Participating in fbFund REV, Facebook’s incubator program run by Dave McClure, connected me with Tim Ferriss who has been immensely helpful and instrumental in helping us launch TaskRabbit in the San Francisco Bay Area.  After fbFund, a round of funding was lead by Ann Miura-Ko at FLOODGATE Fund (formerly Maples Investments) and Steve Anderson at Baseline Ventures.  Ann and Steve have offered invaluable help and insight, and have been really wonderful to work with.  Shervin Pishevar (SGN), Michael Powers, and Payman Pouladdej rounds out this strong group of advisors.

Following the same high standard of working with the right people at the right time, I am thrilled to welcome First Round Capital to the TaskRabbit team.  Their partners are smart, savvy, and most importantly, incredibly supportive of our vision.  As the Founder, I constantly want to ensure that this company is collaborating with the right group of investors, advisers, and mentors.  Anyone can write a check or offer input, but to be able to work with this amazing group is an absolute dream come true.

Many of the craziest of my tiny ventures were not actually about making money, they were more focused on creating movements or trying to make a difference in my small community.  I was always very ambitious, for better or for worse.  It wasn’t until years later at IBM where someone actually labeled me that way, stressing it was a *bad* thing, that I ever questioned that thinking.  Yes, I had the lemonade stand, the garage sale, and the greeting card making business (where I actually created the cards with construction paper and then went door to door selling them in the neighborhood).  I even tried the good ol’ offer of hard labor working to sweep a walk way for $1, rake leaves, organize a garage, etc.  Those were the money making ideas.  Of my other ideas, it was a split between ambitious and insane.  Let me tell you about the insane first.

2nd grade (age 7): My best childhood friend, Johanna, and I got it in our heads that we could build an airplane.  She had a lot of scrap wood in her back yard, and we spec’d it out on a piece of construction paper.  It would not only fly, it would also have the most amazing feature of of giant magnifying glass attached to the top, that could zap things.  I was really into zapping bugs with magnifying glasses at the time.  When my mom told me that it was impossible to build a plane with a glorious magnifying glass on top I had a fit.  A complete and utter fit.  I accused my mother of not believing in me, not supporting me, and ultimately holding me back.  Johanna and I worked on the plane for a month or so, gathering wood, making plans, and eventually, it fizzled.  We dragged all the wood into the forest and made a fort, which was pretty cool, and even secured the fort from intruders with a magnifying glass at every corner.  Note, there is no sun in the forest.

That one was insane, but I had some other good ideas too, that I actually learned from and tried to make a difference with.  There was Pollution Solutions (PS for short), a company I created with my sister, Amber, and my cousin, Mikey, where I was the CEO.  I asked my Dad what was the highest position someone could hold in a company, and he gave me the title of CEO.  We set up offices in my parents basement and worked tirelessly to create posters, flyers, and educate people in the neighborhood about stopping pollution and encouraging recycling.  We even wrote a letter to President Bush (the 1st one) about the importance of ending pollution and got a response back that I think my Mother still has.  After a while, Amber and Mikey, couldn’t take much more of my bossing around, and we decided to close up shop and just play video games.  We ruled Mario Brothers that year.

3rd grade (age 8): At school, with my friends Johanna and April, we kicked off a Recycling program in the lunch room.  We asked the lunch ladies if we could create signs for each trash bin so that the materials would be separated into paper, plastic, and other.  At the time, 1/2 pint milk cartons were standard with everyone’s lunch (and were 25 cents each), so we figured there were a lot of cartons that could get recycled.  The lunch ladies agreed, on one condition, that we actually took the trash home, sorted it ourselves, and brought it to the recycling center.  We were excited at first and thought that they were really behind us in the effort.  April created signs, which I vividly recall included people with square heads showing how to separate paper and plastic.  We watched during the very first lunch period, as people ignored the signs and threw their food garbage in with their milk cartons.  After sorting through one of those bags after school, I was done, and I’m pretty sure this is where my current germophobia resides from to this very day.

