The role of a Product Manager varies company to company so greatly, especially in an early stage startup, that anyone applying for PM jobs still has to ask, "So what will I be doing?"  It's not like being the left fielder for the Mets where you can pretty much narrow it down to, "We'd like you to hit, field, and run the bases."

In some companies, you're not so much a Product Manager as you are a Project Manager.  Features and ideas come from business, marketing, or upper level management and you're just the translater of functional specs to tech speak, checking boxes in MS Project as things get done. This is a helpful coordination function as a product is being built but often has limited usefulness once something is up and running.  At that point, you might see folks from the business side take over the running of the product and its direction.

Other times, the PM is shaping core strategy and really living and breathing all aspects of a product, not just coordinating, but inspiring and collaborating with Engineering, Design, Marketing, Business, etc.  They're the ones that let the CEO go to sleep with a clear head because PMs dream of their products.

The interesting question is trying to figure out what, if any, kind of PM your company needs and at what stage.   Some would argue that you need a distinct Product function as soon as you start building, not only to be the eyes and ears of the Engineering side. Sometimes, swimming in the open water of deep code, the tech team might not poke their heads up often enough to make sure they're not swimming to Jersey.  (As a swim support volunteer in kayaking for Manhattan circumnavigations, I can attest firsthand that this is very important.)  Also, it may be important to have a PM insolate and shield the product from the pull of business demands.  It's important to insure that your scaleable product business doesn't turn into a custom development shop with the addition of every new business development partner.

What has often surprised me is how often engineers seek out someone in a pure product role.  I would have thought that the people doing the building would naturally want to lead the direction of a product, but that's not always the case.  Sometimes, engineers become PMs, but its a difficult thing to do both sides at once.

That often happens in startups, and I believe it is to the detriment of the end product.  You can do all the user testing you want, but its important to have a fresh perspective on a product, especially when it comes to interpreting user feedback.

So what should the background of a good product manager be? 

First of all, you need to have extraordinary communications skills.  You not only need to coordinate a lot of different areas, but you need to make sure everyone feels like their feedback is important and you need to be able to synthesize a lot of different needs and goals.  After all, listening is half of communication. 

I think the next most important thing is empathy.  You need to have a feel for what users want to do with your product and how they want to interact with it, even if you yourself don't necessarily represent that demographic.  A lot of this comes with knowing a lot of different types of people pretty deeply and being genuinely curious about the human condition and how people operate.... being aware of lots of other "selves".

Breadth is important, too.  You need to know a little bit about a hell of a lot of things...kinda like a utility infielder.  (For the record, on my softball teams, I've played leftfield, center, short, third, first and pitched  and that's only in six games so far.)

Attention to detail is important, too, but not necessarily in the way you might think.  Products change and no one gets every last detail right the first time, but I think it's more important to be deep in your work and not just comprehensive.  So, if you're creating a suite of tools, one damn good one is better than five so-so ones.  That will at least hook some users who will anxiously await the development of the other tools.

Is it fun?  Sure...but I have to say that one of the most difficult things is not just being able to sit back and be a run of the mill passionate user, because you're too busy bug fixing, speccing the next feature and thinking about marketing to participate as much as you'd like to in the community of users.

From the Washington Post... (Thanks MJP...)

There is now a Meebo Room in this post...   Click through on RSS to check it out...

Ok...  I took it off b/c it kept autoplaying the videos...

Now that Twitter has been spun off into its own company, and the team there is hustling to keep up with scaling, you gotta figure we'll here a funding announcement sometime soon.  It's not like Twitter is free to run.  All these SMSs are costing the company money everyday.

