Since man first used a stick to dig under some roots and accidentally caused a tree to fall on him, humans have been doing stupid things with technology. Since the invention of the microprocessor and instant mass media, this has only become that much easier.

Thankfully 2009 is gone, and with it one of the most tumultuous decades in a long, long time. In that time there’s been some amazing advancements in technology, but those aren’t nearly as fun as some of the catastrophic failures. So here’s a quick round up of some of my favorite technology failures of the past ten years (in no particular order).

The Zune
Now I bought a Diamond Rio 64mb mp3 player back in the day (it was the first widely available portable mp3 player). Eventually I replaced it with a MiniDisk player that I still use when snowboarding, so I have a soft spot for terrible portable music players. But the Zune is a real loser. Incredibly ugly, hard to use, expensive and generally un-cool, the Zune had no chance of taking down the king-of-the-mountain Apple iPod. While some of the newer versions have gained a slight following among the highly valued “children of people who work at Microsoft” crowd, it still hasn’t caught on among the general populace. Newer versions are steadily getting better, but it’s still a really ugly thing to carry around in your pocket. On the plus side, the Zune did make for one of my favorite moments from the Fox sitcom Family Guy:

Beenz.com/Flooz.com
Sure these two terrible tales started off in the late 90’s, but their triumphant explosions weren’t until post Y2K. If you were living in a cave around the turn of the century, these two sites were trying to create an Internet-only currency (think Disney-cash, but they won’t even take it at Epcot). Both sites ran into a whole slew of issues, the least of which being that it’s illegal to create money in most countries if you aren’t the federal government. Once they got over this minor issue, both sites proceeded to gather hundreds of millions of dollars in investment cash, only to blow through it faster than anything I can print here and not get in trouble for. Beenz ranks as one of the biggest busts of the first dot-com era, and one of the worst ideas of the young century.

Webvan
The only other dot-com on my list (although there are so many more that could have made it), Webvan was a great idea if you didn’t take into account that whole “operating costs” thing. The premise is that people can order groceries for a decent price then get them delivered to your house for free. Wondering how they’re supposed to make money? So did the investors; especially after they dumped millions into buying warehouses, vans, servers and 115 Herman Miller Aeron chairs (at $800 a pop). Eventually the basic rules of economics caught up with the company and it imploded, only to be bought by Amazon.com for pennies on the dollar.

Internet Explorer 6
Anyone who works with developers can answer this question: What is the happiest day your office has ever seen? For the rest of you, the answer is the day that your last client stopped requiring IE6 support for their site. Internet Explorer 6 wasn’t just terrible for developers trying to make a site look good though, the software is so insecure that the US Computer Emergency Readiness Team (a part of the Dept of Homeland Security) actually asked Americans to use any other browser. Thankfully it is falling by the wayside, and the newest versions of IE seem significantly less inclined to turn your machine into a thousand-dollar paperweight.

Segway
Remember before this thing hit the market how the mad scientist that is Dean Kamen said it would replace walking? Even the Oracle of Technology himself (Steve Jobs) was quoted as saying this it will be as significant as the personal computer. Turns out that they (along with everyone else who said something like that) were wrong, and this marvel of modern engineering has been successfully regulated to mall cops and bearded professors. Outside of causing a few laughs for the nation (remember when Pres Bush fell off one), and one hilarious day for me in Austin, TX (segway tour + newspaper stand = me gasping to breathe from laughing too hard), the Segway has faded into very funny history.

Twitter Peek
So it’s a $200 handheld that’s about the size of a Blackberry. But unlike a Blackberry it doesn’t do most of the useful things you need a handheld to do, like store contact info, or be a calendar, or make calls. It just — wait for it — checks Twitter. Sure you can write Tweets too, but who seriously thought this was a good idea? I wonder which guy at the table said something to the extent of, “It’s like a smart phone, but you can’t make calls, or write email, or do anything besides Tweet (which you can do from most smart phones using a free app).” I’m not saying that they should be beaten over the head with a sock full of manure, but I’m not saying they shouldn’t be either.

