Category Archives: Startups

Achieving Empathy for Institutions with Anil Dash

Anil Dash

IN BIG WEB SHOW № 115 on Mule Radio, I talk with Anil Dash, a hugely influential entrepreneur, blogger, and web geek living in NYC.

Things we discuss include:

How government, media, and tech shape the world, and how we can influence them in turn. Our first meeting at SXSW in 2002. How selling CMS systems teaches you the dysfunction at media companies and organizations. Working for the music industry at the dawn of Napster. RFP-EZ. The early days of blogging.

Designing websites for the government—the procurement problem. If we’re pouring all this time into social media, what do we want to get out of it? How big institutions work and how to have an impact on them. Living in “Joe’s Apartment.”

Why, until recently, federal agencies that wanted a blog couldn’t use WordPress or Tumblr and how the State Dept got on Tumblr. Achieving empathy for institutions. Being more thoughtful about what I share and who I amplify on social media. The launch of Thinkup, and a special offer exclusively for Big Web Show listeners.

Enjoy Big Web Show № 115.


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The Black Hole of The Valley

STOP ME if you’ve heard this one: Guy goes into a venture capital firm, borrows money. Uses money to turn neat idea into product. Gives away product (or sells well below cost) to build a following and thus a demand.

Customers love product, imbue it with their life energy and creativity. Community grows, but not cashflow, because money was something to be figured out later. More investors throw more money at the product, on the theory that what it needs is fancier offices or fifty designers united behind no vision in particular.

Surprisingly (at least to the participants), several rounds of throwing cash and bodies at what was once a neat idea fail to generate ludicrous return on investment. Capitalists demand that product idea be changed.

Change of idea fails to generate ludicrous return on investment. Customers, no longer sure what product is about (or even that it has a future) become less passionate.

Usage falters, then rapidly hits event horizon.

Guy starts shopping no longer loved or interesting product at fire sale price.

Eventually big internet company sucks product and product team into itself, where both disappear forever.

Coastermatic’s Tash Wong and Tom Harman on The Big Web Show Episode No. 92

Tash Wong and Tom Harman, co-founders of Coastermatic.

AMERICAN DESIGNER Tash Wong and British designer Tom Harman are the co-founders of Coastermatic and my guests in Episode No. 92 of The Big Web Show (“everything web that matters”).

Tash and Tom recently resided in Brooklyn, NY and completed their MFAs in Interaction Design at New York’s School of Visual Arts, where I was one of their admiring teachers; they are now bound for Hawaii, where they will expand their web-based product empire. Coastermatic, their first joint product, converts your Instagram photos into stone coasters, and was conceived during their time at SVA. (More in the August 2, 2012 issue of Dwell.)

In a fast-paced hour-long podcast, we discuss design, product, and business strategy; finding the right manufacturing and fulfillment partners; the division of labor in a small startup; and other juicy UX and entrepreneurial topics.

Enjoy Episode No. 92 of The Big Web Show.

Readlists: behind the scenes

FROM THE HOME PAGE of today’s newly announced, totally disruptive, completely free product powered by Readability: “What’s a Readlist? A group of web pages—articles, recipes, course materials, anything—bundled into an e-book you can send to your Kindle, iPad, or iPhone.”

For some time now, people who miss the point have seen Readability as an app that competes in the read-it-later space. That’s like viewing Andy Warhol as a failed advertising art director. Readability is a platform that radically rethinks how we consume, and who pays for, web content. It monetizes content for authors and its technology is available to all via the API. It scares designers, angers some advertisers. Its transformative potential is huge. Readlists are the latest free product to manifest some of that potential.

With Readlist, anyone can create ebooks out of existing web content. It’s easy. Sign in with your Readability account or sign up for one, and start making books of your favorite web articles.

There are still some bugs being worked out, but hey.

I was honored to beta test the product and create one of the first Readlists, along with Erin Kissane, Anil Dash, Aaron Lammer, David Sleight, and Chris Dary.

