Tell me that's not art.

As we reported last week, New York is one of the few states where the sport of mixed martial arts is still illegal. The Ultimate Fighting Championship, MMA's biggest league, has lobbied for years to get this changed so they could hold lucrative live events at venues like Madison Square Garden.

But so far they have had no luck with politics. So today Zuffa, the league's parent, took a different tack. The UFC sued New York Attorney General Eric Schneiderman and Manhattan District Attorney Cyrus Vance Jr. to overturn that state's 1997 law banning Mixed Martial Arts on the grounds that the ban violates the First Amendment of the U.S. Constitution.

"This is mixed martial arts, emphasis on the arts," said Barry Friedman, the Jacob D. Fuchsberg Professor of Constituional Law at NYU. "The reason these atheletes are suing is because they have been prevented from their self-expression on some of the biggest stages in the nation." 

Prof. Friedman says that this is the first time, to his knowledge, that an athlete has brought a case to protect his sporting performance as a first amendment right. "The UFC has tried for years to get this done in the legislature. And it's not that they've lost, but they simply cannot get it to a vote. So now we are taking it to court."

The UFC got New York State fighters like Jon Jones and Matt Hamill to sign on as plantiffs, along with a certified American hero, former Marine Brian Stann. "Performing MMA live in front of a crowd is an unrivaled experience and allows me to speak to my fans,” Mr. Stann said in the press release from the UFC. “I was attracted to MMA during my time in the Marine Corps, after I returned from my first deployment to Iraq in 2005 and was looking for a path that allowed me to stay motivated, and inspire others, particularly fellow veterans."

Violence as art, sport as self expression. Will the courts buy it? No way Cy Vance is going to concede this without a fight.

John and Eric fighting in the UCL - photo by Anil Melwani

Eric, a beefy Long Islander with legs like a running back’s and platinum blond hair that enhances his Jersey Shore tan, locked up with his opponent, John. It was the second fight of the night at the Underground Combat League, one of the busiest promotions putting on mixed martial arts fights in New York, where the sport is illegal.

A crowd of around 100 people were crowded into a well-lit basement gym in Manhattan (the organizers asked us not to disclose its name for legal reasons), pushed up against a chain-link cage watching the action. Wrestling mats covered the floor and heavy bags hung from the ceiling. A burly bouncer stood by the front door to make sure no one arrived uninvited.

The two fighters pressed each other against the chain-link cage, exchanging knee strikes to the abdomen. With a surge, Eric threw his opponent to the ground, mounted him, perched on his chest and began raining down blows.

“Get out of there,” screamed the opposing corner. John bucked, trying to stand up. Eric snatched his wrist and fell backward in an arm lock. The crowd roared, hoping for a finish to the bout. The arm bent up at the elbow at a grotesque angle, but John didn’t submit. He rolled out, ended up on Eric’s back and began choking him. In a flash Eric reversed him again, taking top position with 20 seconds left in the round.

“Drop bombs!” yelled Eric’s corner. An elbow to the forehead sprayed blood, leaving a crimson splotch on Eric’s bleached hair. The five-minute round ended, but the referee didn’t hear the promoter shouting “Time!” over the screams of the excited crowd. The fighters exchanged blows for another few seconds before the match was finally stopped. The woman sitting beside us groaned. “That was too much for me.”

After the match, The Observer chewed on some beef jerky that had been left on a snack table by Jim Genia, who was having his book release party alongside the day’s bouts and had invited us along. His book, Raw Combat, published by Citadel, tells the story of New York’s underground fight scene. “This stuff happens in New York, and it will continue to happen here,” Mr. Genia said. He pointed out that when the sport was legalized in New Jersey and Pennsylvania, the underground circuits there all but evaporated.

Mr. Genia’s editor, Richard Ember, was also in attendance. The event was “interesting,” he said. “Although I don’t think I would like another man sitting on my face, no matter what the situation,” he added, adjusting his glasses. “And some of those punches, they looked like they were aimed at the vital organs …”

Mr. Genia’s prediction for the sport’s legalization in New York may be a little optimistic. M.M.A. has some vehement opponents in the state, including State Assemblyman Bob Reilly, who has compared the sport variously to dog fighting and prostitution. “It really is a glorification of brutality and violence,” he told a panel of fighters recently. “Many people believe that violence in the media, or any portrayal of violence, or violence itself as I think happens in mixed martial arts, in fact, makes people immune to violence and in fact promotes violence.”

To some extent, mixed martial arts has been its own worst enemy. In the early days, promoters enthusiastically branded the sport as a savage, no-holds-barred spectacle of pure violence and emphasizing the gorier aspects. Senator John McCain led the crusade against M.M.A. in the late ’90s, dubbing it “human cockfighting,” after which 36 states banned the sport outright.

For a time, it seemed promoters were down for the count, but they pulled a slick reversal. Rather than continue promoting the sport as the most violent entertainment available, they began speaking instead about its similarity to other athletic events and working to establish a set of guidelines. In 2000, New Jersey was the first state to introduce unified rules, which prohibited things like groin strikes, hair pulling and eye gouging. Since then, the sport has been legalized in 45 states. Of the hold-outs (Alaska, Wyoming, New York, Connecticut and Vermont), New York is the largest market by far, and therefore the biggest prize.

M.M.A. does have some strong political advocates in New York, including State Senator Kevin Parker, who holds a black belt in Tang Soon Doo. Asked to describe his fighting style, Mr. Parker kept it simple. “It’s what Chuck Norris does,” he told The Observer by phone.

Over the past few years, legislation that would allow professional M.M.A. in New York has repeatedly been passed by the State Senate. But legalization has been held up in the Assembly, where M.M.A. has several impassioned opponents, including upstate politco Mr. Reilly. “They won’t even bring it to the floor. My thing is, let’s get the proposal out there and see where the votes fall,” Mr. Parker said.

