An addicted insider’s account of our real lives in the era of the realtime, social web.

Confession #115: Remembering Jody Sherman

Jody never took a call by saying “Hello.” He always answered by barking his own name into the phone: “Jody.” As if that voice could have belonged anyone else. He was often in a hurry. There was always something big just about to happen.

During the height of the first Internet boom, I visited Jody when he was running business development for another fast-rising company in San Francisco. He was dressed in a suit, spoke fast as he showed off his office, and said the word “billions” a few times. After I received the opening monologue on how huge this latest endeavor would be, Jody pulled out a fistful of gaming tokens. The office was right across the street from an arcade at Pier 39. “Here’s a bunch of tokens. Anytime you want to play, just stop by office first. I’ve got a drawer filled with these.”

That was Jody. A hyperactive kid in a business suit who wanted to have fun while convincing everyone of how epic and unprecedented this was all going to be.

I was once on the phone with Jody as he was giving me turn-by-turn directions to his apartment. As I got close, Jody interrupted himself: “Sorry dude, I’ve got to take this call.” I just kept driving for five minutes until he came back on the line and asked me where I was. “Oh dude, you went way too far, you’ve got to turn around.” That was Jody. He was the GPS that guided you. He was the call-waiting that interrupted you. You didn’t quite know where he was leading, but for some reason, you couldn’t help but follow. There was something about hearing, “Jody” on the other end of that line.

Jody was ambitious and loyal. He was entertaining as hell. And he was always a little crazy. As the Internet grew up, it spawned a lot of big personalities. But Jody always remained one of the biggest. He made this place a little more unpredictable and a little more fun, and he was a really good guy. He loved to talk. He loved to talk big. It’s hard to explain, but if you knew Jody Sherman you’ll know what I mean by this: He was memorable in the moment. Whenever you were talking to him, you knew the conversation itself would become an anecdote. “I just talked to Jody, you’ll never believe the hilarious thing he said this time…”

Jody made the Internet business feel like Hollywood. He was the fast talking agent, the producer with the big plans, and the guy in the box office window begging you to buy a ticket and a bucket of popcorn. When the lights went down, you’d realize that Jody also played many of the characters in the movie. I suppose now we know that when the movie would end and the theater would empty, Jody would often remain in this world of his creation, alone in the darkness.

Like everyone who knew him, I was shocked to hear of his death. I wanted to know what happened. I wanted to know how a guy who was such an energetic force could be gone. I wanted to ask a billion questions. But in that moment, I found that just one word came out of my mouth: Jody.

Confession #114: The Answer is Just a Click Away

About twenty people walked into the room, sat down and slid their phones, iPads, and other devices towards the center of the table. It was the last session of the conference and the rules were simple. We would work our way around the table twice. On the first pass, each person was required to name one obstacle to achieving balance in their life. On the second pass, each person would identify one thing that has seemed to help them overcome that obstacle. In the end, we would leave the room with a new understanding of the problems we face and new set of tools with which to overcome them.

These were the Type A personalities. The always-on crowd. They ran companies or led big teams. Most of them were at the top of of their professional game. By any standard of modern success, these folks were the achievers. They had the kinds of roles, careers, and lives where you get to maintain some control, to decide how to spend your time, to sit back — every now and then — and figure out your priorties.

One by one, each person described an obstacle. I need to manage my team more effectively. I need to make more efficient use of my time. I need to spend more time connecting with my kids before they’re too old to need me. While the themes were varied, the obstacles really weren’t. In each case, the key obstacle being described was resting on the table, for a rare moment, just beyond arm’s reach.

Everyone was basically complaining about technology.

I need to turn off once in awhile. I work with people all over the world, so there’s always someone online who’s ready to collaborate. My email inbox has become so cluttered that I spend more time managing it than the rest of my life. I’m distracted all the time. I’m never fully present when I’m with my family. Even when I know I should be taking a break, I feel the vibrating phone in my pocket and I get sucked back in.

Then came the second pass around the table. One by one, people described their solution — the fix they had found that made it a little easier to overcome the obstacle between their current life and a balanced one.

The first remedy mentioned was a company-wide software solution that enabled a manager to keep better track of ongoing projects. The next was a personal productivity app. Then someone described a strategy to fill the time wasted on a morning walk by working through a list of phone calls that had to be returned.

Like the obstacles, the solutions all had one thing in common: They were all technology.

It was like listening to a bunch of people explain how they used heroin to kick their methadone habit.

Technology used to be a way to solve life’s little problems. Now, technology is used to solve the little problems caused by technology. On some level, we know that doesn’t make sense, but we don’t have an app to convince us. Where’s the computer algorithm to prove that the quiet walk without the phone calls is the balance?

