…[T]heir custom date picker is simply brilliant. Hipmunk has a good web interface too, but it has nothing on the iPhone interface. This is why native apps matter.

Thanks for the love, John!

I’m especially pleased he calls out the date picker. That was a lot of work to get right and it’s not the sort of thing you can get away with being wrong in something like flight search and still have happy users.

I absolutely loved that thing, especially by contrast with the rest of my life. School was typically dull: I spent very little time learning about anything that was important to me. I think I could count the number of friends I had with half of one hand – and they were certainly outnumbered by people who disliked me but couldn’t find constructive ways to express those feelings. My home life was no picnic, either.

Yet none of that mattered when I was at the keyboard of my Mac. It was, all at once, a second school, a conduit to another world, an infinitely deep toolbox and a magic wand of indescribable power – running at 60 MHz.

I thought it would be fun to venture down memory lane and revisit my Mac of 1995. Of course, the hardware itself is long gone. But through the magic of Sheepshaver, I’ve been cobbling together the scraps of my favorite childhood memories. Other kids had sports, comic books or Jesus. But the thing I believed in was my Mac.

System 7.5

My childhood experience with the Mac spanned System 6 through Mac OS X 10.2 but System 7.5 was easily the golden age. That would be the first time I had long-term access to a machine I could customize any way I wanted.

Once installed in Sheepshaver, even through an emulated PowerPC processor, System 7.5 is extremely performant compared to 16 years ago. On a Late 2010 MacBook Pro, loading from an SSD, boot time is about two seconds, compared to about 30 seconds in 1995.

The cheerful parade of Extensions and Control Panels marches at the bottom edge of the screen. Performance be damned, I loved collecting these.

Of course, the System 7.5 era was extremely long – an interminable wait for Copland, the next generation operating system that would make unicorns fly from your 4x CD-ROM drive. As time went on, the UI started to look pretty stale.

So it’s important to install one of my favorite extensions from the period, called Aaron, to spruce things up a little:

That’s better. Aaron adds a little flair and dimension to the otherwise flat and bland System 7-era UI and I liked it a lot better. Even at 10, I was starting to be curious about the nuances in UI design.

AOL

AOL was my very first taste of the internet. I believe our first bill came out to $80. So that didn’t last long. Luckily, their unlimited dialup service showed up about a year later, so I would be back in action. Sadly, but unsurprisingly, you can’t actually use the AOL client anymore. Still, I got to poke around with the modem configuration panel that was a frequent source of frustration once upon a time.

ClarisWorks

This little suite was bundled with the Performa. Very little to be excited about here but I spent so many hours cranking out school reports and other projects in its Word Processing, Paint and Vector Art modules.

Hotline

The gravest of my youthful indiscretions was easily my voracious appetite for pirated software. Enter Hotline. Before Napster, before Gnutella, before BitTorrent, there was Hotline. Hotline let anyone set up a file server on their home computer. It included chat, BBS and persistent user accounts, too. Vibrant communities sprung up around these little amateur servers. They dedicated themselves to everything from religious evangelism to technical support to sharing anarchist/conspiracy text files. Of course, being the internet, there would be plenty of pirated software in the mix.

To my utter delight, the mid-90′s version of Hotline I got started with so many years ago not only still works, there’s even a handful of servers still in operation. Back then, I was lucky to pull down files at 2.8 KB/sec via dialup. A limitation of either Sheepshaver or Open Transport, the aged TCP/IP stack Hotline uses, now caps me at 60 KB/sec, but that’s a big improvement I’d have killed for as a kid.

Hotline is a major hinge in my history. With access to so much software, I dedicated myself to learning how to use it. I rarely had access to any documentation beyond what was built into the apps so it was often an exercise in trial and error. It was also fun beyond words.

This began my life-long study of interfaces and user experience. If this hadn’t happened, I have absolutely no idea what I’d be doing with my life right now.

Photoshop

Hotline could be extended with customized icon sets. If one of the two dozen included user icons didn’t strike your fancy, you could create your own. The trouble was that only other users with your custom icon file could see your handiwork.

