TaskRabbit: Leah Solivan

One snowy night in Boston, Leah Solivan ran out of dog food for her 100-pound yellow lab. She wondered: shouldn’t I be able to resupply Kobe without going to the store? That was the origin of TaskRabbit, an online errand service that matches users with “taskers” to do deliveries and other chores. When Leah left her IBM job to start coding the service, the peer-to-peer economy was still in its infancy. But she saw that three important developments—mobile, location services, and social media—were about to converge. She recruited errand-runners from Craigslist, and took an expensive gamble on a 15-minute meeting with Tim Ferriss to get advice and investors. After some management hiccups and a difficult rebranding, TaskRabbit sold to IKEA in 2017. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

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• 0:46Guy Raz?

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• 1:32Guy Raz?

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• 4:23Guy Raz?

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• 5:07Guy Raz?

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• 5:12Speaker 01

  So we're scaling up. And we're also realizing that the product now in 2011, it's just not working. It's just not working. And at this point, there are competitors coming out that are launching mobile-first, mobile-only. And we've been on the web. I mean, honestly, it's like the entire consumer market and expectation just changed underneath us, and we missed it.

• 5:49Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 6:01Guy Raz?

  I'm Guy Raz, and on the show today, how a hungry 100-pound dog on a snowy night inspired Lea Sullivan to launch TaskRabbit, a service that will take care of your errands.

• 6:16Guy Raz?

  Leah Sullivan's idea for a business grew out of a very specific problem she wanted to solve on one snowy evening in Boston. The problem of getting a big bag of dog food for her yellow lab to her apartment. And did she really want to go out in the middle of a snowstorm? Not really. But was there someone else who might be willing to do it for the right price? Now, that was an interesting question. But the thing Leah found most compelling about this problem was not that the solution might one day turn into a business. Instead, Leah, who at the time was an engineer at IBM, saw the problem as more of an engineering

• 7:00Guy Raz?

  challenge, like, do I have the coding skills I need to solve the dog food delivery problem? And if, for example, I were to start an online business for home deliveries, is the market ready for that to happen? Well, the answer to these questions turned out to be a resounding yes. Because not only did Leah know how to code, she also knew how to connect the dots. And at that time, in 2008, she was connecting three very important dots in particular, three technologies that were about to intersect in a critical way: mobile, location services, and social media. Those three developments would, of course, eventually power companies like Lyft, and

• 7:44Guy Raz?

  Uber, and Airbnb, and Instacart, and DoorDash. But as early as 2008, even before any of those companies came on the scene, Leah was coding the beginnings of what would become TaskRabbit. It's a marketplace that matches users with freelancers who provide all types of services, from delivery, to furniture building, to gardening. Working out of a Boston coffee shop, Leah found a group of moms to be her first users, and she recruited people from Craigslist to be the first errand runners. And over the next few years, as the company grew, it also navigated a series of hairpin turns, including some management shakeups and at least one major rebranding that was

• 8:27Guy Raz?

  hated by many of its loyal users. But TaskRabbit continued to grow. And nine years after launch, it sold to IKEA for an undisclosed amount. And Leah moved on, having created one of the best-known mobile marketplaces in the country. Leah grew up in a little town outside of Boston. Her dad ran training programs at a nearby air force base while her mom looked after the family. As a young girl, Leah was really into dance. But when she got to college at Sweetbrier in Virginia, she took her first programming courses and got hooked on C++.

• 9:04Speaker 01

  For me, it was the opportunity to be able to build whatever was in my mind. I mean, I am very imaginative. I have ideas all the time. And I'm not really good at delegation. And so the idea that I could take what was in my head and build it so that someone else could see it, or use it, or interact with it, was really exciting. I mean, I remember, it was the simplest, simplest assignment, which was taking this little JPEG robot and being able to code it so that with the arrow keys on the keyboard, it could move around the screen.

• 9:45Speaker 01

  And honestly, that was enough for me to understand how powerful programming and engineering could be.

• 9:52Guy Raz?

  Yeah. All right, so you fall in love with programming, C++. And this was your first exposure. Like, you weren't like a kid who had like, you know, the Apple II at home, and then like a PC clone, and you were using BASIC, and you were like, I don't know, reading computer magazines in high school?

• 10:11Speaker 01

  Yeah, no, well, so, not really, but a little bit. Let me explain. So, you know, programming in college was my first exposure to actual engineering. In high school, I dated someone who eventually became my husband, who I started TaskRabbit with, Kevin. And Kevin was really into computers.

• 10:32Guy Raz?

  Right.

• 10:33Speaker 01

  And so we would spend, like, Friday nights, I would help him build computers.

• 10:37Guy Raz?

  Oh, wow.

• 10:38Speaker 01

  We would go to computer shows on the week.

• 10:39Guy Raz?

  So you were plugging in the components into the slots?

• 10:42Speaker 01

  Yes, the motherboard, and the bus driver, and like...

• 10:46Guy Raz?

  I've done that once, twice, actually. It's fun.

• 10:48Speaker 01

  Twice, okay. Yeah, it is fun. We go to computer shows and buy parts, and that was very helpful.

• 10:53Guy Raz?

  Yeah. All right, so 2001, I believe, you graduate from Sweetbrier with a degree in computer science, and I think you get a job as an engineer at a small software startup, which I guess eventually gets merged into IBM. And what are you doing for them? Were you coding?

• 11:12Speaker 01

  I actually started as a quality engineer, so I wasn't doing any programming. They wouldn't let me touch the code, but I was the tester. So I would find all the bugs in the code, I would write up the bugs, and then I'd work with the developers and the engineers to fix them. I did that for five years, but I always wanted to be the programmer. I always wanted to be the coder. It was really hard for me to break into that side, though. And I saw other IBM interns coming in right out of school and joining as engineers, and I'm like, why aren't I coding? Why aren't I programming?

• 11:49Guy Raz?

  Because you knew how to do it.

• 11:50Speaker 01

  I did. I did. I finally, I finally worked my way into it. And the only way that was possible is I got another job offer at another startup to be a programmer.

• 12:03Guy Raz?

  Always the case. Story of my life.

• 12:04Speaker 01

  I know. So I was like, I can do this. I can go do it at this other company, or I can stay here and do it.

• 12:08Guy Raz?

  And they're like, no, don't go.

• 12:10Speaker 01

  Exactly. Oh, we really value you. Don't go. And so finally, I get to start coding, and I joined a new team. And I really loved that team in my time there. I still stay in touch with my mentors and technical leads there on that team.

• 12:26Guy Raz?

  Meanwhile, you got married really early, like right out of college, with your, to your high school sweetheart, right, Kevin?

• 12:33Speaker 01

  Yes. Yes. Yeah, I was 22.

• 12:36Guy Raz?

  Wow.

• 12:37Speaker 01

  He actually also worked at Iris Associates, which was bought by Lotus, and then Lotus was bought by IBM. And so we worked together there for many years. And then he left first. He left and started joining startups in the Boston area, focused mostly in the healthcare space. And I stayed.

• 12:53Guy Raz?

  Right. And it was a stable job. I mean, you had probably had health insurance. I'm sure you do. You had health insurance and a retirement plan. I mean, IBM's the mother ship, right?

• 13:03Speaker 01

  Yes.

• 13:04Guy Raz?

  So you were there for like, I think, seven, something like seven years or six years.

• 13:07Speaker 01

  Almost eight years. Almost eight years.

• 13:08Guy Raz?

  Eight years, wow.

• 13:09Speaker 01

  Yeah, yeah. It was consistently one of the top 100 places to work for women, and that mattered to me.

• 13:17Guy Raz?

  Yeah.

• 13:18Speaker 01

  And I thought, I can just stay here. I can move up. I always wanted to stay on the technical side. They kept trying to put me in management, go manage people. I was like, I don't want to manage anyone. But by the end, the last, the last couple of years, I felt a little bit loose in the saddle.

• 13:32Guy Raz?

  Hmm.

• 13:33Speaker 01

  I know for a fact that I was seen as very ambitious. And in fact, there was one incident that occurred on my team where, you know, one of the other engineers said to me, wow, Leah, you're really ambitious. And he said it like it was a problem.

• 13:48Guy Raz?

  Like they're criticizing you for being ambitious?

• 13:51Speaker 01

  Yes. And I was super confused. I, his tone, like, it didn't make sense to me. Exactly.

• 13:57Guy Raz?

  Yeah.

• 13:58Speaker 01

  But you know what? That actually was part of what made me realize that IBM wasn't the long-term fit for me. And I was really ambitious. And I did always have this sort of fire in my belly.

• 14:10Guy Raz?

  Yeah.

• 14:11Speaker 01

  And so I think people saw that. People knew. I mean, that's hard for me to hide.

• 14:15Guy Raz?

  I guess I should, we should also clarify. It wasn't, it probably wasn't even IBM. It was just a big company with a bureaucracy that wasn't gonna, you couldn't, it couldn't, it couldn't accommodate your ambitions, right? You, you had to do something and it wasn't gonna happen at a big company.