When it comes to our physical health, we often find ourselves popping new pills to ease the side-effects of the ones were already taking. Then the new pills have their own side-effects. It can be a neverending loop. But at least there is some evidence that the drugs can heal the original malady.

Being more connected can’t cure us of being too connected. Being more wired can’t make us less wired. Using one more app will never equal using one less app. There just isn’t an app for that.

The idea that we need a technological solution for too much technology is, at best, the Internet era’s great placebo effect. We feel like we’re getting a little better, but that’s just part of the same addiction. We’ll always be just one more piece of technology away from the solution.

We are at the early stages of the information revolution. We will become more connected, more wired, and more distracted. There’s no turning back at this point. And believe me, I’m right there with everyone who sat around that table. As you read this, I’ll be watching my stats and tracking Twitter mentions. The number of browser tabs I have open grows faster than the national debt. When I fly on a plane with no Wi-Fi (the horror, the horror), I’ve usually switched out of airplane mode and checked email and five other apps by the time the wheels hit the tarmac — even if I’ve just landed on a tropical island for a family trip and it’s the weekend. I’m in no position to tell anyone to quit technology. But I am convinced we can make better choices about the way we navigate this era.

And ironically I think I found one potential route while we were all sitting around a table during that conference session. Even though no one noticed it, everyone found, for a little while, some balance in their lives. We put down our devices. We closed our laptops. For a good hour, we just talked, face to face. And we all left the session feeling a lot better than we did when we came in.

We found the solution for technology overload. We turned it off. Who knew that a balanced life was just a click away?

Confession #113: Get Off My Stoop

When news of the unthinkable comes, we all head for the front stoop. Today, that stoop is virtual, and the digital neighbors with whom we share the news of the moment communicate with us via tweets, status updates, and hastily-tapped texts. We whisper in ears, we shout towards rooftops, we tell each other what we think and feel, and what we’ve heard.

Did you hear the shooter’s name was Ryan? Isn’t it shocking that his mother worked at the school where the shootings took place? Can you believe that she was the teacher in the classroom where all those kids were killed?

Things get emotional on that stoop. Guesses become facts. Hunches become certainties. Details are shared with such adamance that they are accompanied by proclamations of their broader meaning in the grand scheme of things. We’re well on to metaphors before we know what actually happened.

It’s always been that way out here on the stoop. We need a place to be together now and we can worry about being right later. Our digital gathering is more crowded than its analog precursor, but it’s still, at the core, the same basic conversation. We know the rules. It’s not a newsroom. It’s not the whole story. We inherently get that all the supposed facts and assumed truths delivered in this forum and in the heat of the moment should be taken with a grain (if not a pillar) of salt.

Historically, we’ve expected that once the din of theories, hypotheses, and manufactured realities had quieted, we could count on getting the real story (or at least part of it) when we heard the thump of the morning paper landing at the foot of that stoop. But these days, the thumping starts right away. Instead of patiently correcting the mistakes and hearsay understandably spewed by the emotion-filled masses, the mainstream media has joined the fray. The thump no longer clarifies, it obscures.

This is the shooter’s name. Thump. His mother worked at the elementary school. Thump. She was the teacher in that classroom where are those poor kids were killed. Thump. Thump. Thump.

As you’d expect, the various bits of false details about the Newtown shootings spread rapidly throughout our virtual front stoop. But they didn’t originate there. These “facts” were coming from (or at least being repeated by) the media sources most of us have come to trust the most. Instead of correcting our hyperactive distortions, the mainstream media added to them by mimicking the haste and inaccuracy of social media. The wildfire of burning inaccuracies needed to be doused by a pail of water. Instead we got a bucket of gasoline.

We’ve seen this trend coming. Gabrielle Giffords was prematurely pronounced dead after being shot in Arizona. Both CNN and Fox got the Supreme Court’s ruling on health care’s individual mandate exactly wrong. The standards once applied to reporting are now often reserved for correction writing.

While these mistakes were symptoms of the same disease — the mainstream media’s race to keep pace with the digital conversation — they were more understandable than what we saw in the Newtown coverage. When a member of Congress is shot, the lede will be whether or not she survived. The headline in a Supreme Court story needs to contain news of what they decided.

In the case of Newtown, we already knew the basic facts. The brutal and unforgettable lede was already written. If you tell me that a lunatic killed twenty kids in an elementary school, that gives me enough to process for a while. I can wait a few minutes or a few hours (or even a few days) to learn about the details about the shooter’s psyche or his relationship with his deceased mother. But these days, it seems, no one producing news can wait.

