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Drowning in a sea of stuff!

The average American family has $3300 in extra unused items just sitting around the house.  $3300!!!  This figure has been in our Swapfish pitch deck, promo video, public talks, and I must have said it over and over and over.  But, tonight it just got real for me.

I was combing through my closet in an effort to downsize for moving on Wednesday and realized within an hour that I had 42 pieces of clothing and accessories I no longer wanted.  Some of these were t-shirts (like my student council t-shirt from Sophomore year I’m finally parting with), but mixed in I also had some Brooks Brothers button downs, Banana Republic sweaters, and some fairly expensive purses.  I estimated that my pile was probably about $500 alone- and I was ready to toss it out the door without a second thought.

This is why we are launching Swapfish in three weeks…if those items were sold on Swapfish, that $500 could feed 1200 families in partnership with the Greater Boston Food Bank.  Wow.

We can’t go live soon enough.

It’s been awhile since I’ve posted, and Swapfish has undergone a partial tweaking of the model.  I won’t reveal what we have in the works just yet, but, it disrupts an entire industry– very exciting!

Earlier this week I was sitting in a Starbucks in Boston and had asked the woman next to me if she could glance at a few versions of a product page we were working on and tell me her thoughts.  She was in her late fifties and was a pharmaceutical research consultant.  She had previously been working on a crossword puzzle before I tried to engage her in conversation.  I expected a brief exchange and then us to go back to what we were working on.  What followed instead was a huge motivator…she began asking me about the company and spent probably 20 minutes asking me questions on how it works and telling me how much she needed it right now with the bag of clothes sitting in her trunk.  We stopped talking for awhile, and then she did something really great. As she went to leave, she broke the silence by pulling out a small notepad and pen, and said “I’m really sorry for interrupting you again, but I want to make sure I write this down so I remember to sign up when I get home and tell my daughters about it so they can save their stuff. What is the name of the site again?”

She probably has no idea how much of an impact that had, but it was big.  Doing scripted market and user testing is one thing, but, having someone fall in love with the idea enough to take the time to ask about it a second time, write it down, and then offer to share it is a feeling that never gets old.  Plus, now we have another reason to hit our launch date…Maureen the pharmaceutical research consultant from Boston needs to clean out her closet.  I promised we’d help.

Encouragement comes in the most unlikely places sometimes, but I’m thankful for it.

As a law student I spent almost every Tuesday night for three years pretending I was a giant prehistoric crab, tending sheep in a pasture in Denmark, being part of secret spy missions, falling in love in less than a minute, holding a breakdancing pose until it hurt, or panicking in various states of distress. Thankfully, these were all in scenes with my improv troupe and not real life occurrences (student life was crazy, but not quite THAT crazy), but, in those moments, the stories we explored seemed as true as anything we were learning in the classroom.

I never expected that improv would be what taught me the most valuable piece of information I learned while I was a student at Harvard Law, but the rule of “yes, and…” has proven to be vitally important in both building a company and building my life.

The “yes, and…” rule in improv is one of the founding principles of building a great scene.  It means that you never negate what your partner suggests, instead, you assume it is true and then think “if this is true, what else is likely to be true?” and build the story from there.  In an improv game it goes something like this:

Improver 1: “The mashed potatoes are finally ready for Nana’s 98th birthday party!” 

Improver 2: “Yes and, I just picked up my favorite pants suit from the cleaners for the occasion”

The point of “yes, and…” is to agree and add something to the scene that helps define it, solve it, or brings new information into the story (i.e. Improver 2 is still in the early 90’s era of the pants suit).  To me, “yes, and…” in the context of the start-up world means to approach every idea from the perspective of “yes we can, and if we did, what would it look like?”.  Starting from yes is a way of exploring, vetting ideas, and finding simple solutions in a positive environment that encourages innovation.  That doesn’t mean you always say yes at the end of the day (we still subscribe to the lean startup and minimum viable product mentality), but it means that every idea at least gets a chance to be heard.  “Yes, and…” doesn’t always mean adding features, it sometimes means taking them away as well.  Such as “what if we didn’t do _____” and exploring what that looks like.

