Calacanis. (Flickr: ElectricSheep)

As TechCrunch first reported,  Inside.com might once again become a functioning web domain, under the administration of Silicon Alley Reporter and Mahalo.com founder Jason Calacanis. And if that sounds to you like a lede from 2000, you probably remember Inside.com as the late-bubble content play—helmed by Kurt Andersen and Michael Hirschorn—that gave us both David Carr and the Segway.

“For 10-plus years I’ve coveted the Inside.com domain name, and I’ve tried to own it,” Mr. Calacanis told The Observer. “I finally got it.”

Although he wouldn’t be specific about his plans for the domain—or what he paid for it—he did note its illustrious pedigree. The address has passed through the hands of Steven Brill and paidContent founder Rafat Ali since the original site went under. When GigaOm acquired paidContent earlier this year, the Inside.com domain came up for grabs.

Mr. Andersen, for his part, can’t believe it’s taken this long for someone to put it to use. “It’s a good name, Inside.com, and I’ve been baffled (but not unhappy) that it’s gone unused for a decade,” he told The Observer. “I find it entertaining and somehow inevitable that Jason Calacanis is acquiring it.”

“I don’t touch Facebook,” declared Michael Romanowicz, 29, a freelance web designer who nixed his profile and more than 300 friends on the social network last year after he decided it was making him unproductive. (Worse, it was showing him too many pictures of his ex-girlfriend.) “I’m a digital professional and I fundamentally disagree with the philosophy of how Facebook has structured their product.”

It’s not that he and the social network didn’t have some great times. “What was really cool was that one of my friends was one of the first few hundred Facebook users, and for some reason he had a super admin access,” he said. They used the account to snoop through strangers’ photos.

But Facebook became “annoying” and “inundating” as it grew, and at some point, it stopped being fun. “So I deleted it. And what I found was that everyone I’ve had a real relationship with, after I deleted the account, sent me an email and was like, hey, how come we’re not friends anymore?” he said. “And I’m like, ‘No, we’re totally still friends! Thanks for sending me an email because that proves that we’re still friends!’”

Last week, Google finally launched its full-on Facebook competitor, Google+, which Wired called a “bet-the-company move,” implying that Google’s future depended on whether Facebook’s 600 million users would take to a new social network. Encouragingly for Google, the corpses of Facebook’s predecessors—often cited as cautionary tales of web consumer fickleness—were also in the headlines: Myspace was bought for a 10th of the $327 million it sold for in 2005 just before it hit 100 million users, and the proto-social network Friendster relaunched with a whimper, as a gaming site that prompts users to sign in to find their friends, with Facebook.

Facebook lost more than six million users in May according to a widely publicized report by InsideFacebook, which collects data on the site. That number was disputed by Facebook and other third-party researchers, who reported a net gain for the month, but everyone’s data show Facebook’s momentum has slowed—and the web’s power users, at least, seem to have moved on. These days, Mr. Romanowicz is more into Instagram, the photo-sharing iPhone app that that launched in October, and GroupMe, the group-texting service that came out in August.

“The tech-savvy crowd has grown tired of Facebook,” Jason Calacanis, dot-com publisher of the bygone Silicon Alley Reporter, wrote this weekend in his email newsletter predicting that Google+ will be a “crushing success.” Mr. Calacanis recently surveyed an audience of techno-hipsters at the Future of Web Apps Conference. The vast majority said they were using new services for things they used to do on Facebook. “I asked how many people were using Facebook more now than last year,” he wrote. “Almost no one raised their hands.”

Mr. Romanowicz’s friend Gordon Cieplak, 27, is co-owner of Handsome Code, a web development shop that carries the slogan “more bicycles, less social networks.” He thought Facebook was “amazing” when it first came out. “I was like, wow, it’s such an incredible user experience and the design is so good,” he said. “I had never seen anything quite like it on the Internet.”

Gradually, the site lost its luster. Facebook is an addictive time sink disguised as a complement to your social life, he explained to The Observer. (People collectively spend 700 billion minutes per month on the site, according to Facebook.) A few weeks ago, he quit in favor of Twitter and Tumblr.

“Among my friends, we all sort of loathe it,” he said. “It’s kind of the same way we loathe cars. They’ve just become part of this, like, legacy infrastructure. Sometimes we use them, but we mostly dislike them.”

