49

the visionary and to be the leader. And

23:51

so, you know, we tried it. We had

23:53

someone come in for six to nine months.

23:56

We ended up hiring too many people,

23:58

scaling up too fast. The burn got really

24:00

high and it was just kind of like we

24:02

need to get back to basics here and regroup.

24:04

Yeah. There's a lot of discussion in the

24:06

world about finding your

24:08

technical co-founder. I think there's less

24:11

about the technical founder finding

24:13

their business co-founder. Right. So how

24:16

would you advise a technical founder to

24:18

think about that? If I could go back

24:20

and do it all over again, I would

24:23

have tried harder from the beginning to

24:25

find a co-founding partner. Before

24:28

I went to the incubator program,

24:31

maybe even before I left IBM, I

24:34

would have taken the time from the very beginning

24:36

to formulate the team that was

24:38

going to build it. And instead I

24:40

was like, oh, I can build this. I'm going to launch

24:42

it. We'll just kind of see what happens. And

24:45

I think if I could go back, I would

24:47

slow down those first few months and focus on

24:49

getting the right team in place. And

24:51

there's a theory of organizational growth in factors of

24:53

one and three. You're one company, one person at

24:55

three, a 10 at 30, at 100, 300, and

24:57

so on. What piece of that journey was hardest

25:03

for TaskRabbit? When we hit

25:05

50 people, I feel like everything broke.

25:07

What happened? Communications broke, cross

25:09

functionality between teams broke, the

25:12

culture broke, everything broke. It was

25:14

like, oh, wow. We're

25:17

not this small company anymore that where everything

25:19

just gels and jives and everything just works.

25:21

And of course, marketing and engineering are on

25:23

the same page because they're working on the

25:26

same things. And it's like, no, it was

25:28

not like that anymore. So I remember when

25:30

we hit 50 people, it was kind of

25:33

like, ew, we need other

25:35

processes in place now and we

25:37

need organizational structures. We need HR.

25:39

The whole company needed to transform

25:42

at that in-person customer service team.

25:44

And you actually need more structures

25:46

and policies and scripts and all

25:48

kinds of other things in place.

25:50

And so those transitions are hard,

25:52

but they're necessary. So what

25:55

did you learn from the CO

25:57

hire that didn't work out, that informed? bringing

26:00

Stacey Brownfield-Pott and

27:00

Stacey Brownfield-Pott and

27:30

Stacey Brownfield-Pott company.

28:01

So when IKEA was named the buyer, it

28:03

raised a few eyebrows. Leah

28:06

says the idea at first was just to

28:09

partner with IKEA. Okay. So

28:11

IKEA was a company that

28:13

was on my dream list

28:16

for a long time, because from

28:18

day one, the highest volume task

28:21

on the site was always IKEA

28:23

furniture assembly from day one. I

28:26

mean, I was like going to IKEA, you

28:28

know, outside of Boston, getting these flat packs

28:30

with my little Allen wrench, like putting IKEA

28:32

furniture together. So it was

28:35

always a popular task. Okay.

28:37

So they were on our dream list for a

28:39

long time. Stacy got on board, was

28:41

on Stacy's dream list as well. And we're like, we've

28:43

got to get into IKEA. We

28:46

want to do a partnership with them. We want to

28:48

be in-store. We want to be part of their checkout

28:50

process, you know. But they were really

28:53

very elusive, very difficult to get

28:55

to. Private company, family owned out

28:57

of Sweden. Right. How do you contact

28:59

IKEA? Right. No idea. You're going for

29:02

Swedish meatballs or being a chocolate people? Yeah, I

29:04

don't know. No, it was really hard. We

29:07

worked all kinds of different angles,

29:09

approaches. We finally, literally after a

29:11

couple of years, got this

29:13

random consultant who was

29:15

taking a bunch of companies on tour

29:18

from Europe to the U.S. One of

29:20

the companies on his tour group was

29:22

someone from IKEA. We're like, bring the

29:24

tour group by the office. We want

29:26

to meet the IKEA person and everyone

29:28

else that's there, too. The tour group

29:31

came by the office. We,

29:33

Stacy and I paid very special attention to

29:35

the IKEA exact, made sure she had our

29:37

business card. We got her business card. And

29:39

then that was the end. And that that's

29:42

where we were able to kind of follow up. We

29:45

pitched doing a partnership with them in-store.

29:47

That was the dream. And

29:50

at that point, we were live

29:52

in London internationally. London was

29:54

our fourth largest market. It

29:57

happened to be IKEA's first largest market in

29:59

the world. stage

34:00

raise and my Series

34:02

A investor kept saying, like, we're tapped out.

34:04

Like, we, like, we've invested this whole fund,

34:07

you know, like you were one of the

34:09

last investments in the fund. And

34:11

I'm like, that fund had already exited. They

34:13

had already done well. Like nothing that they

34:15

would have put in a task grab at

34:17

that point was going to move the needle

34:19

on that return profile. So they're not

34:21

going to put any more money in, right? That

34:24

was the biggest surprise to me as an

34:26

investor was I was completely missing some

34:28

of the dynamics that were very important

34:30

to my fundraises. So how does that

34:32

inform what entrepreneurs should be asking you

34:35

and other investors when they're raising money?

34:37

I would ask them, what are you saving

34:39

for me as a company? What

34:41

do you got earmarked for me in this fund,

34:44

right? And I think understanding that along the way

34:46

would have been helpful in planning

34:48

how and when we did fundraises. And

34:51

I had no concept of that, which

34:53

I think a lot of founders probably don't. But

34:55

that's all your investors are thinking about. That's all

34:58

they're thinking about. So it's completely

35:00

different than how you are thinking.

35:03

That's phenomenal advice. Thank you. It's a great

35:05

conversation. Appreciate you being here. Thanks for having

35:07

me. Since leaving

35:09

the CEO seat at TaskRabbit, Leah has

35:11

refined her reflections on the experience and

35:13

used them to transform her investing. With

35:15

that kind of self-awareness and flexibility, you

35:17

can hear how she'd make a great

35:19

advisor. And that, my friends, is no

35:22

easy task. I'm Jeff

35:24

Berman. Thank you for listening. Our

35:34

10-year anniversary as a company was coming

35:37

up. And I said,

35:39

you know, I really want to do something big.

35:42

And we settled on the idea that we were

35:44

going to take a grand

35:46

vacation together. That's

35:48

Capital One business customer and Pinnacle

35:50

Company's founder, Chris Renner. At

35:52

the time, we had about 23 employees.

35:57

And we chose to invite

35:59

them.