It’s an interesting experiment to take a day and approach everything from the “yes, and…” perspective.  For me, it makes me realize that sometimes barriers are really only constructs in my own mind, and that the world is full of a myriad of possibilities waiting to be explored.  With Swapfish, the “yes, and…” culture has led to an amazing feature set and an innovative and exciting business model.

We’ve all been in meetings with people who start from “no, because…” and with every idea rattle off the million reasons why it can’t work.  There are always a million reasons something can’t work, the trick is to find the one or two reasons why it can.

That’s the power of  “yes, and…”.




Last night at the Local H concert there were probably around 150 people packed into a small venue watching the band.  Almost everyone had smartphones and cameras, and the most devout fans would occasionally snap photos or shoot quick videos.  However, with so much jumping and fist pumping going on, it was hard work (trust me- I almost got knocked over once).

I was struck by the opportunity the band had to leverage the 150 people in attendance to spread their music and message.  They had 150 fans, who all liked them enough to pay money to see them, standing there as a captive audience, likely each with a social network of around 500 people. If, at some point in the show, they would have asked everyone to help them make it big by taking out their phones and recording a video or photo of the band and tweet it/facebook it right then, they could have instantly had their music exposed to roughly 75,000 people last night! Multiply that by the 21 shows on their tour, and that’s nearly 1.6 million people who could have heard about Local H. Even assuming a 1% conversion rate, that’s 15,000 new fans!

Companies do this all the time, you go to a website and it prompts you to share to facebook and twitter.  Most of the time, bands will do this on their website as well.  However, visual media is much more powerful than just reading “John bought tickets to Local H”.  In fact, I showed up to the concert because two of my friends had shared a video on their facebook page of Local H awhile back.  Bands should learn from great companies and use their fan base at every moment to share the message.

Plus, that way I could shoot photos of the band while the big guy next to me is also safely using his phone, and not thrashing wildly in my direction. : )

Last night I went to a Local H show at a small venue in Boston.  If you aren’t familiar with the band, it’s a two guy gig from Chicago, filled with intensity and angst, and found most often playing to a crowd of male 20 and 30 somethings throwing themselves into one another.  (check them out here:

So what does this have to do with building great companies?  Watching the difference between the opening band, The Dig, and Local H, got me thinking about what makes a band “make it” and what makes a band stuck playing in people’s garages.  This is much the same way that some companies succeed and are rocketed to superstardom while others fail.   As a music junky often seen frequenting the smaller clubs around Boston looking for the next new thing, I’ve noticed a few key traits that artists who make it big have.  Companies could learn alot from the Gaga’s of this world.

1) A consistent and unique brand. Think about the biggest stars you can think of, Madonna, Elton John, KISS, Grateful Dead, Green Day (these were the first that came to my head).  Regardless of the performer, they all have a common thread- they live their brands from start to finish.  The Dead play in what seems to be whatever they rolled out of bed in that morning and are the same on stage and off, Gaga wears crazy outfits 24/7 when she goes out.  When is the last time Lady Gaga was seen just wearing a polo shirt and walking into a Whole Foods? Probably not recently.  One of the differences between The Dig and Local H last night was that Local H lived their brand, and were consistent with their look, while The Dig, did not.  Great companies are like this as well.  Every single detail of the corporate brand needs to be consistent and constantly executed.  Whole Foods can’t have energy guzzling stores or bag only in plastic.  Customers, like fans, notice inconsistencies.  The same way you would feel cheated if Tool played a concert in khakis and a polo, companies must make sure everything about their brand matches the expectations of the customer.

2) They have to be bigger than their music/product. The artists that succeed go beyond just creating music, they create a mood, an attitude, and a lifestyle that give their fans a sense of belonging.  The same way Gaga has “Little Monsters” or The Dead has “deadheads”, great companies need to convey a message and lifestyle people can identify with.  Subaru, REI, Timberland, John Deere, all do a great job of this. Customers and fans don’t just want to listen to songs or buy a product, they want to feel like they are part of a community.

3) They engage their fans and play for them, not for themselves.  Although every band needs to love what they are doing, they also have to remember in a live show that they are not just playing for themselves, but are entertaining and connecting with their fans as well.  Great bands take time for audience participation, they have them sing a part of the song, clap along, go out in the crowd, pull people on stage, etc.  Mediocre bands play their music the same way in their garage as they do on stage.  (caveat, unless you are a jam band where you make up for it by simply playing for hours, but, that’s also true to their brand, so it works).  Companies are like this as well.  The great companies spend time learning from their customers and getting them involved in the process and really building a connection, not just a product.

