Posts from May 2009


Last week my friend Mark Pincus noted, via twitter, that I was not at the D conference and wondered if I knew something others did not. I replied back to Mark that I'm not a big fan of attending conferences.

I don't go to TED and never have and don't think I ever will. I don't go to Demo or Techcrunch 50 or any of those kinds of events either.

I spent the weekend in Vegas with a bunch of people who go to the Lobby conference every year, including its organizer David Hornik. David was trying to convince me to come this year, but I told him the idea of a ten hour flight to Hawaii was not attractive to me. I suggested to David if he did it in a place where us east coasters could get to a bit easier, I might consider it.

Travel is a hassle. Its time consuming and gets in the way of doing other more productive things. I'll gladly travel to the west coast or europe to visit our portfolio companies and meet with new investment opportunities.

But the idea of travel to get together with the same old group, the tech biz insider club, doesn't appeal to me at all.

I do like attending events that happen in NYC, like I am doing tomorrow morning. I am speaking at Federated Media's Conversational Marketing Summit. I'll spend the morning there, get some networking in, and be back in my office for our monday meeting in the afternoon. That's how I like to do conferences, short, sweet, and easy.

I think our industry places too much emphasis on conferences in an era where there are amazing tools to congregate online and find like minded people. I am not suggesting that face to face meetings aren't important, they are critical. But schmoozefests at fancy resorts aren't the kinds of face to face meetings I want to do.

And 'by invitation only' or high priced events are particularly bad in my mind. The most interesting people you can meet are the outsiders, the up and comers, and the hackers who can't afford to lay out $4000 to attend an event and are never going to get an invite to an event where you have to know somebody or "be somebody" to get in.

So I avoid those most of all.

Back in the 90s, I was unknown to the powers that be and could not get into TED. I don't forget that and that's why I'll never go to it. I don't want to play that game. If I ever got an invite to Davos or Sun Valley, I'd have a really hard time saying yes. These power parties are not for me.

I've got this blog and the rest of social media where I try hard to be approachable and where I can meet interesting new people. And I take an average of twenty to thirty meetings a week. That seems to work pretty well for me. And I think I'll just keep doing it that way.

Reblog this post [with Zemanta]
#VC & Technology

If The Message Is Important, It Will Find Me

Matthew Ingram wrote a post a while back and quoted a market researcher quoting a college student who said:

If the news is that important, it will find me.

I think we've all experienced the changing distribution of news and information via social media and understand what that college student was saying.

But I've reached the same point with messaging as well. Like many of you, I participate in a host of messaging services; email, texting, BBM'ing, twittering, facebooking, instant messaging, and blog commenting to name a few of them.

It's become impossible for me to read every message that is directed at me. I try hard to get to all of my messaging but I've reached the point where I don't sweat it anymore. I know that I won't see every message that is sent to me and that's OK with me.

Our family uses BBM (Blackberry messaging for those of you not familiar with it) as our "batphone" and that is the one channel that is not cluttered for me. Unfortunately, right now my BBM software is not working on my phone, and I need to fix that.

But other than BBM, I've decided to take the approach that if the message is important, it will find me. It's very liberating. I'm curious if any of you are taking this approach as well.


Cloud Based Messaging

Over the past couple days I’ve been thinking and working on cloud based messaging.

The work has been to get off client-based email once and for all. Over the past month, I’ve slowly but surely transitioned from someone who uses the microsoft email system (outlook/entourage/exchange) to someone who uses Google’s Gmail.

I realize that I’m late to this trend, but I’ve been on this path for a long time. When Gmail launched, I opened an account and have been forwarding my email to Gmail since. Its a huge searchable archive that I rely on regularly to find things. I’ve also used Gmail occasionally when my outlook and entourage crash, as they do regularly (at least for me).

I’m one of those people who saves everything. My mail file is between 10gigs and 20gigs depending on how often I archive, empty stuff, and clean it up.

Many people have been telling me for some time that I need to move my mail to the cloud because a mail file as big as mine is not workable in a client/server model.

I had a brief flirtation with outlook running on parallels on my mac but that resulted in a nasty crash of my entire hard disk and regardless of whether it was parallels or something in OSX, that pushed me over the edge. While my new macbook was getting a new hard drive, I went back to my old macbook and used Gmail exclusively.

