Ideally, the service would have some kind of gallery viewing ability, with privacy settings for photos/albums. There should be a way to prevent hotlinking. It should support different image formats (at least jpg, png, gif) and allow me to upload very large uncompressed stuff. It doesn’t really need to serve as backup, but being able to download the original file (say in raw format) would be nice. Video hosting would be cool too. I’d rather not pay, but if the service is good enough I’m certainly willing to shell out. I’m not a professional photographer and don’t need to sell my stuff, I just want to have a clean and centralized way to organize and share it.

I’m open to anything, including installing self-hosted software on my own server, using some kind of cobbled-together solution with Amazon S3, a straight-up paid service, or something in between. I know there are a lot of options out there like smugmug, picasa, shutterfly, etc. but I’m hoping I can get some first-hand knowledge instead of just trying to peer through all the BS. C’mon internet, don’t let me down.

I replaced that by following a bunch of new twitter accounts for those same sites and related people. To avoid getting completely bogged down by twitter instead of rss, I set my twitter client to automatically scroll as new tweets arrived, and created a couple lists for “don’t miss” important accounts (close friends). I still scroll back sometimes, usually if I’ve been disconnected for a while, which doesn’t happen too often. But overall I’m just checking it passively, and any interesting links go into a separate browser window that I go through at a convenient break time instead of on the spot.

The big question was, would I still get the news I was interested in? Would I miss anything? Would I actually cut down on my “wasted” internet browsing? Initial results say yes, who knows?, and definitely. I mean, if I’m missing something, I’m not really going to know that I missed it, am I? (For those of you sitting in the back, if you can’t hear me please raise your hand.) But I don’t feel like I’m missing anything. And it also seems like I spend less time reviewing things that don’t interest me. The twitter character limit and not being able to immediately view posts like in GReader makes skimming over unimportant content quicker. Or more avoidable, or something. Overall, it feels like a definite productivity improvement.

Now trying to decide what the next productivity change should be. Thinking of “dark” hours (i.e. times when I’m not allowed on the computer, or maybe just the internet), which is difficult since my work is so closely tied to being on the computer. Thoughts?

What Moneygram does differently (from what I’ve seen, have you seen other sites do this?) is allow you to add your own personal phrase to the image. I think this is great, especially because the phrase I chose, paired with my image, makes me laugh everytime I see it, and I know it’s definitely the right site. It’s this kind of personalization that seems to be severely lacking in a lot of security “confirmation” techniques. Honestly, it wouldn’t take a genius to figure out where I went to elementary school, or the ever-popular mother’s maiden name.

The key here is that you’re recognizing a specific thing, as opposed to having to recall it, which is much more difficult. People hate passwords mainly because it isn’t easy to remember a bunch of different, complicated code words/phrases. But it’s really easy to recognize something unique, especially if you created it. It seems like this could somehow be a viable alternative to passwords. I’m not going to try and propose an actual solution here, but if we could make authentication more about recognition (and fun) and less about memorization and bland alphanumeric strings, our online interactions might be made a lot more secure.

A nap nook - my second favorite kind of nook.

See, the whole concept of an eBook reader has been hamstrung from the start by the lack of a common, open format. There are plenty of other hurdles: the lack of color screens, the incredibly slow refresh rates of E-Ink displays, the high cost of adoption. But the real setback in my mind has always been the fact that a physical book doesn’t limit who can read it, or where, or when. You can lend a book to a friend. You can sit in a bookstore and leaf through a book before purchasing. If you buy your books from Barnes&Noble, and your friend buys their books from Borders, that doesn’t mean you can never read your friends books, or vice versa.

A good analogy is the mp3 player. The file format mp3 came along while the only way to consume digital music was still off of physical discs that spun around and were read by “lasers.” But thanks to the internets, and small hard drive space, the mp3 format took off, followed by hardware mp3 players. Think about it: they’re called mp3 players, not emusic players. By the time Apple rolled around to dominate the market, as much as they wanted to use their own fancy proprietary format (AAC), every iThing supports mp3 files. Even the music you buy through iTunes or Amazon can be had DRM-free and device-agnostic.

This has not been the case with ebook readers. Amazon’s Kindle uses their own special format that nobody else can use. If you want to read some other type of file on a Kindle, like a PDF, you have to use their special file conversion software to work some voodoo magic and have it anointed by Bezos blood before it can pass through the fiery tunnel of Whispersync and reach your device. And that’s IF that other file type is supported.