First off, who are the likely VCs... or rather.. where would the money come from?  Sometimes, when deals are this hot, you almost expect them to take money from some completely unexpected source.  I could see all these bigshot Valley VCs marching in trying to throw endless amounts of money at the company at ridiculous valuations (you know, because of that big hockey stick) and I imagine that's probably somewhat of a turnoff.  (Hopefully anyway.)   I wouldn't be surprised if you see a big band of angels get together and pony up a million dollars to solve scaling issues and get this thing scalable.... and if that's the case, Calcanis would be all over it.  As it is, he wants to pay for a premium level of the service.  Plus, given is "Entreprenuer in Action" role at Sequoia, whatever that means, he certainly has a connection to deeper coffers if they so desire.  Sequoia would also be a prime candidate because of the Google funding, and Google bought Evan William's first big success, Blogger, so I'm sure there are probably some connections there. 

Ok, so once the money gets raised, what are the likely things that Twitter goes off and becomes?

From Hannah the Instigator...

Instead of tagging something "readlater" in del.icio.us, a tag you're not likely to ever go back to again and without a way to check if you actually read it, tag it "for:" yourself.  This way, when you tag stuff for:yourscreename", it sits in your "for" inbox until you actually click on it to read it.   

Tara wrote a post about trust yesterday that struck me.   I've been doing a lot of thinking lately about what social means and should mean in terms of technology, especially as our social technology starts to make its way into the more private areas of our lives, like our finances.  Do Web 2.0 philosophies hold up in the design of social software for the most important parts of our mainstream lives?  I am sensing from my non-techy friends a kind of Web 2.0 backlash against all the openness and sharing, and while I still believe that open is better, I believe that when, where, and how are key questions that Web 2.0 has yet to flush out in order to start moving away from the bleeding edge.

So, back to Tara's post.  She wrote the following statement:

"The Open Source world needs to make the assumption that people are, basically, good in order to succeed."

I disagree and don't think that's how it actually works.  People aren't actually good.  They're self interested. 

However, it is generally in your own self interest to be a good person most of the time, because then other people will be good back to you and then you also don't have to deal with the penalties for being an asshole (poor reputation, retaliation from others, alienation, prison, perhaps...).   

That's a key difference, especially when it comes to the design of social software.  Take seller ratings, for example.  I bought some nice pieces from Bethany Cooper the other day.  Do I trust her?  Not particularly.  I don't know her.  Although, if I had to make a bet, unless she's an idiot, if she's interested in succeeding in such a public platform, she's probably not in the business of screwing people over on a regular basis.  So, she's probably good, but since I don't have any reason to trust her, I'll make my judgment based on the 1200 positive experiences that people have had with her according to her seller rating... which amounts to 100%.  In this case, while people are likely to be good, technology doesn't force us to depend on trust.

She could still, however, steal candy from babies in her spare time, so there's also context around trust.  I may not trust her to drive my car, but I trust her to send me some beautiful handmade stuff on time.   

Open source works the same way.  Are people involved in the open source community generally good people?  Maybe, but not always.  Are they contributing to the open source community out of selflessness or some interest in the greater good of humanity?  Maybe, but not necessarily.  In fact, many open source contributors are writing code that solves their own problems.  At that point, giving that code back, so that others might improve on it and also share code with them in the future is of greater value to them than hoarding code and not sharing.  Sounds "good" but what's really going on is that they've recognized that they're simply better off, from a utility standpoint, sharing.

It's the Prisoner's Dilemma. Two prisoners are being interrogated separately and if they squeal on each other, they have a better outcome than if only one of them squeals.  However, if they both keep their mouth's shut, they both get off easy.  Without communication and information on what the other person has done before, it isn't likely that these two will cooperate, but if you repeat the experiment a number of times, eventually, they'll learn that the better outcome is to work together.  Is that trust, or just two people maximizing utility in a world of free communication and discoverable information?

Trust has nothing to do with it.  It's about incentive, reputation, and access to information.  Don't ask me to trust you... give me the tools for you to figure out whether I'm trustworthy... or tell me some friends we have in common.

That's why, for example, when social applications like Facebook and Vox were built, they focused on privacy... making sure that the right people saw the right information about you.  Privacy is going to be a huge factor in the mainstreamification of Web 2.0, especially in the current culture of fear that's being spread.

Trust me.

Fred and I had an interesting e-mail exchange the other day about his theory that "Every web service should be social."   