Facebook had fewer than 200 million users when Slate’s Farhad Manjoo declared it a universal good in 2009. “It’s time to drop the attitude: There is no longer any good reason to avoid Facebook,” he wrote, accusing non-users of harboring an “affectation” to make a “statement.” “‘I’m not on Facebook’ is the new ‘I don’t even own a TV,’” Rainn Wilson wrote recently on Facebook, a comment 792 people liked.

But Facebook has become the lowest common denominator on the Internet in its effort to conquer the world, and this may be its downfall among a certain class of technophiles—once your grandmother starts poking you, it may be time to find a new hobby.

The Observer asked Mr. Cieplak if he feels cool about not being on Facebook. “To the same degree I feel cool about not living with my parents in my 20s,” he said.

The anti-Facebook cohort cites a range of reasons, philosophical and psychological, for quitting Facebook. “It is a system designed to not make you feel good; it’s designed to make you click more and go deeper into the hole,” said Cody Brown, 23, who co-founded a Web start-up called Nerd Collider. “It can be totally soul-sucking. They also have something like 52 reasons to send you email.”

David Shapiro, a pseudonymous Clinton Hill–based blogger, 22, quit Facebook after about six months on the site. “Facebook is this massive social experiment that is totally untested and could be fucking with people’s self images more than anything in decades,” he said.

The most common refrain, though, is that Facebook is no longer relevant when there are shinier toys to play with. “What’s funny is, right after our interview I signed up for Facebook part deux (Google+),” Mr. Romanowicz told The Observer in an instant message.

Two-year-old Petey Rojas, son of Peter Rojas, a founder of the popular gadget blog Engadget and the gadgets question-and-answer site gdgt, is not on Facebook. But he has a Twitter account waiting for him when he comes of age. His mother updates @PeteyRojas with quotes from the toddler (“You know my friend Caleb? He’s dangerous!”) and a mix of links; it has 247 followers. “It’s more like a placeholder, in the same way that I own URLs for him,” Mr. Rojas said. “I always tell people, if you have a child, you should buy the domain name as soon as you decide what the name is.”

He hasn’t reserved Facebook.com/PeteyRojas. “By the time they’re old enough to use Facebook—13, technically—will they even care at that point? Will Facebook even be something that people care about at that time?” he said. He quit the network himself a year ago because he wasn’t using it. “The only thing I did on Facebook was manage my privacy settings,” he said.
Facebook fatigue among early adopters won’t necessarily spread to mainstream users. Then again, it might—social networks are, after all, social. Screenwriter Aaron Sorkin, having won an Oscar for The Social Network, recently announced he was through with the site. “I have a lot of opinions about social media that make me sound like a grumpy old man sitting on the porch yelling at kids,” he said during a panel in Cannes.

But Facebook certainly seems worried about being ditched, judging by the hoops users have to jump through in order to leave. If you’d like your account “permanently deleted with no option for recovery” (these words are in bold), you must “submit a form.” This takes you to a page warning that your profile will be permanently deleted with no option for recovery, and tells you to click “submit” if you’re sure, implying that this click will instantly and irrevocably destroy your Facebook profile. Actually, it opens a verification page with a password prompt and spam test. If you pass, a window pops up: “Your account has been deactivated from the site and will be permanently deleted within 14 days. If you log into your account within the next 14 days, you will have the option to cancel your request.” Then, Facebook sends you an email with a link to cancel the request.

The delete option is buried, though, under the option to “deactivate,” which merely freezes and hides a profile, “just in case you want to come back to Facebook at some point.” When you deactivate, a page comes up with the heading, “Are you sure you want to deactivate your account?” above pictures of your friends with captions: Mark will miss you. Alejandro will miss you. Vanessa will miss you.

“When I deleted my account, I had this Swedish intern that I was in love with,” Mr. Romanowicz recalled. “She was so cool. And Facebook must have recognized that I had viewed her profile over and over again. Facebook was like, ‘If you close your account these people will miss you.’ I was like, this is fucking hilarious.”

Mr. Romanowicz ran into the Swede recently, by coincidence at a bar. “We danced for a little bit,” he remembered. “It was a good close to that small love affair.”

