From Boston Software Engineer to Running A Venture-Backed Startup in San Francisco

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By Leah Busque (Founder & CEO, TaskRabbit) The Beginning of TaskRabbit

It was a cold night in Boston in February 2008. My husband, Kevin and I were getting ready to go out to dinner and had just called a cab when we realized we were out of dog food for our yellow lab. We thought of our options -- have the cab stop on the way home to pick up dog food, or run to store real quick before dinner. None was very appealing.

Both my husband and I are in technology so we tend to have some geeky conversations. That night it turned into -- “Wouldn’t it be nice if there was just a place online we could go, say we needed dog food, and name the price we were willing to pay. We were certain there was someone in our neighborhood willing to help us out.”

In that moment of inspiration (or desperation), TaskRabbit was born. Little did I realize that my life would take a dramatic turn.

The Beginning of TaskRabbit

I spent four months talking to anyone who would listen about the TaskRabbit concept. One of the people I met was Scott Griffith, the CEO of Zipcar. I didn’t know Scott before, but a friend of a friend introduced us. I spent 30 minutes describing my vision for TaskRabbit and at the end of the conversation he said, “I think you are onto something here. I think you should see how far you can take it.”

In fact, this response “see how far you can take it” was a common theme with the people that I met. Thankfully, no one said, “You are insane, this is an awful idea!.” So four months later, in June of 2008, I decided to quit my job at IBM and build the first version of the TaskRabbit website. I cashed out my IBM pension to float us for the next six month, hoping that would be enough time to see what I could do with the idea.

Before that fateful night, I spent 7 years working as a software engineer at IBM, building enterprise software.

I loved my job and I really enjoyed the people I worked with at IBM. But that flash of inspiration had taken a hold of me -- I just couldn’t shake the feeling that I had more to offer and more skills to develop and share beyond programming.

I holed myself up for 10 weeks in the summer of 2008 and coded the first version of TaskRabbit. It was a rough MVP, but it was enough to determine if there was any interest from the market. I figured if I could launch TaskRabbit in one Boston neighborhood, I could measure the interest in the overall market. In the fall of 2008, I launched TaskRabbit in Charlestown, the neighborhood where we lived. It took off and grew very organically. Soon people from all over Boston were posting jobs.

Finding Advisors and Mentors

I pinged Scott Griffith and said, “Remember when you told me to see how far I could take TaskRabbit? Well, I left IBM and have the website launched in one Boston neighborhood.” He immediately came on board as my first Advisor and mentor, which was an incredible milestone for me. From there, Scott introduced me to two early investors in Zipcar, who decided to lead a seed round of investment in TaskRabbit. This was nine months after I left IBM, three months longer than my original six-month plan. Those last three months were difficult, but I knew I was close. Scott also encouraged me to apply to the fbFund Incubator program that was running in the summer of 2009.

The fbFund program was such a tremendous opportunity to meet other entrepreneurs, investors and advisors. One of those advisors was Tim Ferriss, who visited us at fbFund. I had read Tim’s book, The Four Hour Work Week, and loved his perspective on living efficiently, understanding what your time is worth, and outsourcing your life. It was perfect synergy with TaskRabbit.

The problem was, I heard on a Friday that Tim was going to visit fbFund the following Monday. Unfortunately, I was scheduled to be back in Boston. I checked last-minute flights and at $750, it was really steep for a bootstrapped entrepreneur. I struggled with the decision to connect with him remotely via phone or to meet with him in person at fbFund. I thought if I can turn this $750 into a $1 million dollar+ seed round, it would be totally worth it. So, I hopped on a plane and flew to SF for the day, determined to bring on Tim Ferriss as an advisor.

After meeting with Tim for 15 minutes, he loved the idea of TaskRabbit! Tim came on as an advisor a week later and introduced me to some of the top seed fund investors in Silicon Valley.

One of his first introductions was to Ann Miura-Ko of FLOODGATE Fund. We met over breakfast one morning in Palo Alto and she immediately saw TaskRabbit’s potential. At the time, I was the still the only person on the team, but that didn’t stop Ann from leading our seed round to help build out the team and really prove out the model. Baseline Capital and First Round Capital also participated and we ended up raising $1.8M. Looking back, it was the best $750 I have ever spent.

Team Building

I hired my first full-time employee, Brian Leonard, who joined as our VP of Engineering. We then decided to move the team from Boston to San Francisco, where we established TaskRabbit’s second market. Fast forward to today -- we have been in SF for over a year and have 10x our growth over the last 12 months.

Once we felt confident in the model we’d established in Boston and San Francisco, we knew we were ready to take TaskRabbit to the next level open additional markets. To do that, we needed the next round of capital. So, we took to the road (Sandhill Road, that is) to raise our Series A financing.

We met many investors along the way and were lucky enough to receive warm introductions from our original powerhouse investors. When we met the partners at Shasta Ventures, we knew they would be the best fit. With their focus and passion for consumer Internet brands, they understood the tremendous opportunity we were building and wanted to help.

From Engineer to Entrepreneur

As I write this, I am sitting in a hotel room in Los Angeles, getting ready to launch our third city. It has been the perfect time to make this reflection. As a female technical founder, I can’t really say if the road has been any different for me than it is for my male counterparts. I have nothing to compare it to. What I do know is that I am so grateful for the tremendous mentors, advisors, investors, and the team I have built. Making the leap from an engineer to an entrepreneur hasn’t been easy, but I remember my defining moment where I literally thought -– this isn’t rocket science, I’ll figure it out. I should just go for it.

Startup Lessons Learned

  1. Tell anyone who will listen about your idea. Don’t worry about keeping things stealth or about the competition. Take in everyone’s feedback and use it to shape your own independent perspective.
  2. Never pass up a good networking opportunity, and nothing can replace an in-person meeting. Always show your passion for your idea - you never know where these meetings will lead.
  3. Iterate quickly and constantly look for customer feedback. Make it really easy for customers to pick up the phone or drop you and email to share their experiences. Continually make improvements and push code focused on these improvements at least once a week, if not every single night.
  4. The right investors will have the same passion and obsession with the business that you do. The conversation will feel less like a pitch and more like you’re collaborating on the business model. The investors who want to sit down and brainstorm with you, and have interesting perspectives to share, are going to be your best partners.
  5. Don’t overthink things -– just do it. Being an entrepreneur is an attainable goal. If you have an idea that you are passionate about, trust yourself, you will find a way to make it happen.

Women 2.0 members save $20 on your first task on TaskRabbit with code "WOMEN20"

TaskRabbit Founder Leah Busque will be speaking at TEDxSOMA on Saturday, June 18, 2011. Get your ticket here.

Leah BusqueAbout the guest blogger: Leah Busque is the Founder & CEO of TaskRabbit, a community of people joining together to get things done. Prior to founding TaskRabbit, Leah was a software engineer at IBM. A Boston native, Leah is a volunteer math tutor for the Boys and Girls Club of Boston, and returns often to Sweet Briar College as a guest lecturer for women and entrepreneurship. Leah holds a B.S. in Mathematics and Computer Science from Sweet Briar College. Follow her on Twitter at @labusque.