5th grade (age 10): One of the last ideas that I remember being pretty excited about was very cleverly (I thought anyway) named by Johanna and I – K.I.D.S.W.A.R.  KidsWar stood for “Kids In Doomed Shirley Want Airport Refused” … a little dark with the whole “doomsday” thing, but I always had a flare for the dramatic as well.  You see, growing up in Shirley, there was an Army Base called Fort Devons that was very much a part of the culture of the town.  Around the age of 10, the government was doing cut backs and closing down military bases all over the country.  Many of my friends were part of military families, and my Dad served as a civilian in the Airforce for over 30 years (Hanscom Airforce Base).  The closure of the base was sad, but when there were rumors that they would replace the army base with an airport, the town became up and arms.  Johanna and I decided to form a contingent group of kids from our class, to learn about the bad effects an airport would have on the town, and then get people to sign a petition to vote against the airport.  We organized a group of 10 kids, held weekly meetings, and even invited a speaker to come to my house to give us a presentation on the airport plans.  We created a petition, it was the first time I heard the phrase “we the undersigned”, which seemed so formal to me (and still does), and got people around the neighborhood to sign it.  We then sent it to our town’s selectmen, and in the end, the airport never made it to Shirley.  This little project actually taught me a lot about organizing a group behind a cause, educating ourselves about the issues, and then eventually taking action to ensure our voice was heard.

I wish I could say I focused on money making schemes as a child and found really clever ways to produce a side business, but the truth is, I was more interested in causes and organizing people to try to make a difference.  I think this is why TaskRabbit resonates with me so much, and executing on the ultimate vision of connecting a neighborhood to live more efficiently and help each other out re-invigorates me every morning.  I guess that resonates and the fact that we’ve found a way to make money with it too!

What crazy schemes did you come up with as a kid?  I want to hear them!

5. Help me set up my new office in Dogpatch!
Kevin and I are living in Mission Bay, which is right next to the Dogpatch neighborhood. We’ve started exploring a little bit, and this is such a cool spot. All kinds of industrial lofts with big views of the Bay.

4. Locate stores that have a keg of Russian River Pliny The Elder
Who wouldn’t love this task. Alcohol? Check. Keg? Check. Learning about a new local beer? Awesome! I had to look up the info on this beer, since someone obviously thinks its good enough to get this research done. I’m familiar with the Russian River Valley and wines they produce, and know I know about this fabulous beer too!

3. 2 eye masks so The Boyfriend will sleep without complaining
Doesn’t the title say it all? Too funny! I completely understand what these guys are going through, because I can not sleep without my eye mask either. It becomes an addictive little habit to sleep in a cozy darkness. Almost like a security blanket wrapped around your eyes. Hopefully a crisis was averted with the completion of this Task!

2. Workout accountability phone calls
Brilliant! With a description of: “Call me at a specific time each day to make sure I have done the workout I promised to do.” When the Task was complete, the Sender left this review of the Runner: “Erica was fantastic! Besides just making the calls to make sure I did what I promised to, she added bits of motivation and encouragement with a very peppy attitude. Thanks!”  I love it!

1. Wait in line for my iPhone 4
I confess. This was my Task … BUT … I wasn’t the only one who had the idea. Last Thursday was a BIG day at Apple Stores around the country. My Runner, David E., waited in line for 4 hours. 4 Looooong Hours! There was a Chipotle cart of burritos roaming around, and some free swag and beverages.  This, apparently, tried to make the wait bearable. David texted me when he was 15 minutes away, which gave me ample time to get there. In fact, when I arrived, I was numero uno in line and only waited about 30 seconds to get into the store. The sanity saved here was priceless!

Growing up we spent summers in Florida visiting my Grandparents – Poppie and Nana to me.  We would always drive, Boston to Orlando – 3 days in the Dodge Caravan, where my sister and I would each get our own row.  It was pretty plush, but back then I can’t even remember what we had to distract ourselves with.  No electronic games, no movie screens, no headphones to play music.  I remember sleeping a lot and getting really fidgety and ultimately slap stick silly with my sister in the back seat.  We must have drove my parents crazy, although it was their choice to drive.