Disclaimer: I am on the advisory board of Readability and cofounded The Deck advertising network with Jim Coudal and Jason Fried. Readability removes clutter (including ads) from the reading experience; The Deck sells ads. Conflict of interest? Here’s another: I design content websites so as to make Readability unnecessary (because I design for readers); yet I strongly support Readability as a platform and above all as a web idea that is at least 15 years overdue. Either designers will design for their end-users, or third-party apps will remove designers from the transaction. As a designer, I’m not afraid of that. Rather, it inspires me.

Enjoy Readlists.

My Glamorous Life: The Power Compels You

I DREAMED that my friend Jason Santa Maria took a job at a popular new startup that had exploded onto the world scene seemingly overnight. A fascinating visual interface was largely responsible for the popularity of the company’s new social software product. It was like a Hypercard stack that came toward you. A post full of exciting social significance just for you would appear in a self-contained deck with rounded corners. The next post would pop up on top of the first. The next, on top of that one. And so on. In my dream, people found this back-to-front pop-up effect thrilling for some reason.

Having imagined the interface, I next dreamed that I went to visit the startup. There were so many cubicles, so many shiny people running around, holding morning standups and singing a strange company song, that I could not locate my friend Jason’s desk. Someone grabbed me and told me the founder wanted to see me.


THE FOUNDER was an ordinary looking white guy in his late twenties. I was surprised that he wore beige chinos with a permapress crease. With all the TV and newspaper hubub around his product, I guess I’d expected a more stylish and charismatic presence.

The founder told me he was concerned because his mother, apparently a cofounder or at least an officer of the company, was of the belief that I had contempt for their product and disliked her personally. I assured him that I liked the product. Further, I had never met his mother, never read or heard a word about her, and felt only goodwill toward her, as I bear toward all people in the abstract. I don’t hate people I don’t know.

“It would be cool if you told mom that yourself,” he said. And suddenly two assistants were whisking me off to speak to her directly.


THE AUDITORIUM-SIZED waiting room outside the founder’s mother’s office was filled with at least a thousand people who had come to talk to her before me. They seemed to have been waiting for hours. There was an air of boredom and rapidly thinning patience, mixed with excitement and the kind of carnival atmosphere that surrounds things that blow up suddenly in the press. It felt like the jury selection room for a celebrity murder case. Only much, much bigger.

The two assistants escorted me to the very front of the auditorium, to an empty row of seats abutting the door to the founder’s mother’s private office. “Special treatment,” I thought. I was thrilled to be cutting to the front of the line, apparently as a result of the founder’s directive to his assistants. The front row chairs were reversed, facing back to the rest of the auditorium, so I was put in the somewhat uneasy position of staring out at the mass of people who had been waiting to see the founder’s mother since long before I arrived.

After a while, Ian Jacobs of the W3C was brought to the front of the room and seated near me.

We waited as other people were shown into the founder’s mother’s presence.


AFTER FIVE or six hours of drowsy waiting, I realized that the room was set up to mirror the software’s interface: people from the very back of the auditorium were first in line, and were shown into the founder’s mother’s presence first. Gradually, the hall of applicants emptied from the back to the front. Those of us in the very front of the line were actually the last people of all who would be admitted to the holy presence. It was a smart marketing touch that apparently permeated the company: everything real people did in the building in some way echoed the characteristics of the software interface — from the end of the line coming first, to the way the rounded conference tables echoed the shapes of individual news posts in the software’s back-to-front news deck.

What a smart company, I thought. And what a good joke on me, as I continued to sit there forever, waiting to see someone I’d never met, who held a baseless grudge against me, which it would one day be my task to talk her out of.

The maker makes: on design, community, and personal empowerment

THE FIRST THING I got about the web was its ability to empower the maker. The year was 1995, and I was tinkering at my first website. The medium was raw and ugly, like a forceps baby; yet even in its blind, howling state, it made me a writer, a designer, and a publisher — ambitions which had eluded me during more than a decade of underachieving desert wanderings.