• 14:32Speaker 01

  That's right. And I think in hindsight, what I've realized, just a pattern in my career, a pattern in my life is, and really, I mean, back into college too, I only like to work on problems that I feel like I can uniquely solve.

• 14:48Guy Raz?

  Yeah.

• 14:49Speaker 01

  And if, if, if I feel like there's someone else who can also do it and do it just as well, like, I become very disengaged and very bored.

• 14:58Guy Raz?

  Yeah.

• 14:59Speaker 01

  And uninterested in working on it. And, and so I think that was where the ambition came from. And, you know, like, I was always thinking, like, I can do more. I want to be doing more.

• 15:11Guy Raz?

  All right, so you start to get itchy feet, right? You're starting to think, okay, I'm just getting bored here. And you're, you know, in your late twenties, right? And what's going through your mind? What do you, I mean, do you start to think like, maybe I could do something on my own? Maybe, I mean, were you searching for something? Or were you just, what do you remember about that time around 2007, 2008?

• 15:38Speaker 01

  Yeah, so at that point, we were living in Charlestown, a neighborhood of Boston. I was working out of the Cambridge office for IBM. And I did start to think, you know what? I have the skill set. I have ideas, like, maybe I should just go code some things. And I started a blog, mostly about technical engineering projects, ideas. There was one idea I had in the real estate space where I was, you know, doing these, going to open houses and doing write-ups about them and then letting, you know, buyers engage with the blog entry.

• 16:16Guy Raz?

  Oh, wow. Oh, you would write a review of the house, like, this house sucks, don't bother?

• 16:20Speaker 01

  Yes.

• 16:21Guy Raz?

  That would save a lot of time.

• 16:23Speaker 01

  Yes, and it was anonymous, right? It was all anonymous and no one knew it was me.

• 16:27Guy Raz?

  Terrible staging, don't go to this one.

• 16:29Speaker 01

  Yeah, absolutely. And it was really, yeah, it was really fun. I mean, I've since now invested in a company that's sort of doing, yeah, like, is doing a version of this. It's very exciting. But yeah, that was back in 2006, 2007. And so I also built a dog walking site for our dog walker so that he could expand his business. And then I started building dog walking sites for all of his dog walking friends. And then I had the idea for what became TaskRabbit.

• 16:59Guy Raz?

  So tell me how that happened? I mean, what, how did the TaskRabbit, what would become TaskRabbit? How did that idea first come to you?

• 17:09Speaker 01

  Yeah, so I was in this very entrepreneurial mindset. I was looking for a problem to solve. And so it was February of 2008. It was cold and snowing outside. It was, we're getting ready to go out to dinner in Boston with some friends. And we realized we were out of dog food. And at the time, we had this 100-pound yellow lab named Kobe, who we kept very well fed.

• 17:38Guy Raz?

  100 pounds?

• 17:39Speaker 01

  Yeah.

• 17:40Guy Raz?

  That's a, that's a human. That's not a dog.

• 17:42Speaker 01

  It's a big guy. He's a big guy.

• 17:43Guy Raz?

  It's another human in your house.

• 17:44Speaker 01

  He was, he was the best. Um, and so we realized we're out of this dog food and I'm talking with Kevin and I'm like, "God, there's gotta be a way to get this dog food. We're really gonna, we're taking a cab to dinner. We don't want to drag the dog food with us to dinner."

• 17:58Guy Raz?

  And you're talking about a 30-pound bag of dog food?

• 18:02Speaker 01

  Yeah, a big bag of dog food. That's right. That's right. What if all the stores are closed on the way home? It's snowing outside. And I was like, you know what? Wouldn't it be nice if there's just a place online you could go? Say you needed dog food, name the price you're willing to pay. There's probably someone in our neighborhood right now that'd be willing to help us out. And maybe there's even someone at the store at this very second and we should be able to connect with them.

• 18:30Guy Raz?

  Yeah.

• 18:31Speaker 01

  And the iPhone had just come out. And so I grabbed my iPhone and I was like, "We should be able to connect with whoever, who's ever at the store right now." I said, "Okay, if a site like this existed, what would it be called?" And I typed into my iPhone, uh, into GoDaddy, RunMyErrand.com. And the domain name was available for $6.99.

• 18:54Guy Raz?

  Great.

• 18:55Speaker 01

  So I bought it on the spot. And I was like, "Okay, well, we now own RunMyErrand.com. What are we gonna do with it?" And so we ended up going to dinner. We met friends at dinner. Like, it was that dinner where we're talking about this idea with friends.

• 19:10Guy Raz?

  You start talking about this idea. And let's say I was at dinner with you. I would have said to you at the time, because I'm like a buzzkill. Not anymore, but I would have been then. I would have said, but now I might still say to you. I say, but what about Peapod? That's around. Peapod exists. I know it existed in Boston in 2008. You could get Peapod to deliver food to your house.

• 19:30Speaker 01

  That's right. There's also a grocery company, I think Home Run or something like that.

• 19:34Guy Raz?

  That was around, right?

• 19:35Speaker 01

  Cosmo. Yeah, Cosmo had just like flamed out. All kinds of, you know, sort of dead companies in this space.

• 19:45Guy Raz?

  But before you got that discouraging news.

• 19:48Speaker 01

  Yes.

• 19:49Guy Raz?

  At that dinner, your friends were like, oh, my God, this is amazing, Leah. You should do this. This is incredible. Was it like that kind of dinner?

• 19:55Speaker 01

  Yeah, it was, but they weren't in tech either. So they were doctors. My friend, it was like a Sweetbryer College roommate who was going to medical school. I mean, they were kind of like, huh, that's interesting, you know?

• 20:07Guy Raz?

  And it sounds interesting. Like, I might have also said at the time, you know, I would totally use that. Yeah, I hate going on the snow. And this is before Uber. This is before like.

• 20:15Speaker 01

  Long before.

• 20:16Guy Raz?

  That we've now come to depend on, unfortunately, or fortunately, depending on your perspective. But.

• 20:22Speaker 01

  Yes.

• 20:22Guy Raz?

  I might have said to you, yeah, I would totally. If somebody could just like bring it to my house, I could just go online and.

• 20:27Speaker 01

  Absolutely, yes. It was, people were excited. It made sense. They're like, hold on, someone must be doing this. Like, this already exists. I mean, it was a lot of like, this must exist already. But I think the key, like, I knew as an engineer that no one was using mobile yet technologies. The App Store was just emerging. It was very early. I knew no one was using location-based awareness. And so as an engineer, again, I was like, I want to find the person at the store at this moment. How do I find that person?

• 20:59Guy Raz?

  Yeah.

• 21:01Speaker 01

  And then the other key for me, from a technical standpoint, was Facebook was just emerging and coming out of the college scene.

• 21:09Guy Raz?

  Yeah.

• 21:09Speaker 01

  And honestly, the biggest piece of feedback we got in the early days, including at this dinner, was why would I trust a stranger to bring something to me or to come into my house? What if they're, you know, an ax murderer? I mean, people would say this to me all the time.

• 21:25Guy Raz?

  Yeah.

• 21:25Speaker 01

  And so I saw Facebook as a way to leverage the social graph to build trust between people. So if I could tell you that, you know, you need your dry cleaning picked up and the person that was going to pick up your dry cleaning was two degrees of separation from you and your friend Bob, like, you're going to be OK with that.

• 21:47Guy Raz?

  But initially, the idea was to just have people run errands for you. It wasn't like to come and fix things in your house. It was just like, go get your dry cleaning, go get your groceries.

• 21:54Speaker 01

  Yes.

• 21:55Guy Raz?

  Right, OK.

• 21:55Speaker 01

  Yes, yeah.

• 21:56Guy Raz?

  And deliver food, whatever it might be.

• 21:59Speaker 01

  Yep.

• 21:59Guy Raz?

  And you had all of these, I mean, you had this kind of unfair advantage because of your background as an engineer. Like, you, you, did you understand intuitively how you could do this? Like, how, like, did you understand that the technology existed to make this possible?

• 22:19Speaker 01

  I did, and that was the key driver for me. I think as an engineer and as someone who wanted to work on something, I saw those three technologies, social, location, and mobile. And I, that was what was interesting to me at the time. It was like, I can mash up these three technologies and create a new platform that no one has launched before.

• 22:41Guy Raz?

  It is amazing because it is a very simple concept. It's have somebody deliver something to you. But the challenge was a technology challenge. It wasn't a...

• 22:52Speaker 01

  Yeah.

• 22:53Guy Raz?

  I mean, the idea was simple. You weren't coming up with... I mean, this is, people have been delivering stuff for centuries.

• 23:01Speaker 01

  That's right.

• 23:02Guy Raz?

  It was, how do you connect the person to the person who needs the service? That was what you had to solve.

• 23:09Speaker 01

  Yes, and I've always said, I am not the first person who had the idea for TaskRabbit. Many people have had this idea, many, many people. But it was the way that I leveraged the technology that was available at the time that made it all work.

• 23:26Guy Raz?

  By the way, same story with Google and Facebook. They did not invent those technologies, they just made them better.

• 23:32Speaker 01

  Yes, yes.

• 23:33Guy Raz?

  Right?