I hesitated to go that far, mostly because I'm feeling a little personal backlash against the idea of every service being explicitly social.

Take WebMD, for example.  Maybe one day, I'll be able to login to WebMD and get all my personal medical history there, but for now, its a good place to get questions answered like, "What is this purple growth on my pinky toe?" 

That's not exactly the kind of question I want to broadcast to a group, nor do I want an armchair diagnosis from Louise from Chattenooga.  I also don't want to be friends with other people with purple growths on their pinky toes.  In fact, if WebMD were suddenly morphed into a more explicit social sharing community about health, I actually might be less inclined to use it and so would others, because its not necessarily the kind of think the mainstream is comfortable being social about.

However, that doesn't mean the fact that 34% of all 27 year old males in Bay Ridge have this issue isn't useful to me.   "People like you...", a concept Amazon pioneered and really nailed, is indeed a very powerful social feature.  But, if you asked most people, you wouldn't normally think of Amazon as a "social" web service.

Would Amazon be even better if they became a social network and aggregated all my reviews, purchases, etc. into profiles?  Can I have Amazon friends?   Clearly, not every user would necessarily want their Amazon purchases so prominently displayed, but giving people the option to publish a public profile could be an interesting move for them.

So, what I'm saying is...   aggregated social data can be a fantastic addition to a site, but making the core of your service to be explicitly social may not be.  It goes back to the idea that a service needs to work if you're the only user and you don't care about the community.  del.icio.us worked at one user in a way that Digg never would. 

Allowing users to commune...  that can also be an added feature, but it's important to make sure that it doesn't alienate users who aren't interested.   There are many people who don't want their web experience to be social.   They see the web as convenient, easy, on demand, but social isn't necessarily want out of their web, even if us designers and product managers and VC think that makes the web universally better.

Social doesn't always mean friends and a public profile... it can mean data aggregation, design, filtering...   and be careful about alienating the people who want to just buy their Slurpee without having to tell the guy at the 7-11 counter about their kids and where they're from. 

Fred Wilson asks what the "Anti VC" is...

Videohybrid has a copy of Spiderman 3 that you can watch right now.

I tried to sit down and watch it the other day, and about 3 minutes into it, I stopped.  I was bored.

It wasn't the movie.  It was the experience.  I really like going to the movies.  I like going with my friends.  I like the huge screen and the Snow Caps and previews, man do I love the previews.  I could seriously just watch two hours of nothing but previews... all the best parts of upcoming movies.  Fantastic.   All in all, despite increases in price, I still think paying the twelve bucks or whatever it is to go to the movies is totally worth it and one of the best values you can get for your money.  Bowling (at least in NYC) is more expensive, and so is pool.  You can't really drink for that kinda money for two hours...   not much you can do for six bucks an hour, really.

And that's really what it comes down to.  Provide a great experience, and people will pay for it.  If content owners spent nearly as much time trying to create a great user experience at a fair price as they did trying to police content, they wouldn't see declining revenues.   

I might watch Casino Royale on the web, b/c I've seen it already, but that doesn't mean I'm not still going to buy the DVD.  (Tried to once already... sold out at Best Buy.) 

Finally, I'm a product manager with a product. 

Voki is now public...brought to a level by which it can only improve through actual usage by real consumers.

What's personally interesting for me is that I thought that this would be the kind of milemarker that I would sit back on and take a breadth...carefully watch what people do with it, put the specs aside and listen to the market, talk it up.

Well, yes, I need to do all of those things, but there's no breather here.  Launching a product is not the end of a phase, it's really just the beginning.  All of those endless debates about what's more intuitive, what should a screen be called, where should a button be placed... now they become issues for potentially thousands of people in a very real way. 

Thought you were knee deep in it now?  Try being a sewer worker during the Superbowl when everyone flushes at the same time.  Such is the responsibility that comes with being a product guy. 

Still, though, it's important to recognize the hard work that got Voki to this point.  It would not have been possible without a lot of hours from Oddcast's creative and technical staffs, none of whom were completely relieved from various day to day fires that need to be put out related to other products throughout the company.  Still, they found time to make a new product happen.