So, why am I excited about the Nook? Because it looks like maybe the final puzzle piece that will topple the ebook format quagmire. The Nook uses the EPUB format, an open format which has also been embraced by Google’s vast store of digitized books, as well as Sony who recently converted their entire store to the format. This essentially leaves the Kindle as the lone proprietary ebook store. And while Google and Sony jumped on the epub bandwagon first, Barnes&Noble is in a unique position to actually compete with Amazon for content. Any ebook reader that comes out from now on will basically be required by market forces to support epub, and from there the road gets a lot smoother.

But that isn’t all. B&N is uniquely taking advantage of their brick-and-mortar stores to do some very booklike things that have been glaringly absent from the current options. You’ll now be able to lend ebooks to a friend for a short period of time (although  how many times you can lend a book, or to how many different people, is in question. This thread says that it will be very restrictive, but things can always change. Better to start heavy-handed and get looser than the other way around). You’ll also be able to take your Nook to a B&N and read a book from their online store right on your device, without purchasing. I think this is brilliant, since it really addresses how people actually shop for and handle books. There’s also a great licensing opportunity here. Much like Amazon allows anyone to sell an item through their online store, B&N (or someone else, Borders perhaps) could allow other bookstores to sell digital content through the B&N store and offer similar in-store reading and lending opportunities. Boutique bookstores could actually have a chance to draw customers back to their stores thanks to an ebook reader. I’m not saying it will happen, but it could.

The Nook also has some other nerd-lovable features. To get around the slow refresh, grayscale limitations of E-ink, there’s a capacitive touchscreen LCD at the bottom to help you navigate your library of books and other control features. On top of that, the device is powered by Google’s open mobile OS Android. These two things could open up a world of possibilities. Just a few mundane thoughts: a Pandora app to stream music while you read, or a twitter app to comment on what you’re reading. What I’d really love to see, though, is a coverflow-like page skimmer. It’s already been noted that the Nook will feature a coverflow interface for browsing your books to identify them by the cover, but how about while reading being able to “flip” through pages? One of the biggest inadequacies of ebook readers until now has been poor navigation, the loss of being able to easily jump forward and backward through a novel to find a particular passage based on your memory of physically where it was located in the book. I might cry with joy when I am able to flick through miniature pages on the touchscreen to navigate whatever I’m reading. This might not be available on the Nook when it first hits stores, but it will get there eventually. I’d put money on it.

Should you buy a Nook? There’s still the problem of the cost ($259 upfront, plus buying new books). And even though the content pool has gotten a lot bigger, there’s still a lot not available, including newspapers and out-of-print material. And there are other potential winners coming from companies like Plastic Logic (who have partnered with B&N) and Apple that will have bigger screens, maybe full color, and who knows whatever other features. The Nook is certainly not the perfect ebook reader, and it will get surpassed, but I think it will be the first to break open the ebook floodgates to the public, which is reason enough for an early adopter like me to jump on board.

Not to say that this is the most well-composed top-100 tech list out there. For one thing the list is actually a top-104 with four picks grouping a pair of influentials, including Googmeisters Sergey B. and Larry P. sharing the top spot. I’m also pretty sure that #6 Yong Nam and #70 Woo Hyun Paik are not the same person, despite this list’s appearances. There is also a hint of European bias, not to be unexpected from T3, but worth noting along with a complete gloss over of investors. While on the whole investors may not be “influential”, it’s ridiculous that a few of them aren’t on here. Are you really telling me that Gerhard Schaas – the CTO of a UK-based high-end home theater company – is really more influential than Marc Andreessen or Tim O’Reilly?

But of course the biggest issue I see with this list is the unhealthy amount of Y-chromosomes. Out of 104 listees, only 9 are women (10 if you count Jonathan Ive), and they don’t even crack the top 30. Martha Lane Fox leads the group at #37. Her Tech100 profile tag line? “One of nine women on the Tech 100.” No shit sherlock. You couldn’t come up with anything better? I guess T3 felt it was better to blatantly state the gender gap as opposed to try and ignore it, but I feel bad for Ms. Fox.

