Results tagged “tech”

New York-Style Tech

July 15, 2016

A technology community driven by values, not just profits.

New York Public Library

I’ve been part of the New York City tech scene for more than 15 years, from back when it was “Silicon Alley” trying to be an imitation of the West Coast, to its more recent iteration as a world-class technology community unlike any other in the world. While I’ve been deeply critical of the things people working in technology have gotten wrong, I’ve recently often found myself trying to re-emphasize something that our community has gotten right.

The other day, I was looking at Matt Turck’s analysis of the New York City tech ecosystem, a detailed look at tech in New York from a venture capitalist’s perspective. It offers a compelling and well-reasoned argument for a strong economic future for New York’s tech scene. But what most jumped out at me was what it missed about what’s special in New York City, something that has nothing to do with the rate of return for investors.

Put simply: New York City is unique in that its tech community is grounded in principles of social and civic responsibility. It’s an important distinction, one that we’ve got to work hard to protect and nurture. And just like New York-style pizza, I’m hoping lots of people in other cities think that what we’re making here is good enough that they try to emulate it in their own communities.


What do I mean by a civic-minded tech community? We see a few consistent traits that jump out:

  • An actual community. Thanks to groups like the New York Tech Alliance and its signature monthly NY Tech Meetup event, we have the ability to gather and organize in centralized ways, a powerful and necessary infrastructure for organizing. As a NYTA board member, I’ve been able to see firsthand the convening power of having a prominent, unified group representing a tech community where “tech” doesn’t just mean employees at startups, but rather everyone who’s using tech to transform their work in various industries and across the public sector and academia as well.
  • Engagement with policy and policymakers. On issues ranging from SOPA/PIPA to net neutrality, executives from New York tech companies were among the first, most persistent, and most effective voices engaging with policy makers to try to improve our laws. Their willingness to hop on an Amtrak and head down to Washington, D.C. to talk to lawmakers is matched by the more local efforts that so many in the NYC tech community do at the state, city, and neighborhood level.
  • Community service. Whether it was after major events like Hurricane Sandy, when many in the tech community worked to volunteer around the city, or in more ordinary daily efforts like mentoring young students interested in technology, there’s a solid expectation of service that I see expressed between members of the community. It’s that kind of peer support that’s necessary to sustain a culture of service, and it’s been reassuring to see support extending from ordinary grassroots tech workers all the way up to the most prominent and influential investors and entrepreneurs in the city.
  • Corporate commitment. While New York’s tech scene goes far beyond startup companies, we see meaningful, significant commitments to responsibility being made by some of the most prominent and influential companies in the community. From Kickstarter legally committing to being a Public Benefit Corporation to Warby Parker pursuing B Corp certification to Etsy working to uphold B Corp principles even as a publicly-traded corporation, there’s a visible and consistent tradition amongst our most successful companies to honoring their commitment to our city and to the world.
  • Inclusion. No, the tech industry in New York City is not yet inclusive enough and does not yet provide opportunity to everyone in our city. But by gender, race and economic class, New York’s tech industry is miles ahead of any other major tech community in the United States. What’s more, our civic and social leadership are more broadly inclusive, making it much more likely that we’ll actually achieve significant change. This even extends as far as significant, broad-based commitments to public, universal programs like computer science education that’s available to every student, in every borough, instead of through commercialized, limited-access platforms.

This is a start, not a finish

We still have a lot of important work to do to improve our tech efforts in New York City — most urgently around inclusion. I am not trying to describe what we’re doing here as a utopian wonderland of perfect technology, and indeed we have inherited many of the same structural barriers and biases that plague the larger technology realm.
But the everyday commitment to being mindful of our communities and our obligation to the world is real, and has only increased over time. I’m hoping that by reiterating this unique strength of our community, we can remind ourselves keep putting in the effort and care to maintain a focus on our values.

Pizza delivery

To be clear, I’m not saying that only New Yorkers care about their communities. Lots of individuals in every part of the country, and every part of the world, care deeply about these things. But when I think about what motivates me most to work with people in the New York City tech scene, it’s that I can usually count on people sharing a sense of ambition to do something more than just making money.
And, though I still think New York-style pizza is the best, I’ll happily admit that nearly every city in America has at least one place that offers pretty decent pizza. A lot of the time, they call their offerings New York-style pizza just to make clear that they’re trying to be like the best. Similarly, I suspect that every city that develops a substantial technology community will nurture a core group of creative people who give back to their city and think that technology reaches its best potential when it benefits the most people.

Thank you to endymion120 and benymarc for the photos.

A checklist of stupid things men will say when they find out I only retweet women

February 12, 2014

I wrote a bit about why I only retweet women. As an exercise, let's guess what stupid things I'll hear in response! If we check off all these items, then we've won Internet Sexism Bingo. And by "won", I mean "lost".

  • "You should just retweet the best people!" I do.
  • "This is reverse sexism!" No, if I were calling for a few centuries of you being treated as property and said you shouldn't be able to vote, that would be reverse sexism.
  • "You're just doing this to get laid." Oh, son. You know what I do to get laid? I treat women as humans while being super smart and attractive. This is a trick that works really well, so I've kept doing it solely for my wife's benefit.
  • "This is political correctness gone amok!" I get it, you miss being able to use racial and gendered slurs, and feel censored. So be free: Please publish the denigrating slurs you love so much on your LinkedIn profile.
  • "You don't deserve all of those Twitter followers!" Yeah, I know. I wrote about that four years ago. Now you have some idea of what it might feel like to not have male privilege, except it applies in realms such as physical safety and equal pay, instead of just meaningless follower counts.
  • "Can you get me a verified checkmark?" No, man. No. I don't know how, and it doesn't mean anything anyway. But you can read a bit about what happens when you're chosen to be verified, if you want.
  • "Are you going to start retweeting men again?" Probably not? I don't feel like I've missed out on anything.
  • "This is censorship!" You are a dumb person who doesn't know what that word means.

Okay, let's see how we do!

Update: Oh good, Leah made an actual bingo card. I think we've gotten dudes who've checked off every space already.

Stupid Simple Things SF Techies Could Do To Stop Being Hated

January 22, 2014

I've seen a lot of hand-wringing from techies in San Francisco and Silicon Valley saying "Why are we so hated?" now that there's been a more vocal contingent of people being critical of their lack of civic responsibility. Is it true that corruption and NIMBYism have kept affordable housing from being built? Sure. Is it true that members of the tech industry do contribute tax dollars to the city? Absolutely. But does that mean techies have done enough? Nope.

