The Blog

The Best $750 I Ever Spent Bootstrapping My Startup: One Plane Ticket West

It was Friday and it had been a long week. I was back in Boston after spending the last two weeks in Palo Alto, participating in the Facebook Fund program (fbFund).
This post was published on the now-closed HuffPost Contributor platform. Contributors control their own work and posted freely to our site. If you need to flag this entry as abusive, send us an email.

By Leah Busque (Founder, TaskRabbit)

Editor's note: Vote Leah Busque for TechCrunch's Founder of the Year!

It was Friday and it had been a long week. I was back in Boston after spending the last two weeks in Palo Alto, participating in the Facebook Fund program (fbFund).

Over the past 12 weeks, in fact, I was flying back and forth between Boston and San Francisco, alternating weeks on each coast. My company TaskRabbit ( at the time) was up and running in Boston, and I was splitting my time between the two cities in order to get the most out of the fbFund incubator program while continuing to grow my business in Boston.

A few nights after settling back into Boston, I received an email from Dave McClure saying that Tim Ferriss will be at fbFund the following Monday and was offering 15-minute meetings with the incubator participants. I had read the Four Hour Work Week, and Tim is someone who I'd admired for a long time. His philosophy about living more efficiently and focusing on the things that are most important really resonated with me. They were also clearly consistent with my vision for TaskRabbit. I knew immediately that Tim would be the perfect addition to my advisory board.

But, I had just returned from Palo Alto, and was settling back into my routine in Boston. Hopping back on a plane with two days notice, and flying cross-country was going to be very expensive. I went online to look at pricing and sure enough, the round-trip ticket was $750.

At the time, I had been bootstrapping the company for almost 18 months. My husband and I were racking up credit card bills, and another $750 was a lot to consider. I remember thinking about how much I could do with $750 - I could purchase a boatload of marketing collateral, buy Ads on Google, or pay our server hosting for the month. It was a significant amount of money and really had to justify the trip. I asked a couple friends for advice - should I fly out there just for the day for $750? Their advice: "Why not just email him or have Dave introduce you via email?"

But, my gut just kept egging me on - there is no substitute for an in-person meeting. Finally, I decided to follow my instinct and book the trip. I figured if I could turn the $750 plane ticket into an advisorship with Tim Ferriss, it would be totally worth it. Further, what if he could make introductions that would lead to a seed round of investment for TaskRabbit? There would be no more racking up the credit card bills!

I remember booking the trip with conviction. I was getting on that plane and refusing to come home with anything less than a new advisor. During the late-night flight on Sunday, I re-read the Four Hour Work Week, so I would be on top of my game. When I arrived to the fbFund office on Monday, Dave and the rest of the team had no idea I had flown in for this 15-minute meeting, and I played it cool.

I waited patiently for my turn and thought about my strategy before going in. 15 minutes can go by in the blink of an eye and I had to ensure that I had enough time to win him over. I decided that 15 minutes was not enough time to really have a thoughtful conversation about an advisor role, so my goal was to get a second meeting booked.

I walked in, shook Tim's hand, and was excited to get his feedback on the product. We talked about the homepage design and how I might be able to optimize the conversion rate with a few tweaks. They were great points; Tim has an incredible eye and solid track record for moving the needle in these areas. We also talked about his theories on living more efficiently and how that fit with the TaskRabbit vision.

Near the end of our 15-minute meeting, I prepared myself to ask the big question. I took a deep breath and said, "Would you be at all interested in having another discussion with me, I found this 15 minutes to be exceptionally helpful, and I would really appreciate any further time you might be able to share."

He hesitated a bit; he gets bombarded with these requests all the time, and I was certain he was thinking - who is this crazy woman in front of him asking for more of my time? In the end, he agreed and in true 4HWW fashion asked me to reach out to his assistant to set something up. I thanked him and said that I really appreciated his time.

Two weeks later, Tim and I caught up over lunch at a small Thai restaurant in San Francisco. Thankfully, it was the week I was already scheduled to be in the Bay Area, so there were no additional travel expenses. I brought my latest pitch deck and we had a wonderful and engaging conversation about go-to-market strategy and how I might spend my first $50,000. Near the end of the meeting, I asked about his appetite for joining our Advisory Board, which he agreed to immediately.

That afternoon, he made an intro to Ann Miura-Ko, co-founder and partner at FLOODGATE Fund. Ann led our $1MM seed round of investment 30 days later, along with Steve Anderson at Baseline Ventures (to whom Tim also sent my pitch deck). It was a huge milestone for me and the company and the first major round of funding.

This funding allowed me to move across the country, establish TaskRabbit headquarters in San Francisco, and build an amazing and talented team.

Lesson learned - you just never know where opportunities will lead so you really have to follow your gut and instincts to make some of these decisions.

Looking back, it was the best $750 I ever spent.

Editor's note: TaskRabbit Founder Leah Busque will be speaking at the PITCH Conference on February 14, 2012 in Mountain View, CA. Get your ticket now!

About the guest blogger: Leah Busque is the Founder of TaskRabbit, the pioneer in service networking. TaskRabbit is an online and mobile marketplace that connects folks in a community to get things done. Since its founding in 2008, Leah has grown the company to more than 35 employees and expanded service to Boston, San Francisco, Los Angeles, Orange County, New York and Chicago. Prior to founding TaskRabbit, Leah was a Software Engineer at IBM. Follow her on Twitter at @labusque.