• 23:34Speaker 01

  And that's the cycle of innovation. I mean, just building sort of on the backs of what has come before you.

• 23:40Guy Raz?

  Yeah. Okay, so now, from what I understand, you're working at IBM and you're still employed there. You're not going to leave your job, but this idea stays in your mind. So much so that you really start to do the kinds of things that, that I think really smart entrepreneurs do, which is you first start to research it. You first start to kind of, you talk to people, you try to understand whether this is possible and viable.

• 24:06Speaker 01

  Yes.

• 24:06Guy Raz?

  But you reached out.

• 24:07Speaker 01

  The first person that was sort of pivotal that I reached out to was Scott Griffith, who was running Zipcar.

• 24:14Guy Raz?

  Wow, and Zipcar was really started to take off in 2008. I remember using it back then.

• 24:19Speaker 01

  Yeah.

• 24:19Guy Raz?

  I would just get my card and, you know.

• 24:21Speaker 01

  Absolutely, it was taking off. And he had taken over from the founders, from Robin Chase. And it was in Cambridge. And I met Scott through a friend of a friend. I mean, it wasn't an obvious connection. But again, we had been out to dinner one night with friends and talking about this idea. And my friend says, oh, my gosh, you know who you should talk to? My friend Scott, he would love this idea. I used to work with him back at my old company. I had no idea he was the CEO of Zipcar. She failed to mention this.

• 24:54Guy Raz?

  Yeah.

• 24:55Speaker 01

  And I emailed Scott this note. I'm like, hi, Scott, my name is Leah and I'm working on this new idea. And to his credit, you know, he wrote me back Sunday morning and he was like, wow, this sounds interesting. Why don't you come by my office this week? And then I see in his signature that he's the CEO.

• 25:11Guy Raz?

  Of Zipcar.

• 25:12Speaker 01

  Of Zipcar. And I, I lose my breath. I'm like, oh, my God, I can't believe I just emailed the CEO of Zipcar. Cold email.

• 25:21Guy Raz?

  So, all right, so, and when you told him the idea, how did you describe it?

• 25:26Speaker 01

  So I went to his office and I said, much like you're thinking about Zipcar, where you share cars in a neighborhood, I want to create a platform in a marketplace where you can share errands and share services. And he immediately was like, wow, I think you're on to something here. Let's meet again next week. And so he, he just was so brilliant and so nice. And he said, why don't you come by every week for an hour and sit with me and we can brainstorm. I was still at IBM.

• 25:57Guy Raz?

  Yeah.

• 25:58Speaker 01

  And so I started meeting up with Scott once a week. I'd go by the office, tell him more about the idea. I'd talk to him about challenges I saw in the marketplace. He would tell me about Zipcar as well, and his experience is there.

• 26:10Guy Raz?

  Yeah.

• 26:11Speaker 01

  And finally, after a few months of that, you know, he said to me, you know, Lea, I really feel like you're on to something here. Why don't you just see how far you can take it? And it was sort of his nice way of saying like, what are you still doing at IBM?

• 26:28Guy Raz?

  When we come back in just a moment, how Lea taps into Craigslist and her local coffee shop to launch Run My Errand, just in time for the onset of the global financial crisis. Stay with us. I'm Guy Raz and you're listening to How I Built This.

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  The agents bring speed and scale and people bring taste, judgment and control. Learn how you can get more out of your site from a Framer specialist or get started building for free today at framer.com/built for 30% off a Framer Pro annual plan. That's framer.com/built. Rules and restrictions may apply. AI isn't just opening new business opportunities, it's changing the way businesses get work done. The questions they ask, the decisions they make, the routine tasks they can hand off. That's the idea behind NetSuite Next, the next generation of NetSuite with AI woven into the tools your business already relies on.

• 28:21Guy Raz?

  NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also reshaping how people and teams work together, and that shift is already underway. That's why NetSuite wants to put a new expert-created business guide in your hands today. It's called Aligning for the Agentic Era: How AI is Changing Everyday Work. And right now, it's yours, absolutely free. Inside, you'll discover how AI could reshape work across your entire organization and how to position your business to prosper from it.

• 29:06Guy Raz?

  If your revenues are at least in the seven figures, get NetSuite's free business guide, Aligning for the Agentic Era: How AI is Changing Everyday Work, at netsuite.com/built. The guide is free to you at netsuite.com/built. netsuite.com/built.

• 29:25Speaker 02

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• 30:10Speaker 03

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• 30:22Speaker 04

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• 30:32Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2008 and Lea is still working full time at IBM. But in her spare time, on nights and weekends, she's thinking about how to get Run My Errand on its feet. And she's workshopping her business plan every chance she gets.

• 30:52Speaker 01

  I would sit next to someone on the bus going into Boston. I'd be like, hey, do you want to hear about this new idea? I mean, I would talk to anyone who would listen to me.

• 30:59Guy Raz?

  Yeah.

• 30:59Speaker 01

  But one of the places where I got a lot of great feedback was a little coffee shop in Charlestown called Zoomies. And I'd go hang out there and I would code and I'd program. And there were a bunch of moms that would come into the coffee shop with their kids. And I'd say like, hey, do you have a second? I'm working on this new thing. Like, would you use a service like this? How much would you pay? What like, what sorts of jobs do you need help with? What, what do you need done? The owners of the coffee shop were so fabulous. They, they were very nice to let me hang out there, you know, for hours and hours and talk to their customers.

• 31:31Guy Raz?

  Using, using their wifi.

• 31:32Speaker 01

  Using their wifi, eating their muffins. It was all good.

• 31:36Guy Raz?

  Yeah. Spending $7 for four hours of wifi.

• 31:41Speaker 01

  Yes. And, and so in Charlestown. This one square mile neighborhood of Boston, I figured out that there was this mothers association. And I'm not a mom at the time, right? I'm still like, I don't have kids. So I don't fully understand, but I think moms are busy and like, they'd probably use the service. So I go to the head of the Charlestown Mothers Organization. And I say, okay, I have this idea. I've talked to a lot of the moms in town and I want to build a beta for you. I want to build a beta just for you. 900 moms in one square mile of Boston. You know, will you advertise it through your newsletter if I build you this beta?

• 32:19Guy Raz?

  Right, okay, I understand that part. That makes sense.

• 32:22Speaker 01

  Yep.

• 32:22Guy Raz?

  I'm wondering how you can do the other part, which is to find the people to do the task.

• 32:27Speaker 01

  Oh, that was easy. I just went to Craigslist.

• 32:29Guy Raz?

  Huh, okay.

• 32:30Speaker 01

  Yeah, so I build a site for the moms, closed beta, and I post an ad on Craigslist. And I say, I'm looking for some help running errands. And I get hundreds, hundreds of inquiries. I'll help you, I'll help you, you know? And so I'm like, wow, okay, there's a lot of demand out there for people that want to run errands. And so I started meeting potential, at the time, we called them runners because it was run by errand.com.

• 32:57Guy Raz?

  They would come meet you face to face?

• 32:59Speaker 01

  Yeah, I met everyone face to face to start because I was terrified that, you know, there was going to be a trust and safety issue early on. And so I met them all at Zumiez Coffee Shop, 30 minute interviews. And I brought on 30 of them to start the site.

• 33:15Guy Raz?

  Yeah. You know, I'm just curious, just, it's a bit of an aside, but this is the time when Uber and Lyft and, you know, Airbnb are really kind of starting to come together. Still not known yet, not widely used yet.

• 33:31Speaker 01

  Right.

• 33:31Guy Raz?

  What would become known as like the gig economy or peer to peer economy. Did you even know about that? Had you, were you kind of looking around and saying, you know, this is going to be a thing?

• 33:42Speaker 01

  Not yet. That was still so early. It was so early.

• 33:46Guy Raz?

  Yeah.

• 33:47Speaker 01

  I mean, yeah, I mean, Uber hadn't started yet. Relay rides was started in Boston. And that was kind of like a Zipcar, but with people that owned their cars, right? Now it's Turo.

• 34:00Guy Raz?

  But you weren't, but you weren't like looking at the landscape and saying this, this peer to peer economy is going to be, because it's amazing that you were already thinking like this. I mean, and who, I mean, who knew that it was going to become a huge thing?

• 34:15Speaker 01

  It was the engineer in me. I was really driven by the technology.

• 34:18Guy Raz?

  Yeah.

• 34:18Speaker 01

  That was it. I had no exposure still to Silicon Valley or what was happening. You know, like, I didn't really know what was going on on the West Coast. And so I was driven by the technology and what I, I saw what was possible with the technology.

• 34:32Guy Raz?

  All right. So you land like 30 people to be errand runners. And you've got this group of moms.

• 34:41Speaker 01

  Yes.

• 34:42Guy Raz?

  And then what? Then what? How did you get them to like, because it's a chicken and egg problem. Like you need the, you need the problem, I need the solver. You need the solver, I need the problem. So how did you get them to, you know, to, to start?

• 34:54Speaker 01

  Yeah. So I, I posted in the Charlestown Mothers Association newsletter that runmyerrand.com was open to them and them alone. And that I had vetted, you know, these 30 taskers or runners at the time.

