BoomTown did an interview last night with outgoing RealNetworks (RNWK) CEO Rob Glaser after the announcement yesterday of his departure from the company he founded and led for 16 years.

That will be posted later today, but here is a profile of Glaser I wrote after spending time with him in Seattle, when I was covering the Internet for The Wall Street Journal.

It’s from Feb. 12, 1998–yes, that means Rob and I are genuine Web antiques–and focuses on Glaser’s decidedly complicated relationship with his former employer, Microsoft (MSFT).

As you will see, it comes from a much different era of the Internet, when Microsoft was much scarier, RealNetworks represented innovation and the medium was still in its infancy. My favorite line is a description of Glaser as “radiating so much intensity that his face resembles a clenched fist.”

Here it is:

Rob Glaser learned the software business as one of Bill Gates’s most aggressive proteges at Microsoft Corp. So he knows all too well the anguishing strategic decision that most software entrepreneurs inevitably confront: Go head-to-head against Mr. Gates and risk annihilation. Or cooperate with him–and risk annihilation.

Now an Internet entrepreneur himself, Mr. Glaser thinks he has another strategy: A delicate dance with Microsoft that combines a little bit of competition and a little bit of cooperation.

His newly public company, RealNetworks Inc., popularized the use of realtime audio and video on the Internet’s World Wide Web. It already has more than 18 million registered users of its free “streaming” software for receiving multimedia over the Net. It also has a rapidly growing business selling server software for transmitting audio and video to Website operators.

But it stands squarely in the path of the strategy that has drawn Microsoft into trouble with antitrust regulators: Emulating innovative products, integrating them into its operating systems and then giving them away free. RealNetworks’ daunting task is to prove it can do a better job of outmaneuvering Microsoft than Netscape Communications Inc., the browser pioneer whose market share and profitability have been devastated by Microsoft’s integration strategy.

Mr. Glaser insists he and the software giant can coexist. “I learned an amazing amount from Bill,” he says, speaking in staccato bursts and radiating so much intensity that his face resembles a clenched fist. “We knew we could either compete head-on like Netscape or do something a lot more interesting.”

His strategy is known internally as “coopetition.” Out of mistrust, Netscape two years ago rejected an unsolicited offer from Microsoft to become a partner and investor. But Mr. Glaser approached his former colleagues last summer seeking just such an alliance. In July, he sold a nonvoting 10% stake to Microsoft for $30 million, and licensed RealNetworks’ technology to the software giant for another $30 million. Microsoft also agreed to bundle RealNetworks’ software with Internet Explorer.

In making the deal, Mr. Glaser helped himself to Microsoft’s cash and prestige and calculated that Microsoft wouldn’t consider streaming technology to be as strategic to its future as the browser.

“What we were trying to do in the partnership is to set it up so that our success would not disadvantage their core business,” Mr. Glaser says. “Microsoft is a very paranoid company and so we have tried to create an environment where while they might be covetous of some of our success, analytically they would not fear it.”

The deal gave Mr. Gates the opportunity, if he so desired, to clone RealNetworks’ products during the period when they were licensed to Microsoft. “There’s no question they could use our own technology to become extremely vigorous competitors and try to put us out of business,” says James Breyer, a director and member of Accel Partners, a venture-capital firm that helped finance RealNetworks.

So Mr. Glaser needs to stay ahead of Microsoft by rapidly improving his software, accumulating enough customers to become the standard for sending audio and video over the Internet and diversifying into related businesses.

Last month, for example, he announced an agreement with one of Microsoft’s archrivals, Sun Microsystems Inc., to finetune his software to perform better on Sun’s popular Internet servers than on Windows-based servers.

“They are neither friend nor foe, but Microsoft is most certainly the environment we live in,” says Mr. Glaser, now 36 years old. “It’s how we work within that environment that will make all the difference.”

Mr. Glaser’s own personality seems suited to the relationship’s contradictions. He has been a committed liberal since his days at Yale University, where he wrote a column called “What’s Left” for the student newspaper. He initially named his company Progressive Networks to reflect his politics. And he donated 700,000 RealNetworks shares to causes related to freedom of speech and environmental issues after the public offering, and promises to contribute 5% of the company’s future profits as well.

