Leah Busque founded TaskRabbit after running out of dog food one February night in 2008. She quit IBM four months later, bought runmyerrand.com for $6.99, and launched the site in Boston. A $750 flight to pitch Tim Ferriss led to his mentorship and a $1 million seed round from Floodgate.
Chapters
Hello. So tonight I'm gonna share with you the founding story of TaskRabbit. And some of you may feel like you've heard this story before, but I'm gonna tell you the story behind the story. The true story of how I founded TaskRabbit. It started on a cold winter night in Boston. It was February of 2008. Boston. Um. I remember it was February because it was snowing outside and it was really cold. And my husband and I were sitting in our kitchen and we were getting ready to go out to dinner. So we had called a cab to pick us up, take us across town. Note that I said cab, not an Uber or Lyft. This is 2008, people. Um, and the cab was on its way when we realized we were out of dog food. At the time, we had this 100-pound yellow lab named Kobe, who we kept very well-fed. And we thought, "Oh no, how are we gonna get this dog food? Are we really gonna have the cab stop on the way to the restaurant? Are we gonna drive the dog food with us to the restaurant? What if all the stores are closed on the way home?" Why is this such a big problem? It's dog food. It should be simple. And that night the conversation turned into, "Wouldn't it be nice if there was just a place online we could go, say we needed dog food, name the price we were willing to pay. We were certain there was probably someone online that could help us out, maybe someone in the neighborhood, maybe someone who was at the store at that very second. Why couldn't we just connect with them?" So my husband is also in technology, so we always had these very geeky conversations in the house. And I grabbed my iPhone at the time. It had just come out 4 months earlier. This is the dark ages. You know, no one was really using location-based awareness yet in their apps. No one was building on mobile. No one was building on the iPhone. There was no App Store. No one was using the social graph, social networking. Facebook was just just coming out of the college scene. But I was an engineer and I worked at IBM for 8 years and I love technology and my husband Kevin was the same way. And so I became really passionate and really excited that evening about what if we mashed up these technologies, you know, the iPhone and mobile and location and social and what if we were able to connect real people in the real world to get real things done. Like, is that kind of insane? And so I grabbed my phone and I said, "Alright, if such a site existed, what would it be called?" And at the time, the first thing that came to mind was runmyerrand.com. And I typed it in and the domain was available. Domains are never available. So I bought the domain name for $6.99 on the spot that night. 20 minutes later, I hated the name, but I thought, you know what, maybe, maybe I should see if there's something here before I obsess over the name. So the cab came to pick us up, and I gave Kobe lots of extra treats and threw him some chicken I think we had in the fridge, so he didn't starve that night. But over margaritas and Mexican food, we sort of started talking about this idea that evolved into TaskRabbit. And it was a pretty crazy night because by the end of the— by the end of that dinner, we were meeting a bunch of friends, we had a business plan for TaskRabbit, and someone vomited in my sock drawer. So it was like one of those just like crazy nights, right? But We woke up the next morning and we're like, "Hey, do you remember that idea we had? Remember that domain name that I bought, runmyurn.com? Do we really think that's still a thing?" And even in the light of day the following day, it seemed like a good idea. So, 4 months later, I quit my job at IBM to build the first version of the site and get it launched in Boston. Now that's the founding story for TaskRabbit, but how did I actually found TaskRabbit? I believe that ideas are not inventions. I believe they're discoveries. And I think our job as an entrepreneur is to be able to discover those ideas, because they're all around us. They're like air. We breathe 'em in, we breathe 'em out. and we have to be able to uncover them. So the real story about founding TaskRabbit isn't that I came up with this idea. Sure, there's this moment of inspiration. Kobe was out of dog food one night, and the timing was great, right, because these technologies were coming into play, and I thought about how we could mash them up together, but really it came down to How was I training myself to think entrepreneurially at that time? The truth is, is that leading up to that night, leading up to that moment of inspiration, I had been obsessing for months about leaving my job at IBM. I was kind of bored. I was thinking, "There's gotta be other things that I could be doing." I was already starting to think entrepreneurially, and I was in a certain mindset. And I think, as I look back, that was the key. If I hadn't been in that entrepreneurial mindset when that moment of inspiration hit, when we were out of dog food, I never would have discovered the idea for TaskRabbit. One of my friends, Adam Grant, has this amazing book called "Originals." Hopefully some of you have read it. If not, I highly recommend. It's awesome. And in it, he describes this concept a vuja day. Now, vuja day is the opposite of déjà vu. So, you know, déjà vu is when you see something for the first time but you feel like you've seen it before, like you've been there before. Can be explained as a simple glitch in the matrix. But vuja day is the opposite of that. It's when you've seen something 1,000 times and you're able to take a step back and look at it differently. And that's what I did that night when we were out of dog food. I confess it was not the first time we had run out of