First, some perspective: The leaders of the technology industry in Silicon Valley are among the richest people who have ever lived in the history of the world. That's some crazy shit right there. And I know firsthand, from living in New York City where we have an egregious, unacceptable and immoral level of economic inequality that these are difficult problems to face. But the two biggest reasons techies in New York don't face the same blowback are because 1. We have the finance industry to shield us by being more disgusting than tech in almost every regard and 2. Our local technology community has a very strong ethos of community involvement, with the expectation that people who work in tech will also be involved in their community to solve bigger problems. It's just that simple.

So, what can folks who work in tech in San Francisco do to defuse the widespread resentment of their impact on the city? Here are a few simple suggestions:

  • First, people in tech should use their voices to push the leaders of their companies and industry to do the right thing. It is just as easy for a CEO to ask the city to accommodate affordable housing as it is for them to demand tax rebates. And if a CEO believes their employees expect this kind of request, most tech company execs will do anything to keep their engineers happy. If Google is the symbol of entitlement in San Francisco right now, Larry Page could simply and consistently amplify the voice of those already working on housing solutions and make a huge impact.
  • The employees who ride the buses could put up simple signs at the stops: "[X] out of the 300 people who ride this shuttle each day have pledged to volunteer once a month at a city shelter or facility, and to support labor rights when they vote & shop." People in the neighborhood could watch the number go up as the riders pledge, and the sign could proudly announce the name of the people's employer, instead of hiding it in secrecy as a source of shame.
  • At a more structural level, startups which provide deluxe on-site benefits could extend their daycare, meal and on-site walk-in health care to people who have WIC or EBT cards and can show that they live in the neighborhood. The bonus here? You can meet actual people in your neighborhood. The cafeterias could charge a fair price for those extra lunches, or even better, simply talk to the people who come in to see which ones would make good employees. One hire from the neighborhood talent pool would more than pay for the cost of six months' worth of free lunches.
  • People who care about these issues in technology could draft a simple platform of social goals and civic initiatives which they want to help with. (Just use a Google Doc for this; Don't overthink it.) Once that's done, people could simply indicate their support for the platform by liking it or putting a little badge/overlay on their avatars. Pick a nice name or logo, and it'd be perfect to put on a pin on your fanny pack or to silkscreen onto your startup hoodie. Then you'd be publicly declaring your commitment to your city and community — I promise a bus full of people wearing those pins won't get anything thrown at it, if it's a meaningful symbol of real engagement with the community.

The ridiculous thing is, these ideas, while nowhere close to real solutions, were meaningful first steps that I came up with in five minutes after a friend raised this issue in frustration. As far as I've seen, none of even these simple initiatives have been tried yet. The reason techies are getting a hard time in San Francisco is because they haven't done even the first steps. Now, to be clear: We need to get our shit in order in New York City, too. While most of our startups aren't big enough to have the infrastructure to do these things, and we don't have commuter shuttles, there's no reason we couldn't adapt versions of these initiatives. But already, disaster-related hackathons like those around Sandy have helped our neighbors, hosting Mayoral forums that raise substantive issues has contributed to our political discourse, drafting meaningful public policy suggestions has driven the dialogue about how we best serve all our citizens, and volunteers across the city put their tech skills to work serving the needs of their neighbors. All of these things are just as possible in San Francisco.

I'm not saying these take the place of real, substantive, long-term engagement and investment. They obviously do not. But these could be useful bits of progress if they lead to people in the technology industry approaching their civic institutions with humility and respect, listening to their neighbors honestly and openly, and making commitments instead of demands. I joke around a lot about San Francisco as a New Yorker, but having lived in San Francisco for years, I know it can be a great city. So act like it, and be worthy of it.

My Meeting with Pax

September 13, 2013

I'm sick to death of this whole stupid topic, and fighting off a brutal chest cold, so I'm going to ask your forbearance on this piece; It'll be a little less even-handed and detailed than I usually try to be, and if my language is ambiguous, I hope you'll take a charitable interpretation to what I say.

Earlier this week, people noticed that Pax Dickinson has been saying horrible things online for a while and then he was held accountable for them. Early on in the discussion, I pointed out that his attempts to act like an asshole had succeeded, and so I became a sort of tangential part of the story, mostly for this tweet and its replies:

People who know me know that my offer was sincere, because while I was not trying to get Pax fired (though I certainly am not sorry that he was, and everyone including Pax agrees it was the right decision), I was definitely trying to find some way to understand if a constructive form of accountability could be attached to this incredibly shitty circumstance. I would still like to see Business Insider's management explain how they're structurally addressing their failures that allow a toxic culture to thrive for years with no accountability.

Today, Pax and I finally sat down as planned. The first indications to me that this was going to follow a predictable pattern was that his initial email to me described his tweets as being the voice of a "persona", and that his final planning email mentioned that he wanted to change venue to a different place than I'd mentioned publicly out of deference to his wife's desire that he be ultra cautious.

I hope that Pax's friends in the pick up artist community take a few moments away from writing date rape manuals and sending me death threats to reflect on the fact that their new hero has at least some tiny bit of respect for the wife he's been married to for 15 years. How crushed they will be.

Pax showed up about 10 minutes late, having been busy with the latest stop on his press tour, and as I had agreed, I called him an asshole to his face and paid for his coffee. We talked for about 20 minutes. He offered up a pretty boringly conventional defense of male privilege, and when I described the role of actual satire and comedy in punching up instead of punching down, he revealed that he sees attacking feminists and equality activists as punching up. There was some pointless bickering from me about the inanity of that perspective, but overall things were fairly civil; I've met guys like this before and I didn't have any illusion that I was going to dissuade him from a perspective which his social group rewards with attention and the perverse impression that acting like an asshole is somehow being brave. There were the obligatory mentions of how his wife and some of his coworkers are women, so obviously he can't be sexist. And there was a philosophical underpinning to his provocation, that Pax is trying to broaden the definition of what constitutes acceptable debate or discussion. That left me a bit amused, as I can't think of a more self-defeating way to try to accomplish that goal.

There was also a pretty dogged pitch for his startup, which will get all kinds of warm huzzahs from the intersection of MRAs, Bitcoin fans, NSA critics and Redditors. I was pretty amazed that he went for it. He flat out said that he wants his startup to be funded and wasn't sure if it'd be possible after all of his, and I replied that it realistically wasn't going to happen without the say-so of someone like me, and I wasn't inclined to give some VC the nod on this. On reflection, I'll be explicit: If you're a venture capitalist, and you invest in Pax's startup without a profound, meaningful and years-long demonstration of responsibility from Pax beforehand, you're complicit in extending the tech industry's awful track record of exclusion, and it's unacceptable.

[Update: Since the section above was misinterpreted by some, I'll clarify. I'm not an investor or VC; I just know that when those folks look to invest in someone, investors check references by talking to those who've interacted with them. If they asked my opinion, I'd share this perspective: Pax did something his employer deemed a firing offense, but said that there was no changes he should make, nor constructive lessons learned, from the experience. Seems like a bad investment.]