Bluetooth Headsets
Before you get all up in arms about how wonderful Bluetooth technology is, please put down your Perrier and stop freaking out. I’m not saying that the headsets themselves are bad, but like the Trans Am and giant belt-buckles, Bluetooth headsets are used by terrible, terrible people. Unless you’re a trucker (or anyone else who spends all day driving) please take them out of your ear. I promise that when the President calls looking for the nuclear launch codes, I’ll flag you down.

From Boston to Bangalore and Toronto to Tunis, our little holiday endeavor has spread across the globe faster than risqué pictures of Lindsey Lohan.

The Backstory

Before the business world shut down for the holidays, we at Pop Art launched our 2009 e-card, The Holidizer. Running with the success of “Imma let you finish” and “The Bacon-izer,” Holidize.me was designed to let you put a cheery animated holiday scene over your choice of site. The Holidizer also generated a shortcode, letting you easily share the new URL.

Spreading the Word

Once it was launched we set about exposing the world to what we had done through a multi-channel social media campaign.

Step one was an email blast out to about 1,700 people who have signed up to receive our quarterly newsletter. With above-average open and click rates, we started off on the right foot.

Once we got that initial push it was off to the Twitter-sphere where we dragged in the whole staff to help with the effort. We asked the Pop Artists to holidize their favorite sites and post the shortcode to their Twitter feeds, and soon the retweets were flowing like water.

Through a few targeted tweets — and a bit of luck — we were able to get onto a few high-profile blogs and Twitter feeds including Ad Pulp and Agency Spy. The groundswell began as the card spread through the blog-o-sphere.

And then we hit the big time.

On the morning of Monday 21 December, we made it into AdFreak’s 2009’s Best Agency Holiday Cards. AdFreak is the blog of Ad Week (the second biggest advertising publication by global readership) and the article itself was written by James Cooper (the Interactive CD of Saatchi New York).

From there it really took off with blogs posting and reposting write-ups on the site all over the globe. In the end we had hits pouring in from every continent except Antarctica, and we definitely declared the experiment a success.

In the end we learned a few things:

• Make the site easy to tweet (http://holidize.me is shorter than a bit.ly shortcode).
• Get everyone involved in spreading the word.
• Talk directly to bloggers that you care about reaching — this means building and maintaining a dialouge — don’t just @reply and cross your fingers.

And here’s the big one:

• Make sure people will care about what you’re trying to make go viral.

• I can say “back in my day” when referring to anything before 2006.
• I get to dole out useful information to students and other people trying to get into advertising

So get off my lawn, pull up a chair and shut up while the adults are talking.

Hints on Starting Your Career from Someone Who Still Remembers Going Through It

Back in my day — see, I told you I could do it — portfolios were actual books with actual printed pages. Every year seniors all over the ad departments of universities across the country would blow a month’s worth of beer money printing them and sending them out to potential employers. Pop Art’s Creative Director, Dave Selden, has written a great set of rules for design portfolios, but for all the writers out there, I wanted to add one small thought.

Remember: You’re selling your mind.

Everyone’s book will be full of awesome spec ads. They’ll look mind-blowing, be hilarious and show a crazy amount of potential — or at least the good ones will.

So how do you stand out in the crowd? Make sure the book is about you. Let me tell you a story about my first internship in the industry:

Right after college I started working on my book (it needed an overhaul from the senior year version). While getting everything together — and working at a bar — I managed to pick up a few hobbies, including home-brewing beer.

When I was putting the book together, an old professor of mine recommended that I throw in some non-advertising pieces about who I am. So I added a page about growing up in Texas, a page about my fear of historical revisionists and a page with home-brew recipes I made. Then I began to shop it out.

One lucky morning I sent my book to the former Editorial Director here at Pop Art. He called that afternoon and set up an interview for the next day.