Over the next few days, I'll be detailing some of the thoughts and decisions and "todo's" related to the product and I'm excited to be able to give an insider's perspective into the process of product management.   It will be fun to talk about a product that is out there and one that hopefully iterates and innovates over time.   If we're doing out job right, it will be obvious that we're listening to our community and working hard to make Voki more useful, easier, and yes, more fun. 

But right now I need a favor...  from every last one of you.

I'd really like you all to be a part of this...  check that...  I really need you all to be a part of this.  If you've been reading this blog for a while, or if you just recently joined, and you've ever got any value out of it, I'm glad.  I've never really asked for anything in return, but today I will.

You see, I really believe that the best products are made better by passionate users, and so, right now, that's what I need...users.   But don't use come in, poke it once, and leave.  Really use it and tell me what you think.

Here's what I'm looking for:

1. Register for an account.
2. Go to My Voki.
3. Click "Create a new Voki" and, well, create a new Voki.
4. Send it to a handful of people by clicking "Voki for others" and select that scene that you just created (or a completely new one).  Send it to me, too, if you want.  And don't just send a boring "Hey, check this out e-mail."   Send something cool.  Something funny.  Be creative, angry, sexy, moronic, obnoxious, sweet, sincere, alluring...  whatever you want.  Talk about what you're really passionate about.  Tell others about the war, or net neutrality, or about Paris Hilton's arrest.  If it's really good, we'll post it as a "Featured User".
5. If you have a blog or a MySpace profile or anywhere else you keep widgets, post it, even if only for a few days to see what people think... and to see what you think of being able to change your Voki's look and message on the fly.

Asking a lot?  Maybe...   but you have to understand, Voki is something I really want to be fantastic.  I don't want a lot of users because I want to go sit on a panel somewhere... I want a lot of users because I want to be able to say that I helped build something that people use... that when it's my birthday, I get to hear the voices of my readers because they're sending me Voki.... when I happen upon your blog, you're telling me what you're up to for the day, or just greeting me.

But I can't do that unless it's good, and I can't do that without the feedback of users.  So, try it out, stick with it for a little bit, and tell me what you think.   E-mail me at charlie@oddcast.com.  Don't pull punches either.  Tell me exactly what you think and I'll be posting the feedback right here and what we're doing about it.  It will be an interesting exercise in transparency and honesty.

So thanks for helping me out... thanks for reading... and seriously, sincerely, I look forward to hearing your voice soon, on a Voki.   Because, and I've said this before, it's not really about the avatar or virtual worlds, or being like Second Life or anything like that... It's a voice app, and voice is emotional.  I think of Voki as a creative skin for your voice and I believe in voice on the web.  We spend a lot of time by ourselves in silence on the web... often times glossing over the idea that there's a real person on the other side of the IP address.  Voice is a reminder, to me, of the human side of the web... and even with a little animated fish in front of it that lipsyncs for you, it can be a very powerful thing.

And while you're at it, RSS people, click through to my blog to see the first public Voki in my sidebar.  Go ahead and comment on it!  (It will take a second or two to appear... )  Play ball!

Because I'm interested in the research and I'm an admitted fanboyd...

[x ] Yes, and you *must* use my real name.
[ ] Yes, but please use a pseudonym and don't use any identifying information.
[ ] No, please just use this for your own weird thoughts.

1. Why do you use Twitter? What do you like/dislike about it?

I use Twitter to keep up with what a particular social group is up to after work...  Only my tech friends really use it, and so I use it to make my city smaller...increasing the "random" run-ins and stop bys.

2. Who do you think is reading your Tweets? Is this the audience you want? Why/why not? Tell me anything you think of relating to the audience for your Tweets.

I don't understand why many of the people who are subscribed to them are.  Seems like a lot of the people don't really know me, so I'm not sure why they would care when I go play softball or what bars I'm at.  At least when strangers read my blog, they might gleen some interesting technology info or something...  but my twitters are the day to day minutia of my life...  Sometimes, I'm not even interested in them.