But he became a notoriously hardcharging and sometimes arrogant manager after he joined Microsoft in 1983, at the age of 21. Some colleagues dubbed him a “screamer.” When deadlines approached for projects, several former colleagues at Microsoft say he became increasingly revved-up, downing one Diet Coke after another and erupting at even tiny mistakes. “My intensity sometimes manifested itself in less positive ways,” Mr. Glaser concedes.

“Like Microsoft, Rob was smart, young, perhaps a little hard to take, and convinced he was absolutely right about a lot of stuff,” recalls Mike Slade, a friend of Mr. Glaser’s at Microsoft who now runs an Internet publishing company, Starwave Corp. “But that was what was rewarded at the company and everything was going too fast there for a lot of management training.”

The pace did take its toll. Even though Mr. Glaser rose to become vice president of multimedia systems and one of Mr. Gates’s favorites, his last years at Microsoft were rocky. Some at the company point to an internal power struggle with Microsoft’s head of technology, Nathan Myhrvold. “They both wanted to be Bill’s boy genius and visionary for the company,” says a colleague. “Obviously, Nathan won.”

Mr. Glaser dismisses tales of infighting, blaming his departure on a diminishing feeling of “joy” in his work. “I began to think that Bill had the best job of all,” he says. In 1993, at the age of 31, he resigned, with about $15 million of stock in his pocket.

His retirement didn’t last long. Soon after, he saw a version of the Mosaic browser, the first graphical interface software for navigating the Web. He had an epiphany, he says, realizing that the Internet could eventually become a major purveyor of audio and video.

Mr. Glaser sank about $1 million of his own money into a start-up that would first produce software for compressing and transmitting sound. With additional funding from friends, such as Lotus founder Mitch Kapor, RealAudio 1.0 quickly made its debut in April 1995.

RealAudio was greeted with more than a little disdain from the Internet elite because it was a tinny and unsatisfying experience for most users. But it gave the Internet a voice, and Mr. Glaser kept plugging away, improving fidelity and striking deals with more content providers to use it on their Web sites. The hook: Free player software for consumers.

He is attempting to repeat the process with RealVideo. It currently provides small, jerky moving pictures but will, he believes, someday transform the Internet as data transmission speeds increase. In a recent demo of the player, Mr. Glaser selected a music video by the languid singer Jewel, he joked, “because she doesn’t move around too much.”

Meanwhile, Microsoft has been developing its own Media Player and NetShow streaming software, partly with technology acquired by purchasing VXtreme, a RealNetworks competitor.

The Microsoft products are now free. But the company may decide to charge for the latest version of NetShow coming out this year, which would be good for RealNetworks. Meanwhile, Microsoft will continue to bundle RealNetworks’ player software with the Microsoft browser, also good for RealNetworks. And the day after RealNetworks’ Sun deal, Microsoft announced an agreement to make its own Media Player compatible with RealNetworks’ server software, yet another positive development for RealNetworks.

“The user only wants it to work,” says Rich Tong, a Microsoft marketing vice president. “So it is good business to work with RealNetworks to set standards for compatibility and expand the market for all of us.”

Skeptics assert that RealNetworks has forged only a temporary truce with Microsoft. Like Netscape, it must continually confront the challenge of trying to make money on technology that Microsoft gives away. RealNetworks charges $29.95 for an enhanced version of the player it gives away free, and $695 and up for its most powerful server software.

Some large companies are snapping the products up. Mercedes Benz, Eastman Kodak and Lockheed Martin are buying RealNetworks’ latest software, RealSystem 5.0, to bring their internal networks to life. Boeing Co., for example, uses RealNetworks’ software to communicate with employees world-wide and conduct training sessions. A variety of media concerns such as Metro-Goldwyn-Mayer, the Public Broadcasting System, AOL, Fox News’s 24-hour newsfeed and Paramount Pictures use it as well.

Mr. Glaser recently cut a deal with Macromedia Inc., the largest provider of animation-editing software, to transmit animated material over the Internet. RealNetworks is also operating multimedia Web sites for other companies, and has a joint venture with MCI Communications Corp. to create a broadcast network on the Web.

All these initiatives are running up big bills. Earlier this month, RealNetworks reported that revenue more than doubled for 1997, to $32.7 million from $14 million the year before. But heavy research and development spending tripled losses to $11.2 million, or 40 cents a share, from $3.8 million, or 14 cents a share. The company’s high costs, plus the looming threat of Microsoft, have depressed the stock, which hovers at around $16 a share, only slightly above the $12.50 a share it opened at when it went public in November.