In his latest effort, Mr. Parker presented some compelling evidence to his fellow legislators about the safety of M.M.A. compared with more traditional contact sports. Despite the opposition of the American Medical Association and the deaths of two fighters following state-sanctioned bouts (Sam Vasquez in 2007 and Mike Kirkham in 2010), studies from John Hopkins and the British Journal of Sports Medicine suggest that the sport is actually safer, in terms of brain damage and fatalities, than its counterpart, boxing. And following the recent studies about brain damage in football, gridiron great Herschel Walker, who has taken up M.M.A., told USA Today, “People shy away from it because they think it’s a brutal, brutal sport. Guys, M.M.A. is safer than football and boxing. And people tell me they don’t believe it. Am I not the most credible person to give you the answer to that?”

This weekend, the sport’s biggest promotion, the Ultimate Fighting Championship, will make its network debut on Fox after years during which it was televised only on pay per view cable. Coincidentally, it will be going head to head with a welterweight boxing match featuring Manny Pacquiao. Proponents of M.M.A. like Mr. Parker are eager to draw attention to the irony: in New York it’s legal to kick someone in the head during a karate match or knee someone in the face during a muy thai fight. Boxers can punch each others brains out and grapplers can choke each other. But combined into the modern sport of mixed martial arts, these acts are illegal.

That said, Mr. Parker may not be the best advocate for M.M.A. In 2005 he punched a police officer and, in March of this year, attacked a photographer from the New York Post. When we mentioned to the senator that Brazilian jiujitsu was a hobby and invited him to our gym for a sparring session, he replied, “That sounds like something we’ll have to do. But not till I’m off probation.”

Though the sport remains illegal in New York, the state is home to some of the top fighters and trainers. Jon Jones, the U.F.C.’s light heavyweight champion, and the youngest man to hold the strap, was born and raised in Endicott, N.Y. Georges St-Pierre, the league’s welterweight champion, travels from Montreal to study Brazilian jiujitsu at the Renzo Gracie Academy on West 30th Street (disclosure: this reporter also trains there). Lightweight champ Frankie Edgar studies muay thai with Phil Nurse at the Wat Gym in Tribeca.

Some see issues other than health and safety behind New York’s ban, pointing to a union dispute in Las Vegas. The owners of U.F.C., Frank and Lorenzo Fertitta, also own several nonunionized casinos in Las Vegas, which Nevada’s Culinary Union is eager to organize. The union is an affiliate of Unite Here, a national labor organization that has spearheaded opposition to M.M.A. in New York. “The Culinary Union is spending millions of dollars of all these people who pay dues to keep us out of [New York],” U.F.C. president Dana White said at a recent press conference “because my partners, the Fertitta brothers, are the largest nonunion gaming company in the country.”

“It’s a blood feud,” said a veteran labor attorney in Las Vegas, who requested anonymity.

But Unite Here’s “Memorandum of Opposition” to the bill legalizing M.M.A. points to “coercive contract provisions” that they see as exploitative. The Observer reached out to the organization, but has so far received no comment.

Back at the underground fight, The Observer chatted with Matthew Polly, an author who was doubling down on the book release party with the debut of his own title, Tapped Out, being published by Gotham. “It’s kind of the George Plimpton approach. What happens when a middle-age fatass tries to train with the elite of the M.M.A. world. Basically I get my ass kicked.”

Mr. Polly, a Rhodes scholar who dropped out of Princeton to study kung fu, was standing around in his socks on the wrestling mats. Like many, he was an adherent of the labor dispute theory. “Look, you follow the money from the unions to the politicians who are holding up this process and you’ll get your answer.”

“Why are you asking this guy? He’s only had one fight,” joked Joey Varner, head kickboxing coach at one of the premier gyms in Las Vegas, who had trained Mr. Polly for the book and flown in to celebrate. “We sent him home crying most nights.”

We asked Mr. Varner if M.M.A. would ever be legal in New York. “I sure hope so. You ever seen how they fix a broken orbital bone? They literally have to take part of your face off and screw your skull back together. That’s not the kind of thing you should have done without insurance.” Leagues like the U.F.C. have insurance to cover fights and training.
“The worst thing about amateur M.M.A. is the idiots with egos,” he added. “Of course the promoter is going to let you fight. He wants you to get knocked out, so he can have someone twitching on his highlight-reel DVD. In the pros, guys know how to protect themselves.”

In the bathroom, The Observer ran across the combatants, Eric and John. With limited resources, the Underground Combat League can’t provide a separate locker room for fighters.

The two men hugged and started chatting. Their match had been declared a draw. Each was still covered in the other’s blood. “I can’t believe you got out of that arm bar,” Eric said, shaking his head.

“It was tight man, real tight. But I ain’t going out like that,” John replied.

“Yeah, I heard it popping, but you didn’t quit,” Eric said. “We’ll do it again someday.”

There aren't many startup CEOs who can claim to have side careers as standup comedians. But Jeff Glasse has a particularly hyperactive mind. After spending years in film production and software development, Mr. Glasse decided that he wanted to reinvent the way people recorded video. His startup, Kogeto, has created the world's first handheld panoramic camera available at a price anyone can afford.

The seeds of Kogeto came while Mr. Glasse was working at at the educational company Teachscape. He was assigned to win a grant from the Bill and Melinda Gates foundation that would capture detailed footage of teachers in action. He designed a small, unobtrusive camera called Lucy that would capture a 360 degree view of the classroom, allowing instructors to go back and see what methods were working with the class and when they started goofing off.

Mr. Glasse was so inspired by his work with Lucy, he left Teachscape to go try his luck with a startup. The new company, Kogeto, created a small, handheld panoramic camera that attached to a users iPhone. The project found a huge audience online, selling 100,000 units instead of the 20,000 Mr. Glasse was hoping for. And the big boys have noticed. When Kogeto debuts this month, it will go on sale at Apple's flagship stores, a testament to Mr. Glasse's innovative fusion of software and industrial design.

Game, set, match.

The Observer took in a few rounds of racquet sports last week at the stunning Tennis Club Grand Central, a single court hidden within the train station. The event mixed tennis pros with tech types, including First Round Capital's Charlie O'Donnell and Social Media Week's Toby Daniels.