But I am an optimist, and always try to find some opportunity for at least a tiny positive outcome in a shitty situation, so I asked if there was anything productive that could come out of our talking. He seemed pretty skeptical, and the first idea I had was that some of his technical skills were valuable enough that documenting them in a way that could be useful to others might be worthwhile. At this he seemed to perk up, and I said if there were materials that people could use to learn skills at a conceptual level, that might at least yield some good. Pax agreed there was potential, and I told him if he made something like that, I could get it to the right people who could put it to good use.

Then, foolishly, I tweeted about the meeting, briefly mentioning this last part of the conversation. My wording was terse in obedience to Twitter's limits, and a few folks understandably misinterpreted my intentions.

So, to be clear: I have no interest in playing an agent of Pax Dickinson's redemption. I do not want him anywhere near kids of any sort, let alone teaching anyone. I am not concerned with creating opportunities for him or reopening the doors he's closed through his actions.

I do think Pax knows how to do some things that are valuable at a technical level. If he chooses to direct those abilities in a way that's useful to society, I think that'd be a good thing. I think it would help atone for the hurt Pax has caused.

More broadly, I am trying to live a life where I am as unreasonably kind as I can be. If that means having coffee with a guy who's been a supremacist asshole, I'm okay with that. In fact, some of the lessons that have stuck with me the most this year were imparted to me by a man who's done even worse, having served two decades in prison for killing someone. I don't forgive him that wrong; It wouldn't be my place to do so even if I had the power. But it's a good exercise for me to try to see the common humanity I share with even those who do the things our society defines as the worst things. I do not pretend it's the right choice for everyone, but it is for me.

My most lasting impression of this stupid half hour at a coffee shop was from right in the middle of the conversation about how we speak truth to power. I pointed out that his words were bullying because he was aiming at those who have less power than Pax does, and he said, with great animation:

"But you guys are winning! The progressives and feminists are winning in everything, in politics and media!"

So yes, we did find some common ground during our conversation.

NYC's Mayoral Primary: How to Choose

September 10, 2013

Today is New York City’s mayoral primary, where the two major parties select which candidate will represent the party.

Due to my being on the board of the NY Tech Meetup, I got to be part of a small group that interviewed almost all of the major candidates. (Basically, everyone except Anthony Weiner, whose presence I didn’t particularly miss.) If you have the time, I strongly recommend watching all of the video interviews with the candidates. Though they obviously focused their conversation on the fact they were talking to members of the technology industry, each presentation began with a 10-minute talk about their candidacy overall, and the questions that followed weren’t limited to being about technology.

A broad range of representatives from the technology world were present, including people involved in policy, education, entrepreneurship, civic organizations, and even venture capital, well described by Fred Wilson. I am incredibly proud of NYTM for organizing and hosting all of these candidates; When I ran for the NYTM board, my greatest wish was that the Tech Meetup community would become a political force, working as a positive actor in New York City. As I said then, “We must be a community that is able to hold officials accountable.” I think today’s election marks a point where the technology community can truthfully say that we have reached that milestone.

Now the question is what we do with our power. Do we use it to enrich ourselves, or to help our city?

Foot in the Door

Access to the candidates is a powerful opportunity for all of us in technology. From this point on, I’ll diverge from describing what the NY Tech Meetup community has done to representing my own point of view, which doesn’t represent the NYTM board or our members.

As an ordinary citizen, I don’t often get to talk to the likely next mayor of New York City, so I asked the candidates the question that I thought mattered most: Given the success and privilege that the tech sector has seen so far, how would we be asked to serve and give back to our city? I framed the question in terms of how we could help address injustices like our city’s Stop and Frisk policy, but the key point here was that we should be asked what we can give, not just telling what we want to take.

Price of Independence

For me, this exercise is mostly an intellectual one; I don’t belong to a political party, so I can’t vote in the Democratic or Republican primary, and there’s no runoff for independent candidates ahead of the general election. It’s very likely that we’ll see a post-Bloomberg return to having a major party win in the general election, so though I’m friends with Jack Hidary, one of the leading independent candidates, and I found independent candidate Adolfo Carrión to bevery fluent in the issues of his constitutency, I don’t have much of an opinion about their chances of an upset in November.

Leading Contenders

Before getting a chance to spend half an hour with each of the candidates, my bias amongst the Democratic candidates had been slightly toward Christine Quinn. Though I share the near-universal disgust for her horse-trading to enable Bloomberg’s third term, the prospect of having a true ally for LGBTQ rights in office, and the prospect of our first female mayor were very appealing, especially given that I perceived a lack of substantial policy distinctions between the Democratic candidates. The interview with Quinn also shows her strength, especially during the Q&A: She feels real. She talks like a normal person, and has a great instant rapport with a room in a way that doesn’t feel like a pandering politician. I was impressed, and surprisingly charmed, and her literacy in the minutia of making policy happen in the city is absolutely the strongest of the field. Despite the misgivings many have about her brusque manner, I would have no major qualms about having Quinn as mayor, given the long history of prickly types who’ve inhabited the office.

Another surprise to me was Bill Thompson. I’d been cautiously impressed by his performance in an earlier town hall meeting where I’d seen 3 or 4 of the Democratic candidates speak. He was passionate about housing equity issues that few other candidates addressed. In his NYTM interview, he had by far the most detailed and inspiring plan for using technology to help the city. You can see him outline his 10-point tech plan in the video, but my takeaway from the admittedly impressive plan was more “I wonder who he got to write that for him?” rather than “He has really brilliant ideas about this!” I do respect leaders who are smart enough to get great policy advisors, though, and this put Thompson into my second place overall for desired candidates.

Tech Cred

Any detailed response to how candidates might either help the tech industry or take advantage of tech to make the city run better was well-received, but most candidates generally regurgitated the 7-point policy platform that the NYTM outlined on its site (see bottom of the page). Any deviation from those expected nods to their hosts was very welcome.

One of the few other candidates to do a strong job in thinking of ways to use tech was Joe Lhota, the lone Republican candidate to sit down for an interview. Given that his main opponent is running on the farcical reputation of having built the Gristedes grocery chain (Slogan: “Slightly less shitty than C-Town!”), he’d be hard pressed to not do well in the Republican race. That being said, a close alignment with some of Giuliani’s most indefensible policies, was off-putting, and worse was that he oddly took credit for some MTA open data efforts that I actually helped to launch under his predecessor Jay Walder. Given that Lhota could have easily, and fairly, just focused on the remarkable job that he did getting MTA back up and running after Hurricane Sandy, this seemed like needless stretching for credit with techies.