But someone has to wait. Little value for journalists or their readership is created in the race to be first. We need a media that races to be right. We expect the news to be the first rough draft of history. But it can’t be this rough. In an era of accelerating and always-on information moving at the speed of Twitter, where clarity and accuracy are the rare exceptions, we find ourselves counting on news professionals more than ever. The job is critical. But it can’t be accomplished unless journalists rise above the din instead of getting sucked into it. They need to get off our stoop.


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Confession #112: Screen Rage

At five years-old, it’s no fun getting interrupted while you’re focused on something. As a parent, I compensate for that by employing a series of intricately planned measures to guide my son from whatever he happens to be doing towards whatever it is that I want him to do instead.

The extremity of these measures depends entirely what’s being interrupted. If he’s playing outside with his sister, the steps I take are fairly mundane. I give him a few, gentle time checks (“five minutes until dinner” … “3 minutes until dinner” …), and then offer something enticing enough to make putting down the ball seem like less of an intrusion (“Tonight’s chicken has both teri and yaki on it!”).

If I need to transition my son from building a cardboard village with grandma to going to bed for the night, I need to combine my time checks with some subtle threats and an Obi Wan Kenobi-like response to his three hundred or so repetitions of some variation of, “No. I don’t want to. But you said. Why are you doing this to me?”

The techniques are all pretty simple and effective. Until it’s time to get him to put down the iPad.

The time checks, subtle threats, and feeble attempts at reasoned parenting are useless. You don’t bring a knife to a gunfight, and you don’t bring traditional parenting strategies to a fight to wrestle a possessed child back from a retina-display, 3.1 million pixel, demonic poltergeist.

Anyone who’s been within a thousand miles of one can tell you… There is no tantrum like a Put-Down-the-iPad Tantrum.

First I need to prepare. I put on my hazmat suit, helmet, and thick, dark goggles to make it less likely that I too will be pulled into the light. Any parent of an iPad-era child will be familiar with the other tools in my arsenal: Ear plugs, body padding, iron manacles, shock paddles, a straight jacket, an inflatable kayak (speaking in tongues while the head spins exorcist-like 360s can release a significant amount of saliva), WiFi jammers, tear gas, tasers; and for re-entry, candles, classical music, smelling salts, and several black and white paper printouts of familiar places and loved ones.

And even with all that, I give myself about a 50% shot of bringing my son’s attention back to the terrestrial world before the iPad battery runs out.

Of course, as in most cases, our kids are simply modeling our behavior. Having a disproportionately enraged reaction to being interrupted during screen-time is a characteristic that’s hardly limited to five year-olds. I regularly find myself snapping at my kids or feeling overly irritated with adults when faced with the seemingly simple demand that I drag my gaze away from my screen when I’m in the middle of something (anything really). And since I’m always-on, and my screen provides access to so much of what I do – work, social life, leisure time, writing this article – I’m permanently  in the middle of something. My son was born around the time of the original iPhone. So I’ve been asking him to “Just give me a second” for his whole life.

It’s not just that we’re often distracted. It’s the short-fused anger that bubbles up when life pulls us away from our screens. Sadly, it might not be that surprising to see a technology addict in this state of mind. But the same behavior often surfaces among folks who are recent smartphone converts. I’ve seen people who have historically maintained a swami-like calmness to their demeanor snap angrily at someone who interrupts them when they’re focused on their new screen.

Even for the formerly ascetic, it’s a slippery slope. Om … Om … Om … OMG!

Wanting to focus and being irritated by distractions and interruptions is nothing new. I’m sure my dad missed a few of my childhood moments while he was at the office. But now the office is seamlessly connected to games, music, texting, email, social networking, entertainment, and everything else. The hierarchy of things worthy of earning our focus has largely collapsed. If it glows, it’s worthy. The screen doesn’t care what you’re doing. I see modern parents miss childhood moments while they’re playing Words with Friends. “Just give me a second…”

In a way, staring at a screen is lot like being alone in your car. When someone cuts you off, you adopt a totally different personality; one defined by urgency and often explosive anger. No one can hear you scream as you speed down the highway with the music blaring and windows rolled up.

Screen rage is the new road rage. Except everyone can hear you scream.

These days, about the only thing that’s more frustrating than being interrupted while we’re interacting with our screens is trying to get the attention of someone else who’s interacting with theirs. Maybe this occasional glimpse into the digital mirror gives us hope that there’s a light at the end of the tantrum tunnel.

Of course, that light could just be coming from another screen.

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Confession #111: They Know You’re Reading This

I was recently complaining to a teller at my bank that the another bank down the street had given my 3 year-old daughter a stuffed horse for nothing more than walking past the front door. I jokingly asked her what gifts my own bank would be willing to offer to compete for the affections of my daughter. Then I said, “Oh, you probably don’t like it when I mention the competition when I’m in here, eh?”

