Having an Entrepreneurial Mindset

Well take us back to 2008 when you started TaskRabbit, when you were out on your way to dinner one night

and you realized you forgot dog food. You ran out for your dog.

That's right.

And you thought, wouldn't it be great if you had someone right now to just come by, pick up the dog food, and deliver it. How did you go from that one single idea to pioneering a whole new sector really?

Well, it didn't happen overnight. That's for sure. And I always tell the story like it was that moment of inspiration, which is completely true. I was out of dog food one night. I came up with the idea for TaskRabbit. I quit my job at IBM four months later and started the site, but I wouldn't have actually even discovered the idea for TaskRabbit unless I had been thinking for many months, even years I would say while I was at IBM, about what I wanted to do next. And I sort of got myself into this entrepreneurial mindset of looking at problems that I would hit in everyday real life, and taking a step back and thinking, are there new solutions here? So I think because I was in that entrepreneurial mindset, when I was out of dog food that night, that's really how the idea for TaskRabbit was formed. So you have an engineering background, and you in a way had been prepping yourself all along for this moment when the brilliant idea came along. I'd say about 5 years into IBM I was sort of getting bored, maybe a little bit antsy. And I was thinking, you know what, I have all these other skills that I know I have, that I'm not using on a daily basis.

What were some of those skills?

Well, you know it's funny because at IBM, there is this one time of year where they let the developers actually talk directly to the customers. And it was this big conference they called Lotusphere. And it was tens of thousands of people from all over the globe would travel to Orlando, Florida. We would fly down from where Lotus was located up in Cambridge, Massachusetts, down to Florida. And we'd have this meet the developers lab. And I loved meeting customers. I loved talking to customers. I loved getting their feedback. I loved solving problems for them in real time. I remember one day this woman came in with her laptop and she was really frustrated, and really stressed out, maybe even a little bit angry, because she couldn't get you know, her mail file to archive properly. And I remember debugging the problem for her on the spot, fixing it in the code, patching it up on her laptop.

Wow.

And she was so happy when she left. And I was like, you know I just wish I got to interact with customers more. And so I realized that doing something entrepreneurial, that would help me utilize that one skill set I wasn't using at IBM.

But it took reflection on your part, and a certain self-awareness on your part, right, to kind of reach for that next goal.

It did. You know, I went to a small women's college. It was a liberal arts college, where I studied math, computer science and dance. And so I think...

That's an unusual combination.

I know, right? But I think that I was always exposed to a more general, more holistic view of the world, and of learning, and of education. And so I don't think that I'm built to just focus and kind of fall into line into one niche area.