But Mr. Glaser exudes confidence. His intense personality seems calmer these days. Once divorced, he now has a steady girlfriend and is traveling more frequently, including a summer trip to New Zealand, Australia and French Polynesia, where he made the decision to take RealNetworks public. His 13.5 million shares are worth $218.5 million. And he thinks he has Microsoft figured out. “People in Silicon Valley see things unnecessarily in black and white: You either hate Microsoft or you are a vassal of them. I am saying there is a third way.”

Davis (pictured here) is a senior partner at Davis, Shapiro, Lewit & Hayes. The entertainment law firm–which is based in both New York and Los Angeles–has an emphasis in music, digital rights, and branded entertainment, and works with a wide range of digital media companies, including YouTube.

After a BoomTown post in late October on Smith’s plans, CBS (CBS) confirmed the move, which will take place in January, noting that his new firm would remain an adviser to the media giant under a multiyear contract.

Davis is an interesting choice for the firm, which Smith hopes will emulate Hambrecht & Quist, one of the more influential among Silicon Valley investment banks during the first Web boom.

Along with Davis, Smith has been joined by CBS’s Mike Marquez.

Smit has also been collecting a high-profile group of advisers to the still-unnamed firm, including Danny Rimer of Index Ventures, former Netscape Communications CFO Peter Currie, and David Golden, EVP of former AOL CEO Steve Case’s Revolution LLC.

Quincy Smith, the high-profile CEO of CBS Interactive, is planning on leaving his job at the media giant in January to start an advisory firm in Silicon Valley, according to several sources.

But, in an interesting twist, Smith (pictured here) will remain an adviser to CBS (CBS) under a multiyear contract, sources added, making it his first client.

UPDATE: CBS confirmed the move BoomTown earlier reported, in a press release below.

Apparently, Smith will focus intently on video monetization, authentication and other digital issues for the company. CBS is calling it a “transition to a new role,” in its official statement.

CBS Interactive President Neil Ashe will take over Smith’s duties, but without the CEO title, which was a relatively new one for Smith.

CBS is television’s most popular network again this season and its interactive properties are among the top ten in aggregate in both traffic and video.

“I’m very pleased to extend our relationship with Quincy, who is one of the finest minds working in Interactive media today,” said Leslie Moonves, president and CEO of CBS Corporation, in a statement. “Quincy helped put CBS Interactive on the map and we are now a Top 10 presence in premium content.”

Said Smith: “It’s a huge honor to count CBS as my first client. In three years, this company has grown its Interactive profile immeasurably, and yet there is so much more to be done. I love CBS and its people and I look forward to working closely with them to help CBS become the premier video content company, regardless of platform or screen.”

MediaMemo’s Peter Kafka wrote in May about the possibility of Smith departing CBS, where he has worked since late 2006.

As Kafka wrote, Smith has long wanted to start a new media consultancy and has also wanted to return to Silicon Valley.

In fact, the man BoomTown has dubbed the “Energizer Bunny of the Web” was an early employee at Netscape Communications in the Web 1.0 heyday, tried his hand at venture capital and worked on tech deals for media banking firm Allen & Co.

At CBS during the Web 2.0 era, Smith has been aggressively guiding the company into a series of transactions, including the $280 million acquisition of Last.fm in 2007 and the $1.8 billion purchase of CNET last year.

Smith has also been involved with digital issues related to CBS’s strong television assets. He has championed–unlike other media giants–widely distributing CBS content online and keeping control of its advertising sales.

People close to Smith say he often talks of trying to emulate Dan Case, the late brother of AOL founder Steve Case and the former CEO of Hambrecht & Quist, one of the more influential among Silicon Valley investment banks during the first Web boom.

Sources said that the time has now come and that the move is expected to be announced very soon.

It is also likely that Smith’s top business development exec at CBS, Mike Marquez, will also leave to join him at the still unnamed firm.

BoomTown suggestion for a name: Q 3.0.