She surprised me with her answer. She said that she had her checking and savings accounts at that competing bank and that she’s always found their service to be great. I was surprised. Why would a teller at one bank do her own personal banking at another bank down the street?

She told me that most of the tellers she works with have their accounts elsewhere because they don’t want friends and colleagues at their own bank to have access to their private information.

The exchange was a clear reminder that privacy issues are everywhere. Anytime you share any information with anyone or any institution, you should expect it to be shared in ways you never expected.

This week, the top story in the Internet world was that the mobile social network Path had been uploading users’ email contact lists to its servers. The purpose of the upload was to make it more likely that users would find friends and colleagues who were also on Path. The problem was that Path was uploading the email data to its servers without users knowing it. A firestorm of criticism erupted. And within a day or so, Path responded by putting a stop to the offending practice and deleting every email address they had collected.

Path deserves credit for the swift and appropriate response to the criticism it faced. But the whole incident was one more reminder that almost everything you do on the Internet puts a dent in your personal privacy, whether you’re aware of it or not.

When I first heard about Path’s plan to delete all the email addresses it had collected, I wondered if Facebook would respond by agreeing to delete those embarrassing photos from 2006 that you already manually deleted 6 times in the past. As it is now, the photos you delete from Facebook never really get deleted. They’re still accessible via direct link (and of course, by anyone at Facebook who has access to the data). Once you put something on the Internet, you should assume it will be somewhere out there forever.

Maybe that’s no big deal when were talking about a few collegiate kegstand photos that you’d rather forget. But it is a big deal when you consider that almost everything you do or share on the Internet is being tracked by someone.

The Path story got big because it’s exceptional in two ways. First, thanks to one guy who wrote a blog post, we all were made aware that Path had a policy of borrowing your email contacts without your consent (and that iPhone apps easily allow for such a transgression). And second, when confronted with valid complants, Path acted swiftly to change its policy and right its former wrongs.

There’s nothing all that exceptional about the notion that your data is being collected and saved, and that just about every click you make and every piece of data you share is being tracked by Internet companies and the marketers who pay their bills. Companies like Facebook are so valuable precisely because of the effectiveness with which they transgress your privacy and piece together a portait of you that can be sold to advertisers.

Pennsylvania professor Joseph Turow explains how you’re tracked in the modern world.

Websites, advertisers, and a panoply of other companies are continuously assessing the activities, intentions, and backgrounds of virtually everyone online; even our social relationships and comments are being carefully and continuously analyzed. In broader and broader ways, computer-generated conclusions about who we are affect the media content — the streams of commercial messages, discount offers, information, news, and entertainment — each of us confronts. Over the next few decades the business logic that drives these tailored activities will transform the ways we see ourselves, those around us, and the world at large. Governments too may be able to use marketers’ technology and data to influence what we see and hear.

They are watching. And they know you’re reading this right now.

And it’s not like you can just go offline and avoid the tracking. If you get a postcard advertising a lung cancer screening from your local hospital, it’s not by coincidence. Everything about the offline you is being shared across corporations as well. In the age of data mining, it just takes a few clicks to piece together enough information about your age, address, income, and insurance status to figure out if you’re a likely smoker and therefore a good target for a lung screening pitch.

I have a friend who used to fill out nearly every online and offline form with a different title (Mr, Mrs, Dr, prince, king…). Then over time, he tracked the mailings that came to him with those various titles attached. Over time, he could easily track who sold what information to whom.

Today, it wouldn’t even make sense to try to keep up. We share our data with everyone and everyone is sharing our data with everyone else.

It’s worth putting this Path story into this broader perspective and reminding ourselves that we are only at the tip of personal data mining iceberg. By the time my 3 year-old daughter is my age, she might walk into her bank and have the teller ask: “Hey, didn’t we give you a stuffed horse back in 2012?”

Confession #110: Kitties, Komen and The New Editor of Mainstream News

There’s a new editor in chief of mainstream news.


About a year ago I was putting the final touches on an article for a major media outlet. I honed, I proof-read, I tweaked. My self-absorbed goal was to have to the most popular item on this big media site for at least a few hours, and based on the topic and content, I really thought I had a shot. And then, minutes after my piece was published, the site’s editors put up a story about baby panthers.

And just like that, it was over.

There are a few rules that hold true even in this ever changing media landscape and one of them is that no one beats a good kitty story. While story placement and promotion matter, readers have a big part in determining which stories will rise to the top of the most popular lists on news sites. As a rule of thumb, editors choose the top stories while the reading public decides which stories will be the most popular by way of their shares, Tweets, Likes, and the like. Editors decide what to cover. The public decides what to read and share.

But I have a feeling the public is getting a promotion. In two major cases, conversations historically reserved for editorial meeting rooms have been extended to the social web.