Of the thousands of active Hotline servers in operation during its golden age, two emerged as dominant tribes vying for the loyalty and patronage of the masses. Known as BadMoon and SoSueMe, the servers collected thousands of customized user icons and then distributed them as authoritative custom icon sets.

Of course, I wanted to get in on this. ClarisWorks’s Paint module really wasn’t up to the task, so I had to find and learn Photoshop 3.0. This little head-start on graphics tools ended up being important – years later, I’d be able to design my own UI elements thanks to this early noodling.

It meant days of downloading but it was worth it.

One striking thing about Photoshop 3.0 is how very little has changed after all this time. The color picker is identical. There are the many cluttery pallets for layers, brush diameter, colors, and channels. Later versions would introduce layer styles, which were awesome but a little rigid, and endless other bits of junk. The overall workflow, aside from crappy Save For Web, remains much the same. (This is why I now use Opacity to design UI – it’s built for how I actually work.)

ResEdit

I loved ResEdit when I was a kid. Apple’s resource editor let you poke your nose into most system files and applications, revealing image assets, icons, interface elements and plenty of other technical goodies I didn’t really grok at the time. It was surprisingly deep, including a little MacPaint-like editor for the icon files along with a drag-and-drop interface editor. At the instigation of David Pogue and Joseph Schorr, I recall using it to make the bloated trash can look filthy and overflowing.

Gaming

No exploration of Mac history would be complete without a look at some of the platform’s greater gems of gaming. PC’s may have had more games by volume but the Mac didn’t have any shortage of fun, either.

Escape Velocity

I sunk so many hours into EV, it’s not even funny. A nerd who grew up on Star Trek and other scifi, I found this game’s premise of space exploration, commodity trading, secret missions and interstellar combat extremely compelling. Entire Saturdays vanished into its gaping maw.

Marathon 2

Before Halo, Bungie made Marathon. It was a rich story of treachery and tragedy among the stars. Crazy AIs and three-eye aliens all trying to get you killed while you blast things with enormous guns. No full-motion video cinematics here, though. If you wanted story, you had to read.

SimCity 2000

I was terrible at SimCity. My budget rarely balanced, my people always complained.

I loved it anyway. SimCity 2000 is still surprisingly playable, too. Definitely a timeless piece of work.

End of an Era

The way many expected the System 7.5 era to end was pretty bleak: Apple collapses, the Mac dies, and its software and hardware begin to decay into uselessness.

Of course, history went a different way. I’m glad that Apple survived long enough to ship Mac OS 7.6 and OS 8, that in the time since Apple has rebuilt itself into the juggernaut of its industry. Mac OS X beats the hell out of anything that came before it. I still remember picking up my copy of Macworld at the supermarket and learning how Apple bought NeXT – and hoping that the future would bring brighter days for everyone’s favorite “beleaguered” company. And it did.

Still, I’ll always look back with fondness on those days of innocence before a Unix shell was a keystroke away, before every UI interaction was beautifully animated, before we measured even the tiniest of hard drives in gigabytes, before collaborative multi-tasking and protected memory. When using the computer was new and exhilarating. When the Mac was more than just tool – when it was an escape to another realm of existence. Those were the days when a little boy, without coming anywhere close to realizing it, laid the groundwork for all the wonderfully fun things he’d get to do years later as a man. I learned way more from my Mac than school ever gave me.

Thanks for the memories, Apple.

The app even won Best Design at LAUNCH 2011.

I was wrong. I got another, more personal email a week later.

And another – right after Nokia announced they were dropping MeeGo for Windows Phone 7. This was more than I could take. With that vote of no confidence, who would be crazy enough to invest in Intel’s non-existent platform? I responded:

I know you’re doing your job, but it’s not going to happen. Intel lost in mobile. Sorry. Putting my money behind horses who have a real chance. Thanks and good luck.

I put it out of my mind. Later that day, though, my persistent friend gave me one last push:

…If history repeats itself, it will be open architecture systems and industries that will eventually dominate. It’s only a question of when. ( I think soon.) Think of where the PC market was in the early days when there was still multiple proprietary solutions competing for the market space of the home computer user.  The IBM standard eventually dominated the larger market.