Here’s Smith in a cameo for a video spoof after he paid $5 million for Wallstrip, the funny business video site which has since been severely sidelined:

QUINCY SMITH SIGNS MULTI-YEAR ADVISORY AGREEMENT WITH CBS CORPORATION

CEO of CBS Interactive to Depart in January 2010 but Will Continue Working with Company on Video Content Monetization, Among Other Projects

CBS Corporation announced today that Quincy Smith, Chief Executive Officer of its CBS Interactive division, will transition to a new role with the company beginning January 2010 as he starts an independent advisory business. In this new role, Smith will advise CBS on strategies and opportunities for growth across the Company’s interactive businesses. Smith, who had led CBS Interactive since November 2006, will remain with CBS Corporation as the division’s CEO through the end of 2009. Neil Ashe will continue as President of the division.

Smith will continue to be closely involved in CBS’s initiatives related to next-generation monetization of video, including oversight of the Company’s effort to explore authentication as a new, additive method of distribution. He will also advise on partnering with technology companies to expand CBS’s interactive presence, as well as explore new growth opportunities related to content, services and applications.

“I’m very pleased to extend our relationship with Quincy, who is one of the finest minds working in Interactive media today,” said Leslie Moonves, President and CEO of CBS Corporation. “Quincy helped put CBS Interactive on the map and we are now a Top 10 presence in premium content. His entrepreneurial spirit and his passion for the business have helped this Company attract some of the most creative minds working in digital media. I know he will continue to be successful in all he’s yet to do, and we’re very happy to have Quincy working with us in this new role at CBS.”

“It’s a huge honor to count CBS as my first client,” said Smith. “In three years, this company has grown its Interactive profile immeasurably, and yet there is so much more to be done. I love CBS and its people and I look forward to working closely with them to help CBS become the premier video content company, regardless of platform or screen. I especially want to thank Leslie for his leadership and counsel, and for giving me this opportunity to continue working with CBS.”

Smith came to CBS Interactive in 2006, and in three years helped build a division that has become a top ten property in terms of worldwide visitors and video views. CBS’s acquisition of CNET in 2008 added industry-leading Web sites like CNET.com, GameSpot, TV.com, chow.com and BNET.com to a portfolio that had already included top ranking properties like cbs.com, cbssports.com and last.fm. Today, CBS Interactive sites span nearly every category of premium content on the Web, across news, sports and entertainment.

Previously, Smith was an executive with Allen & Company, where he was involved with multiple transactions and advised companies such as Comcast, Google and CBS. Prior to Allen & Company, Smith was a Founding Partner of The Barksdale Group, a venture capital firm. Previously, Smith spent five years at Netscape where he ran Investor Relations and Corporate Development and played a role in over 20 joint ventures, investments and acquisitions including Netscape’s ultimate sale to AOL. Prior to that, Smith was an investment banker for Morgan Stanley.

Brad Garlinghouse’s appointment to a new job at AOL today as its new communications czar is yet another sign of an interesting trend for those keeping score of the comings and goings of top Internet execs.

Garlinghouse came to the Time Warner (TWX) online unit after a year-long break, preceded by six years at Yahoo (YHOO).

As anyone who watches the digital space knows by now, this kind of management musical chairs is common and never-ending.

In fact, borrowing a quote by IAC/InterActiveCorp (IACI) CEO and chairman Barry Diller from an onstage interview I did with him at the sixth D: All Things Digital conference and switching out Hollywood for Silicon Valley: “[It] is a community that’s so inbred, it’s a wonder the children have any teeth.”

But, given all the movement of late, this insider seat-switching seems more frantic than ever, as allegiances shift, competitors become friends and colleagues become rivals faster than you can tweet.

When he left Yahoo last summer, in fact, the digital chatter was that Garlinghouse would take a job either as a venture capitalist (he had been one once) or helming a start-up (that too, at Dialpad.com).

In fact, sources said, Garlinghouse had been considering two mobile gigs, but opted for helping to try to overhaul a troubled Web giant.

Fixing messes was the impetus of Owen Van Natta, who left a top job at social networking giant Facebook in early 2008 and by the end of the year, headed over to run Project Playlist, a controversial online music-sharing service.

But then he had hightailed it by spring to try his hand at reviving MySpace, as its CEO.

His boss, News Corp. (NWS) digital head Jon Miller, did the same, getting the hook (unfairly to my mind) at AOL several years ago and then creating an investment firm with former MySpace head Ross Levinsohn.

The pair considered being part of a bid to oust Yahoo management in 2008.