Mr. Calacanis. (Photo: flickr.com/photos/joi)

Three months ago, the Transom broke some news to Jason Calacanis, former publisher of the New York-based dot-com bust chronicle Silicon Alley Reporter. Mr. Calacanis was sitting in the corner of a South By Southwest party, contemplating whether he could use the edge of a table to open a Heineken, when we told him his former employee Josh Topolsky had just quit as editor of the popular AOL-owned tech blog Engadget. “What?!” Mr. Calacanis said, lunging for his BlackBerry: “Hey @joshuatopolsky,” he tweeted. “I have a blank check here with your name on it. Let me know where to send it.” He sat back and took a smug swig; a server had opened the bottle. “I love making public offers,” he said. “It’s win-win. If they take it, I win. If they don’t take it, I win because it’s baller.”

Mr. Topolsky didn’t bite. Instead he and at least five Engadget bloggers signed on to a new venture backed by Jim Bankoff, who while at AOL coordinated the purchase of Engadget and its associated blog network, from Mr. Calacanis.

Mr. Calacanis was in town for a tech conference last week (not the Webbys—“I can’t believe that’s still going on”) and we met him again in a corner, this one at the W in Midtown, where his beverage, coffee, presented a different challenge, a fly. “I was like, oh my God, do not worry about it. Do you know how many flies are in this bagel? I don’t care,” he told the Transom, stirring.

“It really is a major red flag for AOL that you can’t keep a group of five or six bloggers happy,” he said. “Like velociraptors, the most dangerous dinosaur that ripped people up in Jurassic Park? If you have like a pack of those that work for you, you don’t have to tell them, go kill that. All of a sudden they’re just like, ‘What? There’s something there?’ They pounce. They just go kill it. You just have to keep them fed, that’s it. If you don’t fuck with it, they’ll do an amazing job… Of course they left because of meddling. They wouldn’t say it publicly but they told me AOL was meddling too much.”

We asked if there were any bloggers he wanted to offer a job via the Transom.

“I’m actually keen on landing Erick or MG from TechCrunch,” Mr. Calacanis said, citing another tech blog which recently sold to AOL. “I’m fairly certain they owned less than two and one percent respectively of TechCrunch when it sold. I’d offer them much more than that and get them their big pay day.”

Blogging is “largely dead” though, he said.

The Wall Street Journal had a story recently that said texting was dead, we noted. Mr. Calacanis agreed.

Is anything else dead? we asked.

He cocked his head, thinking. “Mm, not sure,” he said.

Wanderfly currently offers more than 1,200 destinations around the world. The company launched in Oct. 2010 and culls its findings from more than 20 content providers like Expedia, Foursquare and Facebook.

TechCrunch says Wanderfly will use the new money to adding social-media capabilities, creating partnerships and syndication deals with partner websites.

mtaylor [at] observer.com | @mbrookstaylor

Hunch users can create a profile and answer breezy questions from the "Teach Hunch About You" section. Queries include "Which fries would you prefer to munch?" and "Are you more likely to spoon or be spooned?" All of them were written by other Hunch users. Then users can ask the site questions (the search box includes a prompt: "Today I am making a decision about ..."), and receive responses curated from their answers to Hunch's questions and stats from other, similar users.

Some tech bloggers compare Hunch to Jason Calacanis' Mahalo Answers. But that New York tech scene veteran's "human powered search engine" is different from Hunch, which combines user opinions and machine algorithms to curate personal answers for its users. Mahalo Answers takes opinions from actual users and quotes their direct responses to specific questions.

"Hunch is wonderful (at first glance)," Mr. Calacanis wrote to The Observer in an email. "I just played with it for buying a car and it came up with a Tesla and Corvette in the top slots for me—I own both.

"In terms of a competitor to a knowledge exchange like Mahalo Answers I don't think it's comparable," he added. "In a Q&A type service folks are interacting with each other, and in a system like this it's rules based. I actually think they are complimentary."

For example, Mr. Calanis explained, a Mahalo Answers user could give advice on buying a digital camera and say "check out Hunch's digital camera test" to help out another user.

"These decision trees have been around for a while, but my guess us Hunch is going to do great because it will be, simply, better executed than the decisions trees on sites like PC Magazine and CNET in the past," Mr. Calacanis added.