Our road trip was more than manageable with all of the pieces of technology we had in the car to keep us busy – 3 laptops, a 3g card, 2 iPads, 2 iPhones, a video camera, and the ultimate power adapter to keep everything charged.  It felt like the freakin bat mobile.  At any moment we could download a new song, or audio book (ahemmm … I am now obsessed with the Twilight Saga).  We could get anything we needed at our whim.  I could stay connected to email and voice mail, even throughout the spotty areas on Kansas and Wyoming.  How the times have changed!

People also mentioned that they had fun following along on our trip every time I checked in on Gowalla and Foursquare.  Taking a look at my feed, you can clearly see our progress each day, and some of the fun site we saw.  I was diligent about checking in on both platforms, with the goal of assessing the number of users across the country that are using each product.  In the end, I definitely saw much more activity on Gowalla across the board.  Foursquare seems to have more of a following in the press, but I’m not so sure they are winning the majority of consumers.  Gowalla’s product is far superior in my opinion.  It was created by some pretty kick ass designers who provide a high quality visual and user experience.  We shall see who comes out on top in the end, but as far as our cross country trip is concerned, I am giving the win to Gowalla, solely based on the number of users checked in at each location I checked.

Since Foursquare and Gowalla seem to be neck and neck, I realized that our cross country drive, will give me a unique opportunity to assess the scale of each product. I’ll be passing through over 3,000 miles of highway, stopping off at major metropolitan areas such as Nashville (for my sis’ wedding!), St. Louis, Denver, Salt Lake City, etc. Not to mention all the tinier places and rest stops along the way – maybe even a giant ball of string or two.

So here’s my plan. At each stop, when I have the unmanageable urge to check in and get a new badge, become a founder, or pick up a virtual taco, I will do so on 2 applications – 4sq & Gowalla. At each point, I’ll measure how many other people have checked in at that location and in the end, I should be able to tell who has the better reach across the country over all.

You can follow my experiment on twitter, as I push out my checkins and updated stats along the way.  There are obvious differences between the two products, so this will just measure the amount of scale and reach these applications have across the nation.  I personally have a favorite, and would love to hear your thoughts as well.

Road Trip – Preparing for Boston -> SF from Leah Busque on Vimeo.

I’m going to try to video blog from the road too.  There is a lot to do in the next 24 hours – not sure how its all going to shake out, but I always manage to get there.  First stop will be Nashville, TN on Saturday for my sister’s wedding.  I just hope we make it on time!

Thinking about what the top 5 things to pack for a major road trip.  Here’s my list so far, let me know if you have other recommendations:

1. AT&T 3G card so I am always connected
2. Audio books for that long and exceptionally flat stretch through the middle of Kansas
3. A cooler full of snacks: vitamin waters, almonds, and other nom noms
4. The camera / video recorder to capture the whole trip
5. My iPhone, iPad, and Macbook to upload all the fun for YOU to see!

What else am I missing?!

In the 18 months TaskRabbit has been doing tasks for people, we have experienced tremendous growth.  The company has expanded from me working alone in my apartment in Charlestown, to five full time employees and an office in Cambridge. We have more than 300 runners completing tasks in the Boston area. And we are continuing to grow.  It’s a dream come true.

Both Boston and San Francisco are home to some of the brightest minds in innovation and venture and we will look to both coasts when we seek an additional round of funding to support our growth.

Kevin and I are pretty excited.  We’ll be driving across the country, with our 100lb yellow lab Kobe in tow.  The timing worked out that my sister is getting married in Nashville, TN this weekend – at 2:30pm on Saturday.  We’ve got 24 hours to drive from Boston to Nashville staring Friday afternoon.  Of Memorial Day Weekend.  One of the busiest driving weekends of the year.  And hitting New York City at rush hour.  We should be fine, right?!  I am a little concerned, but we have to make my sister’s wedding, so that’s what we’ll do.