It’s taken me about a month but I’m pretty comfortable on Gmail now. I still find collapsing emails into conversations an issue at times, but I’ve also found it helpful at times. That was always my big hangup with Gmail.

There are two other things that have really helped me get comfortable with Gmail. The first is keyboard shortcuts. I never took the time to learn them before. I did this time and I now use Gmail mostly without a mouse. That rocks.

The second thing and the reason I am thinking a lot about cloud based messaging is offline Gmail. I use plane, train, and other “offline time” as a time to catch up on email. I hated the idea that I couldn’t do Gmail on a plane. With Google Gears installed, you can now use Gmail in offline mode. I’ve just finished four hours of catching up on email in the browser while being offline. It’s one of those experiences that changes the way you look at web apps.

Gmail caches your most recent mail (and attachments) so you can get a connected experience offline. I wish it would also cache the pages behind the links in my email.

I also wish Twitter’s web app would be available in offline mode. I would love to go back through my timeline for the past few days like I can now do with email and send replies and direct messages. And of course, I’d love to have the pages behind the links in twitter cached as well.

All of this is possible and I think its coming (don’t take my comments specifically about twitter, I haven’t even talked to them about this idea).

I spent some time this morning watching the Google Wave video. I had the same reaction to its UI that I’ve had with Gmail (and FriendFeed too). It looks complicated and cluttered.

But I love the way the messaging all happens in the cloud and its designed for many to many messaging. That’s what happens with the comment conversations in disqus that we have on this blog. We are emailing back and forth but the conversations are public and hosted in the cloud.

So there are some big trends here that I’ve been thinking about.

Web apps are gaining the ability to be functional offline. Which makes them work as mission critical messaging systems. And messages are being hosted in the cloud which creates the kind of scalability needed for a world in where we generate hundreds of messages a day to groups not individuals and want them archived forever.

Mobile is also a big part of this. For messaging, the triple play appears to be cloud based storage, a web app that can be used offline, and great mobile support. With Gmail offering native support of the native Blackberry mail app this summer, I’ll have my triple play. Just in tme to swap out Gmail for Wave!


Let's Play Some Games Today

I had some technical issues with this blog yesterday afternoon that got in the way of doing this as part of my post on our newest investment Heyzap.

So I figured we can do it today instead. I’ve selected a bunch of strategy games from the Heyzap collection and they are available via the widget below. Try it out and let me know what you think.

I’m thinking about making a Heyzap games widget a permanent fixture in the right sidebar and I’d like to hear your thoughts on that too as well as what kinds of games you might like me to include in it. – embed games

Reblog this post [with Zemanta]
#VC & Technology


Our firm, Union Square Ventures, just announced our most recent investment in a YCombinator backed startup called Heyzap.

Heyzap is a bet on the "deportalization" of casual games on the web. I wrote a post a while back about the deportalization of the web. And since then, we've only seen this trend grow. And we think there is no reason why game playing on the web will be any different than any other behavior on the web.

My partner Albert wrote a post on the Union Square Ventures blog about this investment and the reasons we made it. I hope you'll take the time to click on over and read it and let us know what you think.

#VC & Technology

Why Isn't Paypal More Successful?

I just bought a replacement part at an online store I've never shopped in before. I was dreading the checkout process since I have not committed my various credit cards to memory. But thankfully this store offered checkout with Paypal. I clicked on it, entered my paypal credentials, and was out of the store in less than a minute.

It was an awesome experience, as simple and easy as checking out at Amazon. 

And yet, Paypal has not really taken off among my friends and family as a way to pay for stuff online. The Gotham Gal doesn't like Paypal and avoids it at all costs. I find that most people I know feel the same way.

Why is that? Is it that Paypal works like a debit card and the money is taken out of your checking account immediately? Is it that the Paypal implementation used to be clunkier and most people have bad memories of failed checkouts? Is it that most people have committed their credit card info to memory and don't mind filling out the web forms? Or is it something else?

All I know is that when I see a checkout with Paypal option, I take it every time. And if everyone else did, Paypal would be so much bigger. But it's not. And that's worth thinking about. Because there is a very big opportunity to reinvent the way payments work and Paypal is front and center in that opportunity.