My point here though is not that I think this list is inherently or purposefully sexist or something. I just personally find it disheartening that the state of the tech community is still so predominantly male. There’s maybe a couple of other women that should have made this list, though please correct me if I’m wrong. Marissa Mayer of Google comes to mind, as well as President of Oracle Safra Catz (and p.s. how is Larry Ellison not on this list?!?), but that’s about it. And that just sucks.

While the business world, like pretty much everything, continues to be a male-dominated legacy, I feel like the tech world should be a bit different. There’s no reason that a tech-geek chick couldn’t be the next Mark Zuckerberg, or Walt Mossberg, or Berg McBergersberg (note: Mr. McBergersberg is not an actual tech influential). I guess it just bothers me that there’s probably a lot of great innovation and progress to be made that we’re missing out on because it requires some female sensibilities or insight. And I hope a few years from now these Top-X lists will start looking less like a Dan Brown fan club sports pub collegiate computer science classroom and more like a Harry Potter fan club wine bar collegiate biology classroom. Or something. Sorry, I couldn’t come up with a good analogy, but you get the idea.

The truth, of course, is that this was as much about me getting to play with a new gadget as it was about taking a stand against Apple’s “injustices.” I certainly wasn’t the first to make this kind of jump, nor am I in any way important or influential (see: Michael Arrington, TechCrunch). But after switching phones I found myself repeatedly having to explain in painful detail exactly WHY I got rid of my amazing iPhone to scores of less tech-informed family and friends. And every time the subject came up, I found it increasingly difficult to paint the “Apple and AT&T are the bad guys” picture because all I really wanted to do was talk about how freakin cool Google Voice and background apps are.

Now a month into my self-imposed iPhone exile, I’m forced to address the question: was it worth it? I’d say the answer is a firm but unenthusiastic Yes. Here’s a list of what’s great and not so great with my switch to the myTouch 3G (agnostic of Tmobile’s network vs AT&T). If you’ve been considering the same switch, or are in the market for a new phone and haven’t decided to get an iPhone just yet, I hope this can help with your decision.

Big Wins

• Google Voice kicks so much ass it should get its own Nike endorsement
  My biggest hurdle with the switch was getting all of my contacts to start using my new phone number. This required several emails, text messages, phone and in-person conversations, plus quite a lot of setup on my part organizing my Gmail address book. But boy was it ever worth it. The voicemail transcription feature alone is reason enough to start using Google Voice, for reasons I hadn’t even considered until after I switched. A) The transcriptions are often fairly accurate, but when they’re not they can be hilarious. I’ve started answering my phone less just so people will leave me voicemails for potential unintentional comedy. B) Being able to read voicemails is such an amazing experience. Google Voice strips out people’s natural pauses and “ums” and the text translation allows you to skim through a voicemail so much faster than listening to it. I feel like I’ve added years to my life by no longer having to listen to someone say “So, uhhh, we should like, go get food later…and, yeah, cool, ummmmm bye.” Add in the benefit of being able to check your voicemail during meetings/movies/other times when it would be inappropriate to hold your phone up to your face, and hopefully you can see the major win here. I won’t even bother explaining all the other great features of the service. It’s just so worth it, and having it run natively in the background on my phone – exactly what the iPhone can’t do – is enough to make me happy with my switch, and until that changes for the iPhone there’s no way I’m going back.
• Cheaper bills, shorter contracts
  Tmobile’s unlimited data plan is $25/mo. AT&T’s iPhone unlimited data plan is $30/mo. Also, if you’re a student (which my wife is), you can get a whopping 15% off your monthly bill. Not to mention Tmobile had a plan going at the time where I got 1000 minutes/mo at their lowest price tier ($40). And with Google Voice, I get free text messaging (about as huge as the other perks mentioned above). Aaaaannnnd, although the myTouch is $200 with a 2-year contract, Tmobile (unlike Apple/AT&T) let’s you pay $300 for the phone with a 1-year contract. At the end of the day, I paid a $115 early termination fee to AT&T which I will easily recoup in the next 12 months from my much lower phone bill, and by then I will no longer be under contract and free to switch phones again. I also sold my iPhone on Craigslist for a cool three Benjamins, so I basically broke even on the switch, which I find pretty great. How often do you get to upgrade an expensive gadget at essentially no extra cost? Hopefully when my contract is up in a year Apple will have their act together, and the new (my pure speculation) version of the iPhone with video-chat camera, 64Gb storage, Wifi-n, and background apps (including Google Voice) will be available.