It was all part of Get Served, a tech-meets-tennis event put on by hostess with the most-est Emily Gannett and her IRL productions. We didn't quite make it to the finals, a doubles match involving AdWeek's Dylan Byers. Sadly Mr. Byers and his partner lost to a pair of stunning sexy-tagenarians, who proved consistency, not power, is the real killer on the court. Better luck next time, Mr. Byers.

After all the balls were played, The Observer joined former Wired writer Eliot Van Buskirk, who now runs the music app blog Evolver.fm, to have our swings recorded and analyzed via video. Mr. Buskirk, a former tennis coach at Harvard, had the better forehand, but we proved once again to be the master of the backhand (compliment).

From there it was off to the bar, where we sipped some 18-year-old cherry oak-aged Macallan single malt and discussed the finer points of startup life with Mr. Red Tie himself Gary Sharma, ER Accelerator's Murat Aktihanoglu.

Ms.  Gannett grabbed us and steered us towards the photo booth. "Get your picture taken with Roger Federer." And there he was, that rough smile, dimpled chin, astonishingly large head. He seemed smaller in real life ... and had a bit of a gut.

"Pretty good right? I found him on Craiglist," Ms. Gannett explained of her photo Federer. Personally The Observer would have used Zaarly, but same difference. As we headed out for the night, Foursquare co-founder Naveen Selvadurai was checking in for a photo with Faux Federer. Priceless.

"The days of, 'Do we publish on Facebook? Do we tweet?' are over," Buddy Media CEO Michael Lazerow told Betabeat. "Either you do it, or you're crushed. Do it or go out of business." Hearst Magazines must have got the memo, because its Digital Media unit just announced a partnership today to use Buddy Media's platform to enhance its presence on Facebook. From its Midtown headquarters, Buddy Media will create "sapplets" (short for social applets) that overlay on the Facebook pages for titles like Cosmopolitan, Seventeen, and Marie Claire.

Sapplets like Buddy Media's  Interactive "Personality" Boutique, which recommends products based on answers to a personality quiz,  introduce a game-like aspect into the Facebook page and encourage interaction. They also offer a handy new advertising vehicle for Hearst, which is probably why Kristine Welker, Hearst Digital Media's chief revenue officer, was the point person on the deal. Hearst is further removing friction for potential advertisers by launching multiple brands (13 titles and websites will eventually be involved) at once. That way, if an advertiser wants to reach a certain demographic, they don't have to negotiate with each magazine individually.

"Instead of doing one-off siloed programs, they're almost selling it as part of a cable network that lives on top of Facebook," Mr. Lazerow explained. But why "sapplet"? Did the world really need another word for a widget? "I can't speak for the world, " he said sharply.

Although both Ms. Walker and Mr. Lazerow say this partnership is unrelated to the recent launch of Hearst's well-funded App Lab for emerging technologies, it's hard not to notice the similarities between the two. After all, in addition to creating tablet versions of Hearst magazines, the App Lab is also branding game-like apps, like  House Beautiful's paint colors app and Esquire's iPad puzzle app, in an effort to attract advertisers that's not exactly editorial.

Mr. Lazerow sees the Hearst deal as an example of pay-off from a gamble he made back in 2007. "With Google, it was paid clicks. Everything was search-based. Facebook reoriented the world around people and sharing. When you can no longer scale by buying more clicks, you have to get people to share. That was a bet we made."

It didn't hurt, added Mr. Lazerow, that Buddy Media is in close physical proximity with Hearst and Conde Nast, another publishing client. "We decided to stay in New York as the technology moves away from hardware--stuff we don't do incredibly well--and moves towards content, storytelling, and media," Mr. Lazerow told Betabeat. "We pay a little more to be in New York for people and real estate, but the upside is so much bigger than if we were in Atlanta or Chicago, or even the Valley. It helps that we're right down the street."

“Stand back! I’m here!”

As it turned out, “Doctor” Pogue was there as a representative of the “Industry Rescue Service” and his bedridden patient was “AM/FM.” Mr. Pogue vamped surprise, pieced the situation together out loud—the patient was a metaphor for the dying radio industry—then whipped out a laptop, and “prescribed” his “patient” an online radio site.

The video was typical of Mr. Pogue’s style: folksy and accessible, relentlessly service-oriented and generalized. More than anything, it was goofy and affable.

“We’re talking about a guy who was trained as a pianist and a magician,” said Jeff Yablon, a tech writer who met Mr. Pogue in the early 90’s, when Mr. Yablon was the president of the Computer Press Association and Mr. Pogue’s writing career was still in its earliest stages.

Mr. Pogue’s entertaining tech coverage has conjured a massive and devoted following, but his greatest trick might be convincing the stately Times not to make him disappear—despite raising some of the more thorny conflict-of-interest questions the paper has confronted in recent years.

Mr. Pogue has been accused of being an insidious shill for one of the most powerful technology companies on the planet, Apple, and was reported to be dating a publicist who represents many of the same companies he covers for the Times.

Seven days prior to the video’s release, Mr. Pogue and his estranged wife were each charged with disorderly conduct by police in Westport, Conn., after he allegedly hit her with—what else?—an iPhone.

In the video, the bite mark he reportedly received on his arm during the incident had apparently healed, or was well-concealed. It wasn’t noticeable. Not a single scratch.

If anything, it was classic David Pogue.

An Ohio native, Mr. Pogue graduated summa cum laude from Yale University in 1985 with a distinction in music. According to the biography on his website, Mr. Pogue moved to New York City after college, and worked a series of jobs in Broadway theater, with an ambition to compose for musicals. He eventually took up teaching at the New School and the Learning Annex, and went on to program and write manuals for various music software programs.

From there, he began teaching composers and Broadway stars how to use their computers, which evolved into—as he put it on his website—“Hollywood and literary celebrities, from Mia Farrow to Harry Connick Jr.”

“The first time I came across David Pogue he was working as Liza Minnelli’s geek-for-hire,” said Mr. Yablon. “He was doing social media marketing before that term existed. The routine was, ‘You know me, I work with these big names, you can trust me, I’ll set you straight on technology.’”

Mr. Pogue has often outlined his entertainment background as a foundation for his current work, once telling a music website that, as the youngest of three children, he is “a natural-born entertainer.” And, after a rare interview with Steve Jobs was criticized for a lack of skepticism, Mr. Pogue defended himself by saying, “I am not a reporter. I’ve been an opinion columnist my entire career … I try to entertain and inform.”