The Next Layer Of The Social Media Stack

Last week Seth Goldstein's company Social Media put on a social media bootcamp for marketers and he asked John Borthwick and I to start the day off with a panel discussion around social media.

During that discussion, we got to talking about what's next in social media. I suggested that the "next layer of the stack" will be services built on top of the primary social media channels. Here's a short video clip that captures the thought.

The next layer on the stack… from Social Media on Vimeo.

I read this weekend that there are over 11,000 registered third party apps built on top of Twitter. I suspect that there are a similar number (or more) for Facebook. As the primary social media channels (including blogs and blog comments) become fully open platforms, I believe we are going to see a host of interesting (and valuable) services get built. It's already happening.

You can see a few short clips from the panel discussion here.
#VC & Technology

Social Media - What Needs To Be In The Cloud?

Cloud I had an interesting email discussion yesterday with a friend. He suggested to me that media doesn't need to be in the cloud to create a great social media service. He said that the files can be stored locally and only the data needs to be in the cloud. I'm not so sure about that.

I've been scrobbling my music listening data to for a few years now (since Oct 2005 to be specific). So my data is in the cloud. But to be honest I don't get much social media value from that. 

The best experience I get from scrobbling my listening data is's neighbor radio which is a service that allows me to listen to a radio station programmed by my "musical neighbors". But it's really a solitary experience.

Compare that to what happens on Tumblr, for example. I post music on tumblr every day, one song a day. And I get feedback in the form of comments, likes, playcounts, and reblogs. I get to see what people think of the music I post. And I also get to see and listen to what other people are playing and listening to. I can do the same thing; comment, reblog, and like the music I find there.

The same is true of many other social music experiences out there; passing links to music tracks on twitter, listening at the hype machine, engaging at

So the question is if we can get a truly social experience with the files stored locally on our machines or networked storage devices and just our data in the cloud. Or do we need the media itself in the cloud?

My gut instinct is that we need both the media and the data in the cloud. They don't need to be in the same place or service however. I would love tumblr/listen (you have to be a tumblr user to use this service) to incorporate my scrobbling data to create a more personalized version, for example.

The primary reason I think we need the media in the cloud is that is the only way I know of to ensure that I can listen to the same thing you can listen to. If we continue to rely on file based media, then you might say you love I'm Turning Into You by Wheels On Fire but unless it's online (it is, right here), then I would not be able to listen to it and let you know what I think and more importantly share it with my friends. As an aside, I found this great song because I follow Luke on Tumblr and he posted it a few weeks ago.

The same issue is true of TV shows, films, photos, games, news, and other forms of media we consume both on the web and off of the web. If we continue to rely on files as the way we consume media, the social activities around our consumption will be muted. If we move to streaming all media in the cloud, we will see an explosion of consumption driven by social interaction.

There's clearly an issue of bandwidth versus storage costs in this whole equation and all things being equal it certainly would be better for media to be stored and consumed locally, but I think the power of social media and social interactions will change the balance in favor of cloud based media. What do you think?

Note: The photo in the upper right of this post is of Mt Shasta and was taken and posted to Flickr by SP8254.

The Disruption Talk

A few weeks ago this community helped me put together a talk on Disruption that I delivered at Google a week and a half ago. I've posted the slides twice (draft and final) and now the talk is live on YouTube. Here is it. I'd love to hear what people think. It's long, about 55 minutes.

#VC & Technology

Headed East

It's memorial day weekend and I'm headed out east with most of the family. We've had a house on the east end of long island for about a decade and we generally only use it from memorial day to labor day. But during the summer months, it's a great place to be.

This summer, we've got a new blog to keep everyone up to date on the happenings out east. It's called Curbed Hamptons and it launched yesterday. And there is also a twitter feed you can follow to keep up to date on the latest goings on out east.

Both come from the crack team at Curbed who also produce Curbed, Racked, Eater, and Gridskipper. In the spirit of full disclosure, The Gotham Gal is an investor and an advisor to Curbed and so we've got a vested interest in the success of all of these blogs. Check them out and let me know what you think.
#Blogging On The Road