dog food for our poor dog Kobe. We're delinquent doggy parents. Now I have 2 children and I promise you they eat every single day. But it was really about how do I, how did I get into that entrepreneurial mindset? And I was actually talking with Adam about this exact thing, because I said, you know what, I just— that concept in your book really resonated with me because I felt like that being out of dog food, that inspiration that night, that was a Vuja De moment. And he's like, yeah, but how did you get into that moment? How did you— why did your brain lead you there? And so I took a step back and I thought about it, and I said, you know what, the truth is, is for months I had been thinking about different ideas and trying to look at the world differently and not going on autopilot. I think sometimes it's so easy to just go through your life on autopilot. You have your routines, you hit challenges, you kind of move through them. But if you can take a step back and you can slow yourself down, that's when you can really start to see things differently. Now, for me, getting into this entrepreneurial mindset felt a little bit awkward at first. I mean, I was, I was going through, you know, normal things every day, but stopping and talking incessantly about them and asking my husband Kevin what he thought. You know, it can feel really awkward, but if you can force yourself to get there, then I think it can be a really, really powerful thing, and you can take the ordinary and turn it into something extraordinary. So, how did I take this idea for TaskRabbit and raise my first round of funding and turn it into, you know, where we are today? Well, I had the idea, quit my job at IBM, built the first version of the site, got it launched in Boston. Now what? It's September of 2008, the stock market is crashing, very tough economic time. Worst time to be raising money. By the way, I didn't even know how to raise money, um, at the time. But I got accepted into an incubator program that brought me out here to the Bay Area called FB Fund. And it was run by Facebook. And Dave McClure, before he did 500 Startups, started this incubator. And so I was flying back and forth between Boston and San Francisco, a week in Boston, a week in San Francisco. Completely bootstrapping the company on my own, and I flew to Boston and had just spent the week in San Francisco and got an email from Dave saying, "Hey, we have a special guest coming to the office on Monday." This is Friday. "His name is Tim Ferriss, and he's willing to meet with companies that are here." And I was like, "Oh man, I just flew back from San Francisco, and I'm in Boston, and I'm supposed to spend this week in Boston, and actually this company is live in Boston, and there's no one else but me like running this thing right now. So I go online and I look at plane tickets, and I see that it's like $750 to get a ticket back out to San Francisco that Sunday night and be there for Monday. And I emailed Dave and I was like, "Hey, I'm not supposed to be in town, but this sounds really exciting, you know, how much time are we gonna have with Tim?" He's like, "You have 15 minutes." 15 minutes with him. Okay, so $750, 15 minutes with Tim Ferriss. Like, is this really worth it? Like, I'm— this is going on my credit card. I don't know if I should do this or not, but I thought, you know what, if I can turn $750 into the million-dollar seed round that I'm hoping to raise, then it'll be worth it. And that was my threshold. I was like, anything less than that is not worth it. And so I bought the plane ticket, I got on the plane, I flew to San Francisco, met with Tim for 15 minutes that Monday, and I said, "All right, my goal is to get him on as an advisor because I think he could really help us." And his book, The 4-Hour Workweek, had just come out, and he writes all about living efficiently, and TaskRabbit is like the perfect thing that fits in his portfolio. And so I thought, in 15 minutes I'm not going to convince him to come on as an advisor, but I could definitely get a second meeting. So that's my goal, in 15 minutes just get a second meeting. So walk into the Facebook office, you know, get the meeting with Tim, sit down with him, start showing him— at the time it was still actually RunMyErrands.com— showed him the site. And, you know, it's like 10 minutes, 11 minutes, 12 minutes, he's talking and I'm like, oh my god, It's almost 15 minutes and I haven't been able to ask him for a second meeting yet. And so it gets to 15 minutes and I was like, you know what, this has been so helpful, you know, can we meet again? Would you be willing to spend more time with me? And he sort of hesitated because he's like saw the crazy look in my eye, but he agreed to it and he said, you know what, you can email my admin and she'll set something up. So walked out of the room and immediately, you know, emailed his admin and she said, you know what, Tim actually, you know, can do a call with you next week. And I was like, Oh man, a phone call? Like, I just met him in person. Like, I feel like I'm better in person, and I've gotta turn this plane ticket into a million-dollar seed round. How am I gonna do this? And so I said, "You know what? I'm gonna be in San Francisco at that time in the neighborhood." And decided to stay and ended up meeting Tim in person over lunch. We really hit it off. And at the end of that lunch, he agreed to come on as an advisor. And he is the one that introduced me to Anne-Marie Coe from Floodgate Fund, who led our $1 million seed round. So, woo! It was nerve-wracking, but I made it happen. And I think for me, the biggest takeaways from that first year of discovering TaskRabbit and raising that money was ideas are everywhere. I needed to be in the right mindset to find that idea. And then just willing your way forward, willing things to happen. There was no way I was gonna let that plane ticket not turn into that seed round of funding. Thank you.