In 1988, Mr. Pogue began a regular column for the Apple fan magazine Macworld. In 1992, he wrote the second book in the “For Dummies” series, Macs for Dummies. He has written more than 50 books, making him, in the words of his own biography, a “ridiculously prolific author.” Only two of the books are fiction: a 1993 “techno-thriller” entitled Hard Drive and a 2010 young-adult book, Abby Carnelia’s One and Only Magical Power. (The Times’s own review noted that “Pogue, the personal-technology columnist for The New York Times and a former magic nerd himself, clearly has a lot of affection for kids.” In the second sentence of the review, the review’s author admits to crying at the end of the book.)

In 2000, Mr. Pogue brought his entertaining brand of explanation to the Times, where he was hired as the Personal Technology Columnist, and, since then, his State of the Art column has appeared regularly on the front page of the Thursday Business section.

He arrived at a crucial moment. Around the time of his hiring, the objects of Mr. Pogue’s affection and study—personal technology—started to transcend their roles as utilitarian aides and objects of geek affection and become fashionable accessories increasingly central to the lives of those who adopted them. When Apple released the iPod in 2001, Mr. Pogue became the go-to layman for the company’s new gadgets, and when the iPhone arrived, he filled his prose with apostlelike praise. (His Times video on the first iPhone is the second-most watched video ever uploaded by the newspaper, with nearly one and half million views.)

Mr. Pogue’s influence metastasized along with Apple’s market share, and his 1.3 million Twitter followers now dwarfs the digital presence of other marquee Times writers such as Thomas L. Friedman and Maureen Dowd. It’s more than four times the number of followers that Jenna Wortham, the Times’s decidedly hip, young tech reporter, has; Mr. Pogue, in fact, has more followers than the entire tech reporting staff of the Times combined.

“He’s like the Oprah of gadget writers,” said Michael Sebastian, the managing editor at PR Daily. “A single tweet from him can put you on the best-seller list.” Earlier this week, the appropriately named Cult of Mac tweeted out: “@Pogue...our servers just melted melted from your sorcery.”

“A review from David Pogue is the holy grail,” said a spokesperson from Open DNS. “After he wrote us up, we experienced the single biggest day of growth in the company’s entire history.” In the 24 hours after Pogue’s review appeared in the Times, Open DNS saw account creation jump 370 percent.

Mr. Pogue’s success has created some ethical entanglements. He has been attacked for taking paid speaking engagements, such as one for the Consumer Electronics Association’s “CEO Summit” near Los Angeles in June 2009. That fall—one month after then-public editor Clark Hoyt used an entire column (entitled “He Works for the Times, Too”) to admonish Mr. Pogue—he spoke at Disney World, in an event hosted by the defense contractor Raytheon Company.

In his column, Mr. Hoyt had challenged three media ethicists with Mr. Pogue’s case; all three agreed that Mr. Pogue’s interests were conflicted. His employment status remained unchanged. That same year, the Times fired a writer named Mike Albo, for taking a paid trip to write about junket travel culture for a separate publication—his first, and last, infraction. “Comparing this situation with one particular instance is not fair,” said Times spokesperson Eileen Murphy when asked to compare Mr. Pogue’s case with that of Mr. Albo. “There are different sets of circumstances involved. They’re handled on a case-by-case basis. We handle these situations in accordance with our policy. We are confident that our standards editor has made the appropriate judgment in each case.”

Jeff Jarvis, a best-selling author and journalism professor known for his strong, loudly broadcast opinions on media and tech, compared Mr. Pogue’s self-styled status an “entertainer” to that of Michael Arrington, owner of the blog TechCrunch, which was recently purchased by AOL. “When Mike Arrington says he’s not a journalist, he is really dismissing the label, because he began as an investor,” Mr. Jarvis explained. “I think Pogue is more specious, more for convenience. He expects us to trust him, but at the same time, he asks not to be held to the same standards.” Mr. Jarvis concluded: “I don’t buy his shtick about being an entertainer, not a journalist.”

Mr. Pogue’s harshest critics have focused on his undying praise of Apple products in the Times, and the potential conflict with his best-selling books on the company. Mr. Pogue has gone to bat for Apple’s products quite often, in his signature over-the-top style. An April post mocked the outrage over revelations that Apple was storing location data in its phones. “Ooh! Apple is spying! Ooh! The government is tracking! Ooh! Big Brother is watching!” he wrote. It also ominously noted: “The one legitimate concern [of Apple’s location tracking] is that someone else with access to your computer could retrieve the information about your travels and see where you’ve been. Your spouse, for example.”

A week after Mr. Pogue’s domestic dispute, Dan Lyons, a longtime press foe of Mr. Pogue’s, claimed an even more personal conflict. Mr. Lyons wrote for The Daily Beast that Mr. Pogue had been dating Nicki Dugan, a public relations executive who works out of San Francisco. A journalist dating a public relations executive is hardly novel, but Ms. Dugan is a vice president at OutCast, which represents some of Silicon Alley’s most prominent tech companies.

The Times responded by saying that Mr. Pogue had approached technology editor Damon Darlin in December with the news of his relationship, and that Ms. Dugan didn’t pitch Mr. Pogue stories. The Daily Beast produced several instances where Mr. Pogue seemed to write glowingly of OutCast clients and disparagingly of OutCast competitors. When speaking with The Observer, Mr. Darlin questioned that reporting, noting that OutCast doesn’t represent Amazon, but an Amazon business-to-business product. Mr. Lyons also cited a review by Mr. Pogue of a competitor to Netflix, which is an OutCast client. “No intelligent person would construe that as a positive review for Netflix,” Mr. Darlin noted. Finally, refuting Mr. Lyons’s argument that Mr. Pogue’s writing about Groupon and Skype was conflicted by another OutCast client, a venture capital firm with investments in both, Mr. Darlin argued that this is “a pretty thin string.”