Miller’s freedom lasted only until he got an offer that he presumably could not refuse from News Corp. head Rupert Murdoch recently. (Full disclosure: News Corp. owns Dow Jones, which owns this site.)

The list goes on, chock full of ex-Yahoos, in fact.

Its one-time COO, Dan Rosensweig, left the company in 2006, for example, and joined the well-known private-equity firm, Quadrangle Group.

But, soon enough, he was scooped up by Activision Blizzard (ATVI) to run its Guitar Hero division.

Yahoo Network head Jeff Weiner also departed from the Internet giant, in mid-2008, for a stint at two VC firms.

He landed at LinkedIn, the business-networking service where he was named CEO in late June.

Greg Coleman ran Yahoo ad sales until mid-2007 before taking a job at AOL earlier this year, which he lost after it got new management soon after.

At Yahoo, Coleman sparked with former advertising sales head Wenda Harris Millard, whom he ousted. She went onto Martha Stewart Living Omnimedia (MSO) and left there this spring for the Media Link consultancy.

Presto! She is now helping MySpace’s Van Natta fix the social networking site’s ad business.

Current Yahoo U.S. advertising head Joanne Bradford actually came from Microsoft last summer, via her own short visit to the troubled ad start-up SpotRunner.

Former Yahoo search techie Qi Lu now runs digital for Microsoft (MSFT), along with a big gang of ex-Yahoo techies he has recruited.

And Scott Moore is even better at the switcheroo. He was at Microsoft running MSN U.S. content, switched to Yahoo as its media poobah, left last year to consider a start-up and then headed back to Microsoft as head of U.S. content this year.

But former Google (GOOG) execs have also been busy shuttling hither and yon, mostly to innovative start-ups.

Of course, many find refuge at Facebook (COO Sheryl Sandberg, PR major domo Elliot Schrage and many more) and Twitter (GC Alexander Macgillivray and COO Dick Costolo).

Recent departures–such as Sukhinder Singh Cassidy, who landed at Accel Partners for now–are also likely to find new homes soon enough.

And, of course, there’s always Garlinghouse’s new boss, former Google ad head Tim Armstrong, who took over at AOL earlier this year.

We’ll skip former Joost CEO and former Cisco (CSCO) exec Mike Volpi (who is now a VC); former Netscape Communications/short-term VC/ex-banker/current-for-now CBS (CBS) digital head Quincy Smith; and Joanna Shields, who has worked at Real Networks (RNWK), Google and Bebo (which was bought by AOL)–for now.

Because, around and around and around it always goes, as you can see in this funny video below, which I posted previously:

[Musical Chair designed by Jacob Mathew.]

In the ongoing game of musical chairs among top managers at Internet companies, former Yahoo exec Brad Garlinghouse–famous for his controversial “Peanut Butter Manifesto,” which correctly chided the Internet giant for becoming so lugubrious several years ago–is taking a job at AOL very similar to the one he left at Yahoo last year.

Garlinghouse, 38, has been named president of Internet and mobile communications at AOL, putting him in charge of the New York-based Time Warner (TWX) online unit’s powerful email and instant-messaging properties, including ICQ and AIM.

He has only been in talks with AOL–which used Spencer Stuart’s Internet-top-exec-finder-in-chief Jim Citrin–for a few weeks, in a deal that came together quickly, he and the company said.

Garlinghouse, a longtime Web entrepreneur and exec, had reportedly been considering a number of start-up and venture-related jobs since he left Yahoo last summer after six years there.

Sources said he was seriously considering becoming the CEO of a mobile firm.

He was most recently at Silver Lake Partners, as an “in-house senior advisor,” the private equity firm that recently bought the Skype Internet telephony firm for $1.9 billion. Garlinghouse also reportedly helped work on that deal.

“It’s really exciting to be to able to rebuild and revitalize an industry giant,” said Garlinghouse in an interview with BoomTown earlier today. “I make no bones that these [properties] are in need of that…but there is also a huge opportunity to do something cool.”

Garlinghouse has to hurry. Despite being among the top communications players online–a group that also includes Yahoo (YHOO) and Microsoft (MSFT) and, more recently, Google (GOOG)–AOL has lost relevance with key audiences, even as social networking properties like Facebook and the microblogging service, Twitter, have innovated in the communications space.

The hiring of Garlinghouse, well known in Silicon Valley circles, is meant to counter that.

