Keep Making those Connections

Inevitably as you're building a company you'll always run into roadblocks. What kinds of roadblocks did you run into that were hampering innovation, and how did you coalesce your team to overcome those barriers?

Yeah, I mean in the early days, it was really, really hard to raise money in 2008 and 2009 for an unproven entrepreneur with no network You know, investors weren't writing checks. And so it took a lot of hustle, a lot of bootstrapping, a lot of maxing out my credit cards, to really make it happen, and eventually I was able to get two Boston area angel investors to put in $150,000 to the company, which really made a huge difference to me at the time. That's really what got me sort of to the next step where then I was able to come to the West Coast and participate in an incubator program that Facebook was running called FB Fund, and then that really opened up the door to Silicon Valley investors, which really in 2009 got the idea for social networking and these emerging technologies in a way that, you know, other investors I was talking to didn't.

And so it was really important, I think, all of those little baby steps and all of those little struggles, and you know, maxing out the credit cards and just doing whatever it took. You just never know what the next connection is going to lead to or the next person you're going to meet, if that's going to be the person that makes the difference. And there's so many of those stories along the way, over the course of 10 years, that I could just have never planned. It was really about just persisting through all of those challenges and then right around the corner, you know, something amazing happens.

So it's about persistence, but would you say it's also about remaining open to whatever may come along?

Absolutely, I mean I have this slide in this presentation I've created. And it's this map of all the connections I made from day 1 when I first had the idea for TaskRabbit. And it's about 10 different nodes of connections I made that then led to Ann Miura-Ko at Floodgate Fund investing a million dollars into the company. But along the way, if any one of those people- I didn't meet, or I wasn't at that dinner, or I wasn't at that networking event, or I didn't have that conversation, it never would have led, at least in the same way and the same path, to that investment. And then off of all those nodes, there's like a hundred other connections of people that I talked to and I made. I mean, I think as an entrepreneur, it's really your job to be open, as you said Thuy, to whatever possibilities come your way, but then also to make those possibilities into something that's going to help your business. And I think that's the magic of entrepreneurship, just making something out of nothing.

Preparation meets opportunity.

Absolutely. It's a good way to put it.