TaskRabbit

“We tasked our office agent to just make was it like a hundred dollars, a thousand dollars? We just gave that prompt. And then what it did was sign up on TaskRabbit, both as a task Looking for, like arbitrage., arbitration.”

“I've gone from running a company by the quarter, really every three months you have OKRs and objectives and things that you have to get done, to thinking about what can we, what value can we create in 10 years? So I have to think a lot longer term in what I'm …”

“And so once I decided to start a venture firm, all those people who wanted me to do something else, some of them invested in my fund, super excited, to this day, send me great opportunities.”

“It was a 36%. I remember this number because I was like, So flabbergasted when I found out about it, 36% participation rate, and it happened to be pretty much director and above, right? The younger folks weren't using it in any way.”

“Most people don't know, but we actually, Leah and I, at the time when we founded TaskRabbit, we actually cashed out some IBM pension to go and start TaskRabbit. We bootstrapped TaskRabbit for a couple of years before we took the first investment.”

“So in the end, the asset base fee for task rabbit early on was 1.67% or 167 basis points.”

“Our first employee was actually a lawyer. And this was a person, you know, generally not fresh out of law school, but somebody young enough to essentially interpret, interpret ERISA, the IRS regulations, Department of Labor, SEC, et cetera. And that was really…”

“Like the first 10 Lyft drivers were TaskRabbits because John at the time didn't know how to do background checks and like we wrote background checks. For TaskRabbits, right?”

“The thing that I also said I would never do again would be a transaction-based company. I love the recurring revenue model, like AR is, like, just where it's at. At TaskRabbit, it was like, all right, get all these tasks posted, and then at the end of the day,…”

“If you look about, you know, look at TaskRabbit, we were too early. Like we should have waited five years, followed on Uber or something like that. Like we could have done that a totally different way, but definitely some timing, right time, right place, solvi…”

“So they bought TaskRabbit for a small amount, 50 to seventy-five million, somewhere in there, a few years ago.”

“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.”

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

“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…”

“And at that point, we were live in London, internationally. London was our fourth largest market. It happened to be IKEA's first largest market in the world.”

“You'd buy IKEA furniture on checkout. You could sign up to have TaskRabbit, deliver it, and assemble it. Drove up average order value immediately for IKEA.”

“I had a very complicated board dynamic at different points in my TaskRabbit journey, and I was always super sensitive to the imposition that an investor can have on a founder, and I always wanted to be that investor That was going to be really helpful and was …”

“Technologies like AI, it's a big game changing technology, but the costs are still so high to launch something. I think startups, you know, need to raise a lot more money to get started right now today. Than I did. I mean, I started with 250 K from angel inves…”

“And I typed in the domain name runmyeran.com, and it was available on GoDaddy for six 99, so I bought it. And then for the first 18 months that we existed, we ran under that name.”

“As I look back at it was like 27,000 dollars I had earned in my pension plan, and I was like, well, I could take this out and pay the tax penalty, and this is what I'm gonna use to start the company.”

“It took six to eight weeks to get something built that I felt like was ready for people to use. And then I said, okay, I need to find people that are gonna do the jobs. And so I went on Craigslist, put it out, put out an ad for someone to run errands.”

“I didn't plan the timing like that, but it turned out to be the perfect time to launch a company like TaskRabbit.”

“I started with 30 taskers that I handpicked.”

“I learned very quickly that by offering a service where you could get anything done, one, people had no idea what to post.”

“I think my mistake there was that the company was still so young, it was still so early, To remove the founder as the leader. A COO would have been fine. And in fact, the second time around, we brought in an incredible COO that's been on this podcast before, S…”

“We had someone come in for six Six to nine months We ended up hiring too many people, scaling up too fast, the burn got really high, and it was just kind of like, we need to get back to basics here and regroup.”

“If I could go back and do it all over again, I would have tried harder from the beginning. To find a co-founding partner. Like before I went to the incubator program, you know, maybe even before I left IBM, I would have taken the time from the very beginning t…”

“When we hit 50 people, I feel like everything broke. Communications broke cross-functionality between teams broke, the culture broke everything broke.”

“From day one, the highest volume task on the site was always Ikea furniture assembly from day one.”

“They haven't absorbed the brand into their own, and they continue to do all the other jobs and tasks that TaskRabbit usually does.”

“I would ask them, what are you saving for me as a company? What do you got earmarked for me in this fund? Right? And I think understanding that along the way would have been helpful in planning how we, how and when we did fund raises.”

“We show up, we had task rabbits outside of the event in Brex t-shirts handing out Brexfist burritos to every single person that walked in the venue. So the first experience that they have at Sastra is they get a Brex burrito on when they walk in. Four bucks a …”

“Uber, DoorDash TaskRabbit has basically taken every American who wants to be a gig economy worker or monetize kind of their skills, but it's all been done within manual labor. This is the first time I've seen it be done within kind of like knowledge work.”

“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,”

“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…”

“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.”

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

“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…”

“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…”

“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.”

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

“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.”

“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 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 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.”

“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.”

“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…”

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

“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.”

“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.”

“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.”

“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…”

“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.”

“And actually, between 20 11 and 20 13, we evaluated opportunities to invest in Grubhub, in Caviar, in Postmates, in TaskRabbit, because I was fascinated with this space. We passed on each of those opportunities, not partly because we're somewhat concerned abou…”

“So despite the fact that the company is like Andrew's List, Home Advisors, and TaskRabbit, 90% of people say you is word of mouth to find help.”

“50% of the people had a bad experience, and they told 10 times more people than the people who had a good experience. That just wasn't gonna work for the long term.”

“The assignment rate went up. Our close rate went up to over 80%, not 50% anymore. We knew that we were on to something, and then we brought it back to the U.S.”

“But the more users feel their identities and economics are invested in your product, then you are no longer the sole proprietor. Your users are owners too. They may not hold equity or have a parking space in your office lot, But they are part owners in the bra…”