He will head up AOL’s operations from its Mountain View, Calif., campus–which is also the former HQ of AOL-acquired Netscape Communications–where, said AOL CEO Tim Armstrong, Garlinghouse will “be CEO of Silicon Valley for us.”

Between all its various properties, AOL has several hundred employees in the Northern California area.

Armstrong said AOL–which was founded 25 years ago on the East Coast and has tried and failed many times to get a true foothold in the West–thinks having an important player at the center of the tech industry is critical as it moves to spin off as an independent company by the end of the year.

“We have a triple play in getting a great executive, who is a master in the communications on the Web and who is well known out there,” said Armstrong. “Brad is our senior AOL manager there.”

Along with running all of AOL’s communications properties, Garlinghouse will inherit some of its community properties, although AOL’s Bebo social networking unit–now considered to be an overpriced acquisition error–now resides in its ventures unit, headed by Jon Brod.

Garlinghouse will also be aiding Brod, said Armstrong, with AOL on the lookout for acquisition opportunities in communications and other arenas.

While Garlinghouse declined to be specific about what would pique his buying interest, he was responsible for such big Yahoo deals as its $350 million purchase of Zimbra in the fall of 2007.

He was also key to bringing both Oddpost, which is at the heart of Yahoo’s email offering, and the popular Flickr photosharing service to Yahoo.

Garlinghouse said he has admired what Twitter and Facebook have done, but that they were not destroying traditional online communications, pioneered by AOL, as some assert.

“It’s a vibrant segment and this just means there are a lot of opportunities to enable integration,” he said. “I think of it as an expansion of online communications and I hope AOL can do more collaboration and partnerships.”

Garlinghouse also has to watch AOL’s basic products like email, which was recently passed by Google’s Gmail as the No. 3 email service in the U.S. Yahoo Mail is the top email, while Microsoft’s Hotmail is second.

How much Garlinghouse can do will depend on the future financial strength of AOL. Its advertising business has been hit hard in the econalpyse, with hopes it will return before its money-generating access business continues its slow decline.

Armstrong is now in the midst of looking over AOL’s cost structure and employee base, which most expect will eventually result in another round of layoffs and cuts.

He has been busy creating a different strategy for the company since he arrived earlier this year, as well as hiring (and firing) top execs to create a new management structure.

Now, that includes Garlinghouse.

So, for a look-see at AOL’s latest talent acquisition, here’s a video interview I did with him, just after Yahoo bought Zimbra:

And here’s the full press release from AOL about the hiring of Garlinghouse:

AOL NAMES BRAD GARLINGHOUSE AS PRESIDENT, INTERNET AND MOBILE COMMUNICATIONS

NEW YORK, N.Y.–September 8, 2009–AOL today named Brad Garlinghouse as President of Internet and Mobile Communications, spearheading AOL’s global efforts to expand the reach of its e-mail and instant messaging. Garlinghouse will also take on an expanded leadership position for the company, heading up AOL’s Silicon Valley operations from its Mountain View campus and serving as the West Coast lead for AOL Ventures, the company’s venture capital arm headed globally by Jon Brod. Garlinghouse was most recently at Silver Lake Partners as an in-house Senior Advisor.

Prior to Silver Lake, Garlinghouse spent nearly six years at Yahoo!, where he led that company’s communications and community products. Garlinghouse will report directly to AOL’s Chairman and CEO Tim Armstrong.

” Brad Garlinghouse is an all-star in the Internet industry with an unparalleled background and proven track record, having led Yahoo’s communications products to unprecedented growth,” said Armstrong. “In addition to leading our efforts to grow our communications products, Brad will be bringing his global leadership and business experience as a key member of our company’s executive leadership team. He will also be a major force for AOL in Silicon Valley, working to expand our presence there and in the tech community in general. We’re delighted to have Brad on board and know he’ll do great things for AOL.”

“It’s a tremendous opportunity to join AOL at this pivotal moment in its history,” Garlinghouse said. “Tim has set out a clear strategy and vision for where he is taking this company as it becomes independent again. I’m looking forward to working with him and the rest of the team to realize that vision.”

Armstrong, who joined AOL in April, identified Communications as one of the five key areas of strategic focus for AOL after an extensive 100-day review of the company’s business. Other focus areas include Content, Advertising, Local & Mapping and AOL Ventures.