• 35:07Guy Raz?

  Yeah.

• 35:07Speaker 01

  And then as soon as I posted, you know, some moms were trying it out. They needed dry cleaning picked up. They need groceries delivered.

• 35:15Speaker 01

  You know, just like simple, easy little tasks. I then had created the algorithm, right, which would alert all of the runners, all of the taskers at the time, that a new job had been posted. So they'd get an alert on their phone. And at that time, it was a bidding system. Tasker, runners at the time would pick up jobs. They would do the errands. They would be rated and reviewed, but you know, by the customer. But I, I personally, right, would get an alert every time something was posted. I mean, this was a closed beta. I would be sweating bullets. To see how long it would take for a runner, for a tasker, to pick up the job. I was like, oh, my God, is someone going to pick this up? I mean, like, I didn't know it was a marketplace. If someone would pick it up or they wouldn't pick it up.

• 36:00Speaker 01

  I ended up being the one doing a lot of the early jobs. I had this little scooter that I rode around Boston, Charlestown area. And I would do a lot of the early jobs myself. And so I would then get like firsthand knowledge of what it was like to be a tasker, a runner, to do these jobs. And that actually helped a lot in building out the service, having that knowledge.

• 36:24Guy Raz?

  All right. Now, this is a lot of work. There's a lot going on here. But at what point were you? I mean, did you have to leave your day job? Because, you know, I don't think you left your day job until June of 2008.

• 36:40Speaker 01

  Yeah.

• 36:40Guy Raz?

  Were you just like going to work during the day and then just trying to do all the stuff at night?

• 36:45Speaker 01

  Yes, nights, weekends. I mean, it was a lot. And it really was Scott who kind of nudged me to make the leap. He saw the progress.

• 36:55Guy Raz?

  Yeah.

• 36:55Speaker 01

  And everyone I had talked to, no one had said, you're insane. This won't work. Everyone's reaction was-

• 37:01Guy Raz?

  This is a brilliant idea.

• 37:03Speaker 01

  Yes, everyone, everyone. And so I finally decided to make the leap and quit IBM.

• 37:11Guy Raz?

  Did you have savings, some money that you saved up?

• 37:14Speaker 01

  So I had $27,000 in my IBM pension program that, you know, we could withdraw with a penalty because it was your retirement. But I was like, whatever, let's just withdraw this money. And so I gave myself like six months to make something happen.

• 37:30Guy Raz?

  And meantime, I mean, I guess because you were married and Kevin probably had some income coming in.

• 37:35Speaker 01

  Yes.

• 37:36Guy Raz?

  So you didn't have to worry about like feeding yourself.

• 37:38Speaker 01

  That's right. That's right. It's interesting because you said in the beginning, you had the stability of IBM. I was the stable one for many years while Kevin kind of jumped around at different startups. And we talked and he's like, you know what? This is such a great idea. I'll be the stable one. You go, like, go see what you can do with this.

• 37:55Guy Raz?

  Yeah. So what would the user experience be like in 2008? You know, you'd go on, you had people who were available to run errands.

• 38:04Speaker 01

  Yep.

• 38:04Guy Raz?

  And then what would you do as a, as the person who needed an errand? Taken care of.

• 38:10Speaker 01

  So I built it modeled after eBay, you know, the big marketplace at the time.

• 38:14Guy Raz?

  Yep.

• 38:14Speaker 01

  And so you'd go on and you'd say, I need dry cleaning picked up. I'm willing to pay you $10 to do it.

• 38:19Guy Raz?

  Okay.

• 38:20Speaker 01

  And a tasker would come on, they'd get an alert on their phone and they'd say, will I do this for $10? Or do I want to make a bid on the job? Oh, I'll do it for 15. So some runners, taskers, errand runners, they would bid on jobs. Others would just do the buy now price, right? Um, and connect. And then that was it. And then the transaction would occur offline and then they'd come back to leave each other ratings and reviews.

• 38:45Guy Raz?

  Okay, so it's June of 2008. You've got some of these moms that you're working with. You're starting to onboard some errand runners in the beta.

• 38:57Speaker 01

  Yeah.

• 38:58Guy Raz?

  And, and how does it go?

• 39:01Speaker 01

  It goes really well. And the moms in Charlestown start referring their moms in other neighborhoods of Boston, but it's not open in those neighborhoods.

• 39:11Guy Raz?

  Yeah.

• 39:12Speaker 01

  And so I'm thinking, wow, maybe I should just open this up in more neighborhoods, but that means I need to go recruit more runners in these neighborhoods. But I'm then frantically posting Craigslist ads and interviewing runners all over the city.

• 39:29Speaker 01

  But it's going well. And I get to the point where I think, okay, maybe I should try to do a little bit of marketing or, you know, get the word out more than just word of mouth.

• 39:42Guy Raz?

  Yeah.

• 39:43Speaker 01

  So I march into the Charlestown Patriot Bridge, which is the local newspaper in Charlestown.

• 39:49Guy Raz?

  Yeah.

• 39:49Speaker 01

  And I kind of, I pitched the guy there, the story about Run My Errands starting and how I'm opening it up. It's been in the Charlestown Mothers Association. It's gone really well. And he's so nice and he loves the story and he's like, I'll, yeah, let's write it up. I'll publish it.

• 40:04Guy Raz?

  Wow.

• 40:04Speaker 01

  And honestly, that drove so much traffic. I mean, I think the readership was like 13,000 people. It drove so much traffic to the site and all over Boston. It wasn't just Charlestown. And so I was like, okay, wow, there's something here.

• 40:20Guy Raz?

  Yeah. I think you opened it up wide, right? The beta phase ended in like September of 2008, right? Something like that.

• 40:29Speaker 01

  That's right, in September, yep.

• 40:31Guy Raz?

  But September 2008 was wow. I mean, that was like Lehman Brothers and, and you know, it was just the world is collapsing. And then you had like, uh, the Madoff Ponzi scheme was exposed in December. And then they just the financial crisis in 2009. I actually remember it very well because I was living in Cambridge, Massachusetts in the fall of 2008.

• 40:55Speaker 01

  Okay.

• 40:56Guy Raz?

  For a year. And that was a crazy time, crazy time. It was like, how, you know, do you remember having any anxiety over like, oh, I left my job and I'm starting that? Yeah.

• 41:11Speaker 01

  Yes, I was freaking out as a what am I doing? I had this stable job at IBM and the world feels like it's falling apart. Yeah, no one wants to give me money right now. Investors don't want to write checks right now. Yeah, it was very stressful. But I did realize something, which was the runners, the taskers, the people that wanted to make money on the platform. It was overwhelming.

• 41:37Guy Raz?

  Because people were losing jobs?

• 41:38Speaker 01

  Yes, it was overwhelming. And the, I mean, the, the skill sets and the talent and these people were educated and they'd gone to college. They were pharmacists, they were lawyers, they were teachers, they were being laid off. And they were looking for new ways to make money.

• 41:55Guy Raz?

  So you were getting overwhelmed with people who were responding to the Craigslist ad?

• 41:59Speaker 01

  Yes. And so that motivated me that despite my own personal panic around leaving my own job to do this, that there was something interesting here to be built.

• 42:11Guy Raz?

  Yeah. But from, from what I've read, like in order to attract more users, right? To run my errand, you, you tried a bunch of different, interesting strategies. Like, for example, you, you offered like the first errand would be free. And so I'm assuming you guys would pay the errand runner. So you were losing money on it, but you had to attract users.

• 42:34Speaker 01

  Yes.

• 42:35Guy Raz?

  So that and then, and then like you were trying to talk to, I guess, corporations like IBM, I think even approached IBM to see if they would adopt your service. Right?

• 42:47Speaker 01

  Yes, we tried everything, a lot of what I would call guerrilla marketing techniques. I mean, one of my actual favorite sort of stunts we did in Boston was to do a marketing program during the Boston Marathon. And we called it Run My Marathon. And we actually hired runners, errand runners to run portions of the marathon all the way along the marathon route. But yeah, I mean, we, we just, it was boots on the ground, knocking on doors.

• 43:21Guy Raz?

  Yeah.

• 43:21Speaker 01

  You know, cold talking to these business owners about the service.

• 43:25Guy Raz?

  Meantime, you can't run this without any money. Right?

• 43:29Speaker 01

  Right.

• 43:30Guy Raz?

  So I, from what I understand, you raised a little bit of money, like just to keep it running, is that right?

• 43:35Speaker 01

  Yeah, I mean, it's even sort of a more in-depth story than that, which is, so I had that $27,000 pension that I knew would last us from June, when I left IBM to December, six months.

• 43:48Guy Raz?

  Minus the penalties and the tax.

• 43:49Speaker 01

  That's right. Then we're putting the mortgage on the credit card. Like, we're putting everything on credit cards after that.

• 43:56Guy Raz?

  Yeah.

• 43:57Speaker 01

  And so September rolls around, we've got the beta launch, there's good feedback, people are using it. Scott introduced me to some investors. I start, you know, going around Boston and talking to people. And these conversations with investors are not going well.

• 44:14Guy Raz?