Even if I bought into this (I don’t), wouldn’t Android be the horse to bet on? It’s open. It’s actually in shipping products. It actually has users, right now, today.

I believe that history will repeat itself.

So, this guy, and by extension, Intel, believes that fate will grant Intel perpetual reign over all things computing, despite the fact that they can’t produce a mobile processor anyone wants to use in best-selling products? Despite the fact that they’re late to the party with their self-serving OS?  Despite the fact that MeeGo, by all accounts, kind of sucks?

Okay, I guess history is just going to repeat itself. Because they want it to. It’s like they’ve been reading The Secret or something.

This is a ground floor opportunity akin to purchasing a stock just before it goes up in value.

As if my bullshit detector weren’t already burying the needle.

Keep idly watching this space (open architecture mobile computing) and you will miss the train. Intel is leveraging all it’s 30 years of OEM relationships. The number of distribution channels contained in this network is going to be staggering. It’s not one store or one manufacturer.  This is the democratization of mobile computing.

I think the only one who has missed the train here is Intel. They’ve been idly watching mobile while ARM quietly cleans their clock.

Moreover, even Google has struggled to nail down successful, paid distribution. Intel thinks it can succeed by encouraging the creation of several channels? It’s like they don’t even bother studying what works and why. Apple is ruling the day by getting 100 million accounts all in one database and giving the keys for one-click buying to anyone who wants to come over. Several fragmented channels is not the way to match their power.

That’s my story and I’m sticking to it.

Translated: Intel is delusional and they’re paying me to repeat their fever dreams.

The mobile computer market is nearing a similar democratizing event horizon as the PC market did 25 years ago.  Throughout 2011 Intel chips will turn up in 35 tablets from 15 brands!

How many units are going to be sold of all these many tablets? 15 brands and 35 tablets? Really? Why not just two, really, really good ones? Sounds like a recipe for an instantly fragmented market from a hardware perspective, too.

He ended by encouraging me to hop on the phone with a program manager to learn more. I haven’t taken him up on it.

Now, many of us have been in an room listening to marketing spin a tale of bullshit (“narrative”) to share with outsiders. Maybe Intel knows it’s full of it, right? I’m not so sure. I think decades of being the Processor King has genuinely convinced them that their success is inevitable.

I think they’re wrong. The game has changed. They haven’t.

If you need more detail, here’s the deal.

Once, when I was 17, I picked up a girl and took her out on what I hoped was a date (in case you’re wondering, it wasn’t). About ten minutes into the evening, as we drove down the highway, a police officer pulled us over.

I was speeding. 10 MPH over the limit.

It cost me $134.

Being 17, the lesson I learned wasn’t “Hey, maybe I shouldn’t speed.” Instead, I decided “I need to figure out how to get away with it next time.”

And I did. Reading many sources, talking to a cop who worked with me at Best Buy, and trying things out later, I figured out what to do. In the eight years since my first ticket, no one has given me another one. It helps I don’t drive like an idiot anymore. But even the best drivers can lose track of the speed limit.

The following guide assumes that you’ve been pulled over by the police and the maximum extent of your crime is a traffic infraction. Maybe your stop could have been more complete, maybe you lost track of your speed. This may not help you if you’ve done anything worse than that. Driving drunk? Got some pot in your car? Illegal weapons? Involved in anything else that the police won’t be impressed with? If any of those is a yes, this probably isn’t the guide for you.

Let’s also be clear: I am not a lawyer and the following is not legal advice.

Still with me? Okay, you’re otherwise law-abiding but you did something naughty in traffic and the police noticed:

Take a Deep Breath

You’re about to enter a situation with a distinct asymmetry of power. If you’re not used to that, you might be nervous or intimidated. Don’t be. In the grand scheme of things, you’ve done very little wrong. Take a very deep breath, relax and gather yourself.

Regardless of how lopsided this interaction is going to be, remember one thing: the police officer is a human being, just like you. Your cop might be mean, might be nice, might be a mom, might be nuts about astronomy, might be going through a divorce. Each is their own person, so discard your preconceptions and do your best to understand the challenges they’re facing.