Garlinghouse spent nearly six years at Yahoo! where he most recently served as SVP of Communications and Communities. Prior to that he served as SVP of Communications, Communities and Front Doors, which included the Yahoo! home page. He came to Yahoo in 2003 as VP, Communication Products. During his time there, Yahoo! Mail went from No. 3 to leading all competitors by a wide margin, and the company’s instant messaging service rose to become the leader in that market as well. Garlinghouse also oversaw the company’s Flickr photo-sharing service and Yahoo! Groups.

Prior to Yahoo!, Garlinghouse was CEO of Dialpad.com Inc., responsible for all aspects of the company’s operations, finance, sales and marketing. He was also General Partner at @Ventures, Category Manager of Media Development for the @Home Network, Inc., and Manager at SBC Communications.

Garlinghouse, 38, received his BA in economics from the University of Kansas and his MBA from Harvard Business School.

In Web years, BoomTown is now officially 143 years old.

Why? Well, I was the one who got to write the big Page One piece in The Wall Street Journal after GeoCities was sold to Yahoo in January of 1999 for $5 billion in stock.

GeoCities was, in its way, the Facebook of its time.

But instead of “friends,” its users were “homesteaders,” since the Web then was a place to be pioneered and settled.

As Cher so eloquently sings: Those were the days my friend, we thought they’d never end.

Except they did. Yahoo (YHOO) announced yesterday that it was closing the GeoCities unit down, part of new CEO Carol Bartz’s war against useless assets at the troubled company.

But a full decade ago, the Yahoo-GeoCities transaction was a big, big deal, struck at the peak of the Web 1.0 bubble.

The move shook up the then-Internet landscape, in which Yahoo was the undisputed king.

The sector then had begun to rapidly consolidate, as stronger players snapped up weaker ones in a race for market share.

The Yahoo-GeoCities deal closely followed another deal in which At Home, a high-speed Internet access service, bought search and directory service Excite for stock valued at $6.7 billion. In another key deal at the time, then-independent America Online agreed to buy Netscape Communications for stock then worth $4.2 billion.

Of those then-dominant Web companies, only Yahoo and AOL–now a troubled unit of Time Warner (TWX)–survive relatively intact.

And, what exactly did Yahoo get for its giant payment back then? A money-losing, low-revenue company with a whole lot of users.

At the time of the purchase, the publicly-traded Marina Del Rey, Calif., company had reported that fourth-quarter sales increased to $7.5 million from $1.7 million a year earlier. But the company’s loss had also swelled, to $8.4 million from $3 million, in the year-earlier period.

Sound familiar to some current Web 2.0 stories? I thought so.

Another weird irony: One of GeoCities major investors was a venture firm called Flatiron Partners, whose principal, Jerry Colonna, was on the board.

And who was Colonna’s parter? Well, Fred Wilson, who has a different firm now called Union Square Ventures and is–wait for it–one the the major investors in the 2009 hotsy-totsy start-up, Twitter.

(You can read Wilson’s terrific take from the VC perspective of the GeoCities experience here.)

In other words, the more things change… Well, actually, they don’t change.

So, if you want to take an instructive trip down memory lane, here is my piece below, which appeared in The Wall Street Journal on Jan. 29, 1999:

Those Who Tied Fortune to GeoCities Yell Yahoo! All the Way to the Bank

By KARA SWISHER | Staff Reporter of THE WALL STREET JOURNAL

Last spring, Thomas R. Evans was nervous about leaving his longtime job at the top of a powerful Manhattan media company for an Internet start-up near the beaches of Southern California. So he talked to his boss, real-estate and publishing tycoon Mort Zuckerman.

“I was wondering if this whole Internet thing was real and sustainable,” says Mr. Evans, then publisher of the Atlantic Monthly and U.S. News & World Report. “I wanted his blessing in a way.”

Virtual Payoff

Mr. Evans got Mr. Zuckerman’s nod–and a lot more. You know the drill by now (though it may not be getting any easier to hear). He became chief executive officer of GeoCities , an electronic casbah of about 3.5 million Web sites, and helped lead its initial public offering last summer. Then Thursday, Yahoo! Inc. agreed to buy the young company for about $5 billion in stock. It means the value of Mr. Evans’s stock options soared by 65% Thursday to a dizzying $200 million.