“I can understand why there’s skepticism,” Mr. Darlin admitted, “and that’s always healthy under an intelligent readership. Because of these other questions that have been raised in the past, it’s very easy for someone to make that charge. In this case, that charge doesn’t stick.” Yet when asked if Mr. Pogue had been given preferential treatment by Times editors during past transgressions, Mr. Darlin noted that he wasn’t familiar with Mr. Albo’s situation, and that the Times has “addressed all of this. We’ve been satisfied that under the rules we’ve set up for [Mr. Pogue], and that there is no conflict.”

Responding to an emailed request to speak, Times executive editor Bill Keller referred The Observer to a spokesperson, noting simply: “We have rules. David followed them.”

An assistant in the office of the Times’s current public editor, Arthur Brisbane, responded: “[W]e dealt with this issue last week after the Daily Beast story” and included Mr. Brisbane’s response to a reader about the issue. In it, Mr. Brisbane noted that he had “spoken with [David Pogue] and Times editors and satisfied myself that Pogue has made the appropriate disclosures about his relationship with Nicki Dugan of OutCast Agency. Any time there is a conflict, it does create complications but I think in this case Pogue and his editor have taken the appropriate steps to comply with the newspaper’s ethics policy.”

Sitting down at his laptop, Mr. Einhorn began to poke around Google, trying to figure out who the guy was. "I think he was on a show about firemen," he said. Then he got distracted. "What's that?" he asked, leaning across his desk.

On my middle finger I wear a replica of a prewar signet ring bearing my grandfather's initials. The original was once lost and my grandfather had a copy made, then several years later found the original. The duplicate ring was my birthday present when I turned 25.

"You see, that tells me so much about you as a person," Mr. Einhorn says, turning the ring over in his palm. For Mr. Einhorn, every object has a provenance, a history that exerts a powerful pull on the people around it. Putting all of that into a digital database, he thinks, would remake the Web.

CHECK OUT OUR ILLUSTRATED GUIDE TO THINGD >

Google created the world's biggest search engine by devising the best way to chart the relationships between the billions of pages that make up the Web. Facebook became the world's most important social network by building the best system for understanding the identities and relationships of the people who use the Web. A database that allows users to identify and search every object in the world could be as elemental, and profitable.

Imagine browsing the Web and being able to learn about any piece of clothing, from any image, on any Web site, with just the push of a button. Instead of just cataloging their friends on Facebook, users could begin to build inventories of their possessions as well. Tied into all of this, inevitably, would include sharing, swapping, selling and shopping.

Mr. Einhorn, 29, is thin and excitable, with a buzzed head and stylish clothes he admits his wife picks out. "I think of objects as the last great uncharted territory on the map," he said, playing with a rolling chair in his office. "Who's knows what this guy's story is," he said, referring to the chair. He pushed off the table with his foot, spinning the chair in a tight circle.

He calls his project "Thing daemon," or Thingd for short. A daemon is a computer program that runs in the background, named not for satanic minions but for the ancient Greek concept of a daemon: something that is not visible, yet is always present and working its will.

The daemon is one-half of Mr. Einhorn's plan to create the world's best database of objects. Programs that he and his team created crawl the Web constantly, examining images and identifying objects based on surrounding text, tags, ID numbers, even the shape, size and color of the images themselves. "We've got hundreds of millions of objects in our database," says Mr. Einhorn, "and we're adding more than two million a week."

CHECK OUT OUR ILLUSTRATED GUIDE TO THINGD >

For several years now, Mr. Einhorn and his team have been building their database largely in secret, ignoring press requests, fearing that publicity would spur competition from some formidable foes.

"There are a lot of folks working on this idea," says Tom Pinckney, co-founder of the New York start-up Hunch. Companies like Google, Amazon and eBay are all constructing databases of consumer products. "Right now it's not clear what the best approach is, or who will have the strongest database. But when one player does emerge from the pack, there will be a strong network effect."

Mr. Pinckney compares it to the once-competitive landscape for social networks. "Once Facebook emerged as the clear leader, it just grew faster and faster, while others died off. The same thing will happen when a company in the object space crystallizes as number one."

To compete with giants like Google and Amazon, Thingd needs serious funds, and the company has assembled a formidable set of investors: Andreessen Horowitz, arguably the hottest VC fund in the world today, plus Allen & Co., General Catalyst, Esther Dyson, Jim Pallotta (billionaire owner of the Boston Celtics), Bob Pittman (creator of MTV), Maynard Webb (former president of eBay) and the scions Eric Eisner and Jeff Samberg.

The investors have been attracted in large part by Mr. Einhorn. At 16, he became the first employee of Capital IQ, which structured messy financial data for hedge funds and money managers. He started working nights and weekends, but after graduating from high school, he decided to forgo college and work there full time. Capital IQ was acquired by S&P for $200 million when Mr. Einhorn was just 22.

From there, he founded Inform Technologies, which helped publishers better organize and present their content, and is now used by CNN, CBS, The Economist and Condé Nast.

For all its ambition and investment, Thingd remains a tiny company: It's Mr. Einhorn and just nine developers. But that, he says, is on purpose. "I always told him one of the best rules in business was to add overhead very reluctantly, and he has followed that," says Jim Satloff, who was part of the team that acquired Capital IQ and went on to work as CEO of Inform Technologies. "Joey is a visionary. He sees two or three steps further into the future than anyone. That kind of vision means he can attract top talent."

PETER ROJAS KNOWS the passion people can have for inanimate objects, having created Engadget and Gizmodo, the two biggest gadget blogs in the nation. His new venture, the Betaworks-backed gdgt, is an attempt to tap the wisdom of the crowd to catalog every gadget in the world. "I see what Joe is trying to do, and I admire such an ambitious project," says Mr. Rojas. "You can do a lot with computers, but at this point I just think there is no substitute for having a human being involved." On gdgt, humans, not computer programs, are building the database of things.

"It's just so hard with stuff people are not passionate about," says Mr. Rojas. "Facebook worked because people want to put in information about their friends. I mean, it's one thing to find users who want to contribute information about a new camera or iPad. It's a lot harder to get people to help you build a database of Aeron chairs, with every model and color. What about mattresses, or forks? It's just not sexy. In the end, I think a project of that scale is going to be dominated by somebody like Google."