Ask Hunch, say, "What Should I Order At Shake Shack?" and the site will then ask 10 questions, including "How Much Are You Looking to Spend During Your Visit?" ("Under $5" or "More than $5") and "What is the weather like today"? ("Winter-y," "Cold and wet," "Mild," or "Hot and sunny?"). A results page, according to my answers, gave me three options (Single Shackburger, Single Hamburger, Hot Chocolate) and a "Wild Card," "Pickles and relish make it special." I can then like or dislike each result or write up pros and cons for each one. Another link to "Why did Hunch pick this?" will explain exactly why the engine made those decisions for me based on my answers.

Using the site feels a bit like playing a constant Choose Your Own Adventure game. Each answer to a question leads to a different result—building a "decision tree."

Compare Hunch's detailed Shake Shack results to a Google search for the same question.

Hunch also has other incentives: earn badges and credits, or "banjos" for contributions to the site. That's right ... banjos.

According to the site:

Hunch team member Caterina Fake has often talked about mainstream content vs. user-generated content being the difference between watching a television show vs. telling stories around a fire; or listening to Britney Spears vs. grabbing your banjo, going down to the parlor and putting the band together: Uncle Greg on the jug, Mom on guitar, Gertrude on vocals and Lucy on the mandolin. Dad supplies the bad jokes, the clapping, and the whooping. Given all that, we weren't going to call them "Hunch Points" or something similarly uninspired. The Hunch currency had to be "banjos". In retrospect, it's obvious.

Combine those banjo incentives with a fun, easy-to-use site and Ms. Fake seems to be off to a good start. So far, many of Hunch's users are from the early-adopter tech crowd, so topics and their curated results seem very, well, geeky. And some are simply ... questionable, like "What gender am I?"

A location-based Hunch service, like one specifically created for New Yorkers, would also be helpful for users.

But a combination of blog hype from Flickr devotees, not to mention a marketing boost from another new online "decision engine," Microsoft's big Bing, and Ms. Hunch's site just might survive past the early adopter crowd. 

Originally launched in 2007, Mahalo's Web directory combines search algorithms and content found by real-life editors to present results pages that include text listings, photos and video. It looks a bit like About.com. "We put Yahoo!, Flickr and Wikipedia in one page," Mr. Calacanis told The Observer in an earlier interview. "People understand [the subject] better. You can send that page to mom, and she'll get it."

But now Mr. Calacanis will integrate a Wikipedia-like practice, and allow user editing—for pay.

Mahalo users can sign up and "claim" pages on the site based on their expertise. If they are, say, obsessed with Gossip Girl, they could "claim" Mahalo's Gossip Girl page and be curate its content—updating it when a new character arrives or a scandalous news article is written about one of its stars. As a reward for their Chuck Bass knowledge, that user gets half the advertising revenue generated from Google ads on his or her page. Mr. Calacanis said users get a number of pages based on their "belt" level (white belts, or beginners, get two pages, tops), but they can claim more pages the more they use the site, answer questions, and get kudos from other users. If they're lazy about maintaining their topic page, Mahalo can yank their rights to the page so another user can claim it. (Later, users might be able to start selling pages to each other, Mr. Calacanis told CNET News).

Launched in 2007, tech critics have been skeptical of Mr. Calacanis' Mahalo—some even claiming, with this new version, that he's hiring user editors because the venture is ailing. But he told The Observer he sees potential now that companies like Microsoft (which recently released Bing) are utilizing "human-powered" search engine results.

Ms. Calacanis, one of New York's biggest tech egos, operates Mahalo from the West Coast but told The Observer he misses New York "terribly" and plans a return. He said on stage at the Meetup that after September 11, he couldn't go downtown without crying. (He told The Observer that the aftermath of the attacks is one of the reasons why he left.) But, if Mr. Calacanis does return, he'll come back to a new tech scene, revived with young, more creative companies than when he left, he admitted.

Some of them include those that presented at last night's Meetup, like Aviary, which actually offers artists online photo, video and media tools for free. Vice President Michael Galpert whizzed through some new features including sound integration and editing. Their Web-based suite of tools won the CNet Editor's Award for Technical Achievement in the 2009 Webware100 competition. Don't have Photoshop? Check out their "Phoenix" photo editor, and see why they got the prize.