Pick a Safe Place to Pull Over

The police want to talk to you. They’re going to need a few minutes to do it. Make sure you give them a good spot to work with. If you put them in a place where they’re on edge because of unsafe traffic conditions, you’re already on their shitlist.

Surrender

Being a cop is hard, scary shit. They don’t know if you’re speeding because you’re oblivious or because you’re on the run. As an officer emerges from their car, they have to prepare themselves for trouble. You could be a desperate criminal, ready to kill or maim them to secure your own freedom. Imagine it from their perspective: this is not a fun moment for you but it’s worse for them because they have a lot more uncertainty to grapple with. At least you know what’s about to happen.

Roll down every automatic window in your car. Especially if you have tinted windows, this lets the police see exactly what’s going on inside the vehicle. A backpack, an In-N-Out cup, a water bottle, say. Okay. No big deal. Not scary. Much better than a dufflebag full of drugs, a weapon, or worst of all, an unexpected group of armed bad guys.

You have nothing to hide, so show instead of tell.

As the police approach, make sure you and your passengers rest their hands on the rim of the car’s windows, in plain view of the police. If they can see your hands from several feet away, you’ve spared them several seconds of adrenal windup. They’re more likely to be relaxed, which means they’re more likely to be friendly.

Turn off your car. For bonus points, place your keys on the dash. A car can be a dreadful weapon all on its own.

The goal during the approach is to make sure your cop knows that there is absolutely no reason to be tense or concerned about what’s about to happen. You’re harmless.

Now it’s time to talk.

Don’t Be an Asshole

Remember you’re about to talk to someone who has one of the hardest, most thankless jobs in the world. You enter the conversation worried about points on your license and paying a ticket. They’re worried about never seeing their families again.

Keep your hands on your window ledge and greet the officer as they approach. A cheerful “Good evening, officer” is all you need. Do not be terse, do not be curt, do not be rude. Just say hi.

Follow the officer’s lead. If they want to talk to you about why they pulled you over, they will. You’ll get nowhere by being demandy about the reason. Many times, they’ll just start by asking you for your papers – “license and registration.” Sometimes they want to see insurance instead of registration. I don’t know what influences this. Wherever the conversation goes, be polite and courteous. Show, through your behavior, you’re just a normal person who missed a road sign.

If asked why you’re behaving this way, tell the truth: “You have a hard job, officer. I do, too, so I’m just doing my best to make this easy on you.” Cops deal with a lot of inconsiderate people, so you don’t have to do much to stand out.

It’s very likely that you’re going to have to reach into your pocket or the glove box to comply with an officer’s requests. Announce your intention to do this before moving your hand. “If it’s all right with you, I’m going to move my right hand to the glovebox. My registration is in there.”

While one hand digs around, keep the other firmly planted on the steering wheel, in clear view. After you’ve retrieved whatever you were asked for, hand it over slowly and make sure your hands return to the dashboard or the window ledge. If you forget, your cop will remind you.

The police may ask you if you know why you were pulled over. Many people will tell you that it’s in your interest to play dumb here. I don’t work that way.

See, I don’t like to lie. It’s a pain in the ass. When, for example, two Texas Highway Patrolmen pulled me over a few summers ago, I knew why I was speeding. When asked, I told them.

“I’ll be honest with you, gentlemen. There was a feedlot back there. Thousands of cows! It smelled terrible, honestly. So yeah, I hit the gas because it was making me ill and I needed to get out of there.”

So yes, I waived my fifth amendment right not to incriminate myself. I also made myself a human being. By being direct and honest about what’s going on, I’m hopefully sticking out as different from the sort of person they would usually ticket.

After a conversation, they sent me on my way with a warning. Let’s be clear: I’m hispanic. I didn’t look even remotely like the guys who pulled me over. I was about as thoroughly other as you can get while still speaking english. But I was considerate of the the patrolmen, I talked to them like human beings and they returned the favor by not screwing me with a ticket. I even pitched one of them on the company I was working for at the time.

A little empathy can go a long way. This has application in many other interactions unrelated to traffic violations or law enforcement, but I learned it here first thanks to the financial incentives involved.