Smaller wins

• Background apps
  This is a great feature to have in a phone capable of so much. Just like you can run lots of programs on your computer and switch effortlessly between them without having to quit out of one to start another, background apps on the myTouch (and other Android phones) allow you to do things the iPhone simply can’t, or needs special hacks to achieve. The Google Voice app is just one example. Other things like live streaming video (Qik) and customized phone settings based on your situation (at the office? automatically set the phone to vibrate. Away from home? automatically turn off wifi to save battery) make the phone so much more fun in a lot of ways.
  So why isn’t this a bigger win? Simple: performance. The myTouch processor is simply not as powerful as the iPhone, and things tend to get sloooooow. Battery life might actually be worse. There’s no multitouch (although I don’t actually miss it all that much). The responsiveness and the smoothness of the iPhone is just not present here. I’ve heard that installing a custom ROM (more on this below) can really fix or improve these things, but I have yet to try it. A fair analogy here might be like switching from a Ferrari to a custom-built supercar. You can do a whole lot to your modified kit car that you just can’t in a Ferrari…but it’s still not a Ferrari, and it never will be.
• More buttons?
  While aesthetically the myTouch isn’t a slick as the iPhone (re: Ferrari), all those extra buttons on its face actually come in handy. There are times when the scroll ball is a lot more intuitive/useful than touch input, having physical call answer and end buttons is wonderful (no need to “swipe” to answer a call, a novelty which wears off as soon as you try to use your iPhone with gloves), and the Back button actually navigates you through your app use history, so you can follow a link from your Twitter app to your browser and then with the click of a button you’re back in Twitter where you left off.
• Removable stuff
  The battery comes out. So does the SD card for expanded storage. And the back of the phone (aka battery cover) can be easily slipped off and replaced with another one, which can be completely customized by the Skinit site. I used their online interface to make my own cute Wall-E battery cover and it was a really easy and fun way to waste $20. But it definitely adds some charm and character to the myTouch in a way you can’t really achieve with the iPhone.

Small Losses

• Less buttons?
  Despite having a plethora of extra buttons on the phone, the designers of the myTouch missed a biggie. Little did I know that one of the things I’d miss most about my iPhone was the silence switch. With a simple flip I could turn off the phone’s ringer. While a terrific Android app called Locale lets you set preferences for things like ringer volume based on situations such as your location, it can’t account for those other times like visiting family, going to a board meeting, attending a movie, etc. Tiny iPhone ringer on/off switch – I hope we can be friends again some day.
• The SD card
  Yeah, cool, I get it, a removable micro-SD card is great and all because you control it, or something. Sometimes I just want 16Gb built-in, ok? I just paid $300 for a phone, and now you want me to shell out more money so I can actually put some podcasts on it? The phone comes with a 4Gb card, but that’s so 2007. And this brings me to the next section…