  Yeah.

• 44:15Speaker 01

  They're not going anywhere very quickly. And I remember Scott calling me on Christmas Eve of 2008, saying, hey, like, are you getting the round closed? There were a couple of angels that were the first investors in Zipcar that, that were going to come in. He's like, hey, are you getting the round closed? It was supposed to be $250,000.

• 44:33Guy Raz?

  Yep.

• 44:34Speaker 01

  And I said, I don't know, the money hasn't come in yet. Like, I don't know what's going on. And so in the new year, I go and sit down with the, with the investors and we're there with lawyers, we're supposed to be closing the round. I actually have a co-founder at the time, too, that's going to leave her job. And, you know, I've offered like 20% of the company to, to come on as my co-founder. So we go, we meet these investors and they're like, listen, this financial crisis has hit us hard. We're, we're getting cold feet. We really love what you're doing. We love the idea, but we can't, we can't put all this money down right now. We're just, we're nervous. And so we'll, we'll give you some money, but it's going to come in tranches.

• 45:19Speaker 01

  And you, you have to meet certain milestones to get the next check. And I am like, oh my God, it's been now nine months since I left IBM. Everything is going on credit cards and this round is not coming together.

• 45:34Guy Raz?

  Yeah.

• 45:35Speaker 01

  So we leave that meeting. She decides she can't leave her full-time job to join me after all.

• 45:41Guy Raz?

  So she, you lose your co-founder?

• 45:42Speaker 01

  Lose the co-founder and the investors say, let's start with 50K. We'll give you 50K. Let's see how you do. So we start with 50K. That was March in 2009. And I just, I just make it work. I just stretch it and keep going.

• 46:00Guy Raz?

  Now, how, from a, from a user's perspective at this point, it's only available in the Boston area.

• 46:06Speaker 01

  Right.

• 46:07Guy Raz?

  Like, I have to imagine you're still, you still have a tiny number of people using it. Probably you're bringing in, I don't know, 5,000, 10,000 bucks a month at most, at that point?

• 46:19Speaker 01

  Probably less, honestly, probably less. Boston was a tough market, even at scale with TaskRabbit. Boston was like number 10 market for us.

• 46:30Guy Raz?

  And, I mean, you had $50,000, which is going to give you some runway, especially if it's just you, pretty much doing everything. But it's, it's not, it's, it's limited. You had some revenue coming in, but a really small amount. It was really mainly, it sounds like you were, it was really mainly data you were collecting.

• 46:49Speaker 01

  Yes, that's right. It wasn't big enough yet to sustain anything, let alone pay for the, you know, web server costs of running the site. And so I just kept expanding. At that point though, I was working out of the Zipcar office. So Scott very nicely said, why don't you just come work out of here, you know, for as long as you want. And one day he said, you know, there's another entrepreneur from California coming by. His name's John Zimmer. He runs a company called ZimRide.

• 47:16Guy Raz?

  Yeah.

• 47:17Speaker 01

  I want you guys to meet. We're, we're going to do a deal with them at Zipcar. I said, cool. And so later that day, I meet John and, and he's like, hey, you know what? Um, there's this incubator program Facebook is going to launch this summer. You should apply. I know the people who are going to run it. I'll, I'll put in a good word for you. And I was like, okay, great. So I go back, I tell Scott, he's like, yeah, that sounds really good. Why don't you apply to that program? And in the meantime, we had closed a little bit more angel money, you know, in total, it became around a hundred and fifty thousand dollars.

• 47:48Guy Raz?

  Yeah.

• 47:49Speaker 01

  And so I apply to this program called FB Fund. I do a phone interview for it. And, and then we, we get it, we're offered it. And, and John says, you know what? I think it's like $250,000. Like it's a, you know, an investment from Facebook. And I say, oh, that sounds great. That sounds a great way to raise money. So we get the offer from Facebook to come out to do the incubator program. It's $15,000.

• 48:15Guy Raz?

  Ooh.

• 48:17Speaker 01

  And it's for a chunk of the company. It's like, you know, a few percentage points of the company.

• 48:21Guy Raz?

  Wow. For 15 grand.

• 48:23Speaker 01

  For 15 grand. And I said, well, what happened to the 250? And they're like, yeah, well, it, it's different for everyone is what they tell me. They decide how much they're going to offer you. Okay?

• 48:34Guy Raz?

  Right.

• 48:35Speaker 01

  So I'm talking to Scott about it. He's like, don't do it. That's not worth it. It's 15 grand. Don't do it.

• 48:40Guy Raz?

  Yeah. And so they're offering you 15 grand, but presumably also mentorship and connections. It's Facebook.

• 48:47Speaker 01

  That's right.

• 48:48Guy Raz?

  So what did you do?

• 48:50Speaker 01

  So I decided to do it. I decided to go for it. And even though most people thought it would not be worth doing, I felt like this is the connection to Silicon Valley. There are things happening there. Let's go do it.

• 49:04Guy Raz?

  And the incubator program presumably was in, in California.

• 49:08Speaker 01

  It was. It was in Palo Alto. So I'd spend a week in Boston on the ground.

• 49:13Guy Raz?

  Yep.

• 49:14Speaker 01

  And then I'd spend a week over at the Facebook program. And I told Facebook, I was like, hey, listen, like, I've got this company running in Boston. I can't just go there for the summer. So I just went back and forth all summer. I mean, that was a, it ended up being a pivotal moment. And that program was life changing.

• 49:30Guy Raz?

  And I think I'm assuming if they, if they ran it like Y Combinator and others, at a certain point, they would. You would be able to present to investors. Is that, is that how it worked?

• 49:40Speaker 01

  Exactly. There was a big pitch day at the end of the program. And I remember on the first day of the program, one, I was surrounded by all of these other amazing entrepreneurs and founders and people. And that was the first time in my life I had been surrounded by that type of energy and it was really exciting. So day one, day one, they get us to stand up, introduce ourselves and give our 30 second pitch. And they, it's like 20 companies. And then we get rated on how well we did on day one out of 10. I got like a two.

• 50:18Guy Raz?

  A two, rated by who? By the, by like the mentors?

• 50:21Speaker 01

  Running the program.

• 50:22Guy Raz?

  Okay. Because you didn't, what? You didn't properly explain what you were doing or you didn't have enthusiasm? What was the feedback?

• 50:28Speaker 01

  It wasn't enthusiasm. They, they said that I used too many technical buzzwords.

• 50:34Guy Raz?

  Ah, okay.

• 50:35Speaker 01

  And so I really had to make the shift away from being a technical engineer. And into what is the value proposition? Like what are you actually building here for consumers?

• 50:46Guy Raz?

  Right.

• 50:47Speaker 01

  And so that was very helpful. I mean, I actually worked on the pitch then for the next 12 weeks. And, and at the end, there was a big demo day and, you know, it was online and there were investors there as well. And I was just like, I am making this round happen. Like this is my chance. I have to bring a round together at the end of this program.

• 51:08Guy Raz?

  And I think, what, what, what were you looking to raise? Cause you hadn't really done a seed round yet, right?

• 51:14Speaker 01

  No, I, I, based on the advisors and mentors there, they said, you know, raise a million dollars, raise a million dollars. Yeah.

• 51:23Guy Raz?

  And it's 2009.

• 51:27Guy Raz?

  Right? And now there are people with money, there are people, there are investors, but still, even on Sand Hill Road, I mean, I've heard stories of companies looking to sell at the time for like pennies on the dollar that, you know, today are worth many, many tens of billions of dollars that didn't do it. But, you know, it was like a bloodbath in 2009.

• 51:48Speaker 01

  Yes, it was. And I didn't fully understand yet either, you know, just how to do this or the dynamics around it. But one of the people that was very pivotal in the raise and that came out of Facebook Fund was Tim Ferriss.

• 52:04Guy Raz?

  Tim Ferriss?

• 52:05Speaker 01

  Yes.

• 52:06Guy Raz?

  Who's been on the show?

• 52:07Speaker 01

  Fabulous human being.

• 52:08Guy Raz?

  At the time, 4-Hour Work Week was like all was a huge deal, right?

• 52:12Speaker 01

  Yes. So I had read 4-Hour Work Week and particularly as it related to runmyerrand.com, I thought, oh, my God, if I could get Tim as an advisor to this company, that's going to be a huge win for us. And it just so happened that Tim was going to speak at Facebook Fund on a Monday morning. Now, I was flying back and forth, right? A week in Boston, a week in Palo Alto. So the head of the Facebook program says, okay, Monday morning, Tim Ferriss is going to be here. Surprise. What, you know, everyone can sign up for 15 minutes with Tim on Monday. I'm literally on a flight back to Boston when I get this email. I'm like, oh, my God, do I really turn around just so I can have this meeting with Tim?

• 52:57Speaker 01

  I look online to see how much a plane ticket is to fly back. It was like $700. It was a lot. And I think, okay, it's a 15-minute meeting with Tim. Like, is this really worth it?

• 53:09Guy Raz?

  Yeah.

• 53:10Speaker 01

  But I decide that I'm going to make it worth it. I'm just gonna, I'm gonna make sure that he comes on as an advisor, like whatever it takes. And so

• 53:18Guy Raz?

