TaskRabbit

“Inside there was like a paper return survey, because we still didn't have a website, and so it was a piece of paper that was like an Excel thing that had all the items, and then you would fill out with words what you were going to keep, what you weren't going …”

“So it ended up being about 20% of the team. At that point, we were probably 80 people, and so it was under 20 people that we transitioned out.”

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

“So day one, they get us to stand up, introduce ourselves to And give our 32nd 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.”

“I mean, at that point, I think we were burning probably over a million dollars a month.”

“I think the culture of Bostonians is a very do-it-yourself mentality. 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 …”

“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 gonna pick up your dry cleaning was two degrees of separation from y…”

“And so then they put together a five million dollar term sheet.”

“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. It was too e…”

“And it was the largest round that we raised. It ended up being eighteen million dollars led by Lightspeed.”

“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.”

“I typed into my iPhone into GoDaddy, runmyerrant.com, and the domain name was available for six 99. So I bought it on the spot,”

“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.”

“You know, the main revenue stream was the commissions, and the average task size at that time was about a 150 dollars. And so it, the number, the numbers worked. We took anywhere between 20 and 30% of a task, and that was, you know, net profit to us.”

“Even at scale with TaskRabbit, Boston was like number 10 market. For us.”

“It was overwhelming. And the, I mean, 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…”

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

“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 postin…”

“And the investors say, let's start with 50 K. We'll give you 50 K. Let's see how you do. So we start with 50 K. That was March in 2009.”

“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, and we're like, ok, this works.”

“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.”

“I ended up being the one doing a lot of the early jobs. I had this little scooter that I rode around Boston, a Charlestown area, and I would do a lot of the early jobs myself, and so I would then get, like, first-hand knowledge of what it was like to be A task…”

“So we get the offer from Facebook to come out to do the incubator program. It's 15,000 dollars. And it's for a chunk of the company. It's like, you know, a few percentage points of the company.”

“We were this tiny company in Boston for, you know, almost two years before we even opened the San Francisco market.”

“Having experience now as an investor and having talked to hundreds, if not thousands of entrepreneurs, I really think it comes down to three things. Timing, technology, And TAM, the three T's.”

“I think as a founder, you have so many ideas, you see all the possibilities, and really, you have to pitch all of those possibilities to kind of bring people in and inspire them and get the company off the ground, but when it comes down to execution and custom…”