Bre Prettis gave a 5-minute runthrough of his company, Makerbot, which makes an an "open source robot" that helps people make their own robots that actually make things. Their prototype: The CupCake CNC, a bot about the size of a small TV that will perfectly frost cupcakes. Buy their OpenSourced 3D printer kit for $750 and build an army of bots. We're waiting for a Shake Shack burger builder.

On that Shake Shack bit, you can find that burger joint, along with others, using UpNext NYC, a kind of Google Earth iPhone application of the city that includes 3-D imagery and easy restaurant and service searches (there's a subway map too!). Users can 'like' and 'dislike' certain spots in the city and see other reviews from in the UpNext community. Another mobile service presented last night was, Centrl. Its a location-based application that allows its users to search for discounts, deals and landmarks within walking distance, and integrates social networks like Facebook and Twitter so users can interact with their friends.

Andrew Hoppin, New York State Senate chief of information officer, and C.I.O. team member Noel Hidalgo talked about "open government" initiatives for recently launched Web site NYSenate.gov. Chief executive Max Haot also presented a "pro" version of Livestream, an online live Webcasting service previously named Mogolus that received $10 million in funding from the Gannett Co. last July. They're broadcasting that I Want Media "Future of Media Panel 2009" panel going on right about now...

Now, excuse us while we watch Gawker's Nick Denton, Twitter's Jack Dorsey, the Wall Street Journal's deputy managing editor Alan Murray and other media wonks bloviate about the "future" of the choking-to-death newspaper business. Shhh, watching right now.

He was at the Puck Building last night at the Internet Week Kick-Off party, sponsored by The Observer, the Webby Awards and YouTube and standing in front of a TV screen playing a Web video of J Geils Band's "Centerfold." Nearby venture capitalists and young entreprenuers in sports coats and were sipping wine and one guest was nearly passing out on the couch from a bit too much of it.

Perhaps New York's start-up scene has gone G-rated? "After Sept. 11, New York wasn't the same, and that's part of the reason why I left," Mr. Calacanis said. "When artists and creative people can't afford to live in Manhattan, the worse it got."

"Creative destruction is gonna be the greatest thing that can happen to Manhattan," Mr. Calacanis said.

Ah, and here comes the nostalgia:

"That's how it started back in the early 90s in Silicon Alley," Mr. Calacanis said, who now lives on the West Coast to run Mahalo.com. He noted that the Puck Building was near the heart of New York's original tech scene along Broadway. "It was a lot of out of work people who were working at magazines, advertising agencies and finance companies. When everybody got laid off, people started experimenting with CD-roms, and... then putting all of that on the Internet."

Mr. Calacanis said despite the real estate bubble, bottle service and VIP poseurs souring him to New York, he misses the city "terribly," he told the Observer. "Every week. I'm sure I'll come back. I like it more and more every time I come back."

And he sees potential in new startups, like Tumblr and Meetup. "They're making cool shit," he said and doing it for the love of the Internet, not the dot com dollars. "You have to get in the limelight based on what you do, how creative you are, and not how much money you make."

Two of New York's young star entreprenuers, AnyClip.com's Nate Westheimer and Drop.io's Sam Lessin stepped in to shake hands with Mr. Calacanis. He'll see Mr. Westheimer again tonight, when he hosts the New York Tech Meetup at FIT's Haft Auditorium. Mr. Calacanis is presenting a new version of Mahalo, his "human-powered search" engine. "The creativity here [in New York] is what made it great, the art is gonna come back," he said, before finding a quiet corner to Twitter on his laptop and duck out for some pork and corn at Cafe Habana.

Posted in full at ValleyWag, Mr. Calacanis predicted in his email that "50-80% of the venture-backed startups currently operating will shut down or go on life-support (i.e. 3-4 folks working on them) within the next 18 months." He also recalled memories in New York from the dot com bust in the early 2001:

TechCrunch's Erick Schonfeld reports venture capital firms continue to raise money and invest in startups at a healthy pace. But the results may slow down as VCs experience the trickle-down effect.

Venture capitalists like Fred Wilson of Union Square Ventures (featured in a recent, glowing NYT piece) say the New York tech community is used to wading through difficult economic times. "Those of us who work in the tech business are used to this sort of thing. Capitalism is darwinism and technology driven darwinism has impacted the tech industry more than any other," he wrote on his blog on Sept. 18. "We'll get through it for sure, we always have, but it's going to suck for a while."