30 Thoughts At 30,000 feet

I thought I’d try Jason Calacanis’ new favorite way of writing a blog post on for size. I am on a flight from NYC to Portland Oregon and my entourage email database crashed this morning so I don’t have an inbox to work on (except on my blackberry and that’s getting tiring). So here goes:

1)    Many people have emailed me, twittered me, called me, or simply asked me what I think of Google purchasing Jaiku. Frankly I don’t know what to think. My feeling has always been that startup companies should not waste too much time worrying about the M&A and financing activities of their competitors or perceived competitors. The enemy of most startups is their own internal issues. So my hope and advice is that Twitter keep their heads down, make the service more reliable, robust, and keep adding new addictive features like track and favorite.

2)    The needs of readers and publishers aren’t always aligned. When I read something like Techmeme, I want to “explode” a particular “meme” into a new web page with all the posts stacked up one after the other so I can read them all at once instead of clicking back and forth. This would be huge for readers but publishers won’t like it. The approach of showing the headline plus a small amount of text and forcing the reader to click thru is well developed on the web. Going further than that will annoy a lot of publishers. But not me. I’d be happy to get a lot more readers in return for giving up the ad impressions.

3)    Why do I continue to fly coach on cross country flights? I can afford to fly upfront but something keeps me from booking it. Dave Winer said yesterday that his parents are “decidedly middle class” and he agrees with them that a middle class mindset is best. I can’t claim to be “decidedly middle class” but my parents certainly are and some habits die hard if they die at all.

4)    I went from being a sports maniac two weeks ago to not caring a damn about baseball or football. That’s what happens when your teams blow up in your face.

5)    Ben Kweller may be the best singer songwriter of his generation. His new songs are so great and I say that only from hearing live versions on YouTube. His last record, Ben Kweller, was “sing along good” from start to finish. And he’s getting better and better. I think he’s only 23 or 24.

6)    After I write this post, I won’t have anything to write about for weeks.

7)    Alex Iskold is a freak of nature. He writes code, runs a company, and does amazing blog posts for Read Write Web that are better than most Gartner research reports. I’d ask how he finds the time to do all of that, but I know the answer. Full disclosure – Alex’ company, Adaptive Blue, is a Union Square Ventures portfolio company.

8)    Some Harry Potter movie is showing on the plane. I have never read a Harry Potter book and have no desire to do so. I saw a couple of the movies. Harry does nothing for me. Neither do Hermione or Ron or Dumbledore.

9)    I love the Virgin America ad campaign featuring high profile bloggers. One day I want to sit next to Peter Rojas on a cross country Virgin America flight and play with his gadgets all the way from coast to coast.

10)    What happened to Lauryn Hill? That girl got me to love hip hop and then she just disappeared. Remember when she was on the cover of Time Magazine right before her solo record came out?

11)    Looking forward to taking Josh on a road trip to London in November to see an Arsenal game and the Led Zeppelin reunion. Think I’ll make him a killer Led Zeppelin mix and give him Fever Pitch to read on the flight over.

12)    The new Hype Machine (in private beta) is amazing. Anthony Volodkin has his finger on the pulse of how to turn music blogging into a mainstream listening experience. I wish I could be listening to it now instead of iTunes.

13)    I’ve got iTunes on Party Shuffle and Loretta Lynn’s Portland Oregon just came up. How did iTunes know where I was headed? And Jack White and Loretta Lynn are a great combo.

14)    Has TechCrunch peaked? If Mike launched this wave of startup activity and innovation (as many give him credit for), then does TechCrunch peaking mean the whole thing is peaking?

15)    Why hasn’t anyone been able to aggregate all of my comment activity across the entire web and turn it into a feed that I can put into my lifestream on Tumblr? There are a bunch of companies working on it, but I don’t think anyone has nailed it yet. And I am not just talking about blog comments, I am talking about ratings and reviews on Amazon, Yelp, Menupages, Digg, etc, etc.

16)    I think Isaac Brock (Modest Mouse) looks like John Belushi and acts like him too.

17)    I’d like to see Kings Of Leon cover Paper Thin Walls and Modest Mouse cover Joe’s Head.

18)    I’ve been contacted by five reporters for major business publications in the past week all seeking to talk about “valuations being out of control”, “are we in a bubble again”, and “are you expecting a dowturn”. My instinct is yes on all three but the contrarian in me says it can’t be if everyone thinks so.

19)    A commenter to one of my posts last months said “you have to be consistent”. I reject that notion entirely. I am not consistent at all. I feel entirely comfortable being a raging capitalist in some circumstances and a raging socialist in other circumstances. I’d rather be right than consistent ☺

20)    I wish my children blogged. They all are good writers, with strong fundamentals, but they still struggle to communicate an idea easily and quickly. It takes them a lot longer to write a report or paper than it needs to. I think blogging, or keeping a diary, would be extremely helpful to them. The simple act of writing every day, even when you think have nothing to say, is essential to becoming a confident writer.

21)    The Gotham Gal and I could go to a fundraiser dinner every night of the week if we wanted to. Why do we feel necessary to throw these big bashes, spend all this money, in the name of charity? There has to be a better way. I’d probably give to twice as many causes if I didn’t also feel obligated to attend a function.

22)    Should the CEO of every technology company be a technologist? It seems like it’s easier to teach a technologist finance, marketing, sales, and management than it is to teach a good manager technology. And it seems that key business drivers are increasingly technical. It was true in the past, when Novell beat Banyan with marketing over technology, or when Oracle beat a host of relational database companies with sales over technology, that technology alone didn’t win the day. But let’s look at Facebook versus MySpace, Google versus Yahoo!, Skype versus Net2Phone, and Apple versus the entire music business. The companies with strong technologists as leaders seem to win more often these days.

23)    Has the WSJ announced if it will go free post the sale to News Corp? If so, I missed it. I am certain they’ll do it. It’s the right thing to do for the business and the readers. They’ll join the conversation after being out of it for way too long. It will be the first of many good things Murdoch will bring to the Journal.

24)    Feeling that it’s going to be Hillary versus Rudy for President in 2008. I know the primary season hasn’t even started and it’s way to early to call the race over. But it just seems so logical. Both parties need to move to the center, name recognition is everything these days, and we’ll finally get the race NY was supposed to have for Senator in 2000. If that happens, it’s going to be nasty. But I guess it always is in politics.

25)    I miss Warren Zevon.

26)    Someone wrote in the comments not too long ago, “all VCs do these days is blog about Facebook”. I figure that was aimed at me. I try not to blog about Facebook all the time. But it’s at the epicenter of a number of very interesting things going on right now. I need to think about Facebook a lot and I do that by writing about it. Same with YouTube in 2005/2006. I don’t blog much about YouTube anymore. I wonder if I’ll be blogging about Facebook in 2008.

27)    The best technology is magic. Someone tags a photo of me in Facebook and I am alerted in my mini-feed without even knowing the photo or the photographer. I mms a photo from my phone to Flickr and all my friends on Twitter are notified. I respond to a comment email on my phone and it appears as a reply in the comment thread on my blog. My friend Brad Feld uses the term automagically to talk about this kind of thing. That’s what I look for in technology, in my life, and in my business.

28)    Why do they have to tell you to turn off your laptop 30 minutes before you land. It’s a productivity killer of the highest order.

29)    I like breaking the rules so I’ll keep writing.

30)    Most of these 30 thoughts could have been twittered, probably all of them if I tried.