Leah Solivan

“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.”

“From a venture investor standpoint, which is where my brain works you know, the industry is so fragmented it's slow, it's underfunded and there's not a lot of room, you know, to innovate.”

“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…”

“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 …”

“I think to some extent, to some of the big AI companies, you see the same thing, and so you see the big players like Andreessen, or you see Microsoft investing in OpenAI, like, you need really, really deep pockets to be successful. I think it's harder for the …”

“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.”

“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.”

“I only like to work on problems that I feel like I can uniquely solve. And 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 and uninterested in working on it”

“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,”

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

“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 Zumi's Coffee Shop, thirty-minute interviews, and I brought on 30 of them to start the site.”

“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 I had 27,000 dollars 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.”

“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.”

“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.”

“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, Ann Miraco at Floodgate, and Steve Anderson at Baseline Ventures.”

“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 …”

“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…”

“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.”