We’re profitable, and we’re looking to hire a smart all-around programmer as our first hire. It’s a cliche, but we want people who like tackling complicated problems.

…

Depending on the task, we program in Ruby (on Rails), Javascript (a lot of this), PHP, Python, Objective-C (iPhone), and Java (Android). Flexibility is a plus.

…we like people who don’t put themselves in a box. You should be comfortable thinking about the product as a whole, and how changes are going to impact the hundreds of thousands of people who use it regularly.

…

We’re profitable, make the lives of hundreds of thousands of people better every month, have a rapidly expanding user base, and napping is an encouraged part of our corporate culture.

…

Basically, you’ll get to be the first employee of a small successful startup, while getting a paycheck and equity, and feeling good about the impact you’re having on the world.

It’s so clear. I know what kind of person they’re looking for, I know what’s special about their company, I can start to picture what it would be like to work there. Without having to say much about their people or product, I can tell one thing right away: these are not bozos.

There are no buzzwords, no vague claims about the company, nothing unclear about the kind of person they’re looking for. These are the kind of people you would feel comfortable working with because they’re direct and human.

And hey, did you notice they’re profitable?

It’s a good pitch because within the confines of their stealth approach, it tells you everything you’d want to know without handwaving or hyperbole. For respecting your intelligence, it stands out. It builds confidence.

This is a rarity in tech companies. Other job postings are not so clear. Try this one:

The Front-End Architect will be a senior and leading member of the [Product name] development team and will be responsible for driving innovative consumer applications. The FE Architect will help make technology decisions, lead, design/architect, implement and mentor.

I just picked this one at random off of craigslist. It was the first one I clicked. How can you be both senior and leading? What does it mean to drive an innovative consumer app? What makes it innovative? What will they lead, what will they architect? Of course, it wouldn’t be a bullshit job posting without some poor bastard having to “implement” something.

These people have no idea what problem their hiring is supposed to solve.

Job postings are a great window into a company. They show you just how much clear thinking is demanded  along with how well people communicate. Those are two important factors for working with other people. What about more consciously public communications?

Let’s turn to the granddaddy of software development:

Windows Phone 7: A Fresh Start for the Smartphone

The Phone Delivers a New User Experience by Integrating the Things Users Really Want to Do, Creating a Balance Between Getting Work Done and Having Fun

That’s a headline and sub-head from a press release. (Thanks, DF)

What the hell does any of it mean? What do users really want to do? Absent Robbie Bach and J. Allard, I don’t trust the word “fun” anywhere in a new product announcement from Microsoft, either. They probably mean an optional Comic Sans UI.

Maybe they’re going to clarify in the first paragraph. I’m just being a dick with their opener, I’m sure.

The goal for Microsoft’s latest smartphone is an ambitious one: to deliver a phone that truly integrates the things people really want to do, puts those things right in front of them, and either lets them get finished quickly or immerses them in the experience they were seeking.

I’m missing the ambition here. It sounds like their goal is to create a hierarchical mobile user experience optimized for short bursts of interaction.

Which is what everyone else does.

They haven’t described anything that sounds even remotely like a “fresh start for the smartphone.” What they’ve got is a fresh start for Windows Mobile that brings it up to par with the last three years of mobile OS evolution. By all accounts, they’ve succeeded.

Also, what the hell have they actually built?

The much more interesting story here would be owning the fact that they fell behind, then dug in deep, then, wonder of wonders, finally met a ship date. I’m sure it wasn’t a small undertaking. But they want to convince me they, unique among all companies, have rebooted the smartphone concept.

Contrast that with Google, who, the other day, genuinely unveiled a chunk of the future:

We have developed technology for cars that can drive themselves.

Damn. Really?

Our automated cars use video cameras, radar sensors and a laser range finder to “see” other traffic, as well as detailed maps (which we collect using manually driven vehicles) to navigate the road ahead.

Nothing vague about that. It sounds like something out of science fiction. You could call your mom, read that to her, and she’d understand exactly what’s going on, maybe even share your excitement.

