Interview with Kevin Rose’s Foundation Series

I’ve been a avid watcher of Kevin Rose’s Foundation Series, so when he asked me to do an interview for the show, my response was – “Wow, I’d be honored!”.

One of my favorite Foundation interviews was with Philip Rosedale, Founder of SecondLife. He’s currently running Coffeeandpower, somewhat of a TaskRabbit competitor, but Philip is one of the coolest, smartest, most authentic people I’ve met in the Valley. Great guy and its awesome to have him thinking about this massive Service Networking space with us.

This was of the most fun interviews I’ve ever done. I have a pretty casual style, so the conversational approach was right up my alley. Thanks to Kevin and Graham for coming by TaskRabbit to chat. It was a blast to think back to the early days and reflect on what really influenced me to pursue math, computer science, and ultimately become an entrepreneur. Kobe also enjoyed being conked out on the couch next to me for the entire piece.


“Dear Kobe…” – Real emails from TaskRabbit fans

This email is priceless, and it’s not the only one in Kobe’s inbox.  This was sent to Kobe, TaskRabbit’s Chief Inspiration Officer (yes, he has his own email address – kobe at taskrabbit.com), earlier in the week ….

Hi Kobe,

My name is Colby “Cheez” Knight and I am a 7 year old Australian Shepherd in San Diego. My Dad, Derrick Knight, is driving me nuts! All he ever talks about is TaskRabbit. He is absolutely convinced that it is exactly the service that we need RIGHT NOW to help those out of work and those who have been blessed with jobs and are too busy to get stuff done.

My Dad talks to everyone he sees about TaskRabbit, about how it will allow people like the students at local schools, our military families and others support the affluent downtown, La Jolla and Rancho Santa Fe communities with their tasks. He has all kinds of ideas and connections

to find both taskrabbits as well as lots of the communities of people who don’t have enough time. San Diego is a really unique community as we have such a balance of students and needy families and the ultra-affluent who have second homes or remote homes here in San Diego, La Jolla, Rancho Santa Fe and Coronado.

Dog-to-dog, can you please have your Mom, Leah, contact my Dad and see if they can work something out? He would really love to be a part of this (launching in San Diego or doing corporate/biz dev/growth tasks for her).

I appreciate you listening to a fellow pup trying to help out his Dad.


Colby “Cheese” Knight

I love the creativity here, and what a cute dog! We’ll certainly be in San Diego soon … Kobe will make sure of it!

Montage of TaskRabbit Offices

We spent all weekend moving into new office space and even with the help of our amazing Task Rabbits, it was still exhausting.  Moving is rough.  The new space is going to be an amazing environment for TaskRabbit to thrive, and I am beyond thrilled to have the team set up, cranking away.  I took some time over the weekend to reminisce about all the office spaces TaskRabbit has been in from the very beginning.  Three years ago, we started the company out of our second bedroom in Charlestown, MA.  Actually, I spent probably half of my time at my favorite local coffee shop, Zume’s.  I had a favorite corner there I would spend hours coding away.

As the company evolved, Scott Griffith was generous enough to offer us some space at Zipcar’s HQ in Cambridge, MA.  As a few people came on board, including Brian Leonard, our VP of Engineering, we started to bust out of the Zipcar space, and I didn’t want to over-extend our warm welcome.

The next stop was not too far way, just across the street from Zipcar at the Monitor Building.  The 5th floor was a cheap, pay by the month for an entire room, and we shoved as many people in that room as possible.  In fact, this is where we met our great friends from ThredUp, who set up shop right down the hall.  It was a great environment to be around other startups.  Funny enough, both of us decided to head west after a few months there.

Around that time, we had overlapping space as we participated in fbFund REV in the summer of 2009.  This was an amazing experience, we got to work with other cool companies like Zimride, and this is what led to 500Startups latest investment in TaskRabbit.

Because of the awesome experience at fbFund, I fell in love with the Bay Area and decided to move to San Francisco, establishing our official HQ here on the West Coast.  Brian and I, along with our families sold our houses, threw away a ton of belongings, and made the trip west.  We had a soft landing at Dog Patch Labs, which was a wonderful way to get ingrained in the tech scene here in San Francisco.  We met some great Founders and companies including Instagram, LearnBoost, and our soon to be office mates Recurly.

300 Brannan was our very first office space that felt official.  It felt very real.  Continuing the trend of collaboration with other cool companies, we shared this office space with Recurly.  It was great to be around another startup at the same stage, making similar decisions.  This space was phenomenal, but we grew out of it a bit faster than we initially planned for.  Soon there were two people to a desk and lines for the single bathroom.

Which brings us to our brand new space.  Still located in SOMA, we are all grown up, everyone has their own desk and plenty of room to rock out.  We’ve been fortunate enough to create a very strong company culture, even as we’ve brought on so many new people, so it was really important to find the right space to continue to allow this culture thrive.  Three main criteria – dog friendly (we love having dogs at the office, and Kobe loves friends), an eat in kitchen (we enjoy camaraderie over a large lunch room table), and open floor plan (lots of room to collaborate and innovate across functional areas).  In fact, for this last point, we took down 10 interior offices that were built into the original floor plan, to make it one big open area of our own.

The TaskRabbit family has found a home.  This is where we will grow the team, launch new cities, celebrate our successes, and agonize over our failures – always moving forward, staying focused, and executing quickly.  Welcome home everyone!