After entirely too much coffee and a frightening encounter with the office manager up front, I was pretty terrified. My future boss and I sat down, exchanged pleasantries and started talking about my book.

One of the first things he said to me was, “The ads are great, but is this a real home-brew recipe?” I later learned that he was an avid brewer, and once he saw the recipe, he knew he had to set up an interview. I ended up getting the internship, which parlayed into a job. I’ll never forget something he told me on my first week, “When you hire someone, your work and experience are important, but that most important question a prospective employer will ask himself is, ‘Can I hang out with this guy every weekday, or will he drive me insane.’”

So, the moral of the story is this: Beer got me my first job.

Wait, no. The moral is that showing some personality in my book landed me my first interview. So whether it’s a bound book or a web site, make sure it’s about you and not just your ads.

1. Shave your head.
2. Stop thinking. Hey, firing neurons are hot.
3. Get a summer home in Argentina. We do wine, they do wine. We ski, they ski. We have good food, they have food so good you’ll think your tongue is playing a joke on you.
4. Mint-chocolate chip ice cream cures all your ills.
5. Pick up some new hobbies, like ice fishing, snow shoeing or anything else that lets you travel to the Alps.
6. Liquid nitrogen + shirt = personal AC unit.
7. Camp out in the dairy aisle. If the store’s open 24 hours, just go grab a lawn chair and always have a can of easy cheese in your hand.
8. With enough dry ice and a chisel, you can make anything.
9. Waterproof a laptop and never leave the tub.
10. And then end-all be-all last resort: Sleep at work.

I hope this list helps you to survive. It was going to be longer, but it’s too dang hot to think…

Some Background

Twitter is a social networking and micro-blogging service that lets people “follow” your trail of 140 character posts, known as tweets. It started as a post-board where people would text in what they were doing from their cell phone. While the service launched three years ago, it has blossomed recently, with a 1,384% growth from February ’08 to February ’09. Currently, Twitter is the third largest social media service in the world, behind Facebook and MySpace.

How Can Twitter Help Your Business?

The service is not a solely business-free area though. Twitter has been used rather successfully by a plethora of businesses, some of the most notable being Jet Blue, Zappos, Southwest Airlines, Ford and Jack in the Box. The most prevalent uses of Twitter by businesses fall into one of two areas: customer support and brand building.

Using Twitter to Handle Customer Support

Customer support through Twitter is a more established, and more easily implementable, usage. Monitoring the mentions of your brand through sites such as search.twitter.com, has been used very successfully to deal with potential problems. One notable example is as follows:

If your Comcast cable service were to conk out, what’s the first thing you would do? Right: You’d complain about it on Twitter. In one case, customers in California began tweeting about a service outage two and a half hours before anyone bothered to dial the company’s customer support line. That’s why Comcast keeps a support rep Frank Eliason to monitor customer gripes on Twitter.

— Paul Boutin ‘Customer Support via Twitter? Salesforce.com Makes it Legit,’ The New York Times

Using Twitter in this way is a good way to react to negative sentiment about your brand, but is not the best way to build a positive view.

Using Twitter to Build and Personify Your Brand

On the flip side, using Twitter to help build your brand, when successfully executed, can do wonders for positive brand recognition. This is probably best epitomized by Zappos.com CEO Tony Hsieh.

Currently, Zappos has 351,550 followers (making them the second largest non-news corporate account). Now what does that statement mean? It means that several times a day (the average Twitter user tweets 8.2 times a day), the Zappos brand can touch over three hundred thousand people.

Hsieh doesn’t talk about promotions, or shoes, or his company in general (for the most part) though. He has never tried to sell anyone a new pair of kicks, and except for a few mentions of his office, you’d never know he had a real job.

Unlike many business Twitter accounts, Hsieh personifies his brand and turns it into a relatable entity. To the over 350,000 people who follow him, Zappos isn’t a faceless company selling shoes. It’s an entity that loses its Chapstick every two weeks to the “Chapstick Fairy.” And gets freaked out when it catches a mannequin in the corner of its eye. Zappos’ Twitter account has been able to do what so many companies have been striving for, and turned a brand into a person.