A Different Perspective

And then, one of the last candidates came up to speak and fundamentally changed how I saw the race: Bill de Blasio. His opening 10 minutes spoke frankly and forcefully about income inequality in our city and in our country, in a way that very few politicians of any stripe have articulated. He mentioned clearly that his children would be the first of any mayor’s to have gone to public school for their education. He articulated a clear plan for preserving our gains in fighting crime while undoing the everyday humiliations of Stop and Frisk. He supports his campaign with public dollars, allowing him to avoid being financially dependent on big donors without being a billionaire. And when I asked the same question about how the tech community could serve, rather than the bland platitudes I got from nearly every other candidate, he answered with specifics about how successful startups could pair with individual schools in order to offer students specific examples of the kinds of careers they could pursue post-graduation.

I get to hear a lot of elected officials talk, and I’m a little inured to the predictable cadence of people telling an audience exactly what they want to hear. Telling a room that has Fred Wilson in the audience, “I’m going to tax rich people” was pretty unexpected. I do not find it at all surprising that, in the weeks since this interview was recorded, de Blasio has seen a precipitous uptick in support for his candidacy. I think it’s well-earned and based on substance.

Do I think Bill de Blasio is the most tech-friendly, tech-literate candidate out of the field of contenders for the mayor of New York City? Probably not. I don't support a candidate based on their blind fealty to an already-wildly-successful industry. But like any of these smart people, he’ll have access to as fine a coterie of technical advisors as he’s willing to embrace.

Get Off Your Ass

Overall, we’re lucky. I don’t love any of these candidates, but given the disproportionate amount of attention that’s been paid to lunatic sideshows in NYC’s elections this year, I’m very glad to see that there’s a deep list of smart, engaged candidates. They all had very good ideas, and none of them were embarrassing to watch when talking about how they’d improve the city.

As an independent, I don’t have much of a vote in city politics, and by the time I do, it’ll probably be too late. But if you’re reading this, you might well have a say as to who we put into office. I think the best choice is Bill de Blasio, and it seems many New Yorkers would agree. But I’m certain the worst choice would be to miss a chance to vote on these candidates, so please do watch the videos, read up on the candidates and issues, find your polling place, and get out and vote!

Further Reading

10 Rules of Internet

July 17, 2013

In my years working in technology, I have learned a few things. These lessons have become oft-repeated refrains when speaking to people, so I thought I'd collect them so I have a link to send folks when needed.

  1. Given enough time, any object which can generate musical notes will be used to play the Super Mario Brothers theme on YouTube.
  2. Judging by their response, the meanest thing you can do to people on the Internet is to give them really good software for free.
  3. Three things never work: Voice chat, printers and projectors.
  4. Once a web community has decided to dislike a person, topic, or idea, the conversation will shift from criticizing the idea to become a competition about who can be most scathing in their condemnation. (See The Law of Fail.)
  5. Any new form of electronic communication will first be dismissed as trivial and worthless until it produces a profound result, after which it will be described as obvious and boring.
  6. If your website's full of assholes, it's your fault. (See the post on this topic.)
  7. Most websites treat "I like it" and "This is good" as the same thing, leading to most people on the Internet refusing to distinguish between "I don't like it" and "It's not good".
  8. When a company or industry is facing changes to its business due to technology, it will argue against the need for change based on the moral importance of its work, rather than trying to understand the social underpinnings.
  9. People will move mountains to earn a gold star by their name on the Internet.
  10. The only way to get useful feedback from people on the Internet is to ask questions that are actually answerable, instead of open-ended.

Bonus rules which apply equally on the Internet and off:

  • Never argue against logic with emotion, or against emotion using logic.
  • We hate most in others that which we fail to see in ourselves. (That's pretty much where this blog started, 14 years ago.)

Hold The Door Open

April 25, 2013

Though it's currently in vogue to threaten the President with ricin, the fashion when I was a younger man was to intimidate newspapers with anthrax. During those heady days I happened to work at a newspaper, and as always the terrifying eventually evolved into the mundane, so efforts to protect the staff got reduced to the mailman delivering our packages while wearing latex gloves and a sign being taped inside the main door to our office. The sign had no doubt hastily been prepared in Microsoft Word by someone struggling to deal with the very real possibility of a deadly attack on their coworkers, but by just a few months later, it already seemed an odd artifact of an era of duct tape and color-coded alert levels. The sign said this:


Do not hold the door open for anyone. Later, the sign was revised to something more polite, doing a better job of explaining that this simple glass door was supposed to represent a last line of defense against some unforseeable biochemical attack.

But I think about that sign pretty regularly, as a manifestation of how people who are afraid act. I am a person who has a better life because some kind strangers held the door open for me for just that one extra moment. It was especially appreciated because the elevator in 36 Cooper Square took forever to arrive.

Be Kind

These are two posts that both arrived on Sunday. I don't know if they were coordinated, but they connected in a way that I found pretty powerful.

Cap Watkins, design lead at Etsy, asked us to Be Kind:

I was working out of my apartment fulltime, and hadn't met a single person in the bay area outside the people working with me on PMOG. One day, I decided I wanted to meet some designers in San Francisco. So, I did the only thing I could think of: made a list of web sites I thought were well-designed, figured out who designed them and sent a cold email to the designer telling them I was a new designer in the area and asking if they'd like to get coffee or a beer sometime. In all, I probably sent around 20-30 emails to a variety of creative people in San Francisco.

I received a single reply.

Daniel Burka (who at the time was the creative director at Digg) said that, sure, he'd love to grab coffee. We set up a time and I took the train to the city to meet up with him and his friend Mark. We chatted for awhile and, just before we left, they both mentioned that they were going rock climbing the next morning with friends, and asked if I'd like to join.

Absolutely, I did. ... I wonder sometimes about where I would be now if Daniel hadn't responded to that email. Most likely, I would have gone back home to Louisiana after PMOG. I wouldn't have known anyone in San Francisco, wouldn't have known how to even start looking for new work, etc.

And from Daniel Burka, the Google Ventures design partner mentioned in Cap's piece? A rumination about Doug Bowman:

Nine years ago, I sent a tentatively worded email to Doug Bowman asking if he’d meet up for a coffee when I visited San Francisco for work. At the time, Doug had just launched the new Hotwired site, which was the most incredible, amazing, mind-blowing achievement in web standards at the time. No way did I think that Doug would agree to get coffee with a handful of nobodies from Eastern Canada.

And then he responded. And said yes! And even knew some of the work we’d done (or was generous enough to look us up on the way to the café). And he didn’t talk down to us. And he treated us like COLLEAGUES, not like disciples. And he was just a human.

