Posts from May 2007

I am going to start this post with a disclosure. We’ve known Jason Calacanis since 1995 and have been through a lot with him. The Gotham Gal was his partner in his first venture, Silicon Alley Reporter, in the late 90s. We, The Gotham Gal and me, are personal investors in Mahalo and have been since the start of the company.

So what is Mahalo? It’s a search engine, just like Google, except that the search engine result pages (serps) are built by humans not machines. This has been done before, in fact many times before (Magellan, Look Smart, etc, etc). It’s never been particularly successful. But Jason’s got a model to build serps really cheaply and in my experience with Jason over the years, I’ve come to realize that you can never ever count him out. He’s scrappy, tenacious, and usually successful.

Here a a few result pages. You’ll see immediately how and why it’s different than Google.

Search for iPhone


Search for Barack Obama


And of course, the obligatory search for your own name


You can see that the result pages look a bit more like wikipedia than they do Google. When Jason first described the idea to me, he said he was going to combine wikipedia, weblogs inc, and google. I think he’s done a pretty good job of executing on that basic concept.

Time will tell how popular Mahalo becomes. I think the result pages are a lot better than Google, but they only have about 5,000 result pages right now. If you search for a term that they don’t have done yet, you’ll get something that looks like this with google links below it.


I am frankly shocked that they didn’t do the shake shack in the first 5,000 terms. It would have been in my top ten!

And the name, well I am not going to say much about that other than I can never remember how to spell it but hopefully I am in the minority on that.

I am rooting for Jason on multiple levels. First, he’s a friend of ours. Second, we are investors. And third, I think there has not been much innovation in search in a long time. Google’s dominance of the category has made it an area many of the best entrepreneurs avoid. Thankfully Jason’s the kind of person who is always looking for a challenge and he’s certainly found one in Mahalo.

#VC & Technology

Sony Gets Behind HD Radio


Great news for the radio industry and its efforts to make HD Radio the
new standard in audio broadcasting. Sony has announced that it will be
shipping a bunch of HD Radios this year. The first model out the chute,
in July, is this table top radio, which will retail for $200. You can pre-order one here.

To quote Mick Jagger:

My Favorite Flavor, Cherry Red

Gizmodo has the whole story.

I’ve said before on this blog that this is the year HD technology starts to show up in many of the new radios and this news from Sony certainly points in that direction.

Full Disclosure for those that don’t already know – I’ve been an
investor in and director of iBiquity since 1999. iBiquity is the
developer and licensor of HD Radio.

#VC & Technology

CBS Buys

I just did a search on my blog for the term "". I’ve used that term so many times that there are 16 pages of search results and that’s just for my blog posts. Clearly I’ve been obsessed by this service from the day I started using it in the fall of 2005.

And there are so many reasons why. First, was the first streaming audio service on the web that wasn’t traditional internet radio that really grabbed me. When I first starting playing neighbor radio, I couldn’t believe how good it was. The concept is simple. If you knew all your musical neighbors and could listen to a stream of music that they are listening to right now, you’d have an amazing radio station. The people who have musical tastes closest to you are in effect the DJs. I’ve listened to my neighbor radio at least once a week for the past 18 months and never get sick of it. When I turned it on this morning, the first song was Very Loud by the Shout Out Louds. I love that song and have never ever heard it on traditional radio.

But there’s more. was the first service that allowed me to spy on myself, to actually tell me what I was listening to. Here’s the list of the artists I’ve listened to the most since I started using in the fall of 2005. Here’s what I’ve been listening to this week. Data like that was never available to me (and all of you) before

And there’s the social networking that’s available on I’ve met new people, been turned onto new artists, and heard about shows to go see on The filter is the music we love and that’s a pretty great filter.

So I am writing all of this as a prelude to talking about the news that CBS has purchased for a reported $280mm. That’s a big number but I think it will go down as a smart buy. I think streaming audio is fast becoming the best way to listen to music over the internet. A year ago, file based music (meaning iTunes) was at least 2/3 of my listening activity. Today, it’s about 1/3 and going down. I use the following streaming audio services for the majority of my listening; rhapsody,, hypemachine, blogs, and streampad. I know that I am out there on the edge and that most people still play mp3s on their iPods and laptops.

But I bet that’s going to change over time. Because all the music you want to listen is available for streaming over the net. You just have to find it. And helps you find it with services like neighbor radio and similar artist radio. Radio can be monetized whereas files are free, at least to most of the youth generation. And that’s just not going to change.

We’ve already made one bet on this trend with our investment (with CBS coincidentally) in TargetSpot. TargetSpot was built to monetize streaming audio, meaning traditional radio streamed over the Internet and new forms of radio like and the others I mentioned.

That’s where the $280 million purchase price comes in. That’s a bet that more and more people will start discovering and listening to music over the Internet. And it’s a bet that those page views and streams can be monetized. I think they can and they will. So I think it’s a smart bet that will take some time to pay off. But like MySpace, this buy may look very cheap in a couple years.

I’ll finish with the playlist that I heard on Neighbor Radio while I was writing this post:

Very Loud – Shout Out Louds:
The Boy With The Thorn In His Side – The Smiths
Looking At The World From The Bottom Of  A Well – Mike Doughty
A Shot In The Arm – Wilco

You can’t get that on traditional radio. I can’t even do that well programming my own iPod. I love and I am really happy that it found a great home at CBS.

#VC & Technology

Where Tags and Blogmaps

Steven Johnson, founder and CEO of did the closing keynote for the first day of Where 2.0 yesterday evening. He started by talking about cholera and his book on the subject called The Ghost Map.