I'd love for some of my non tech friends to be on it...  and maybe I'll clue them in, but I don't think you'd really "get it" if you weren't blogging or reading blogs and understanding the value and potential of this kind of openness.

3. How do you read others' Tweets? Do you read all of them? Who do you read/not read and why? Do you know them all?

I read on the phone, but have it set to not buzz during certain hours of the day, like when I'm sleeping.  I do not read all of them...  just the people I'm likely to bump into and a few extras who I happen to find really amusing or interesting.   I know all of the people I read at least digitally... not necessarily in person.

4. What content do you think is appropriate for a Tweet? What is inappropriate? Have you ever found yourself wanting to Tweet and then deciding against it? Why?

I don't know why people have public casual conversations over Twitter... the kind that others aren't likely to be interested in.... I mean, I know why the do, I just wish I could filter it out.  I've never bagged a Tweet.

5. Are your Tweets public? Why/why not? How do you feel about people you don't know coming across them? What about people you do know?

My Tweets are public and I'm fine with it.  To people I don't know, they might seem irrelevent, but certainly not something someone would judge me on in a way that I care about.

6. What do i need to know about why Twitter is/is not working for you or your friends?

Twitter needs better group and notification management tools.  I want to be able to get different messages across both phone and IM at the same time, or at different times.  Basically, I need a calendar that allows me to turn on/off independently of each other what my notifications are with a schedule.  Also, I would like to be able to bundle/group people with this same level of control.

I'm not much of a traveller, I'll admit that.  I can count the number of times I've been out of the country on one hand, and one of those times was Canada, so I'm not entirely sure that counts.  (Just a little good clean Canadian humor, eh... just kidding around.)

So, when the idea of a cross country road trip was proposed to me, I jumped at the idea.  Ok, so actually, I thought about it carefully, and created several maps and spreadsheets on it, but the jumping was there in spirit.

But, actually, the whole planning thing was not only a logistical pain in the butt, but I thought of lots of opportunities for web app to help me out.

So first off, here's the trip:  (PS... All these yellow markets aren't necessarily real stops... sometimes, I just had to make sure Google Maps put me on the right road so I had to enter somewhere random to force it.)

And here's a link to the real map...   

And then to our calendar.    It's quite ambitious...  and no, I'm not driving the 'Stang.  No interest in putting 4900 miles on it.  That's what rental cars are for.  Plus, we're only driving one way.

But what I really wanted was a great integration of a map and a calendar, one that took into consideration driving times.   On top of that, I wanted to layer on events and hotels... ones that took into consideration the time I was going to be there.  For example, by random chance, I stumbled upon a fair in St. Louis going on right around July 4th when I'm going to be there.  Also, it was a pretty manual process to match my driving and my calendar with the various baseball games that I wanted to see, because teams aren't always in town when you are.

Not only that, the group collaboration around this trip was very manual... mostly with passing links back and forth.   I wanted to give my co-pilot the opportunity to comment on various parts of the trip.   Plus, the collected wisdom of others came in handy.  We got advice from others to make sure we hit the South Dakota Badlands and exactly what time to hit them.  Now we know that, but what about others making that same trip.

So what I'm looking for is a Google Maps, Gcal, Travelocity, Yelp, Gchat, Wiki, Blogs, Flickr mashup for roadtrips.   That doesn't seem like it would be that hard to do.  :)

I just saw a great ad on Shockwave.com with a limp joystick asking "Is spyware affecting your performance?"   Hilarious.  Nice job whoever did it for McAfee.

And I'd love to have reposted that ad on this blog... and I suppose get paid for it.. but regardless, why should video be the only form of viral advertising.  Every single ad element out there should be sharable.  Where's the embed code for this ad?  Even if you don't build in a way to pay me, people don't get paid to pass YouTube videos around (for the most part) yet either...  so why shouldn't you be making banner ads that are just as entertaining and just as worth playing?