I’m not exaggerating when I describe this as a seminal moment in my design career. The fact that Doug Bowman treated me like I belonged in the same league allowed me to believe that maybe I really did play in the same league. What a wonderful boost of confidence!

I don't think it's coincidence that Cap and Daniel and Doug work in design, a discipline that at its best is grounded in empathy, but regardless of which field they happened to work in, they offer examples of exactly the serendipity and opportunity that can arise when we hold the door open, just a little bit, for that person entering behind us. All we have to do is not be afraid of who we're letting in.

You may also want to see How Jason Fried's opinion made it into the New York Times.

To Less Efficient Startups

September 28, 2012

Most of the technology world, especially the traditional venture funding infrastructure, is justifiably proud of the extreme efficiency of modern internet startups. It is a triumph for Craigslist to serve hundreds of millions of users with only a few dozen employees, or even for Facebook to serve a billion users with just a few thousand employees.

But we need to support and encourage another model, one that's less economically efficient.

From an economics standpoint, the hugely successful tech companies of our time are marvels of efficiency because it used to take a company with hundreds of thousands of employees to generate so much market value. Unfortunately, this "progress" in efficiency means a concentration of generated wealth among an even smaller, more exclusive cabal of winners when one of these companies succeeds.

Instead of generating tens of thousands of middle-class jobs as industrial-age titans did, these companies make a few dozen people truly extraordinarily wealthy, and then give generous payouts to a few hundred people who were already on a path to success by having been privileged enough to go to top universities and by having the identities that tech and engineering cultures are biased toward today. There is effectively no blue collar path to success, notwithstanding the much-vaunted stories of tech company chefs entering these companies in the kitchen and exiting as millionaires.

Beyond Efficiency

Some of the most interesting startups (the NYC chauvinist in me must point out that these are all New York companies) are not optimizing for raw market efficiency, but instead for opportunity for a broader community. Some examples:

  • Kickstarter is explicitly building an economy to support the work of artists and creators, disciplines that are often not favored by the attentions of the tech industry.
  • 20×200 has a complete structure of support for promotion and payment for artists, as Jen Bekman outlined at the XOXO festival.
  • Etsy perhaps illustrates this best of all; I talked about this a bit when recording Chad Dickerson's talk at XOXO, but his slides from that talk outline their commitment as a B Corporation to many of these principles of helping an entire community, not just preferred shareholders:

I should note that I'm friends with the founders and executives of all of these companies though I'm not part of the community of creators who benefit directly from these platforms. And of course, Ebay has had many of these tendencies for supporting an economy of creators for years; One could argue that Google's programs like AdSense helps publishers in a similar way. But before we go down the slippery slope of saying every small business ad on Facebook and Twitter is proof that many can benefit from efficient companies, we need to draw a line between explicit parts of a company's internal economics and the dollars that flow through their overall ecosystem. Because the players outside the company who are subject to the economics of AdSense or ads on Facebook or Twitter are the first ones to get squeezed if the company needs to optimize its revenues, aside from the fact that they never structurally benefit from an increase in the valuation of the company which provides them with their marketing platform.

How We Do It

I'm not saying existing companies necessarily need to radically change; It's great that many have succeeded with the model so far. But I'm hoping that people who are building and funding companies can put some thought into what success can look like for future tech companies if they also value creating lots of middle-class jobs and lots of opportunities to help blue collar or non-technical workers thrive with meaningful long-time work as their companies take off.

We tend not to think it's cool that Microsoft or IBM have hundreds of thousands of employees. But there's something meaningful, and important, and essential to our society for enormously valuable companies to also provide enormous value in the form of lots of jobs for regular folks. I'll be rooting for the next wave of startups to tackle this problem that has, so far, been too difficult for our biggest web companies.

Politics is a Business. A Big, Broken One. Let's Fix It.

February 24, 2012

I'm an idealist. I want all governments to work in an ideal, uncorrupted state. But I'd settle for the governments which I live under to work in a way that were at least a bit more responsive and transparent. But part of the reason that doesn't happen is because most of the people I see interact with government based upon their feelings about various governmental institutions, rather than the facts of how it actually works. So here are a few key truths:

  1. Anybody who says "The Government" did something is ineffective at best and just plain ignorant at worst, because there is no monolithic "government" any more than there is a monolithic "The Media" or "The Business". Knowing, and embracing, complexity is necessary for those of us who'd like to change the system.
  2. Money drives an enormous amount of the actions of elected officials. This is not perceived by most elected officials as corruption, but rather as a simple fact, a fact about which they are neither shocked nor surprised. You cannot shame someone about a fact they readily concede.
  3. The reason money drives many actions of elected officials is because it's used to get votes, mostly through the purchase of advertising. It's not because politicians are trying to get rich. Politicians are already rich; That's why they can run.

But if these simple statements indicate that the current system is broken, how come this is the one area that's obviously broken that most tech entrepreneurs aren't trying to fix?

So We're All Doomed?

When I say the political system is broken, it might make it seem like I'm some pessimist decrying that the whole thing is hopeless. But I'm not! Because first, I don't think the process of using our electoral system as a multi-billion dollar media subsidy is going to be sustainable forever.

More importantly, the inescapable motivation for the enormous amounts of money saturating our political and electoral processes is that politicians want votes. It's what lets them become incumbents, a fancy political term that means "ruler for life".

Here's the tricky thing, though: Networks, sometimes, can trump money.

Networks Over Dollars

Now, it's not always the case that enormously vested interests with bottomless pocketbooks can be overcome simply by people banding together through newer, smarter, faster networks. But we've seen it work a few times. Early communities that sprung up around blogging and Craigslist were just trying to meet their own needs, but ended up massively disrupting the wealthy, powerful newspaper and magazine industries largely by accident. You know the same story happened to the industry formerly known as the recording business, too. And those disruptions happened without even trying.

When new technology-based networks are still young, they can be massively disruptive without even intending to be. So what would it look like if we disrupted one of these broken-ass, frequently corrupt, largely inequitable networks on purpose? Well, I can think of no industry in better need of that sort of upheaval than our policymaking infrastructure, at the local, state and federal level. We've let many of the organizations that make up these governmental institutions become unmoored, making many decisions not based on fact or effectiveness, but based on decisions shaped by the money chase that elected officials are obsessed with.

Who's Going To Step Up?

The thing is, there is a ton of opportunity in this disruption that's going to happen. Social networks will reshape electoral politics and the world of policymaking in the next half-decade, and it's just a question of who does it, and on what terms. Even in just the few short years since Expert Labs was formed, we've had to change some of our fundamental assumptions; According to the world we were living in when we started Expert Labs, the widespread, incredibly effective and surprisingly rapid protests against SOPA and PIPA should never have been able to happen. Yet they not only happened, they happened without primarily relying on financial sponsorship of alternate candidates as their primary point of influence.