A Middle Ground

While these two ends of the spectrum do work in some cases, a middle ground is probably the best bet for most businesses. A prime example of this is Southwest Airlines. Southwest, which has almost 19,000 followers, does promote trips on their feed, but only sparingly. Most of the tweets are dedicated to passing on interesting tidbits and pictures from flights.

By maintaining an interesting and regular stream of tweets, Southwest Airlines has grown into one of the most successful examples of corporate Twitter use. It uses it’s account to combat negative press, promote new features (they’re installing WiFi on their planes now), and build the brand as a fun airline to fly.

What’s Next for Twitter?

Twitter is constantly expanding, and new uses for the microblog prop up every day. Some of these, like the examples mentioned above, are great, some of these are not. Just to liven up your day, I offer up the world’s worst screenplay. It was built solely through people direct messaging (think of a Twitter IM) lines to Southwest Airline’s Twitter account. It pushed the medium a step further, but lets just say it’s a start.

Currently the only people who don’t make money off of Twitter are the people who built it. They keep talking about doing everything from charging corporate users to allowing PPC style ads. As the amount of Tweeple continues to increase, who knows what tomorrow brings for the micro-blog…

Ok, now that we’ve got that out of the way, the big “Watching Comprehension” question: Did you notice the big, underlying difference between the two?  No, it’s not that one is about biking at night to bad punk music and the other is about jeans rolling through San Francisco.

The big difference is that Jeans has been up since the end of July and has 234,000-ish views, and Bike Hero launched last week and has been seen about 1,338,000 times.  Namely, one is awesome; the other is Pollock in my California Roll.  The big question then becomes: why does one video manage to earn almost 6 times as many views as the other?

Both of these videos are viral ads aimed at a Gen Y audience (full disclosure, this includes me).  Both of them are for consumer products, involve weird stunts, and are starring people in my age group.  Both of them were seeded by Feed Company, and were made by uber-creative agencies (Cutwater and Droga5).  And finally, both of them have been all over the blogosphere (just a few: here, here, here, and here).

The big differentiator between the two, and a big rule to follow when trying to make live-action video go viral: members of Gen Y can see themselves doing the Bike Hero stunt, but there is no way that I can animate my jeans to walk on their own, no matter how hard I try, or how many witch-doctors I visited on my trip to Haiti last year.

Gen Y has grown up so thoroughly barraged by a world of advertising that our radar for “guerilla advertising” is pretty fine-tuned. But things like Bike Hero do exactly what viral videos are supposed to; they slip in under the wire. It does this by seeming completely plausible and relatable.

In fact, it’s not until you watch again and ask yourself why the kids would write out all of “Guitar Hero World Tour” on the intro, that the fact that it’s an ad sinks in and the wow-factor fades.  The mystery of Runaway Jeans lasts about 18 seconds (that’s when the jeans start to escape).

And now the over-arching, take-away from the blog post, if you’re trying to go viral, either make it real, or make it something so utterly bizarre and twisted that Lewis Carroll himself couldn’t dream it up without chemical help (read: Happiness Factory).  You’ve only got one try before Gen Y thinks, “this is awesome,” or just shrugs and says, “this is advertising.”

That is until I looked at www.Bthesite.com, the spinoff blog for the Baltimore Sun.  This site is possibly one of the best examples of newspapers going digital ever.  The layout is awesome and the content is hip (and somewhat user generated). More importantly though, it all seems to be web-specific instead of just a regurgitation of their print content, which is genius, and should be obvious.

So to all you almost failing newspapers out there, this is how you garner younger readers.  I’m 24 years old; I haven’t ever bought a physical newspaper (unless I was killing time waiting for plane), and I never will, but if more papers actually start to care about the interactive space I’ll definitely take notice.

My dearest Baltimore, I’m not planning a trip to Ravenstown any time soon, but I’m going to read your daily tomorrow.