Big Losses

• Media management (aka iTunes integration)
  While some may bemoan Apple’s icy cold grip on your media management by forcing the use of their application (iTunes) with their products (iPods/iPhones) and not letting anybody else in (see: Palm Pre), the fact remains that it’s a dead-simple and pleasant way to manage all of that content. Gigabytes of music, podcasts, photos, ringtones, tv epidodes, movies…you just set up your synchronization preferences, hook up the phone and let it go to town.
  There’s no such unified system with the myTouch (or any Android phone). This thing is about as user-friendly as a starving pitbull when it comes to managing files. You actually have to MOUNT the SD card on the computer through an arcane process of long-holding the USB connection message and…sorry, I’ll refrain from wasting your life the same way mine was when I first wanted to put some damn music on my phone. There are some options out there, like doubleTwist, that can manage media on the phone, and a new Android app from Google called Listen allows you to manage podcasts in a pretty easy way. But I desperately miss the integrated iUniverse, and I’m actually planning to just get an iPod Touch and use that for all my music and video needs.
  I won’t even get into the stupid USB headphone adapter. Whoever thought that was a good idea needs to be fitted with a ball gag “adapter” so they lose all desire to produce sounds from their mouth.
• The Virtual Keyboard
  Here’s a great writeup on exactly why the iPhone’s virtual keyboard gives the myTouch what I can only imagine is the smartphone equivalent of penis envy. If this were the first touchscreen keyboard I’d used I would probably think it’s great, but coming from the iPhone I’m only ever satisfied at best, ragingly annoyed at worst (it sucks, but it’s not that bad. It still beats the MotoQ physical keyboard by a mile. Goddamn that phone…).
  There are also little things to the iPhone keyboard software that I really miss. For example, Android puts the comma and period right on the main screen flanking the spacebar, while on the iPhone you have to hit the special characters key. That would seem like an improvement, but because the Android keyboard on the myTouch is already cramped, that comma and period makes it even harder to hit the spacebar, which is maybe my single biggest gripe while typing. On the iPhone, after you’ve gone to the special character screen and typed your comma, hitting the spacebar switches you automatically back to letters. And the period on the main screen is completely unnecessary, since both phones have the ability to insert a period automatically by hitting the spacebar twice. The iPhone also brings you automatically back to the letters view after typing an apostrophe, something Android doesn’t. Overall I feel like I have to do more key presses with the myTouch just to simply type, but add in the accuracy (and speed) issues and the experience overall is very disheartening. Nowadays I often feel less like I’m typing and more like I’m jabbing at alphanumeric minnows. Which brings me to…
• Applications/Customization and Hacking/Rooting/jailbreaking
  I haven’t tried it yet, but I’ve read that a lot of the speed/keyboard issues on the myTouch can be fixed by hacking, or what’s known as “rooting,” the Android phone. The iPhone equivalent is known as jailbreaking, which was something I did a couple of times during my iPhone’s tenure. Jailbreaking the iPhone gave you access to things like non-Apple-approved applications and special phone customizations (skins, docks and app launchers, even background tasks!). You had to jailbreak to get any of this cool stuff because the iPhone is a closed platform, carefully walled off by Apple. The process, however, is surprisingly simple and more or less painless, with basically no risk of permanently ruining the phone and the option to undo the jailbreak at any time. In fact, you can now get the Google Voice apps that were pulled from the Apple app store by jailbreaking, although trust me here that it just isn’t the same experience as direct integration.
  Why does this matter? Well, Google’s entire concept of the Android platform is an open source phone operating system, unencumbered by rules and restrictions. Except reality doesn’t really play out that way. The phone carries install their own customized versions of Android on the phones, in effect limited their performance and capabilities. Sure, you’re still free to install any applications you want, but changing the core functions and performance of the phone are still off limits. And unlike the iPhone, the process to root (jailbreak) an Android phone is actually kind of complicated and scary (unsurprising considering the media management), although recently that’s improved. So a gloriously free and iPhone-performance-rivaling myTouch can be yours, but it will probably void your contract agreement and take you several stressful hours to complete. I’ll let you all know how it goes.
  Add on the fact that the Android app market is just nowhere near the robustness of the iPhone’s, nor is it nearly as easy to find and get good apps or manage them on your phone (the lack of iTunes-like synchronization rains on another parade). That too should be changing soon, but the basic fact is that there’s no Pandora app for Android, or 1Password, or etc. etc. etc. Except, of course, there is Google Voice. BOOYA IPHONE! In the words of SNL-Sean Connery: Shuck it, Steve Jobs. Shuck it long, and shuck it harhd.

If I had to summarize this agonizingly long article in a single sentence it would be: While the myTouch is a mere BMW next to the iPhone’s Ferrari, if you want to use Google Voice natively (and you DO) then it’s worth grinning and bearing the shortcomings to experience the virtues, and it might just save you a buck or two.

Updated 09/09/09 (just had to write the date): The Pandora app for Android was released today, which is another +1 for the phone, although that headphone adapter is still damn annoying.

I also thought it would be funny to point out how Google Voice has continued to fail with transcribing my name, “Dylan.” So far it has called me Jill, John (multiple times), delyn (so close!), know, and Joe. I don’t even mind, it’s always a fun surprise for me when I get a new voicemail.

Apple and AT&T started crippling the iPhone with their “amazing” App Store. Which really is amazing, but could be so much better if they’d actually open it up and let in all the cool stuff. You can find tons of info on how the App Store approval process makes no sense with a simple Google search, but just a few examples are blocking the video streaming app Qik, crippling the Sling Player app (wifi only), and recently forcing Google to make their Latitude service into a web app instead of native application.

