Leah Busque’s Biggest Task Yet: Building a Community of Trust

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Leah Busque was getting ready to head out the door to dinner with her husband when they realized that they were out of dog food. It was a small inconvenience, but —like any good technophiles— they spent the evening discussing how it could have been circumvented with an app.

Leah had been looking for the right problem to solve for awhile, and that evening got the idea for a platform that connects neighbors to help each other with errands. In 2008, Leah launched the first version of TaskRabbit with 100 ‘helpers’ ready and able to complete errands and by 2015, the company started receiving over 15,000 applications per month to be a Tasker.

We talk to Leah about how she got her start and how she built a community on trust.

How did you get your start?

I was a math and computer science major at Sweet Briar College in Virginia. When I graduated, I found a job at a small startup in Boston that was quickly acquired by Lotus, then IBM. I ended up at IBM for 8 years as a programmer working on enterprise software used by millions of people around the world. I really enjoyed that, but always felt like I had other skillsets and things I wanted to do.

I started to think about what it would look like if I were to leave and do something on my own. I found myself thinking more like an entrepreneur, looking for problems around me to solve. That type of thinking led me to come up with TaskRabbit.

It was 2008, so the iPhone had just come out, and Facebook was just breaking into the mainstream. I became really passionate about the possibilities of social, location, and mobile technologies and wanted to use them to connect people in the real world to get things done. I was certain there was a way to connect people to help with errands and other day-to-day tasks; I just needed to figure out how.

Four months after first coming up with the idea, I quit my job to build the first version of TaskRabbit.

What did those four months look like?

I’m the type of person who gets obsessed with an idea. I talked to anyone who would listen to me: the people at our local coffee shop, people sitting next to me on the bus — everyone.

One of those people was Scott Griffin, then CEO of ZipCar. Scott and I were thinking about our businesses in a very similar way from a vision standpoint. He was putting cars in neighborhoods that people could share, so that a community could live more efficiently together. I wanted to connect people in the neighborhood to share services and errands, so they could live more efficiently together. I remember meeting with Scott on a weekly basis while I was still at IBM, while developing the idea for TaskRabbit.

One day Scott looked at me and was like, “Leah, why are you still at IBM? I really think you’re onto something and you should see how far you can take it.” He threw it down like a challenge, and I took it on. That’s what ultimately got me to make the leap and buckle down to start building the first version of the site.

Now you’re eight years in, what have been some of the biggest challenges?

The biggest challenge early on was technology. There were some big infrastructure, coding, and building hurdles that I needed to overcome.

Trust was also a big challenge. Today, you can hop in a car with a stranger and not think twice about it, but back in 2008 that was unheard of. We spent a lot of time thinking through how to build trust between two people, especially because they would be connecting offline.

There were also a lot of challenges, particularly in 2008 and 2009, around raising capital, finding investors that not only believed in you and your vision, but were willing to write a check while the economy was taking a massive downturn.

Today is very different. It’s more about scale and expansion. We have over 15,000 applications each month from people who want to make money on the platform. I can remember when we started with 10 people just in Boston. It’s really exciting.

How else did you instill trust early on?

We really had to invent how to do that from scratch. For such a long time, the internet was somewhat anonymous. You’d have screen names and wouldn’t use your real name. All that started to change. You had Facebook, Yelp — and other apps using your real identity. We really took advantage of that.

With TaskRabbit, you had to use your real name. Everyone in our community regularly goes through a thorough vetting process that includes a background check, a social security number trace, and several criminal background checks. On the client side, we wanted to make sure that Taskers felt safe that they were going to get paid. So, early on, we verified the identity of clients through credit cards transactions.

Are there any big pitfalls you see when it comes to building a strong community?

You really have to think about both sides of your community. TaskRabbit is a two-sided marketplace. Understanding how to balance those two sides, their incentives, and values is huge. On the Tasker side, we ran a survey and found that more than 70% really value flexibility, even over money. So, we really work hard to ensure that there are the right tools and resources available on our platform to give them that flexibility.

When you’re building community, it’s really important to think about what your brand stands for. TaskRabbit is about being neighborly, open, and collaborative. We hold monthly meet-ups where Taskers get together to swap ideas and best practices. We’ve done a good job at aligning our brand and our company’s core values with how we want the community to operate as well. That attracts a certain type of person to the community that’s going to be really successful in the platform because they’re well-aligned with the company, as well.

How did you decide what features to prioritize?

As a company and as an entrepreneur, can really only do one to three things really well. If you can figure out what those things are — particularly if you look at data to see how the community’s operating, how the business is operating, what people want, what features they want — that’s really going to help influence how you decide to focus.

Where do you see TaskRabbit going next?

It’s a really, really exciting time for the company. We were the pioneers of the sharing economy. We are in twenty cities across the U.S. and have London as our first international market. I still feel like we’ve barely scratched the surface. Our vision is to revolutionize everyday work. That means for clients and taskers, being able to make them their most productive selves every day. There’s still a long way to go.

In April, Leah announced that she was stepping down as chief of the company, in lieu of her new role as executive chairwoman of the startup’s board. TaskRabbit’s chief operating officer Stacy Brown-Philpot became the company’s new CEO.