First, there was the challenge to the Stop Online Privacy Act as it moved through Congress. Several major Internet organizations joined in a coordinated effort to bring the negative aspects of SOPA to the attention of the general public. Big sites either went totally black or at least supported the cause with prominent links to information on the subject. The media dramatically boosted coverage of the story. And in a very short time, public and organizational pressure forced the political backers of SOPA to fold. When was the last time a large swath of the American public even knew the contents of a bill before Congress?

This week we’ve seen an even more powerful shift. There was no coordinated organizational effort. But thousands of voices on the Internet still managed to organize in a way that drove the news. I write a daily newsletter in which I cover the top ten news stories of the day. As part of my daily routine, I visit about fifty top news sites multiple times a day. At the outset, the story about the Susan G. Komen Fund cutting its financial support of Planned Parenthood was covered, but it was not a major story on any of these sites. It was, however, a major story in my Twitter and Facebook streams. People were energized by the news and from the Komen Facebook wall to Twitter and blogs, they had an outlet to express that energy. Within a few hours, major media picked up on the surge of activity around the topic and it quickly moved to the top of front pages.

The story started small. The people decided it was major. Big media responded and gave the story more coverage. And within a day, we had a full-fledged media firestorm that was being driven from the bottom up.

At the height of the coverage, NBC’s Andrea Mitchell interviewed Komen founder Nancy Brinker. During the exchange, Mitchell explained that she was voicing the anger of many people and channeling the energy and ideas surfaced by thousands on Twitter.

That sounds like a pretty good way to decide what’s news.

SOPA and Komen represent a change in how we pick top stories. Even in an era of constant changes in the way we consume and share content, this is a remarkable moment in the history of news and public discourse.

There are of course risks to majority rule when it comes to what makes headlines. Sometimes the pace of the realtime Internet leads to the rapid and rabid spread of misinformation. Brands and individuals can witness the destruction of their reputations before anyone has a chance to see the facts through the fog of retweets.

But with the mainstream press and the Internet-enabled general public providing checks and balances, we might see a much improved process by which we all decide what should be the headline of the moment.

I’m guessing we’ll still be pretty interested in cat stories. Some things will never change.

Confession #109: Something Disintegrates at a Burger King

The other day, while sitting in our car with the windows down, my wife and I had a heated argument. Bad words. Yelling. A fist or two slammed into our Volvo’s center console. Though we both received nominations, we never reached consensus on which one of us was wrong, and the whole thing blew over by time we pulled into the garage.

I tell you this story because I figure you’ll probably hear about it anyway. So it might as well come from me.

That seems to be the lesson offered by Andy Boyle. Boyle was at a Burger King when a young married couple at a nearby table had an argument. The fight was loud enough for Boyle and other patrons to overhear. The fighting couple was certainly aware of that. They chose to argue in public. They, in effect, gave up their right to privacy among those at the restaurant. But should they have assumed their fight would be broadcast on Twitter and eventually featured on ABC News?

Thanks to one guy who decided to take a break from his Whopper and start tweeting, that’s exactly what happened. Andy Boyle opened with this missive: “I am listening to a marriage disintegrate at a table next to me in this restaurant. Aaron Sorkin couldn’t write this any better.”

From there, he went on to live-tweet the fight, describing details of the argument, even going so far as to broadcast photos and videos of the couple.

Getting a large dose of overly personal details from someone’s life on Twitter or Facebook is nothing new. Plenty of people broadcast the content of arguments, share intimate details about their marriages, and even mourn the death of a loved one online. But usually those experiences are shared voluntarily. Most people get to decide for themselves which parts of their lives they want to share on social media.

But maybe the ubiquity of smart phones and new technologies, coupled with a decreasing respect for boundaries, has changed the equation. You no longer get to decide when to share. You don’t even get to decide whether you want to use Twitter or Facebook. If you leave the house, you’re on social media.

Recently, a nude picture was stolen from celebrity chef Anthony Bourdain and sold to gossip site TMZ. When Bourdain got wind of the sale, he decided to go pre-emptive and post the photo to his own Twitter account.

The whole incident doesn’t paint a pretty picture of the state of our often obsessive culture. But I’m sure it didn’t surprise Bourdain. He’s a celebrity. He chooses to be in the public eye. He expects to occasionally have to deal with a violation like this because he knows the rules of being a celebrity.

But if Andy Boyle’s actions are an indication of a broader trend, we are entering the age of the unintended celebrity, where the new rules state that we all run the risks associated with fame without necessarily enjoying any of its benefits. There’s a new reality show and you’re the star, whether you like it or not. Someone should follow you around all day yelling, “action!”