After Nashville, we plan to get on either I-70 or I-80 to make the trek to San Francisco.  Would love any recommendations here.

You can follow our progress on  Twitter and I plan to checkin on Gowalla the entire way.  Maybe even get a few video blog entries in.  Kobe is ecstatic, he loves a good car ride.  Hopefully he’ll love the 3,000+ car ride as well!

The development team there is constantly cranking out awesome new features and functionality.  Just since we started using them, they’ve added Proactive Chat, Click to Call (powered by Twilio), stats and analytics, and customized forms – a lot of high impact work.  We are utilizing it all, and have found Proactive Chat to be especially useful.  After 90 seconds on a page, a friendly box pops up in the bottom right hand corner asking if we can help with anything.

We tested different time lengths, and found if someone was sitting on the same page for 1.5 minutes, they are probably interested enough to be engaged, but they also might be struggling with a question that we can quickly answer.  Its not just a customer service tool, we find that its really turned into a sales channel for us.  If we can spend a couple quick seconds getting someone over that initial “hump” and win them over as a customer it is highly valuable.

One day, Jason, our new Director of Partnerships fondly referred to it as “Snap A Hug” and it stuck.  Go ahead … feeling lonely?  Come on by and we’ll snap a hug you!  In fact, I’d like to snap a hug Jerome and his team for making such a great product and executing on their vision so quickly!

At SBC you are expected to be good at many things.  Dance majors are also applied Mathematicians, and Biochemists are also concert pianists.  As an entrepreneur, I’ve learned you also have to be good at a multitude of things.  You can’t just be a programmer or a marketer, its good to have an interest and even excel in many areas.  When I left IBM I was an engineer – a simple role to convey.  Two years later, I would say I am part engineer, part marketer, part saleswomen, part business strategist, part fundraiser, part communicator, full time janitor, part community advocate …. the list just goes on and on.  Here’s the kicker … I love it all (sometimes even the janitor part)!  As I build a team, I look for others that can do it all and enjoy thriving in an environment where there are minimal boundaries and innovation and independence is encouraged.

I believe a strong Liberal Arts education leads to well rounded, smart and savvy, contributors to our world.  A focus on entrepreneurship in this environment is the perfect compliment, and I am thrilled to see the generation of women going through this program come out with the confidence and skills they need to succeed as a leader – perhaps even founding their own business ideas and companies.

One of the most contentious panels was on Venture Capital – what’s working and what needs rethinking.  With small micro funds represented by Eric Paley from the Founder’s Collective to large growth funds, it was apparent that the perspective on this topic is all about who you are talking to.  Brad Feld from the Foundry Group called attention to the fact that there was only 1 person at the conference under 30 … and it wasn’t me!  He enthusiastically pledged to sponsor one under 30 entrepreneur for next year and others followed, bringing the room to  a clapping praise.  Its a nice start, and it certainly won’t hurt the New England VC scene to include more young entrepreneurs in conferences like these – but as an early 30-something entrepreneur, I couldn’t help but sit there and see the entire conference as a metaphor for what we should be doing better here in New England.  This closed, invite only, expensive scene is difficult to broach for most young entrepreneurs.  The seclusion of the island was a great opportunity for networking and innovation, but it naturally separated out who was able to attend.

When the panel was asked, “what is the scarcest resource missing for making great companies in NE”, it was *almost too* quickly answered “great entrepreneurs”.  This was a bit surprising, since I know of a vibrant entrepreneurial scene here in Boston, but from the perspective of these panelist, apparently this is what is lacking.  How can one be so blind?  I submit what is lacking is a VC scene that actually sees the exciting innovation happening in Boston.  We are lacking investors that are willing to take a calculated risk on the next generation of leaders.  I have been lucky to have support from both coasts, for which I am grateful.

All in all, it was a great weekend, and I learned a lot.  I was happy to be able to attend, participate, and get to meet many other wonderful people.  It was a bonus to experience the island of Nantucket – such a gorgeous place!