Who inspires more confidence: the bullshitters or the straight-talkers? The problem with bullshitters is that they start convincing themselves that this is genuinely how people talk. They bullshit themselves. They lose the ability to communicate with any sort of clarity, making up for it in volume of words.

The best people respond to authentic communication. The best conversations form around genuine excitement from concrete performance. Clarity inspires confidence.

The big, suit-choked, sales-oriented, PR spinmonkey companies are a lost cause. There’s no reaching them. But you and me, we have a shot. Resist the siren song of saying words that mean nothing.

Look how much more powerful it is to be a real person.

“What if we committed to overhauling our culture so that the customer always, always, always came first in our processes and our perceptions? Then people would stop falling through the cracks and getting pissed off on the internet. And word of mouth would get even bigger for us!”

Everyone looked at me like I was an alien.

Sometimes it’s delivered with a sneer, other times exhaustion, and occasionally, there’s even contempt:

“That’s idealistic.”

Ideals, it seems, are academic contrivances that hinder How Real Business Gets Done.

I can’t escape my idealism. Sure, I’ve launched v1 before it was perfect, accepted a minor bug or two in a release, fine. But at no point have I ever sacrificed the core of the user experience to any other cause. User experience is the compass by which I judge every decision.

I configure my values this way because I’ve seen first hand how powerful it can be. Not just in software, in web applications, in innovative, industry-changing businesses…

But also: in dog grooming.

I got my idealism from my mom. Whatever town she’s in, she’s the best dog groomer there is. After years of working for stupid, short-sighted shops, she set her sights on a business of her own. With nothing more than a GED and her ideals, she renovated a space and got to work.

And thrived.

The biggest challenge to scaling her wildly successful business? Finding people who were skilled enough to match her quality of work or genuine love of animals. It was impossible.

My mom had two options: hire on people she knew weren’t up to her standards or stay the size she was. She wanted growth – who doesn’t? But she knew she couldn’t just hire crappy people. Her shop’s growing reputation was built entirely on her quality of work. People loved the idealism that inspired outrageous standards of hygiene for the facility. People whose dogs usually couldn’t stand going to the groomers suddenly lost their fear, because for the first time grooming meant being treated humanely.

Ideals had created differentiation. Bad people would destroy that progress. In the short term, yes, her bandwidth would increase and more dogs could come through the shop. In the long term? She’d be just another grooming shop with tepid business – or no business. The worst part of all, I know now: she wouldn’t be proud of her shop anymore.

So she chose secret option C: Open a grooming school.

In hindsight, of course, this is obvious. It wasn’t then. It was risky. It cost a lot of time and effort to get licensing to train. Putting together course materials and a curriculum is a very different skill set than grooming dogs. Shifting from spending all your time grooming to most of your time teaching? Very difficult.

But it worked.

The revenue from a steady stream of students smoothed out an otherwise highly cyclical business. The option to have dogs groomed by students opened the shop up to new clients who had been unable to afford the previous up-market rates. Constant oversight meant even inexperienced groomers were sweating the details and doing things right. Daily bandwidth increased dramatically with only a marginal impact on quality. Best of all, when a star pupil came through the program, they could be immediately recruited after they finished training.

There were hiccups – students could definitely botch their work at times, but the risk was baked into the price, so it didn’t harm reputation. Picky clients could opt out of the student work at the old rates, and many did. Overall, everyone was happy, including the many animal lovers who discovered how to make dogs part of their professional lives through grooming.

True to form, my mom found a way to have her cake and eat it, too: way more money without sacrificing the quality of her work.

None of this would have been possible had ideals not played a huge role in making decisions. Absent ideals, I’m not even sure she would have gone to work for herself.

I can’t escape my idealism. And I don’t want to. My ideals are a map to build trust, solve problems and, in some small way, make the world a better place. The only article of faith I have is that, with a bit of work, that map leads to success. And in the end, without my ideals, I couldn’t build software, or anything, and enjoy it.

There are limits. You can’t pay for a sandwich with a song. Idealism is not a business model. Idealism is a tool. It’s a fulcrum for making difficult decisions and your flashlight in the darkness of ambiguity. It helps you understand the success conditions for every move  you make.