The one glimmer of hope I’ve found in this whole unfortunate mess is the immediate negative reactions others have had, not to the couple’s decision to fight in a restaurant, but to Andy Boyle’s decision to share the details. Almost everyone I’ve talked to is repulsed by what took place at Boyle’s Burger King table. Some didn’t even want to read the outtakes of the fight. The curiosity about someone else’s life was outweighed by a disgust with the messenger.

In that Burger King, Andy Boyle thought he was listening to the disintegration of a couple’s marriage. He was really hearing the crumbling of his own ethics and self-restraint. We can’t stand by and let an alliance between technology and poor judgement disintegrate all decency, and turn every human exchange into another tawdry and destructive episode on a never-ending social media highlight reel.

If our disgust with this kind of secondhand sharing is widespread enough, maybe there’s still a chance such invasions of privacy will be the exception and not the rule. But I wouldn’t bet on it.

The only thing I know for sure is that the next time my wife and I have a fight, I’m rolling up the windows.

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Confession #108: I Made This on a Mac

I made this on a Mac.

That statement is pretty common these days. But there was a time I would have never imagined creating something on a computer. Sure, I had some friends type up one of my essays or a college application on their parents’ Compaq computer, the glowing green letters clicking across a deep black square. They typed. My words came out of the printer. But it wasn’t creation. It was typing. The actual creation couldn’t be done on such an uninspiring, lifeless machine.

When it came to creating, I stuck with my ball point pen and a pad of lined paper. That’s how it was until the 80s when I got my first Mac and I saw how a computer could be a tool so powerful and yet so unobtrusive that it almost felt like extension of myself. It was easier to use. It looked better on my desk. It was better. It was made by someone who cared that it was better.

I got rid of my pens. Everything I created from then on, I created on my Mac.

It seems so obvious now. Yeah, of course. You create stuff on your Mac. But back then, the people to whom that seemed obvious were part a tiny club. We only made up a couple percent of computer users. We’d see each other at small, dank Mac stores and wonder why the rest of the world didn’t see what we could see.

The Mac looked better. It felt better. And everything looked and felt better on a Mac. The Mac was inspirational. The Mac was a place to create. Documents looked better. When the web showed up, it looked better too.

For years, long before the “switch” campaign, I spread the gospel. I tried to convince my friends, family, classmates and coworkers to see the light and use a Mac. A few designer-types trickled over to the Mac world, but the rest always had some excuse to keep using Windows. But none of these excuses ever made sense to me. I never, ever considered using anything but a Mac from the first day I touched one.

When my then girlfriend agreed to be my wife, I told her it was time to have the discussion about her converting. She said, “Don’t worry, I’ve already talked to the Rabbi and started the process of becoming Jewish. I know our kids will be growing up in a house without a Christmas Tree and I’m okay with that.”

But that wasn’t the conversion I was talking about. I explained to her that our kids would be growing up in a house without Windows-based PCs. And then I gave her my old Mac Plus and said, “Lady, this is your life now.”

She joined my small club.

Then Steve Jobs came back to Apple. And slowly, as the new iProducts came, Steve and I converted more and more of my friends and family. One by one they all came over. Those old faces from the corner Mac stores were now joined by millions in lines outside of grand Apple stores.

What was all the excitement about? The same thing it was about the first time I used a Mac. Inspiration and creation. It’s about a guy making something awesome and by extension telling you to go make something awesome yourself.

Since Steve Jobs died, I’ve already seen hundreds of writers and designers thank him for helping them live creative lives. A few folks have called Steve Jobs the modern day Leonardo da Vinci. Maybe that’s true. But more importantly, he made the products that unleashed the da Vinci in all of us.

And he left an army of us. Our numbers can be seen in the flowers left by the inspired and lined up outside of Apple stores and in the messages that blanket the Internet and in the companies that will make tomorrow’s technology.

Like a few flowers, these words are hardly a fitting tribute. But right now, it’s the best one I can make.

And tomorrow I’ll open up my Mac and try to make something else.

Confession #107: Start-ups, VCs and Assholes in the Age of the Personal Brand

In my corner of the web, the big conversation these days is about a guy named Michael Arrington and his new $20 million Internet start-up fund. Arrington has made a name for himself (both good and bad) as the founder and voice behind the start-up world’s go-to blog, TechCrunch. Over the years, TechCrunch hired a CEO and eventually got acquired by AOL. But Arrington has always been its face, and its heart and soul.

Arrington is a controversial guy. This was true during the earliest days of TechCrunch and it’s truer now. And that’s no mean feat. It’s hard to be loved or hated by a lot of a people for that long in the age of short attention spans. I think he would agree that one of his secrets to success has been his willingess to push the envelope, have public smackdowns, and occasionally come off as an asshole. That takes a certain intestinal fortitude (that, frankly, I wish I had more of). On the Internet, being that kind of a brand is pure gold.