In short, they used the network to overcome the traditional money-based ways of influencing politics.

The funny thing is, I'm not actually demonizing the fact that money and businesses have a role to play in how the political system works. In fact, as Clay Johnson eloquently explained, we should all do well to be more versed in how political fundraising and policymaking intersect. It's absolutely essential to know the ecosystem around web-based political influence if you want to understand its future.

Going Gaga

Perhaps one of the most overlooked parts of this evolution is that there are going to be new winners. Not just new candidates getting elected to office (although that's great, too!) but new companies which succeed in building thriving new businesses by serving a more responsive, engaged electorate through social networks online. In fact, I'm proud to advise one of the most prominent and promising of them, Votizen, which just got a pretty formidable set of investors who share my optimism that a better political infrastructure is also a good opportunity for building a business that helps make the world better.

I'm not the sort of person who usually ends up advising companies backed by "hot" Silicon Valley investors. (Or Ashton Kutcher. Or Lady Gaga's manager.) But putting aside my own picky preferences about how the tech industry runs, I want this one to work. I want our tech industry to see as much potential, as much excitement, as much glamour, and far more meaning in fixing politics and voting and policy as they do in fixing the way we listen to music or organize our photos.

Because even after Votizen succeeds wildly in getting people to band together to vote more effectively, with more focus on the issues they care about and the facts that impact those issues, we've got a lot of other work to do. We still have to get the smartest, most creative people in our country involved in the hard work of advising policy makers. We have to get regular folks to understand that the drugs that treat their family members' cancer, the highways they drive on to go see their kids' ball games, the parks they go to on the vacation days that they're mandated to have — all those things are the product of government, even with its current inefficiencies and imperfections. Hell, we have to have every big institution, whether it's government or business or academia or religion, to make itself accessible and malleable by all of us who are affected by their decisions.

Today, though, it's easy to criticize government, or to just complain about it. But bitching about government isn't like bitching about the weather, where we can't do anything about it. In fact it's the opposite — government is made out of the only thing we really can change: Ourselves. So let's get to work.

Communities of Creators

October 5, 2009

Last week, I found this picture of a group dinner at Guero's restaurant in Austin, TX, taken during South by Southwest in 2002.

Guero's, March 10 2002

At the time, most of us at the table knew each other primarily through the web and through the then-nascent blogging community. But in the seven and a half years since then, many of us have gone on to become entrepreneurs or creators, launching dozens of companies and products. I'm still collecting names and companies in the comments on Flickr, but just a cursory glance shows founders from Blogger, Six Apart, Adaptive Path, Flickr, Gawker, Twitter and more.

I point this out not (just) to name drop — you can click through to the Flickr image to see notes about who was there, read what they've done, or add your own annotations. But I also wanted to highlight one of the most important resources that creative people need to truly succeed: A community of peers.

In the business world, and especially in the technology industry, we focus a lot on the functional requirements of raising money, or on the technical requirements of having certain features or technological capabilities. What I've found, though, is that being part of an active, ambitious, supportive and diverse community of peers is just as valuable, if not more so, than any of the more prosaic prerequisites for success. That's even true in this photo — some of the people whom I met in person for the first time that night or that weekend have gone on to become among my closest friends, the biggest supporters of my work, and have ventured their formidable social capital to support my career. An even more diverse community of others whom I met at similar dinners or other events have played a similar role as well. Yet, at the time this photo was taken, I don't think any of these people had ever taken venture capital money for any project they'd ever done — everyone here had bootstrapped their way to the table.

So, it's easy to focus on the money or the little technological accomplishments, but I am glad I found these old pictures as a nice reminder that we should set aside time for a great meal with smart friends every once in a while. If it's not enough enticement that you're just having a good time, you can also justify it as one of the most worthwhile investments you can make in your future success.

These Things Are Related

September 17, 2009

Here are some interesting recent blog posts and articles, mostly by friends or acquaintances of mine, all of which add up to an interesting narrative. owes much of its success to one such investor, First Round Capital, which opted to back the fledgling company at a time when other VCs demurred. Indeed, the acquisition is First Round Capital's largest exit, beating out the $100 million sale of portfolio company Powerset to Microsoft (MSFT). And although First Round Capital would not quantify the return on its investment, co-founder Josh Kopelman says the deal generated the highest return of any deal the firm has done. Previously its best return came when eBay (EBAY) acquired StumbleUpon for $75 million, which generated more than 14 times First Round Capital's original investment. "I don't think this changes our strategy," Kopelman says. "It is continued validation for our approach."

I did interviews with most of the TechCrunch50 experts backstage and there was a common gripe about the companies launching there: Not enough passion, not enough swinging for the fences, not enough trying to change the world. There were too many people building safe businesses, too many companies just trying to make existing things slightly better, and too many people wanting to be the next, not the next Google. Nothing against Mint, but Silicon Valley wasn’t built on $170 million exits.

Web visionaries like Reid Hoffman and Sean Parker struggled to come up with positive feedback on stage. Robert “I-get-excited-by-nearly-any-start-up” Scoble was so bored he was playing Hangman via Twitter with Paul Carr. Marc Andreessen praised Udorse—a company that he joked would make the world a worse place if it succeeded—because at least it was a new idea. Tim O’Reilly said he didn’t care whether Cocodot, one of the companies he judged, succeeded or failed because it was so meaningless in the world. And Tony Hsieh just said it blatantly: “I didn’t see anything that was trying to change the world.”

In some ways, I feel like Sarah's post is a direct corollary to my own earlier post where I'd suggested that the U.S. Government is the most interesting tech startup of 2009.

The ever-diplomatic Jason Fried of 37Signals riffs on a topic that he and I were just talking about last night, a lamentation of modest ambitions:

Mint’s sale to Intuit really pissed me off.

Why should I care? Because I think it’s indicative of a VC-induced cancer that’s infecting our industry and killing off the next generation. I don’t know the full backstory, but I’d bet this sale was encouraged by a Mint investor.

Here’s a fresh new company that was gunning for an aging incumbent. And not only gunning, but gaining. They had a great product, great design, and great potential. They were growing rapidly and figured out the revenue game. They were on their way to redefining an industry — one that was left for dead by the current custodians.

They were everything their main competitor, Intuit, was not. While Mint was inventing, Intuit was out of it. People used Quickbooks/Quicken out of habit and legacy. People used Mint because they loved it. Intuit was disgruntled, Mint was disruptive.

But here’s what happened: Intuit, last decade’s leader in personal finance, just became the next decade’s leader in personal finance. Mint had their number, but they sold it for $170 million. A big payday for sure, and if that was their two-year goal then they nailed it, but I can’t believe that was the point behind Mint. It had too much potential.