Mr. Rojas is right that not many people feel strongly enough about mundane objects to catalog every make and model. Type "Aeron chair" into the search bar on Thingd, however, and the database returns more than 281 results--Herman Miller Aeron chairs in every conceivable shape, size and color. It has cataloged some 67,000 mattresses and more than 81,500 forks.

But that database isn't very interesting, or accurate, until something gets built on top of it, and people begin to use the data. Human interaction around these objects is what will drive Thingd to the pole position ahead of Google and Amazon and help its software to more accurately identify items and brands. "Facebook wouldn't be very interesting if it was just a collection of info about people," says Mr. Rojas. "A database is just table stakes to do something bigger."

One project at Thingd is a site called The Fancy, which allows users to tag the objects, not the people, within photos; it has become a coveted invite among fashionable denizens of the Web. Even the mainstream is catching on, as evidenced earlier this week, when US Weekly tweeted that its editors had become obsessed with The Fancy.

The goal is to follow Facebook's model. "We needed to get the database rock solid first," says Mr. Einhorn. "Now we're ready to start building on that platform." While The Fancy aims at fashion, another Einhorn site, Plastastic, aims to tap the passion of toy collectors. A site for comic-book collectors is set to go live soon. "Eventually we will open up an API to our data, and anyone will be able to build a great app or Web site about objects that relies on our database."

Mr. Einhorn doesn't have as much experience with consumer Web sites as he does conquering massive sets of messy data. But so far The Fancy is growing steadily, attracting new users and press attention. Mr. Einhorn's board includes the co-founders of the Web's two most successful social applications, Jack Dorsey of Twitter and Chris Hughes of Facebook.

"When I first met Joey, his database was pretty substantial, tens of millions of things," says Mr. Dorsey. "All it was missing was a little oomph, a very approachable front end for the average user. But the new products they are putting on top of it, like The Fancy, is really taking it to the next level. What I love about it is that it's completely natural. You flip through the pages of a magazine or walk down the street and you think to yourself: I like that, I have that, I want that."

The Fancy is still invite only, and Mr. Einhorn isn't pushing to expand too fast. "We've got great investors who are comfortable with us taking our time," he says. He puts his hand on the back of his office chair again. "Who's to say how we should relate to one another? This isn't as simple as liking someone or making them your friend. Commerce is at the heart a lot of these relationships, and that can be tricky."

Leaning back in his chair, Mr. Einhorn recounted an article he read recently about a painting that had fallen behind a couch. After many years, the family got around to moving their furniture and taking a second look at the painting. It was eventually declared a Michelangelo by prominent art historians, probably worth millions. It became clear as Mr. Einhorn talked that as far as he was concerned, the old sofa was as interesting an actor in that story as the priceless painting.

CHECK OUT OUR ILLUSTRATED GUIDE TO THINGD >

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Mr. O'Connell, 37, has worked on developments with his father since he was 7. "It's hard to do anything on my own, my dad and I do pretty much everything hand and hand," he said. "But, yeah, this was definitely more my idea, and I'm taking the lead on this."

The Cheyenne was forced to close this April to make way for a nine-story apartment building being erected by the diner's landlord, George Papas, at 33^rd Street and Ninth Avenue. When Mr. O'Connell read about the closing in the media, he contacted the diner's owners, who put him in touch with Michael Perlman, a preservationist who previously saved the Moondance diner in Soho.

According to Mr. Perlman, who brokered the final deal between Mr.O'Connell and Mr. Papas, over 20 different parties inquired about purchasing the Cheyenne, but Mr. O'Connell was the earliest. He bought the Cheyenne for only $5,000, but he estimates that the cost of just moving the diner to its new site will be closer to $80,000. "Sure, I could have built a replica for less, but you can't match authenticity."

Moving the Cheyenne, which is over 100 feet long and 18 feet wide, and split into two pieces at the center, is a large and daunting task. So big, in fact, that the producers of the History Channel program Mega Movers have decided to feature it in an upcoming episode.

When the Cheyenne gets to Red Hook, it will make its new home on Reed Street across from the Fairway supermarket, where Mr. O'Connell has lived since 2006. He plans to elevate the diner eight feet to insure seaside views. Additional plans include a beer garden out front and an outdoor movie screen in the back.

The cuisine will still be diner-style, "but not a two dollar egg sandwich." Mr. O'Connell is looking for a higher-class eatery and he is calling on local help. Recently, he's talked with Harry Hawk, of the Water Taxi Beach, whose burger beat out competitors from around the city to win Best of New York in 2008 in Dish du Jour magazine.

Mr. O'Connell wants to keep the diner's Art Deco aesthetic intact and will be working with Mr. Perlman, who has a collection of vintage photos and original blueprints, to re-create the feeling of the diner circa 1940, when it first opened in Manhattan

Just keeping the décor won't replace the Cheyenne for longtime Manhattan patrons, but Mr. O'Connell hopes to provide some continuity. The New York Times eulogized the Cheyenne back in July with a full-page article in the City Section by Stacy Torres.

"That story ended with the author having the last meal at the Cheyenne before they closed," Mr. O'Connell said. "I'd like to contact her, and ask her to be my first customer."

At times, Mr. O’Connell can seem like a caricature of the down-to-earth developer. He has appeared in dozens of articles on the area, always in his trademark denim overalls, usually in his silver pickup truck, which he calls his office, and more recently with a copy of Jane Jacobs’ The Death and Life of Great American Cities in one hand, like some patron saint of urban renewal.

“The man is a legendary character in Brooklyn,” said Michelle de la Uz, executive director of the nonprofit Fifth Avenue Committee, who has worked with Mr. O’Connell on affordable housing and job placement for local residents. “And he clearly cares deeply about this neighborhood.”

Mr. O’Connell’s development philosophy focuses on creating a mix of small business and light industry as a counterbalance to the rapacious residential gentrification of Brooklyn. “I could make three times the amount of profit with residential than I’m doing with commercial and industrial,” he said. “And I could get the zoning changes, but for me the key is balance, so you take a little less, and everybody gets a piece of the pie.”