Now that I'm back on my Treo 650, I long for the days of Windows Mobile, wide, slide-out keyboards, and ActiveSync.   I miss my PPC-6700.  :(

But alas, there is hope.  A slimmer new model is on the way...   and I want it.

The problem is, no one at Sprint seems to know when it is coming out.  All the bloggers seem to know that it's in May, and someone even went as far as to say May 14th.  So why can't the telesales people pre-order it for me right now?  Heck, they could even charge my card now?  I just want it.

With a couple thousand blog readers and an upcoming trip across the country, I think I'm a prime candidate to be at the top of the list of people Sprint wants this phone in the hands of, no? 

So why is getting this thing so hard and why are the people trying to sell it so poorly informed.

Last year, the PPC-6700 was released to business users before the general public.  Perhaps the same thing will happen this year? 

I want my 6800!!

Hell, I'll even sign a two year contract to get it.

With Microsoft now rumored to be buying 24/7 Real Media, the arms race is at full throttle.  For nextNYer's, the question of "Where will I be working in five years if I want to work in online advertising?" becomes more interesting everyday. 

I'm sure these topics will be covered at the Future of Online Advertising conference, but if you don't have a $995 to drop and you're looking for something a little more conversational, check out nextMadisonAve, next Wednesday, May 9th, at 6:30PM (22 West 27th Street Bet. Broadway/6th - 6th Floor).

nextNY's "Community Conversations" are done in the round (or rectangle, if we're in a conference room) and are an open forum for discussion for the up and coming members of NYC's digital media and technology market.  We invite prominent thought leaders to help lead the conversation, but they're very participatory.

So, if you want to meet with other digital media entreprenuers and professionals to talk about where the advertising and technology market is converging (other than in investment banker wallets) please join us! RSVP Required on our wiki (just click edit and add your name).

Also, if you know of anyone you think would make a great conversation leader for this event, we have some outstanding invites, but I think we'll have an additional slot or two open.  Please let me know at charlie.odonnell@gmail.com.

When you're talking passionately about a product or service, it's interesting to consider the power dynamic of you and your audience.  Where you respectively sit in terms of the "haves" and "have nots" can go a long way to how your audience perceives you.

Think about the following scenarios:

You're talking to someone about your business who isn't in your field and has no experience with it. 

They either don't understand your product or don't try to understand it, and the exchange is dismissed.  When they don't understand your market, you dismiss their confused reaction.  "You wouldn't understand the problem because you're not our target audience."  You forget that the laws of logic apply universally and so, even to someone who isn't familiar with your field, you should always attempt to speak with sound logic even to outsiders.  Not everyone needs to find your service useful, but they should at least understand why someone else would.

You're talking with peers

This is the blogosphere.  You're talking to others who totally get your space and see the world from the same perspective.  Your passion is admired and even contagious.  The feedback you get from peers encourages you to  keep walking the walk and talking the talk...   and you quickly forget that not everyone drinks the same Kool Aid that you do.  Getting unbiased perspective here is incredibly difficult.

You're talking with someone who needs something from you

This is what happens when you're a VC.

So last night, I had a late meeting and I wound up in Union Square at 10PM having not quite eaten yet.  I really don't like eating alone and so I figured I'd just give Twitter a shot.

Me: Anyone hungry near union sq?

Avi Karnani, two minutes later:  I'm walking back from the office, through union sq right now actually, looking for food.

The most bizzare thing is that its the second time that Avi and I have met up this way... and it's the only two times we've met.  We meant to try to connect at SXSW and it didn't happen... but not too long after, I twittered that I was going to a nextNY bar outing and he just happened to be in the area.  I bumped into him in the bar, only to find out later that it was my Twitter that brought him there.

I think the key to Twitter's geolocation capability is the broadcast model and its simplicity.  I didn't need to have GPS going or post cross streets or anything... and Avi didn't need to identify his location either.  Twitter doesn't know the difference between "union sq" and "peanut butter" but an actual human in NYC clearly knew where I was.

Twitter still needs to figure out group features and ways to market this to localized groups of people, which this works best for, but b/c I'm lucky enough to have lots of techy friends using it in the same area, I'm finding it very useful.