Mint was a key leader of the next generation of game changers. And now it’s property of Intuit — the poster-child for the last generation. What a loss. Is that the best the next generation can do? Become part of the old generation? How about kicking the shit out of the old guys? What ever happened to that?

There are a bunch of veteran entrepreneurs actively investing in and mentoring seed stage startups. Google has a big office here and many people seem to be leaving to go start companies.


New York City has many of the same strengths as Silicon Valley - merit-driven capitalism, the embrace of newcomers and particularly immigrants, and a consistent willingness to reinvent itself. Silicon Valley will always be the mecca of technology, but now that people here are getting back to, as Obama says, making things, New York City has a shot at becoming relevant again in the tech world.

Yes. As someone who goes back and forth between New York and Silicon Valley, I see more companies being started in the Valley. But I am seeing some great consumer internet companies being started out here too. Etsy is a great example. Hunch has to be on this list. And Kickstarter, which just recently launched, and is changing the way that creative projects themselves are funded. A promising beginning. There need to be more startups, naturally, and more seed capital, and a hometown newspaper, as Chris also notes. And the CS grads moving into startups rather than financial services companies. I'm optimistic.

Though Caterina is still optimistic about startups in Silicon Valley, I'll offer up that one of the biggest changes in her perspective since saying three years ago that it was a bad time for a startup is that she's spending a lot more time in New York City these days. Finally, my friend Jen Bekman exemplifies the diversity of NYC's nominal "tech" community, in that her startup and company are squarely focused on the world of fine art. As Jen says:

[T]here’s so much else going on aside from technology — the valley might hold the title of the best place for start-ups in technology, but NYC is the best place for many things.

The diversity of experience on the 20�200 team is incredible and inspiring. Everyone I work with has done a bunch of other things aside from technology, and not one of them set out for a tech career to begin with. Among us are photographers, musicians, artists, writers, lawyers, teachers and wine experts. We all love the internet (a lot! too much?) but what drives us most is our love of art and the people who make it.

Does this happen in Silicon Valley? Perhaps, but my time spent there — which I loved, for the record — was about an immersion in technology. Here in NYC it’s about the thing itself.


Then again, if you live too long inside the echo-chamber, it’s easy to forget who’s going to be using all this technology in the end. The reality check is important, almost as important as being able to hail a cab whenever I damn well please.

The thread that ties all of these things together for me is that technology adoption happens now because of culture and media, not simply for its own sake or because certain types of capital are available. It happens because a vision is ambitious enough to capture the attention of artist and writers and creators of all sorts, not just other technologists or people within the bubble of the existing tech community. And cities like Chicago, Boston, Washington D.C. and, particularly, New York City, have a decided advantage when it comes to connecting to those in the tech community to the rest of the world. We also have an unparalleled history of ambition (and, yes, ego) to match that potential.

I hope entrepreneurs learn a lesson from the few underwhelming startups that are out there, and realize that the model of making incremental improvements on companies that already exist is a recipe where, even if you achieve your goals, you may not have achieved much of a success. And if everyone around you has similarly unambitious goals, then maybe you need to be in a place where that's not true.

Note: I use, and like, and I'm happy for their success and am hopeful that they have a positive impact on Intuit. I am not arguing that their definition of success should be the same as mine, but rather that they may have defined a different set of goals if they had been part of a different community.

Who will save the tables?

April 2, 2009

About a decade ago, the web development industry made a decisive shift towards support for web standards. Though the effort encompassed many related efforts around HTML, CSS, the DOM and related technologies, perhaps the signature work of the movement was to encourage CSS-based layouts instead of the then-common practice of using HTML tables to design a page's visual appearance.


The campaign was extraordinarily effective, to the degree that most new sites that launch today use CSS as their primary system for styling and positioning. And the more socially inept web geeks out there still consider those who use tables for layout worthy of their derision, instead of opportunities for education. Tables have fallen so far out of favor that it's not uncommon for people to be reluctant to use them even for the presentation of tabular data.

In short, for front-end web developers, tables are definitely out of fashion.

More recently, web architects and developers have adopted a new generation of storage technologies for data, such as BigTable and SimpleDB. While these systems still use tables to store data, it's common to have a far smaller number of columns in these tables than were used in older systems. And their advantages in areas like scalability and partitioning, have encouraged lots of developers to consider adopting these new data storage systems despite their unfamiliarity.

In short, for back-end web developers, fat tables are rapidly going out of fashion.

Now, I don't mean to suggest that these technological trends are merely about geeks following what's faddish or popular amongst their peers. In fact, in both cases, the shift away from traditional tables might reflect the fact that our data has to be more nimble in both how it's stored and retrieved and in how it's presented and styled. These accommodations are necessary because the applications being built are more social and human-centric in nature, which means they have to be able to adapt and evolve as relationships and communities mature.

But part of me can't help but feel sad for the tables. I'm sorry, tables! I hope you come back in favor soon.

(Thanks to Mo for the image.)

The Anonymous Satirist

July 25, 2007

I often lament the lack of perspective in tech reporting, so it's always a delight to find a story that typifies what I'd hope technology reporting could be like: Smart, informed, and with a good sense of history. Take Caroline McCarthy's look at the allure of Fake Steve Jobs. Now, CNET's not known for being the most circumspect tech news venue around, but this is a brililiant dissection of why Fake Steve Jobs is so appealing.

Fake Steve, as a concept, is downright old-school. Think about it. In a culture captivated--obsessed, even--by the antics of high society, an anonymous satirist starts publishing over-the-top missives purporting to be from an insider in that privileged niche. In the process, the faux-mogul skewers political elites, entertainers, business titans, and ordinary people in a way that's at once outlandish and provocative, hilarious and appalling. It reeks of Swift or Dickens or Twain (although a friend of mine who's better-schooled in 19th-century literature informed me that the most apt comparison is likely Edgar Allan Poe). Were it the 19th century, or heck, the 1990s, the satirist's medium of choice likely would've been a serial or set of letters in a major news outlet.

And she's absolutely right. The fact that tech culture has become so pervasive as to merge with pop culture, and that personalities are so well-known that they can be used as a springboard for social criticism, is a milestone for the technology industry. It also points out why unmasking Fake Steve would be a little bit like telling a kid the truth about Santa Claus: You may be factually correct, but you'll have ruined all the fun and lost the little bit of magic that we have left.

The Challenge of Technology

July 17, 2006

From the comments on one of my recent posts, here's a perfect example of the challenge of explaining technology. I'd provided a set of links for subscribing to my site.