And now, for me at least, the last straw came yesterday when Sean Kovacs, the developer of the GV Mobile app that lets you connect to and use your Google Voice account, announced that Apple was pulling his app from the App Store (along with the other GV apps). After that news broke, more info leaked out about how Google had even submitted their own GV app some six weeks ago which Apple would not allow into the App Store. Meanwhile, there are native Google apps for Google Voice available on both Blackberry and Android phones (as well as other iPhone-unavailable apps, like Qik), and there remain apps in the App Store that do the same kinds of things GV Mobile did.

If you don’t yet know about Google Voice, I suggest you look into it. It’s still an invite-only service, but Google is making a strong effort to open it up to many users, and for a lot of reasons it looks great. The big ones though are that it gives you a new, “central” phone number that you can use to channel all of your phone calls through, along with the ability to have your voicemails transcribed to text and emailed to you, and free sms messages. All big things for cell phone users and people juggling several numbers (office, home landline, cell, perhaps a business cell, etc).

However, there are some limitations to using the service, the biggest of which is that while you may have a shiny new GV number for people to call you, when you call them they still see your old phone number. An iPhone (or Blackberry or Android or Windows Mobile) app can fix this, which is exactly what GV Mobile and others were doing. And now, inexplicably, that’s over and gone.

Personally, I’m sick of it. I laid out a lot of cash in order to get a device that was supposed to free me from the constraints of typical cell phones. And while it started out on the right path, things took a wrong turn somewhere and now I’m more aware of what I can’t do with it than what I can. If somebody asked me today whether they should switch to AT&T to get an iPhone, my answer would be an emphatic NO. And if you’re already on AT&T? Well, it would be a big MAYBE, depending on what you want it for. Personally, I want streaming video and Google Voice on my phone, and it’s looking like I’m going to have to jump ship again to get it.

If you’re in the same boat as me, you have a few options. You could jailbreak your phone to get some of these restricted apps (Gizmodo has a great step-by-step guide) – Kovacs has released GV Mobile for jailbroken phones. Or you could sell your iPhone to pay for the early termination fees and pick up an Android or Blackberry handset (or maybe the Palm Pre) from Verizon or Sprint. I’d also suggest leaving Apple some feedback, in the hopes that they get the message and repent. Here’s what I submitted to Apple through their iPhone feedback form:

The news today that Apple is not only pulling all of the Google Voice apps from the App Store, but has also already blocked the addition of Google’s exclusive GV app, has infuriated me to the point of considering my options for ditching the iPhone and AT&T. There’s been plenty of examples of the shoddy state of the App Store and the decisions about what gets in or not, and this is for me just the last straw.
I switched from Sprint to AT&T to get the iPhone 3G last year, and I’ve been extremely happy overall with both the phone and the carrier. But the main reason I love the iPhone, and why I tell others to get one, is because of the App Store and how it opens up the platform to be so much more than just a regular cell phone. I’m sorry, AT&T, if Google Voice scares you, but you’re already doing enough to discourage me as a customer with exorbitant sms fees and blocking or crippling other apps like Qik, Sling player, and Google Latitude. But keeping these apps away from me is not doing anything to persuade me to stick with you. I’m not going to stop paying you over $100/mo for cell phone service just because I now have a Google Voice app. It just means I’ll be using a new number, and not texting through your service (which I avoid like the plague anyhow). And Apple: bowing to the pressure of AT&T, whatever the reasons, makes you just as culpable.
If it means switching to Verizon or Sprint and buying an AndroidOS phone or a Blackberry so that I can get apps like Qik and Google Voice for my phone, so be it. I’m sick of this shit, and unless you all do an about face really quick then I’m not going to deal with it anymore.

I don’t have any delusions about my (in)significance to Apple and AT&T, but that doesn’t mean I have to sit idly by and accept their baloney, and neither do you. If there’s one thing these companies will listen to, it’s our dollars, and as long as they’re blocking Google Voice apps I don’t want to give them any more of mine.

Update: A great article from TechCrunch (with some amazing comments) on why Apple may have pulled Google Voice
Update: And a great article from LifeHacker exploring why this is such a big issue, and ultimately not just for iPhone owners.