I won’t stop putting the user first and neither should you. Next time someone dismisses your idealism, look very hard: an opportunity could be lurking across the bridge they won’t cross.

And I guess it’s true. I mean, consider:

There’s Blockbuster. Keeping a broad inventory is a lot of work and expense. It’s easier, and more favorable to revenue, to stock only the most popular stuff. Also, you can definitely make a ton of money by charging late fees.

Hmm. The only problem there is that Blockbuster just filed for bankruptcy.

Okay, okay, that’s fine. How about Comcast? Having installers permanently on the payroll is a pain in the ass – paid time off, benefits, training costs, ugh. Outsource that action, let someone else do the worrying instead. Sure, these techs won’t care about the company culture (such as it is), and since they get paid by the installation, they won’t care about conducting business in a way that leads to a long-term positive opinion of Comcast. There will be less oversight, so they might screw up in ways that are embarrassing. Time management could be challenging for these local outfits and people might be late for appointments… But – revenue!

I guess the wrinkle is that kind of thinking tarnished Comcast’s brand so severely, they had to change the name of their consumer service. Maybe customer perception had nothing to do with it – rebranding is fun and it can’t cost much, right? Any long-established brand would want to do it, eh? Maybe not so much.

Fine, how about Yahoo? They made a really great play – push the portal angle really hard, don’t focus too much on search. I mean, if search works too well, people won’t stay in the portal and then how can you monetize all these millions of eyeballs? Nah, display ads. That’s where it’s at. Sell banners by the boatload. Bulk up that ad sales team!

That only worked until the dot-com bust, though. Now Yahoo’s market capitalization is a tenth of its biggest competitor, Google.

So maybe dicking your users isn’t all it’s cracked up to be, assuming you want prosperity to continue more than the next few quarters.

What about being good to users? How does providing an outstanding user experience change things?

Turns out the iPad is the fastest-selling non-phone product. Despite the fact that, as shipped, the iPad couldn’t print, can’t use Flash, and doesn’t have a camera, people are buying it in droves. 4.5 million units sold in the first quarter it was available. Maybe “being hip” is suddenly important to the broad cross-section of consumers who are buying it, and they have been convinced that upwards of $500 is a fair price for the privilege. More likely, though, is that a focused, task-oriented, touch-based interaction scheme where no one nags you about software updates is more enjoyable and intuitive than a netbook.

Apple is one of the largest companies in the world. Their focus on the user is not limited to the iPad.

Then there’s Zappos. Their values include being good to everyone – customers, employees and vendors alike. Their website has been consistently great for exploring their inventory and making informed decisions about shoes before buying. High quality images, easy to use filtering, detail-packed user reviews, all of it conspires to make purchasing easy. When you get on the phone with their customer service folks, you’ll find people empowered to help without rushing you back off the phone. They’ve long refused to outsource any activity that’s core to their business, including customer service and their fulfillment operations. They want to make sure these user-facing elements of their business are air-tight. This isn’t cheap.

Neither is the billion dollars Amazon spent to buy Zappos last year.

Then there’s Google. Say what you want about their creepy ways, Google revolutionized search. They made it work extraordinarily well, made it focused and made it fast. They’ve invested huge amounts of money on infrastructure to make sure their service is as snappy as possible. Instead of display ads, which would have been the easy but user hostile approach to making money from their traffic, Google borrowed Overture’s Pay-Per-Click advertising model. Paid search ads are perhaps the only form of genuinely useful ads for the user. They can actually solve the problem of your search.

At their IPO, Google shares could be had for around $85, already a respectable price. Today, they fetch over $500.

Creating a good user experience is important. It builds goodwill between your company and your users, yes. But much more importantly, it compels you to make a better product. Constantly re-evaluating your product for the benefit of its users future proofs your business. Look at Netflix, busy obsoleting itself by pioneering living room streaming. When you care about doing things well, your business moves at pace that’s very difficult to overtake. You’re a moving target and your products become much harder to compete with.