From "AbC":

I hate something about this whole feed business. I see techies falling over themselves trying to use the simplest possible language to help the rest of us understand what feeds really are and how they work. It's like a lot of people dumb down the definitions and try to use terms they think we'll understand and be able to internalize.

Hell no.

Tell me exactly how these things work ... tell me a feed is like an HTML file that has the address/URL of where a site's latest content is posted and that you can specify exactly how you want to see the new content - snippets or full blow-by-blow.

I maybe wrong ... because techies are really muffling the real definitions with their softened, purpotedly easy to understand definitions.

I think AbC's wrong. Here's why, courtesy of Joanne:

Thanks for posting this. I've heard of RSS before, but it all seemed like black magic until I tried out bloglines. Your post inspired me to get started!

No offense, but somehow I find the argument (and potential readership) of the Joannes of the world more compelling.

Copy and Paste? Live Clipboard.

March 7, 2006

I guess I'm not the only one thinking about copy and paste. Ray Ozzie is way, way ahead of me. In a development that's clearly been brewing for some time, Ray responds to the demand for better data interoperability:

And what was the most fundamental technology enabling “mash-ups” of desktop applications?

The clipboard. And a set of common clipboard data formats.

Before the clipboard, individual applications (such as Lotus 1-2-3 with its Copy and Move operations) enabled intra-application data transfer – in a world largely designed around a single running application. But the advent of the multi-application user environment, combined with the simplicity of the Select/Cut/Copy/Paste/Clear model, suddenly empowered the user in ways they hadn’t previously experienced.

More on this later, but for now it seems like the only official Microsoft resource on Live Clipboard is this mailing list. I'm sure there will be more discussion on MSDN later.

Reinventing Copy and Paste

March 5, 2006

There's been a lot of conversation lately about reinventing desktop office applications on the web. The first (and sometimes second) versions of all the stalwarts are out there: Word processors, spreadsheets, databases. I can think of Writely and Writeboard and NumSum and JotSpot and of course there's dozens of others if you go out and do some research. (Good roundups and good analyses abound.)

But I spent a lot of time watching, learning about, and customizing office applications the first time they were rapidly evolving and picking up steam. I even made a living for a few years building on top of them. And there's some mistakes being made by this generation of web apps that I hope get corrected.

We can all learn a lot of lessons from the history of DDE/OLE/ OLE3/COM /ActiveX/DCOM /COM+ (you can start reading up on Wikipedia to get some background) and how we went from everyone using best-of-breed standalone apps to one integrated, nearly monolithic Office.

The Holy Grail It basically all started with copy and paste. People who never spent a lot of time in singletasking, character-mode operating environments like the DOS command line don't recall that simply copying-and-pasting information between apps was difficult at the time. And part of the revelation of Windows for mainstream users (or Mac, for leading-edge tech fans), was being able to easily share data in that way. This was different than what Unix users were used to with the command-line pipe, or from what most applications do with feeds today, in allowing structured information flows between applications.

There's a desire to combine data from different sources in an arbitrary way, and to have the user interface display the appropriate tools for whatever context you're in. The dominant model here, probably because of the influence of the early PARC demos, is to have toolbars or UI widgets change depending on what kind of content you're manipulating. Microsoft was really into this in the early 90s with OLE2, where your Word toolbars would morph into Excel toolbars if you double-clicked on an embedded spreadsheet. It was ungainly and ugly and slow, especially if you had less than an exorbitant 8MB of RAM, but the idea was pretty cool.

And it still is. People are so focused on data formats and feeds that they're ignoring consensus around UI interoperability. The Atom API and Metaweblog API give me a good-enough interface if I want to treat a discrete chunk of information (like a blog post) as an undifferentiated blob. But all the erstwhile spec work around microformats and structured blogging (I forget which one is for XML and which one's for XHTML) doesn't seem to have addressed user experience or editing behaviors.

All of this is a long winded way of saying, we don't have much beyond copy and paste right now. If I want to put a NumSum or JotSpot spreadsheet into a Writeboard document, I basically can't do it. Maybe I can do it if all the apps are made by the same vendor and are made available as part of a suite, but we had that with Halfbrain seven years ago.

Now, nobody really adopted the interop specs for embedding rich objects between apps when there was the chance to do this on the desktop fifteen years ago. And this was part of the reason Microsoft Office was able to so completely dominate on the Windows platform by the mid-90s. Nobody else would interoperate in a way that let you easily swap in, say, Quattro Pro for Excel, and nobody else had a consistent way of scripting actions between apps. Of course, the point is moot, because Microsoft used bundling, some brutal and possibly unfair pricing, and an almost pathological underdocumentation of the specs to solidify their lead anyway. And that gave them the time to standardize around VBA as a cross-app scripting language, which took years longer than they had planned.

I can't even imagine trying to debug cross-app scripting on Ajax apps. If it's possible, it sure can't be pretty.

But the battle for office app supremacy on the desktop may have actually been a fight instead of a rout if all the also-rans had added up to something more than the sum of their parts. What was needed was not just mixing and matching at the monolithic suite level, but more granular control over which components would edit particular types of information. It took Microsoft until Windows 2000 for apps to stop just grabbing each other's file formats indiscriminately, and most regular computer users still probably aren't sure what the hell application is going to start up if they click on an MP3. And if you want to automate the simple act of copying and pasting from Lotus 1-2-3 to WordPerfect today, more than 20 years after those applications launched? It's basically just as difficult as it was when Windows 3.1 came out.

So, I'd love to see, as a user, a way for real rich data exchange to happen between the new wave of online applications. I'd like to see some efforts by (at least!) this group of vendors to make it possible to make compound documents between their applications, and then to choose from one or more tools for editing the discrete objects that make up those documents. And I'd like to be able to automate actions between these multiple tools without resorting to Greasemonkey hackery or convoluted browser tricks.

What can I offer in exchange for these features? Well, I'd pay to use the apps that are useful, of course, and I'd help promote the apps by sharing those documents with people. But I can also offer some tiny bit of defense over being completely obviated by the inferior, less open web office applications of the future that have better distribution due to the bundling that will inevitably come to this space. And scriptability means you can get features for free that you haven't even thought of, which is a nice way to combat the bundled single-vendor suites that sacrifice flexibility for consistency and integration.

My theory is that the current wave of web office application developers, like the last one during the dot com bubble, has ignored the lessons of the desktop office suite battles. I'm hoping to be proven wrong.

Other links: Some pieces on this and related topics from the past couple years include my own stories and tools, an overview of web-app tech so naive it makes me wistful for my more innocent days. It's remarkable how similar it is to Dave Winer's What is a Web Application?, which predates it by two years. I found Dave's piece as a link from his review of the state of the art in web office apps six years ago. It reads an awful lot like Richard's review, only now we have feeds on everything and there actually seem to be some users.