This strategy has earned him some epithets rarely associated with real estate developers. Jonathan Bowles, director of the Center for an Urban Future, even called him a (gasp!) “socialist developer.”

“If Greg didn’t own the property he does, much of the Red Hook waterfront would probably consist of luxury condos today, and the neighborhood would undoubtedly have fewer jobs and be less interesting,” Mr. Bowles said. “Just about every other developer in the city has been singularly focused on building high-end housing, but Greg has been intent on providing relatively affordable space for light manufacturing businesses.”

Mr. O’Connell is not without his critics, including John McGettrick, chairman of the Red Hook Civic Association. “I think he’s terrible,” Mr. McGettrick said. “He has acquired huge amounts of government property for next to nothing, made huge promises in regard to them, and delivered next to nothing.”

MR. O'CONNELL WAS born in Queens in 1942, the oldest of four brothers, son of a teacher and a police officer. “All around my neighborhood there were civil servants—cops, teachers, firefighters, boom, that’s how it was, middle-class America after World War II,” Mr. O’Connell said in a flowing Queens brogue.

He went to college at SUNY Geneseo, got certified as a teacher, and after graduation in 1964 entered the police academy. For the first few years, Mr. O’Connell worked as a cop at night and a teacher during the day. Between his two jobs he managed to save up some money, and in 1967, with a small loan from his parents, he purchased his first property, a brownstone in Cobble Hill, Brooklyn.

In the years that followed, he continued to acquire, renovate and rent residential property in the borough. In 1981, after 17 years, he retired from the police force to focus on real estate. A year later, he bought his first property in Red Hook: “I had seen what had happened to areas on my old beat, like Soho. Red Hook has the same ingredients. It was the wild frontier.”

In 1992, Mr. O’Connell purchased 28 acres of Red Hook waterfront from the Port Authority for just $500,000. “Greg took a lot of risk going in there,” said Ms. Uz of the Fifth Avenue Committee. The area had become a hotbed for drugs and prostitution. “The piers he bought were practically falling into the water.”

That was the appeal. “It was a challenge,” Mr. O’Connell said, “and it was taking the long term. If you really want to have an impact, you’ve got to be 20 years ahead. Working the city as a cop had shown me that.”

When Mr. O’Connell first renovated and advertised the 28 acres, the low rent attracted a lot of attention. “Businesses would call up, but when they asked about the location, and I said, ‘Red Hook,’ the other end of the phone usually went silent.” He built up the property tenant by tenant, starting with the smaller spaces and refinancing as he went along.

Since that time, Mr. O’Connell has seen the city’s fortunes reversed, and his waterfront property has become the backbone of a revitalized Red Hook. The property, in part, forms the terminus of Van Brunt Street, Red Hook’s main drag; and Mr. O’Connell is by far the area’s largest landowner, holding about one million square feet. His piers house 150 businesses that employ 1,200 workers. The capstone of his portfolio lies next to the piers: a Fairway supermarket that he developed out of an abandoned building purchased from the city’s Economic Development Corporation and opened in 2006.

Mr. O’Connell’s critics claim he has taken advantage of the community.

“When he acquired the pier, he promised a park, a half-mile public esplanade, promised to support housing because we had lost all our housing,” Mr. McGettrick said. “He reneged on all of those promises.”

The Fifth Avenue Committee just completed a lottery for 60 units of affordable housing in Red Hook, the largest influx of affordable housing to the area in years. Mr. O’Connell provided 16 of the 22 lots involved at below-market rates. There were over 5,000 applicants for the 60 units.

No park has materialized, however, and Mr. O’Connell keeps the pier gated at night. But during the day, he opens the property to the public. On a recent weekend, dozens of tourists strolled along his pier, stopping at a crafts fair and peeking in on an art show thrown by Brooklyn Waterfront Artists Coalition, in a space Mr. O’Connell donated to the group. A woman with a thick German accent turned to her husband. “Ve must see the Fairway before we get back on ze boat.”

Lou Sones, a longtime community activist, was one of many Red Hook residents initially opposed to the Fairway: “I changed my mind after seeing the amount of people and interest it brought into the community.” He’s not so forgiving about the new Ikea, a project Mr. O’Connell supported. “Did Fairway spawn the Ikea? Absolutely. It set a precedent for big-box stores on the waterfront.”

class="text" align="left">Mr. O’Connell supported Ikea in spite of traffic concerns because of the 600 jobs it would bring—unemployment in the Red Hook housing projects is 18 percent—but he says his heart remains with small business. He has become friends with his tenant Robert Kalin, the founder of Etsy, an online marketplace for handmade goods, and donated space in the pier for Etsy.org, the company’s nonprofit arm.

“I don’t use e-mail, computers; I don’t get that stuff, but I can feel what he’s talking about,” Mr. O’Connell said. “At 66, people think you’re ready for the rocking chair, but I’m not.”

The pair are looking to create local, human-scale manufacturing. “We could produce the stuff here and stamp it ‘Made in Red Hook’ then sell it on Etsy,” said Mr. O’Connell, breaking into a big smile. “It’s exciting to think what we’re doing here would go out to people around the world.”

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For the children of the Brownstone boomers, moving back in with the parents has become commonplace.

“I think you could walk door to door in this neighborhood and get the same story,” said Rusti Eisenberg, a history professor at Hofstra University. Her daughters call the Henry Street house in Carroll Gardens their Bermuda Triangle.

A few factors drive this phenomenon. The Brooklyn neighborhoods where these graduates grew up have become hip places to live, and rents there and throughout New York City have skyrocketed. “Another important thing, I think, is that the clash in values between parents and their grown children is not as extreme as it once was,” Rusti said.

The result is a generation of young graduates for whom returning home has become less a sign of defeat than a strategy on the path to adulthood.

Mom and Pop Eisenberg, both 63, finished college in 1967, the same year Dustin Hoffman moved home in The Graduate, but neither Rusti nor Allan considered living with their parents. “Are you kidding me?” said Allan, a psychotherapist, sweating lightly at his kitchen table after a Sunday morning jog. “I never would have dreamed of doing that.”

Annie, their middle daughter, lived at home for three years after college with her partner.