From cholera and Doctor John Snow’s map that ultimately solved the mystery of the disease, Steven moved on to placeblogging, geotagging, and maps, suggesting that by mapping blog posts, we can learn so much about life and the neighborhoods we live in, which is the mission of

Steven touched on some new stuff that is coming like extensible where tags and the ability to automatically capture the posting activities of part time placebloggers like me. The details on all that will be available from in a couple weeks.

He then went on to show some cool new things like blogmaps that showcase the places a given blogger has written about (but also showcases all the other bloggers who are writing about that place). Here is the blogmap for The Gotham Gal. Using the blogmap (which will soon become a widget) you can navigate across a city from place to place and placeblog to placeblog.

Steven also showcased a very cool time-based blogmap of downtown brooklyn that shows how the blog conversation has changed over time. I’ll add a link to that as soon as it goes up on the site this morning.

I am biased for sure, because Union Square Ventures is an investor in and I am on the board, but I found the keynote inspiring on many levels. I believe in the social media/citizen journalism revolution and I think that local bloggers can and will replace local newspapers as the dominant form of local media in the next decade. And hopefully the vision that Steven outlined today will help lead the way.

#VC & Technology

A Few Random Items

1) Steven Wright on Twitter is not Steven Wright. He is a Twitter user named Rex. He also does a Condi page on Twitter. Gotta love that. I just subscribed.

2) I’ve now added the Flickr and Delicious Facebook apps to my profile. They were not written by Flickr and Delicious. Both were written by a high school freshman named Steven Bao. Jake Jarvis and Steven Bao are high school freshman who are living examples of the open web ecosystem. Got to find out if there are child labor laws preventing venture deals with fifteen year olds.

3) Facebook third party apps aren’t the same as Facebook first party apps. Why don’t my Flickr photos show up in my friends mini-feed?  Why can’t I make my Twitter message be my Facebook status message? That’s gotta come next.

#VC & Technology

Getting On The Inside of

Steven Johnson, founder and CEO of wrote a post last night titled "A Call For Help" in which he talks about the challenges of being an author and a founder at the same time. I knew Steven was going to need some help building when we funded the company earlier this year. We talked about how and when to start recruiting a business team and I suggested he do what we’ve done very successfully – blog about it.

So now that Steven’s outlined what he’s looking for (a COO, someone to bring in revenue, and someone to bring in deals), I suggest anyone who would like to be on the inside of drop Steven a line. His email is on the post I linked to.

I suspect you’ll be hearing a bit more about on this blog this week. I am at Where 2.0 and location based services are on my mind.

#VC & Technology

What Trumps Email?

Eventually every technology is trumped by something new and better. And I feel that email is ready to be trumped. But by what?

We all know the limitations of email. It has no native permissioning system so its susceptible to spam and near-spam. Email has become a burden to so many people that more and more are seeking an alternative.

And there are no shortage of alternatives; text messaging, instant messaging, and site messaging for one to one messaging. And blogging, twitttering, and social networking for one to many messaging.

I have heard from readers that email is considered ‘serious messaging’ and worthy of a reply before less serious activities like blogging, twittering, and social networking.

I reject that notion because I cannot reply to every email I get but I can alert whomever is interested via a blog post or twitter message that I’ll be in San Jose for the next two days. That’s going to lead to four or five impromptu meetings, several of which are with people who have found it impossible to reach me via email.

I find myself text messaging more and more every day. It has replaced email as the dominant form of communication in my family. We all carry phones with us and texting gets an immediate or near immediate response while an email sits in my daughter’s AOL account along with dozens of spam emails she has no desire to wade through.

I’ve said it before on this blog. Spam has ruined email for the youth generation. They may adopt email at some point when they reach the workforce, but it will never be the messaging system of choice for them.

Site messaging (particularly in social networks) is incredibly popular among the younger crowd. The permissioning system is their social network and so they value the messages they get. They’ve been filtered. There’s no porn spam on facebook.

Instant messaging remains a popular option and at times its useful. But real time communication has its limits. It demands your attention and I think anything that demands permanent attention is suboptimal in this technology driven partial attention world we live in.

Blogging is a lot like social networking but without the permissioning filter of the social network. It’s useful and as many readers have found, one of the best ways to reach me is via a well articulated comment on this blog. Those rarely go unanswered. Funny enough the messaging system I prefer for those replies is email.

Email still has some big advantages. It does not demand real time attention. You can embed attachments and rich graphics in email. You can write long messages (although I would argue the 140 charachter limit of texting is an advantage as much as a disadvantage).

Maybe no single technology trumps email. Maybe its a collection of technolgies like texting, site messaging, and twittering that together provide a better alternative.

Will our lives be better without email? Hard to say. My life is so much richer because I can ‘touch’ hundreds of people a day via internet messaging (ie email). But it’s also a burden. No pain, no gain I suppose. But I am sure hoping whatever trumps email allows me to touch even more people with less pain. And I see hopeful signs that might just be happening.

#VC & Technology

What If You Aren't (yet) My Friend

I suggested in a blog post yesterday that you could read this blog in Facebook. Well I missed a big point with that suggestion.

You can read this blog in Facebook if you are my friend in Facebook, but not if you aren’t.

I’ve taken the approach with Facebook (and LinkedIn) of only accepting friend requests from people I actually know.

But there are tens of thousands of readers of this blog who are people I want to have a relationship with but aren’t technically my friends.

I’ve said this before on this blog. We need a second kind of relationship in social networks.I want people to see my profile who aren’t actually friends.

Maybe fans followers? Or something else?

#VC & Technology