  Wow.

• 53:19Speaker 01

  I book my ticket back on Sunday night. So I'm in Boston for a day, go back on Sunday night. And on the way there, I read the 4-Hour Work Week again. So I just have it fresh in my mind.

• 53:33Guy Raz?

  Yep.

• 53:34Speaker 01

  I have the 15-minute meeting with Tim and I'm showing him the site and I'm describing Run My Errand to him and he's giving me feedback about the homepage. And it's 15 minutes. So I'm like, oh my God, the clock is ticking down. Like, how do I ask him to be an advisor in a 15 minute meeting? So I decide that that's too much, too much to ask for in 15 minute meeting. All I need to do is ask for another meeting.

• 53:56Guy Raz?

  Yep.

• 53:56Speaker 01

  And so it gets down to like 12 minutes, 13 minutes. He's giving me tons of great feedback. And I'm like, hey, you know, Tim, would you be willing to spend more time with me? Like, could, could we set up another meeting? And he's a little hesitant, to be honest. He's like, well, why don't you reach out to my admin? And like, we'll see what we can make work. And I say, okay, great.

• 54:15Guy Raz?

  And it's kind of incredible because that, I mean, that could have been where things sort of ended. But, but I guess you called his assistant and you, you actually were able to get a lunch meeting with Tim a few days later, right?

• 54:27Speaker 01

  Yes. And over that lunch meeting, we just really bonded and connect over for our work week and run my errand and how they're so collaborative. And I asked him to be an advisor. And on the spot, he says, yes. And he says, and I want to introduce you to my good friends that are investors and Mirko at Floodgate and Steve Anderson at Baseline Ventures.

• 54:50Guy Raz?

  Wow.

• 54:51Speaker 01

  You know, I was like, if I can turn this into a, a million dollars of funding, it'll be worth it.

• 54:56Guy Raz?

  Yeah.

• 54:56Speaker 01

  And so that was just my mindset. I had to make it work.

• 55:00Guy Raz?

  All right. So this was a crucial, this was like a crucial meeting that you had to have. You felt like this was gonna, and it did, it helped, it opened the doors. So you raised that, you raised that million dollars, I think by sort of the, sort of late 2009. But you're in Boston and you're running this out of Boston. And I mean, it sounds like Boston wasn't really, you could see that, and everyone that you talked to loved this idea, but for some reason, it wasn't really taking off like wildfire in the way you had hoped it would.

• 55:35Speaker 01

  That's right. I think the culture of Bostonians is a very do it yourself mentality.

• 55:41Guy Raz?

  Yeah.

• 55:42Speaker 01

  And so that was some friction for this type of service. And I felt like if we could just get to San Francisco, where, you know, it's the tech company capital of the world. Like, this is the consumer market where we actually prove this is a real business.

• 56:03Guy Raz?

  When we come back in just a moment, Halia proves that Run My Errand is indeed a real business. But how when she's really ready to scale it, she realizes she has the wrong team at the wrong time. Stay with us. I'm Guy Raz and you're listening to How I Built This.

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• 57:34Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's the summer of 2010 and Leah and her husband Kevin decide to move to San Francisco so she can relaunch Run My Errand from there. And one of the first things she decides is to change the name of the business.

• 57:52Speaker 01

  I did not like the name Run My Errand about 20 minutes after I bought it off a GoDaddy February of 2008.

• 58:00Guy Raz?

  Yep.

• 58:01Speaker 01

  It did get us pretty far. It was clear. It was descriptive. I felt like what we could build was bigger than errands.

• 58:10Guy Raz?

  Yeah.

• 58:10Speaker 01

  I felt like the, the word Run My Errand was a command and it felt demeaning. And I wanted, I wanted the site and the service to feel uplifting and innovative and push the thinking forward. And so we came up with TaskRabbit.

• 58:29Guy Raz?

  So had you been thinking already at this point, you know, we can't just limit our brand to errands, that eventually it could be more like Angie's List where people do repairs or where people do contracting work, or maybe it's going to be something bigger. Was that, were you starting to think about that?

• 58:48Speaker 01

  Yes. I mean, we saw the main use case was errands, but we even saw early days in Boston, people posting really interesting, different things. They needed help with a birthday party or, um, you know, they needed, um, a costume sewn or, and there was, there was like all kinds of crazy things that people would come up with. And so, you know, we did a little bit of press. We did a lot of the on the ground guerrilla marketing like we had done in Boston.

• 59:18Guy Raz?

  And how was the response in the city?

• 59:21Speaker 01

  It was much faster than it was in Boston. And so from the very early days of launching San Francisco, I could see that just the consumer in the Bay Area was going to use the service differently. I mean, it was under a new name and brand as well, so that helped. But people were really creative with their use of the service. You know, they, they were using it much more often than people in Boston were. The weather was nicer, so there were a lot more outdoor tasks being done.

• 59:52Guy Raz?

  Yeah.

• 59:52Speaker 01

  It was definitely growing faster than we were in Boston.

• 59:55Guy Raz?

  And at this point, I guess you're able to hire someone who can take over the, the coding for you. I think this is somebody you knew from IBM, uh, Brian Leonard. And also, I think pretty soon after you arrived to San Francisco, you started to fundraise for a Series A. This was, and this is going to be big. This was going to be like, like five million bucks.

• 1:00:14Speaker 01

  That's right. That's right. It's, yes. So, we start to fundraise for the Series A. And we, Brian and I, sort of hit up and down Sand Hill Road. And we pitch investors. And even given all of that, the fundraiser was not easy. It wasn't easy. And we talked to a lot of investors. I remember one such meeting where we were on Sand Hill Road, Brian and I, and we park, you know, at the investor's office. And I get out of the car and I like somehow closed the door awkwardly and it slams my right hand in the door. And I'm barreled over in pain. Brian is like, oh, my God, are you OK?

• 1:00:59Speaker 01

  What just happened? We've got to get into this meeting. And I'm like, I'm OK, I'm OK, I'm OK. I'll deal with it later. We just go into the meeting. I walk in, I say nothing. I shake everybody's hand with my broken hand, grimacing, sit down at the table and start the pitch. And at this point, Brian and I, you know, had done this pitch many times. Part of the pitch was also, you know, we're building out the team. Still, it's just four of us. And in this particular meeting, about halfway through, the investors interrupt us. They interrupt and they're like, hold on, hold on, hold on. Does anyone on your team speak Spanish? And I'm confused.

• 1:01:42Speaker 01

  I'm like, well, my father's Puerto Rican. I speak a little Spanish. But like, why? He's like, it just dawns on me. You could, you could really build a huge house cleaning business with this platform. And I was like, what? What is he talking about? And he was thinking that if we spoke Spanish, we could market to the Spanish community and bring them on. It was just was like so far off from what we were pitching that day. And my hand is broken and I'm just completely destroyed by this meeting.

• 1:02:17Speaker 01

  So, you know, we continue to talk to investors and we finally get connected with the team over at Shasta Ventures. And then we meet Todd, who's one of the founders of Shasta. And after several meetings with them, and you know, they invite, they invite me out to dinner, which is so nice. It's very old school. I don't know if this happens anymore, but they're like, let's go out to dinner and we'll discuss terms, you know. And so then they put together a $5 million term sheet. You know, it was, it was so exciting. It was a great interaction, too. I remember Todd saying, you know, we never go back on our work. We've never pulled back a term sheet and like, we're really excited about working

• 1:02:59Speaker 01

  with you. And that was it. And so we, we decided to move forward with Shasta and it was a great partnership with them.

• 1:03:08Guy Raz?

  Around this time, you're closing the, the, this round of financing, I think you close in, in 2011, May of 2011. You decide that, that you should not be the CEO of the company, that you should find outside, an outside person with more experience? Or what, tell me what, what you were thinking at the time?

• 1:03:28Speaker 01

  Yeah, I was thinking, I had always wanted a business partner. I am an engineer. That's, that's how I was trained.

• 1:03:36Guy Raz?

  Which is really smart, by the way. It's a really smart way to think about it.

• 1:03:39Speaker 01

  Yeah, I always wanted that business person. And so at this point, we're like, we're open in two markets, we're four people, but I know we need to raise more money. And I know that having more operational and business help is going to help get that done.

• 1:03:55Guy Raz?

  Yeah.

• 1:03:55Speaker 01

  And so we met a lot of different people over the course of many months. We ran a whole search process.

• 1:04:02Guy Raz?

  All right. So you reach out to, to somebody to become the CEO? And, and who was it?

• 1:04:13Speaker 01

  It was a man by the name of Eric Grossa. He was one of the early guys at hotwire.com.

• 1:04:22Speaker 01

  Hundred million dollar business, had sold to Expedia, referenced very well, and, and I mean, is an amazing human being. I think when I look back, it was more about timing. Because the business was too early to bring in someone that was a step away from the core vision. And the business still needed me to really drive the momentum forward. He was brought into scale.

• 1:04:57Guy Raz?

  Yeah.

• 1:04:58Speaker 01

  It was too early to scale in the way that man can scale a company, right?