4) They’re passionate and give 110% to their audience. The great bands give everything they have to their fan base, delivering the best show and the best songs they can, and letting their fans know that they gave it their all to keep them happy.  Great companies should be like this as well.  A customer needs to know that the company is doing everything they can to deliver a top-notch product and solve their customer service needs.  A customer, just like a fan, should never leave feeling like a company only gave it 70%.  Enterprise-Rent-A-Car is a great example of this, they built a loyal base by ensuring they give it 110% to make their customers experience as great as possible.

So, what does this mean?  It means if you want to be the corporate equivalent of  playing Madison Square Garden, you have to create a consistent and unique brand that should be reflected in your products, your PR, your office layout, and how you as CEO live your daily life (aka, an eco-friendly company should have corporate hybrids, not SUVs). The little details make a big difference in brand consistency. You want to create a company with a mission and community bigger than it’s products (think Timberland, Subaru, etc). Remember that you built your company to solve a pain point for your customers, and keep them constantly involved in the process to build loyalty (i.e. the Mountain Dew campaign for a new flavor is an example). Finally, give your all to your customers and never leave them wanting more (Enterprise Rent-A-Car model).

Next time you are at a show, think about the differences between the headliner and the opener.  I’m sure there are a bunch of things I missed on this list, I’d be curious to hear what others think!

Music break

This song is about making it as a country star, but, it also seems strange fitting for what I am feeling building the company.  Plus, I really like it.

Sugarland: Baby Girl

The Harvard Law Bulletin is featuring Swapfish and the photographer called me today to set up the “photo shoot” for the magazine.  First, the idea of doing a photo shoot makes me smile because it reminds me of the Glamour Shot days of the early ’90s.  I have seen her work in previous issues though, so I am confident that she won’t put me in sequins and Rave hairspray.

However, the thing that excited me most was that during the course of the conversation about backgrounds and outfits, the photographer mentioned how pumped she was for Swapfish and how she could use it with her 5 month-old son.

What followed was a ten minute conversation about how quickly kids grow out of things, how expensive they are, and how she tries to go to resale stores but she drives all the way there just to be frustrated that the store doesn’t have what she is looking for.

Inspiration comes in the most unexpected forms sometimes.  I am so amped by the encouragement we keep receiving!

I was excited to see that “resale” was one of the top conversations on CafeMom tonight.  It was fascinating to read the various creative ways moms save money on clothing for their children.  My favorite was the mom who recycled old t-shirts into underwear through a little sewing magic.  Very impressive!



Law School Prom

Yesterday I took a break from Swapfish to head to Barrister’s Ball, the Harvard Law equivalent of senior prom.  It was possibly the best experience I have had yet at Harvard.  I feel so fortunate to have such a great group of friends who are all so interesting, intelligent, and inspiring, but who also can do the Dougie, shopping cart, and salsa like champions.  The photo below is missing the other six, but, everyone was too busy dancing to get all nine of us together at once.

It’s hard to believe we only have four weeks of classes left.  I am going to miss this place and the wonderful people I have met here.


Cash strapped 20-somethings.

I read about an interesting socially entrepreneurial start-up today creating an AARP for twenty-somethings. (You can check them out here: However, the thing in the article that struck me was the lead-in, stating that one in six twenty-somethings were underemployed, and one in ten had to move back in with their parents.  The article also stated the average 20-something carried $24,o00 in debt.

As a 25 year-old soon-to-be Harvard Law grad launching my own company, I can relate to this statistic.  I have piles of student debt, and am living on hope that I will never end up back in my parents basement (although, free rent while starting a company is always a good thing).

This statistic got me thinking…

The 20-something era is when the majority of parents have their first child (although the age seems to be trending upwards).  A large number of my friends are now having their first, or even second child.  As I think through my friends, some of the brightest, most interesting people I know are underemployed, many of them now with children.  With one out of six twenty-somethings being under-employed, that is a lot of families potentially trying to make ends meet on a less than ideal budget.

Swapfish can help.