“I never felt there was anything I had to hide from my folks, and that was crucial,” Annie said. While Annie lived at home, Miguel would often spend the night. “We knew him pretty well by the time they came back from college,” Rusti said. “It was actually kind of fun to have them around.”

The transfer of values is a comfort in this situation, but there is an irony as well, one the Eisenbergs are well aware of. All three daughters have taken jobs in public interest law or at nonprofits that don’t pay much. “Many kids have imbibed their parents’ liberal, anticorporate values to the point where they can’t afford to do anything,” Rusty said. “It’s hilarious, but it’s also upsetting.”

The daughters have mixed feelings about living at home. Annie says she might consider renting from her parents in the future. Lizzie, who still lives at home, says she can’t afford to leave. Jenny, the oldest, demurs. “I love my parents, but I don’t know about moving back in with them again. They are so messy.”

Not all families are as comfortable sharing space as the Eisenbergs. When Caroline Parsons, 24, moved back home to her parents’ brownstone at 91 Sterling Place in Park Slope, she had just spent a year as an independent adult in Bushwick.

“I love living here and getting to know my parents on an adult level, but there were some specific things that I wanted,” Ms. Parsons said. “I cleaned my own room; I bought my own groceries. This seems trivial, but it was important to me, because once you start sharing those things, you lose the sense of independence.”

Her mother, Donna, 58, agrees: “Plus, middle-aged people like their things to be where they left them.”

“Otherwise they can’t find them,” said her husband Bill, 59.

The Parsons hold court in their kitchen, a lovingly crafted country-style room that reminds Donna and Bill of their roots in North Carolina. If the kitchen is communal turf, the two bathrooms mark a battle zone. After several squabbles with her mother, Caroline was forced to move her towel and toiletries downstairs to a separate bathroom. Things have improved since then. “Although I must say, there is a large towel missing,” Donna said.

“Oh, that’s because I spilled my hair mask on it, Mom,” Caroline said.

“Your what? What color is that?”

“It’s white. Well, pearlescent.”

“Well, how did it get spilled on the towel in the first place?” Donna asked. She paused a moment and laughed. “You see, it’s that sort of thing.”

When it comes to boyfriends, the Parsons take a very different tack from the Eisenbergs. Caroline is allowed to have boyfriends over, and she’s allowed to spend the night sleeping elsewhere, but boyfriends cannot spend the night at the Parsons’ house. Donna insists this is not an issue of morals but of comfort. “My thing is, I wouldn’t want to get up in the middle of the night to use the bathroom, and have to worry about running into some young man.”

“And my thing is, I don’t want guys sleeping with my daughter,” Bill said with a chuckle.

The Parsons both enjoy having their daughter home, but they don’t necessarily agree on what effect it has. “I worry that living here puts her on a different track from people out there hustling,” Bill said. “The stuff you get from interacting with the world adds to your skills in an inexplicable way.”

Donna disagrees. “What can they achieve if they spend all their time trying to pay their rent?”

Donna Parsons’ question is one that occurs to many indigenous New Yorkers returning home. All the graduates interviewed for this story agreed that living on your own in New York City was possible, especially if you had a well-paying corporate job. But for those who hope to someday own property in the areas where they grew up, or to make a career in a less lucrative field, living with your parents makes a certain kind of sense; you can’t afford not to.

“I wish that I had lived with my folks right out of school,” said Case Dorkey, a Dartmouth grad who worked for several years as a high-school teacher. “Instead, I ended up in debt, living back at home by 28, which is something nobody wants to do.”

Mr. Dorkey, now 30, has left teaching and works at a start-up in Manhattan. He has left his family’s home in Cobble Hill, but continues to feel shut out by New York prices. “I see it with myself and among a lot of my friends—still renting, still living check to check.”

Christine Kim, 31, grew up in Queens and went back to live with her parents after college. She worked first as a marketing consultant for a firm that went bust during the dot.com crash, then for Sony Pictures Classic.

“The amount I saved while living at home was enough for a down payment on an apartment,” Ms. Kim said. She bought a studio in a historic limestone townhouse along Brooklyn’s Prospect Park West for $130,000 in 2002, and sold the place three and a half years later for $260,000.

Jenny, the Eisenbergs’ eldest daughter, wishes she had made similar choices.

“It’s funny, because in retrospect, it would have made sense to live at home from the outset like my sisters,” she said. “At the time, though, none of my friends were doing that, so after a month or two at home, I moved out. And once I lived on my own, I felt that going home would be accepting defeat.”

After living on his own for two years, Andrew McKay moved in with his parents on Clinton Street in Cobble Hill when he wanted to make a career change.

“I definitely felt some embarrassment—but actually lots of people understood that it was a realistic thing to do financially,” he said. “I think for a lot of young people it is definitely a career strategy.” Since getting engaged and finding a job at Miramax, Mr. McKay has moved back out and now lives in Park Slope. “That made my parents happy … and my fiance.”

As these grads begin to break from their 20’s into their 30’s, a new question looms. “I think the last piece of the puzzle is yet to be played out,” Rusti Eisenberg said. “What happens when they want to have families of their own?”

As The Observer noted last December, even as the city’s population is growing, there is a simultaneous exodus of young families. “You have what’s been going on in other cities—the people staying are childless, and the people leaving have families,” Joel Kotkin, author of The City: A Global History and a noted expert on the economic trends of cities, told The Observer then.

The Eisenbergs hope that they can use their brownstone to give their daughters the same opportunity they had. “I think it’s possible that Jenny and her boyfriend might move back here,” Rusti said.

“I think they should move back here,” Allan said.

“I think it is in Annie and Miguel’s mind, too,” Rusti said. “Lizzie, she lives here already.”

When the Eisenbergs moved to Henry Street in the 1980’s, it was a working-class Italian-American neighborhood. “All these houses were multigenerational, nobody ever went anywhere,” Rusti said. The Eisenbergs never imagined living that way. “But now,” Rusti said, “we see it very differently, and we wonder if, in the future, we might transform our house for the children.”

Allan nodded his head. “No one we grew up with wanted to move back in with their families after college. But maybe our generation was the anomaly.”