The current Arrington-related controversy has to do with journalistic standards. The concern among many is that Arrington’s new fund (CrunchFund) will be investing in the exact same pool of companies that his news site covers. While such a conflict of interest is not unique, it’s certainly worth some serious thought and Kara Swisher (a longtime Arrington foe) covered the key issues in her recent blog post: CrunchFund? Unethical Ventures? Pig Pile Partners? No Matter What You Call It, It’s Business as Usual in Silicon Valley. The folks at TechCrunch have their own concerns about the way the whole deal is being positioned by the higher-ups at AOL.

Even though Arrington has been informally investing for years, the ethics around a journalist investing in the very kinds of companies he covers (and, equally important, those he decides not to cover at all) is certainly worth a long, hard look.

But if you’re part of the Internet start-up world, that’s not the big story here. The big story is about power and popularity in the age of personal branding.

Several of the biggest Venture Capital players in the Valley invested in CrunchFund, including folks from Sequoia, Redpoint, Kleiner Perkins, Accel Partners, and Andreessen Horowitz. Those are some big names who, combined with some well-known angel investors, rounded up the $20 million for CrunchFund.

For these funds, putting in a small piece of $20 million into another fund is unusual. First, it’s a small amount of money. When someone at Accel or Kleiner sneezes, $20 million comes out. Second, they aren’t even investing this money directly into a start-up – which is their core mission. For big valley players, putting a few bucks into another fund (run by a guy with very little formal experience in the investment arena) hardly seems worth the effort it takes to read and sign the paperwork.

So why are major VCs wasting their time putting a few bucks into a little fund with no track record?

Because the very Internet ecosystem that they funded and helped to create has changed all the rules.

There are a couple of key trends you need to understand to really get what’s happened in the start-up world. First, it takes a lot less money to build a compelling product than it did during the original Internet boom. A couple of kids in their undershorts can build a site or app that can easily scale to serve millions of users. Second, since the Internet industry has matured, there are a lot more former entrepenuers who are looking to rotate some of their sizeable earnings back into other start-ups.

Start-ups need less dough and there are more people looking to write a check. Big venture capital firms can’t sit back and wait for entrepreneurs to nervously show up with their Powerpoint presentations, because it may not always happen in the new start-up marketplace. So these funds have moved downstream and are making more and more small investments in very early stage companies in an effort to essentially buy an option to invest in later rounds should things go well.

So that explains why big VCs make smaller and earlier investments. But why are they so anxious to co-invest a few bucks into Michael Arrington?

Because this is the age of the personal brand. Tools like blogs, Twitter and Google+ have enabled individuals to build their personal brands and their following like never before. Pretty much everyone in the start-up world reads TechCrunch. And Michael Arrington is a bigger brand than TechCrunch.

People who are starting up their new Internet companies are just like the rest of us. They respond to brands. And like the rest of us, they are swayed by public relations and the size of a brand’s following. Arrington has a big brand on the playing field where Internet start-ups are born, so he’ll see deals. And the bigger players are desperate to see those deals too.

But Arrington doesn’t have a track record as an investor. But he only has a small fund. But the skills it takes to cover an industry don’t necessarily translate to those required to be good at investing.

Yes, but he’s got a lot of Twitter followers.

This personal branding barely mattered in the past. The big venture firms had strong track records and so much public notoriety that they knew they’d see the best deals.

Today, plenty of VCs at big firms blog and tweet about the topic of investing and the Internet industry on a regular basis. They probably like the attention. But in this age where personal brand power can trump insitutional brand power, they also sort of need the attention.

And maybe they feel they need to be connected to people like Michael Arrington. There’s not much money at stake, there’s some additional dealflow that could come their way, and they don’t have to worry about suffering any of the journalistic consequences that might arise for those who don’t participate in the fund.

When I first started blogging back in the 1990s, I got inbound links from several newspaper sites on a single day. I also got an inbound link from an already accomplished blogger named Jason Kottke. Kottke sent me fifty times the traffic than all the newspapers combined. That was the beginning of the age of the personal brand. And now it’s bigger than ever. If I was about to launch a Mac product, I’d much rather have an inbound link from John Gruber than any other publication on the web. When I want to market something on the Internet, I think of the indivudual people I want to tell. Those individuals are the brands that matter.

So Michael Arrington has a big personal brand and is dipping his toes into an increasingly crowded market of start-up investors. And the biggest venture capitalists want to see the same deals Arrington sees. Can he transition his personal brand from being a controversial journalist to creating a solid early stage fund?