Shasta Ventures joins the TaskRabbit Crew

In 2008, I left my software engineering job at IBM in Boston and decided to build a little site called RunMyErrand.com.  Three years later, I find myself living in a new city (which just happens to be across the country), managing a company with a new name and brand- TaskRabbit.com, and building a presence in two major markets.  It has been quite a whirlwind.  One of the most important aspects of our success to date has been the truly amazing people I have been lucky enough to surround myself with. I’ve written many posts on how important it has been to assemble the right team.  As an engineer-turned-entrepreneur, I’ve been so grateful for the amazing advisors and investors who have supported TaskRabbit’s growth along the way.  Today, I am thrilled to announce that Shasta Ventures has lead our Series A round of investment and Sean Flynn will be joining the TaskRabbit Board of Directors.  The new capital will be used to grow our Service Networking platform and support aggressive expansion into new cities.  I could not be happier having Sean and the entire Shasta team as part of the TaskRabbit movement.  Beyond the capital, we have a shared vision for the business and, as an entrepreneur, this was the most important factor when deciding which firm to work with.

I have also enjoyed continued support from our original investors Floodgate, Baseline, and First Round Capital.  Ann Miura-Ko, will remain on the Board as well working closely with Sean and me.  I am also excited to bring some new folks into the mix including Collaborative Fund, 500 Startups, and Lisa Gansky, author of The Mesh.  As I look at the group we’ve assembled and how they view and write about the space, I realize we have all the right pieces in place to make this a huge business.  This is beyond thrilling for me as the founder and CEO.

We’ll be hiring folks in all areas of the business, from engineers, to marketing and community management.  We are establishing a very special corporate culture, just ask @sourjayne or @exteba.  People are the most important thing, whether it is your investors, your team mates, or the members for whom you are building the product.  Come join us as we take this Service Networking movement to the next level.


A Very Meshy Christmas

After moving away from Boston and across the country over the summer, this was the first Christmas we’ve spent away from family.  We decided to take the opportunity to embark on a little adventure.  We knew we wanted some snow, it just wouldn’t feel like Christmas to us without it, so I hopped on Airbnb.com and looked at some of the spots San Francisco locals always talk about – South Lake Tahoe and Yosemite National Park.  Both are under 4 hours away from the city, so when I found some awesome accommodations on Airbnb.com, I emailed a few folks and figured out what the availability was like. We were looking for a handful of things: Great location, good price, Dog friendly (a must!), Fireplace – there is nothing better when there is snow on the ground to hover around a crackling fire

Many places were already booked, but we found a spot called the Old Yosemite Cabin that was open through the holiday.  Airbnb.com made it easy to find places that met our criteria and then book the place right on their website.  It turns out Yosemite is a pretty amazing place, and this was an epic Christmas trip!  Some of the highlights included hiking around the Giant Sequoias, viewing El Capitan & Half Dome, cooking a Christmas Bolognese, and going for a horse drawn sleigh ride.

There was also quite a bit of relaxing by the fire, where I started Lisa Gansky’s new book, The Mesh.  It’s all about businesses that are based on sharing, like Airbnb.com for instance.  This is a business model based on people sharing their personal space.  Zipcar is mentioned in the book as a business about sharing cars in a community.  The book highly resonates with me, because I’ve spent the last few years thinking about Service Networking and how to connect people to share their time, skill, and expertise.  It’s an interesting moment in time, what people are calling the “Sharing Economy“.  The technology wasn’t available 5 years ago to do what we are doing today – leveraging social, location, and mobile to create a really powerful network.  It’s exciting to think of all the possibilities and power that lye with a Mesh network – where the community is what drive the business.

So here I am, feet kicked up, enjoying the fire in our Airbnb.com cabin, thinking about Service Networking, and reading about The Mesh.  If only we had used a Zipcar to get out there.  Good stuff!

I am excited to try Airbnb.com again during our travels.  Kobe was not allowed inside the Sequoia Grove, so we’ll definitely have to go back in the spring to explore Yosemite some more.  The winter was fun with all the snow, but some roads were closed, and I bet the summer months boast their own magic.


Assembling the Right Team

Over the course of the past couple of years, I would say the one continuous thread I can see in our success is surrounding ourselves with the right mentors, advisors, and investors.  It is so interesting to trace the networks between groups of people, and realize that perhaps the one small conversation you may have had at a random networking event was the connector.  You just never know who you are going to meet and who else they might lead you to.  We have been so fortunate to work with the amazing group that we do.  From the beginning Scott Griffith (Zipcar), Robbie Vorhaus (Vorhaus Communications), and Tom Erickson (Acquia) have been personal mentors to me, and from there came two early stage private investors, Jill Preotle and Peter Aldrich.  In these very early days, this group guided me and helped shape my vision for TaskRabbit.  They remain a strong thread in the vision today.

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.


My Top 3 Childhood *tiny* Ventures

I just finished Delivering Happiness by Zappos CEO, Tony Hsieh, and it was fantastic.  Truly inspiring, funny, and so insightful.  In the first part of the book Tony talks about all the crazy businesses he started when he was a kid – from a worm farm to a greeting card business, and that it was his goal to figure out a way to make money, even at a very young age (later he learns that service and company culture are just as important as making money).  This lead me to reminisce about some of the absolute crazy ideas I had as a kid, and wonder … what was I thinking?!

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!