• 1:05:02Guy Raz?

  Yeah.

• 1:05:03Speaker 01

  I mean, he's brilliant. Yeah.

• 1:05:04Guy Raz?

  He brought incredible businesses.

• 1:05:06Speaker 01

  Yes.

• 1:05:07Guy Raz?

  And, and you guys were still just getting started.

• 1:05:11Speaker 01

  That's right. That's right. But, you know, we did go out and raise our Series B with Eric. So Eric and I then hit the road. And I gotta say, like, oh, my God, it was such a relief.

• 1:05:23Guy Raz?

  Yeah, because investors are looking at the two of you and they're saying, okay, great product, great engineer, and then super experienced operations person.

• 1:05:32Speaker 01

  Exactly.

• 1:05:33Guy Raz?

  So here's a check.

• 1:05:35Speaker 01

  Here's the check. And it was the largest, it was the largest round that we raised. It ended up being $18 million, led by Lightspeed. It came fast because we had brought on this amazing talent.

• 1:05:49Guy Raz?

  All right, now meantime, there's no way that TaskRabbit is profitable, because most startups are not profitable for a long time. Some are still not profitable after a very, very, very long time. But what was the business model that, that you start to land on at this point? Obviously, this is a question investors are asking. How are you going to make money?

• 1:06:08Speaker 01

  So it was always just a commission from every task that went through the site. And that was always the business model. So we were always making money. And the unit economics looked good. We were profitable on a task basis. We were always making money on every task, you know, at that point. Now, at this time, you're also starting to see Uber and Lyft and Airbnb, all these other, you know, peer-to-peer economies really start to take off and start to emerge.

• 1:06:40Guy Raz?

  Yeah, end of 2011. Yeah. Yeah, yeah.

• 1:06:42Speaker 01

  And so we're kind of in the midst of this monumental moment for

• 1:06:49Speaker 01

  Consumers.

• 1:06:50Guy Raz?

  Yeah.

• 1:06:51Speaker 01

  And TaskRabbit actually feels pretty slow and sluggish compared to Yes, yes, compared to the Ubers and the Lifts. And it's not happening as instantaneously as the consumer starts to get trained to expect.

• 1:07:10Guy Raz?

  Yeah.

• 1:07:11Speaker 01

  And so this is the point in the business where like, wow, we, we need to make instant connections and things have, have to happen in real time.

• 1:07:21Guy Raz?

  But just to ask about the, the business model for a moment, I mean, the, the model of taking a commission from every task doesn't seem to me to be sustainable in the long run because you would have to have milli- hundreds of thousands of tasks happening every day to hit profitability. Cause if it's like, I don't know, 40 bucks, I don't know, maybe I'm wrong, but it seems like there had to be other revenue streams that you had to focus on. Is that, is that right? Did that happen?

• 1:07:48Speaker 01

  You know, the main revenue stream was the commissions and the average task size at that time was about a hundred and $50.

• 1:07:57Guy Raz?

  Okay, right.

• 1:07:58Speaker 01

  And so it, it, the number, the numbers worked. We took anywhere between 20 and 30% of, of a task and that was, you know, net profit to us.

• 1:08:07Guy Raz?

  Right.

• 1:08:08Speaker 01

  So yeah, that, that was always the main business model.

• 1:08:11Guy Raz?

  All right. Now Eric was brought in to really scale the company. You had now a pretty nice war chest.

• 1:08:17Speaker 01

  Yes.

• 1:08:18Guy Raz?

  But you were, in the process of trying to scale, it sounds like the adoption rate wasn't actually, it wasn't moving as quickly as you'd hoped.

• 1:08:27Speaker 01

  Yeah, that's right. Cause it never really felt like a rocket ship. It always felt like we were on the brink of getting on the rocket ship, right?

• 1:08:34Guy Raz?

  Yeah.

• 1:08:35Speaker 01

  And so the lever in the model was always this repeat usage metric. Like if you could get someone to post two tasks a month or one time a week, that was the huge lever in the model that like really made all the numbers work. But on average, people were posting about one time a month at the time. And so we're like, okay, why is it only happening one time a month? Where is the friction in the model?

• 1:09:00Guy Raz?

  Yeah.

• 1:09:00Speaker 01

  At the same time, Eric is really, like, he's starting to scale the company, the way he knows how to scale companies. It's like bring on sales and marketing and, you know, I, you know, I need more engineering. We need business development people. We need operation. Like, so we're scaling up. And we're also realizing that the product now in 2011 is it's just not working. It's just not working. And at this point, there are competitors coming out that are launching mobile first, mobile only. And we've been on the web, like we have, we have a mobile product, but it hasn't been given a lot of attention because we've been so focused on the web.

• 1:09:43Speaker 01

  I mean, honestly, it's like the, the entire consumer market and expectation just changed underneath us and we missed it.

• 1:09:51Guy Raz?

  I think Eric would end up being CEO for like less than a year before you kind of took reassume that role. Can you, can you tell me what, what happened ultimately? Cause it doesn't sound like it was, it was like dragged down, you know, I hate you, I hate you.

• 1:10:10Speaker 01

  No, no, not at all.

• 1:10:11Guy Raz?

  It was just the wrong fit? What, what, what, yeah.

• 1:10:14Speaker 01

  It was the wrong timing and it was the wrong fit. And it turned out that we needed to really change the trajectory of the product into this mobile first, fast paced, on-demand service, which was more analogous to Uber and Lyft and all these other services and all these other competitors, frankly, that were popping up. But we had scaled a team that was built to run a traditional web business.

• 1:10:46Guy Raz?

  Yeah.

• 1:10:46Speaker 01

  And so we decided as a board, you know, that I would step back in and, and become CEO again. It was slightly reluctantly. I mean, I really felt like I had failed. I mean, that this process had failed, right? I mean, I, I wanted help. I wanted a business person.

• 1:11:05Guy Raz?

  Yeah.

• 1:11:05Speaker 01

  And that didn't work. And now I have to step back in and I also need to like change the trajectory of this giant ship that's going in the wrong direction.

• 1:11:17Guy Raz?

  Were you worried about your burn rate?

• 1:11:19Speaker 01

  Extremely worried about the burn rate. I mean, at that point, I think we were burning probably over a million dollars a month.

• 1:11:25Guy Raz?

  And you had, you had money in the, in the bank, but still.

• 1:11:28Speaker 01

  We did, we did. We had over $20 million in the bank. I remember, you know, so it was kind of like, okay, you've got. A lot of funding, but the burn is high. We've hired a lot of people. And we've also built a team that may not be the right team to execute what we need to do next.

• 1:11:48Guy Raz?

  All right. In the middle of 2013,

• 1:11:52Guy Raz?

  you had to lay off about 30% of the team. You restructured the company. Tell me what you were thinking in the summer of 2013.

• 1:12:03Speaker 01

  Yes. So it ended up being about 20% of the team.

• 1:12:09Guy Raz?

  How many people, do you remember?

• 1:12:10Speaker 01

  At that point, we were probably 80 people. And so it was under 20 people that we transitioned out. I had to look them in the eye and say, you know, this, this isn't working anymore. And we've got to, we've got to move on. At the time, I was six months pregnant with my first baby, Amelia. And I remember going into the office that morning, just feeling totally sick to my stomach. You know, I deliver the news to this group of people, you know, in segments and chunks.

• 1:12:51Speaker 01

  And we had enough money in the bank to really make sure that we took care of them financially. So that was important, but it was going to be a huge morale hit. At the same time, you know, this is my first pregnancy and I'm nervous because I, I feel like, you know what, I haven't felt the baby move today. And it's just a lot of stress and like, maybe it's okay, but like, I don't know. And so I call my doctor in the afternoon and she's like, I need you to come in. So I go in, they monitor. The baby's sluggish. She's like, no, this isn't in your head. You're not making this up.

• 1:13:36Speaker 01

  Like, are you under a lot of stress?

• 1:13:40Speaker 01

  Like, oh, my God, am I under a lot of stress?

• 1:13:44Guy Raz?

  Yeah.

• 1:13:45Speaker 01

  And, you know, it turned out everything was okay.

• 1:13:50Guy Raz?

  Please, let's get to the end of that story.

• 1:13:51Speaker 01

  Everything's okay. Baby's okay. Amelia's nine now. She was okay.

• 1:13:55Guy Raz?

  Yeah.

• 1:13:57Speaker 01

  But it was, it was just like my body was reacting to the amount of stress I was under.

• 1:14:02Guy Raz?

  Yeah.

• 1:14:02Speaker 01

  And, you know, my doctor said to me, she said, listen, I told her what had happened. And I'm like crying, you know, she's like, listen, you're not going to kill your baby. She said that out to me flat. You're not going to kill your baby. I was like, okay, all right. And I was, I was kind of, all right, that's what I needed to hear because I need to go back and take care of some things, too. But, you know, she monitored me for a few hours. I came back to the office, like, things were settled down.

• 1:14:31Speaker 01

  You know, and we moved, we moved forward. We all moved forward.

• 1:14:38Guy Raz?

  All right. Meantime, so you've got, there's just a lot going on, right?