But that isn’t what baffles me. Craigslist on its own is doing just fine. They’re still the go-to site for online classifieds. What I can’t figure out is why, without any innovation or improvement in 10 years, that’s still the case. Where is the disruptive newcomer to unseat the mighty Craigslist? Doing a little searching for alternatives yields a lot of options without a lot of good results. The sites are either poor clones (Backpage), poorly designed and cluttered (vFlyer), or gimmicky and just poorly put together (RealPeopleRealStuff). Even the big players are starting to jump into this arena: Google offers Google Base and eBay has opened their international classifieds site Kijiji to the States, but both are still lacking killer features that might net them real market share.

Businessman and Dallas Mavericks owner Mark Cuban recently wrote in a blog post:

There will always be a company that replaces you. At some point your BlackSwan competitor will appear and they will kick your ass. Their product will be better or more interesting or just better marketed than yours, and it also will be free. They will be Facebook to your Myspace, or Myspace to your Friendster or Google to your Yahoo. You get the point. Someone out there with a better idea will raise a bunch of money, give it away for free, build scale and charge less to reach the audience. Or will be differentiated enough, and important enough to the audience to maybe even charge more. Who knows. But they will kick your ass and you will be in trouble.

So what’s it going to take to kick Craigslist’s ass? Here’s my list of features I’d like to see in a new classifieds site (or hell, I’d be just as happy if Craigslist would implement them). Give me these with a simple interface and good design and I’ll jump over in a heartbeat:

• Video and higher-quality pictures

  C’mon guys, this is the age of YouTube, of the Flip Mino and the iPhone 3GS. Why do people still go to garage sales? Because they want to SEE the things they’re buying, from all angles, they want to feel them and judge their size and look for imperfections. If I’m selling a DVD player, I don’t want to invite a stranger into my house just to show them it works. Pretty please let me upload video to my ads. RealPeopleRealStuff does this already, how hard can it be? And while you’re at it, 4 low-quality jpegs is not sufficient to display my wares. Storage is cheap. Amazon, Google, etc. are happy to provide server farms at your disposal. Let’s use em.

• Location awareness

  Newer browsers (Firefox 3.5, Google Chrome) are building location awareness right into your laptop. Web-enabled smartphones with GPS can pinpoint you in seconds and are already providing location-based services to help you find restaurants, gas stations, etc. But even web behemoth Ebay’s classified site Kijiji still relies on subdomain-specific listings like detroit.kijiji.com. How about giving me the option to set a radius from my location (5-500 miles) and show me all posts within that range?

• Real anonymity

  I want to sell something on Craigslist, but I don’t want to freely give out my phone number or email address. But oh, lucky me, Craigslist will post an anonymous email address on my listing and forward me the replies. How sweet of them. Except, now that I’ve got some replies in my inbox, my only option is to expose my real email or phone #. I’d prefer an account to log in to with an inbox, threaded replies, and the ability to respond to would-be buyers without giving out real contact information. Anyone can do this every day on Facebook, Twitter, MySpace, etc. Why not on Craigslist?

• Make it extensible

  If the new web services have taught us anything, it’s that providing an API and a way to expand your presence to other parts of the web is vital, nay, essential if you want to survive, and with good reason (which I won’t get into here). When I post a classified online, I want to be able to broadcast that information quickly and easily across my social networks. Give me widgets, give me RSS feeds, and even better give me a way to track this stuff. I want link tracking, visitor trending, I want to tie my posts into Google Analytics. Classifieds by nature get a spike of traffic when they’re listed which steadily falls off as they age. I want to see that traffic curve so I know if it’s time to relist my item, or if I just need to settle for a lower price because people are looking but not biting. And if nothing else, give me a simple way to put my listing on Craigslist as well (vFlyer already does this, to an extent (warning: this link goes to an INCREDIBLY boring video tutorial)). If you’re going to unseat the king, you’ve got to do it in his own castle.

This isn’t a question of if, but of when. It’s true that for any new classifieds site to get any market share, it will need to generate and eventually take traffic away from Craigslist, but if you give people compelling enough features with great function and design, it’s only a matter of time. A service with the attributes I described above is not out of reach for a new tech startup, and making it a viable business would be simple – I know I’d gladly pay a few bucks a month for a premium account that lets me post video, track link stats, etc. I personally can’t believe we’re approaching the second decade of this new millennium while Craigslist is still partying like it’s 1999. I want my Craigslist 2.0. So, who’s going to step up?