So can you dick over your users to goose your revenues? Absolutely. There’s a lot of short term juice in alienating the people you need most. Unfortunately, money is an addicting, distracting force. Before you know it, you’ll be dependent on the cash your user hostile approach to product requires. Ask Yahoo.

Anyone playing the long term game should approach the problem differently. Do it right and you’ve got the potential for a billion dollar business. Even if you never get there, gushing praise from your users is a lot more fun, and profitable, than simmering rage.

They really, truly give a damn about something.

It’s important to calibrate what I mean about this. Being a stickler about Star Trek trivia, parts of speech or state capitals doesn’t count. Affinity for political knee-jerk doesn’t qualify, either.

Giving a damn is about sacrifice and investment. It’s paying with something precious in the service of something you really, truly value.

My favorite leaders, consistently, gave a damn about good leadership. Years ago, during my college internship, I’d stroll into my boss’s office, politely interrupt whatever the hell it was he was doing, and have a conversation. This guy was the director of the department, working on a Master’s degree on the side, and was the busiest guy I’d ever met. But as long as nothing was on fire, he’d give me half an hour to answer my questions about anything. I figured out much later that the reason he did this was that he gave a damn about leadership and helping people grow.

This isn’t something you can half ass. Either you really, trully give a damn about leadership – or you’re just another one of those bosses.

Leadership is a universal one, but this works with anything. I’d rather hire someone green who truly gives a damn about the work than someone with both experience and apathy. Many things can be taught – giving a damn is not one of them.

It goes beyond picking your team or picking your boss, though. The very best companies, large and small prove that they give a damn, too.

In Delivering Happiness, Tony Hsieh explains that Zappos treats their customer service as a marketing expense to be padded instead of an operational expense to be reduced. It’s a very Keanu “whoa” moment when you ponder that. It flips everything around in your head – while being so entirely correct, you can’t imagine anything different. Organizationally, Zappos gives a damn about doing the right thing for people and backs this up with a significant investment.

Down the road from where I live, an immigrant family owns the best damned Chinese restaurant on earth. The food is consistently delicious, but it doesn’t end there. I’m greeted warmly, my picky custom orders are delivered with fastidious accuracy, and every meal is accompanied by a free appetizer or some on-the-house ice cream. These guys truly give a damn about creating an enjoyable restaurant.

If being a good boss is giving a damn about leadership and running a great business is giving a damn about customer service, what about great software?

Great software boils down to giving a damn about user experience. Take a look at your browser history. How much horseshit do you have going on in your digital life? Web applications take the cake for shameless apathy. When an exception turns up – when someone, miraculously, gives a damn about making their software work well, it’s a special moment.

Hipmunk is just such a miracle. Look at this homepage:

The text fields are huge, meaty, clearly-labeled things. Easy to find and click on. Instead of being relegated to a forgotten sidebar, the search activity itself is the focal point of the page. There are no distracting promotions or other crap you don’t care about. “You’re here to search for your flight, so let’s make it happen!” cries Hipmunk, grabbing you by the cheeks and shoving you into search land. Want to leave tomorrow? Type “tomorrow” into the date field.

For reference, let’s compare to another site.

Look at that shit!

From the two examples, which app gives more of a damn about helping you find your flight?

Travelocity can’t even be bothered to make their time of day dropdown fit the default selection.

Meanwhile: Hipmunk’s outstanding search results interface.

There is a sort option called agony. It’s the default. Hipmunk’s creators thought a moment and realized that lengthy flights and layovers are an important detail to make clear from the beginning. The layout lets you see a timeline for your flight date, letting you quickly understand when you’re leaving and when you’re arriving in local time. It’s also a great way to visually compare the lengths of multiple flights. These guys… well, you know what I’m going to say.

No matter what you’re doing, giving a damn matters. The things you do that you don’t give a damn about, I guarantee you’re doing poorly. You can’t give a damn about everything, but please, I beg you, find at least one thing.

And if you do give a damn: I cannot wait to meet you, work with you, be your customer or use your software.

Developing for the desktop has been fun and an interesting change of pace from iPhone development. A full post-mortem is on the way.

In the mean time, it’s a great feeling to add a bit of OS X freeware to the world.