• 1:14:45Guy Raz?

  You also realize that the, the model you have, which is kind of like this bidding system or the book now system, it was confusing. There were people who liked it because they could, you know, haggle over a price and, and even some of the, the, the TaskRabbit, what were they called, the errand runners?

• 1:15:02Speaker 01

  Taskers.

• 1:15:03Guy Raz?

  The Taskers, yeah, like they, some of them liked it, but you knew that there was too much friction with this model, that it wasn't easy to get. And I remember this, I remember going on TaskRabbit in like 2013 and being like, this is confusing.

• 1:15:15Speaker 01

  Yep.

• 1:15:16Guy Raz?

  It's like, I don't want to bid. It's, I'm not good at haggling. Like, I just, just tell me the price.

• 1:15:20Speaker 01

  Yes.

• 1:15:21Guy Raz?

  And so you, you really, the team started to come up with a new, a completely new model that you eventually, you guys called it the Booker T model. I guess after like Booker's and the Model T, is that right?

• 1:15:32Speaker 01

  Yes, that's right. That's right. And this was an idea that came out of The product team.

• 1:15:37Guy Raz?

  And what was gonna, what was gonna be different? It was going to just be like, here's a price and here's how it works?

• 1:15:43Speaker 01

  It was gonna be a direct booking platform. And what we needed to do was remove more friction from the bidding. So we got rid of bidding, you know, and so people could just post, I wanna pay this much money and then taskers would take it or leave. You know, there wasn't a lot of back and forth. So that helped.

• 1:16:01Guy Raz?

  And when you introduced this, from, from what I understand, you actually started in, in London, in the UK to test it out.

• 1:16:09Speaker 01

  Yes.

• 1:16:09Guy Raz?

  Uh, but when you brought it to the US, like, I think there was a pretty strong minority of users, pretty strong, maybe strong and vocal minority of people who, uh, who hated it.

• 1:16:20Speaker 01

  It was a very loud minority.

• 1:16:22Guy Raz?

  Yeah. And they really hated it.

• 1:16:25Speaker 01

  Yes.

• 1:16:25Guy Raz?

  And what did they say?

• 1:16:28Speaker 01

  Oh, my God, this was so hard because millions of people were using TaskRabbit in the US. And thank God, we launched this new product in London because we saw it work. We saw the mobile product work, this on-demand booking platform. It worked. The metrics doubled, the repeat usage. We're like, okay, this works. Now we need to take a million people in the US and 60,000 taskers that are on the platform. And we need to transition them to a completely new way of working. We actually brought a tasker from London, from the UK, who was operating in the London market. And we had her train taskers in the US, city by city, in these little community gatherings.

• 1:17:13Speaker 01

  Thank God, we launched that London product. Because if we hadn't, we would have been completely overwhelmed by that vocal minority. And we, we could have pulled back. We could have completely decided not to move forward, just based on the feedback, because it was so visceral.

• 1:17:30Guy Raz?

  Yeah.

• 1:17:31Speaker 01

  But, but we saw it working. We knew it was gonna work.

• 1:17:34Guy Raz?

  Where did you see the, what was the most popular task? Was it IKEA furniture building?

• 1:17:41Speaker 01

  Literally since day one, IKEA Furniture Assembly was always in Yeah, I mean, it was always in the top five tasks and it number one all the time.

• 1:17:51Guy Raz?

  Taskrabbit, it became in my mind, I remember it was like, oh, you just want to just get a Taskrabbit person to do it if you don't have time.

• 1:17:58Speaker 01

  Yes.

• 1:17:59Guy Raz?

  I remember people saying that in like 2014, 15. I remember having those conversations.

• 1:18:04Speaker 01

  It was always, always IKEA Furniture Assembly and it's so funny because it took years and years to to make contact with them and you know, finally we did, obviously, but um, but that was great for us. That was great.

• 1:18:17Guy Raz?

  And meanwhile, you guys actually start to become profitable around this period and and you also start to have conversations with IKEA. I mean, I mean, and you knew that tons of people were coming to Taskrabbit to get their IKEA furniture built. So it was like a like a match made in heaven. So initially, when IKEA started to talk to you guys, was it was it talking about a potential acquisition or did it start with like a partnership conversation?

• 1:18:44Speaker 01

  It started with a partnership conversation and they knew that we were live in London and London is one of their biggest markets and London for us was number four out of all the markets we were launched in. So we were doing very well in London.

• 1:19:01Guy Raz?

  Yeah.

• 1:19:02Speaker 01

  And they wanted to talk about a partnership in store so that they could drive up sales, right? And have people buy more IKEA furniture because it would then be assembled by a Taskrabbit.

• 1:19:14Guy Raz?

  And so initially was let's, yeah, let's have some kind of partnership.

• 1:19:18Speaker 01

  Yeah, and it was great. So we launched in the London market, a partnership between IKEA and Taskrabbit. And what I really got excited about with IKEA is particularly being in their headquarters, you could feel that they had similar values around sustainability and culture, just their way of thinking about the business. It felt really aligned with Taskrabbit.

• 1:19:47Speaker 01

  And that got me really excited about working with them.

• 1:19:49Guy Raz?

  All right, so IKEA acquires TaskRabbit in 2017 and not long after you leave, you step away from the company.

• 1:19:59Speaker 01

  Yes.

• 1:20:00Guy Raz?

  Do you feel, I mean, you're five years plus removed from TaskRabbit now. Is it, I mean, do you have any emotional attachment to it or not anymore?

• 1:20:11Speaker 01

  Oh, God.

• 1:20:13Speaker 01

  I do. It's, it's, so as a founder, I always felt like, wouldn't it be amazing to build something that lives beyond you?

• 1:20:24Speaker 01

  And that's what I got to achieve. And that was incredible. Now, the flip side of that is there's this company that lives beyond me that I have no control over anymore, but everybody associates with me. And so sometimes I'm on the opposite end where people are like asking me questions about like, oh, and, you know, what do you think about this with TaskRabbit? And what do you think about this decision or that? And I'm just like, wow, I like, I have no input, no, I'm very detached, very detached. I know a handful of people at that company today. So it is sort of odd for me because it was my baby. It is my baby. It was the first, the first baby.

• 1:21:09Speaker 01

  And so it is this very conflicting feeling at times. I'm proud that it lives on beyond me. And I also sometimes feel a conflict that I'm no longer a part of it.

• 1:21:22Guy Raz?

  Yeah.

• 1:21:24Guy Raz?

  I mean, this is an amazing story. Like you started this in an apartment in Charlestown, Boston, and did everything. I mean, you, you, you built the site and all the functions and features and you recruited the users and you recruited the taskers and you formed the LLC and you did it for a year and a half before you hired somebody. I mean, that's amazing. And that's, and then you built a brand, a brand that people know. They're, they know that name.

• 1:21:54Speaker 01

  Yeah.

• 1:21:56Speaker 01

  I mean, looking back, it was a lot and.

• 1:22:01Speaker 01

  Could I go back and do it all again? Oh, my God, I don't know. Could I go back and even do that whole product pivot change in 2014? I don't know. But I'm really, really glad that I did, when I did. I'm proud of the journey that I had, that we had. But it was a lot.

• 1:22:26Guy Raz?

  Do you, when you think about, you know, what happened with TaskRabbit and your, and everything that you created and built, obviously with great, smart collaborators, do you think that what you achieved there was because you worked really hard? Or do you think there was luck involved, too?

• 1:22:44Speaker 01

  I think it's definitely both. I think that there are definitely times that, through circumstance, I was very lucky. For instance, being able to be out to dinner and get connected with Scott Griffith from an old coworker. Like, you can't plan some of these things to happen. There was a lot of serendipity. And I think at the same time, given the serendipity, you have to be able to capture it and execute on it.

• 1:23:16Guy Raz?

  Yeah.

• 1:23:17Speaker 01

  And so, for me, I feel like it was very much both. It was both.

• 1:23:23Guy Raz?

  That's Lea Sullivan, founder of TaskRabbit. Right now, Lea is helping lead an early-stage venture capital firm called Fuel Capital. By the way, she and her former husband Kevin divorced a few years after the sale to IKEA, but they still remain friends, and Lea is now remarried. And from time to time, she still hires taskers. In fact, a while back, after TaskRabbit went fully remote, Lea heard that they had to get rid of the eight-foot wooden logo that used to hang outside the office. She hated to think of someone throwing it out, so she hired a tasker to deliver it to her house. And it now sits in her garage.

• 1:24:04Guy Raz?

  Hey, thanks so much for listening to the show this week. If you want to contact the team, our email address is [email protected]. And if you want to follow us on Twitter, our account is @HowIBuiltThis and mine is @GuyRaz. On Instagram, we're @HowIBuiltThis and I'm @Guy.Raz. This episode was produced by Kerry Thompson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Sam Paulson. Our production staff also includes J.C. Howard, Casey Herman, Liz Metzger, Alex Chung, Josh Lash, Catherine Seifer, Elaine Coats, Chris Messini, Carla Estevez, and John Isabella. I'm Guy Raz, and you've been listening to How I Built This.