Who knows? If it works, his brand will be bigger than ever and the power in the venture world will shift even more dramatically towards the individual player. If it flops, the VCs will only have lost some loose change and Mike can always go back to being the biggest (and now more controversial than ever) name in tech journalism

Either way, we’ll be following.

(Full disclosure: I am an angel investor, writer and aspiring asshole.)

Confession #106: Does the Internet Make You More Connected?

The other day my friend Mordy asked me this question:

Are you more or less connected since you started spending so much time on the Internet?

I’m more connected to people I don’t know.

I’m equally connected to the people I do know.

I’m less connected to myself.

The other day, I was watching Arcade Fire play at the Outside Lands music festival when I thought to myself: I wonder if Michael Sippey is here right now? Michael is one of many friends I’ve made on the Internet. We all share common interests (the main one seems to be the Internet itself) and frequent a lot of the same virtual conversations. From following Michael Sippey on Twitter, Facebook and our common music streaming service, I know that he is a fellow Arcade Fire fan. It’s just one of the personal details and threads of commonality I share with a growing community of fellow web professionals and others whose path I regularly cross. This community wouldn’t exist for me without the assistance of the Internet and the suite of social software that now rides its rails.

I’m a member of several of these virtual groups, large and small. I count on these folks for much of my news. On blogs and Twitter, we share inside jokes and opinions, and riff off each other in the same way I do with my friends in real life.

It turns out Michael Sippey was at the same show and even in the same section, but true to form, the only interaction we had was via a couple follow-up emails. Keepin’ it virtual is the new keepin’ it real.

The Internet has had a dual effect on the level of connectedness I feel with the people I know in my offline life. On one hand, the basic communication tools now available make distance almost a non-issue. My conversation with Mordy that led to this post took place over instant messenger where we communicate nearly every day – far more often than we ever did before the Internet, even though back then, we were only separated by a few blocks, not a few thousand miles.

On the other hand, when I am actually with my friends and family, I find myself (and increasingly, my companions) distracted by a smartphone that’s either the object of my gaze or being fingered in my front pocket.

In a recent Pew Internet survey, 13% of cell owners said that they’ve pretended to be using their phone in order to avoid interacting with the people around them. I’m assuming the other 87% of cell owners were not pretending at all, and were using their phones because they just couldn’t help themselves. I recently walked through a hotel restaurant where every single person was interacting with a device of some sort. They were together spatially, but that was about it.

The actual number of social interactions I have with friends hasn’t been impacted by the Internet. But I do worry that the quality of those interactions has taken a hit because everyone in the room is not only connected to each other, but also to everything else in the world.

So when it comes to my connectedness with people I know, I’d say it’s about a draw. The overall frequency of our interactions has increased, but my ability to focus on them and only them has become more challenging in this age of distraction.

The distractions play an even more aggressive role when it comes to my connection with myself. Most of the moments once reserved for a little alone time have been infiltrated by the realtime Internet. I never just wait for a bus, or just stand in line at a bank, or even just sit and think as I sit stuck in bumper-to-bumper traffic. At these moments, I pull my phone out of my pocket faster than a gunfighter pulls his weapon out of its holster.

The only time I really experience any self-reflection these days is when my computer sleeps and my screen goes dark.

And I’m not alone. According to Pew, 42% of cell owners used their phone for entertainment when they were bored. If those 42% of people are anything like me, that so-called boredom now arrives sooner than the random thoughts that can lead to self-reflection, creativity or just a few seconds of nothingness. I can draw my phone faster than my mind can wander.

Of course, the draw of our devices is about more than relieving boredom (a goal the devices only occasionally achieve). It’s about getting a fix; reacting to a feeling of urgency that you’ve got to keep up with whatever it is that’s coming into your stream right now. Part of the power of the realtime web is that it can quickly make you feel like you can’t live without a flow of data that you easily lived without before you discovered it.

That’s the Internet’s reverse placebo effect: you feel as though you were missing something important before you signed up for the latest service. It’s a drug for an ailment you never had.

At that same Arcade Fire concert, a guy in front of me held his camera phone towards the big screen that flanked the stage and hit the video record button. He stood like that for a long time, separated from a live concert by two screens. Maybe he gained some social benefit by sharing the video with a friend or a broader Internet audience. But the concert provided him an opportunity to lose himself in the music and the moment. He let a screen block that experience.

I’m thankful that I can use the Internet to connect with my old friends and my newer, virtual communities. But I’m worried about the price of that always-on connection. Without the Internet, my friend Mordy never would have asked me the question that led to this post. With the Internet, it’s a lot less likely I’ll ask similar questions of myself.

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My name is Dave Pell, internet superhero. This blog provides an addicted insider's account of what's happening to us in the era of the realtime, social web. You can read more about the site, grab the rss feed, follow me on twitter, join the Facebook page, or get email updates.