I say “it made me” but I made it, too. You get the power by using it. Nobody confers it on you.

I also got that the power was not for me alone: it was conferred in equal measure on everyone with whom I worked, although not everyone would have the time or desire to use the power fully.

The luckiest makers

Empowerment and desire. It takes extraordinary commitment, luck, and talent to become a maker in, say, music or film, because the production and distribution costs and risks in these fields almost always demand rich outside investors and tightly controlling corporate structures. (Film has held up better than music under these conditions.)

Music and film fill my life, and, from afar, I love many artists involved in these enterprises. But they are mostly closed to you and me, where the web is wide open, and always has been. We all know gifted, hard working musicians who deserve wide acclaim but do not receive it, even after decades of toil. The web is far kinder to makers.

To care is to share

Not only does the web make publishers of those willing to put in the work, it also makes most of us free sharers of our hard-won trade, craft, and business secrets. The minute we grab hold of a new angle on design, interaction, code, or content, we share it with a friend — or with friends we haven’t met yet. This sharing started in news groups and message boards, and flowered on what came to be called blogs, but it can also slip the bounds of its containing medium, empowering makers to create books, meet-ups, magazines, conferences, products, you name it. It is tough to break into traditional book publishing the normal way but comparatively easy to do it from the web, provided you have put in the early work of community building.

The beauty is that the community building doesn’t feel like work; it feels like goofing off with your friends (because, mostly, it is). You don’t have to turn your readers into customers. Indeed, if you feel like you’re turning your readers into customers, you’re doing it wrong.

If you see a chance, take it

The corollary to all this empowerment is that it’s up to each of us to do something positive with it. I sometimes become impatient when members of our community spend their energy publicly lamenting that a website about cats isn’t about dogs. Their energy would be so much better spent starting bow-wow.com. The feeling that something is missing from a beloved online resource (or conference, or product) can be a wonderful motivator to start your own. I created A List Apart because I felt that webmonkey.com wasn’t enough about design and highfive.com was too much about it. If this porridge is too hot and that porridge is too cold, I better make some fresh, eh?

I apologize if I sometimes seem snippy with whiners. My goal is never to make anyone feel bad, especially not anyone in this community. My message to my peers since the days of “Ask Dr Web” has always been: “you can do this! Go do it.” That is still what I say to you all.

Big Web Show Episode No. 47: Foodspotting Founder Alexa Andrzejewski

FOODSPOTTING FOUNDER ALEXA ANDRZEJEWSKI (@ladylexy) is our guest in Episode No. 47 of The Big Web Show, to be recorded in front of a live internet audience on Thursday, April 28, at 3:00 PM Eastern via 5by5.tv/live.

Foodspotting, a visual local guide that makes finding and sharing food recommendations as easy as snapping a photo, has received attention from Techcrunch, Mashable, The Wall Street Journal, and CNN blogs, and was named one of Time Magazine’s 50 Best Websites of 2010.

Before launching Foodspotting in January 2010, Alexa was a user experience designer for Adaptive Path, where she helped both startups and established companies create great experiences that improve people’s lives. From redesigning MySpace to conducting the research that underlies the Palm Pre, Alexa has helped clients reimagine products from the ground up.

Through speaking, writing and teaching, Alexa strives to advance experience-minded thinking and methods to all who will listen. Recent appearances include An Event Apart Seattle, WebVisions, Big Omaha, SXSWi, the Web 2.0 Expo in San Francisco and New York, UX Week, and LIFT in South Korea.

The Big Web Show (“Everything Web That Matters”) records live every Thursday at 3:00 PM Eastern. Edited episodes can be watched afterwards, often within hours of recording, via iTunes (audio feed | video feed) and the web. Subscribe and enjoy!