Andrew made this based on #5 of the Web 2.0 Sucks List...  Hilarious!  I love LolCats.

If you're looking to meet up with other up and comers in the NYC digital media and tech scene, drop by Coppersmith's after work this Friday.   

April 27th… Coppersmith’s 6PM-9PM

793 9th Avenue (bet 52nd/53rd).

Tell us to look for you by RSVPing here.

1. The finger pointing culture of fear will always dominate a culture of openness.  Media thrives on taking people down and creating a general fear of the worst possible outcome.  Whether it's trying enact anti-MySpace laws or firing everyone who says a dirty word or two, until we hold our noses and fully embrace freedom of expression in this country, we're going to hold back the real potential of the internet as a medium of conversation and open exchange.  Everyone will be too scared to publish anything thought provoking for fear of being stoned by glass house dwellers.
   
2. The thinking, not just the building, has gotten small and lightweight...  Too many people building  features, not applications, or, gasp, companies.  People are confusing design with innovation.  Just because you add AJAX and rounded boxes to something does mean you have innovated.
3. Web 2.0 hasn't even come close to breaking open the carrier choked mobile world.  E-mail and WAP?  That's what I'm paying unlimited data for?  Come on.  We can do better than this.
4. Web 2.0 is a conversational vacuum. I'll prove it.  Unless you live in the Valley, walk outside your door and try to find a Twitter user... You've got six hours.  Go.  Trust me, we're talking to ourselves.  (Don't get me wrong...  I really like Twitter...  We just need to remind ourselves about how close to the edge we all are out here.)
5. Spelling and grammr (beta)  have gone to hell in a handbasket.  I'm in ur domainz, droppin' ur vowelz.
6. M&A Wack-a-mole stopping innovation in its tracks...  Dodgeball, del.icio.us, MyBlogLog...   Some of the most innovative startups have been swallowed into the black holes of big companies, abruptly halting their innovation paths.  Unless we get some more robust business models, some more risk seeking entrepreneurs,  maybe a real IPO market, most of Web 2.0 is going to wind up becoming the corporate walking dead of long forgotten or poorly understood acquisitions.  Consumers suffer when entrepreneurs won't make a go of it on their own and make a bigger impact on their online experience.  (Pleasant exceptions being the  Office-like apps at Google...)
7. Content licensing is still a bottleneck.  Web 2.0 is all about people and sharing, two things that music and video content owners don't seem to be big fans of.  For now, much of what we share is illegal or user generated.  Freely shareable stuff probably makes up about 2% of the millions of hours of content ever created professionally.  I'd like to blog a clip from the A-Team...  Not only can I not access it easily, I can't clip it easily, and I sure as hell can't publish it legally.   Yet, no one current monetizes it on the web, so it just sits and collects digital dust.
8. The really juicy data will always remain locked up...    I'd very much like to be able to share my purchases, particularly restaurants, at my own discretion.  Of course, that data is at Mastercard, and I think I'll start wearing "I love the RIAA" shirts before Mastercard starts creating personal RSS feeds or APIs for users to take their own financial data to various applications.  The same with my credit history.  I need to sign up for lots of junk mail to get a credit report... and don't even get me started on my own medical history. 
9. A lot of powerful people don't participate.  How many VC's out there fund widget companies without having a blog or a MySpace profile?  Any Sony bloggers out there?  What about brand managers that want to do Second Life campaigns without ever having been inside.  How about my elected representatives?  They get out there and kiss babies during election time, but how many blogging elected officials are there?  (And not watered down campaign blogs... actual blogs written by the actual people.)  We could do great things if we weren't so segregated into a small group of people punch drunk on Kool Aid and a great deal of people who've never even heard of Kool Aid. 
10. MySpace is the most popular social network. Seriously, is this the best we can do?  Spam, hacking, viruses, one song at a time, and no developer network or API?  Facebook is such a better product, but it's really pretty limited as a self expression tool.  Plus, neither really comes close to being able to be my digital home on the web as much as my blog is.