Yahoo! Agrees to Buy GeoCities in $5 Billion Stock Transaction

That’s some kind of money for nine months’ work. After you’re done banging your head on a wall, consider that members of the new financial elite in Silicon Valley are being created in less time than it takes for a kid to finish his first-grade year. That puts oil, real estate and finance magnates to shame. Mr. Zuckerman, for example, spent a lifetime building his $1 billion financial empire.

Asked how he was doing Thursday, Mr. Zuckerman says: “Not as good as Tom Evans.”

Mr. Evans, who commutes between GeoCities’ Marina Del Rey, Calif., headquarters and his home in New Canaan, Conn., is quick to point out the ephemeral nature of his wealth. He must wait six years for his options to be fully vested. And his net worth could evaporate if Yahoo’s highflying stock sinks.

“It does not seem real, because it is not real, because this is based on the long term and is dependent on where this whole industry is going,” says Mr. Evans, 44 years old. “Anyone coming into this industry assumes a certain amount of risk because no one really knows how it is all going to turn out.”

Litany of Lucre

It has turned out well so far for the new moguls at GeoCities. According to public filings the company made last summer, the biggest individual winner is co-founder and Chairman David Bohnett, 42, who owns about three million shares outright, now worth $367 million, based on Yahoo’s closing price Thursday. Mr. Bohnett insists he is overlooking that bit of extra money. “I do not see this as a financial event,” he says. “And we did not start this company with money in mind.”

Chief Technical Officer John Rezner, 35, who worked nine years for aerospace company McDonnell Douglas Corp. before co-founding GeoCities, holds 827,000 shares worth $103 million.

The management team that came in with Mr. Evans last year–taking over from Mr. Bohnett to help with the IPO–is also well-situated. Chief Financial Officer Stephen Hansen, 42, who formerly held the same position at Universal Studios Hollywood, has options for about 600,000 shares of stock, which would be worth $74.7 million at current prices. Michael Barrett, 36, advertising vice president and former online executive with Walt Disney Co., has options for 280,000 shares, worth about $34.9 million.

There are, of course, all kinds of gnashing of teeth over whether the Internet entrepreneurs deserve such riches. But obtaining great wealth through luck or artful maneuvering is nothing new in American business history. Take the stock manipulators of the 1890s and the leveraged-buyout artists of the 1980s. It may be some consolation that GeoCities’ founders can claim that they developed something that is used by many people. In its December Web-traffic report, research firm Media Metrix says the “GeoCities.com” Web site ranked third, behind America Online Inc. and Yahoo, with nearly 19 million different visitors.

Mr. Bohnett says the company was born from a “passion for giving people a chance to speak up.” Founded in 1994, GeoCities was one of the first Web-based communities, where users post individualized sites to express themselves.

Dubbed “homesteaders,” these customers create the bulk of the content on GeoCities. Their Web pages are organized into “neighborhoods” of personal interests and hobbies, such as personal finance or motorcycles, and monitored by a network of volunteers.

“My goal was to stake out a broader territory and create a community of interests, just in the same way Yahoo was helping people find their way around the Web,” says Mr. Bohnett, who led the company in a variety of top jobs, including chief financial officer, CEO and president. “Then we were going to monetize that base of users as the business model emerged.”

That model for profitability hasn’t yet arrived, in part because the company spends heavily to increase its market share. Thursday, it announced a net loss for last year of $18.2 million on revenue of $18.4 million.

Mr. Evans, a dark-haired man with a preppy demeanor and razor wit, has plenty of experience building businesses. He worked his way up in Mr. Zuckerman’s organization from sales and advertising jobs, and eventually served as president and publisher of several magazines.

After being approached several times about new-media positions, Mr. Evans says he decided to jump to GeoCities when the importance of the Internet became clear to him. “I think that by the time I really took a look at it, the whole sector had matured and gotten really interesting for those of us in the traditional media companies,” he says.

While Mr. Evans is loath to discuss the valuations of Internet companies, his former boss Mr. Zuckerman doesn’t dodge the opportunity to be philosophical about Web mania.

“It’s like they said in high school: ‘Boys will be boys and girls will be girls,’” Mr. Zuckerman says. “I don’t want to change anything, I just want to get in on it.”

Back in the heyday, Peter Currie was the money man to see in Silicon Valley.

As CFO of Netscape Communications, he led the start-up into history, as the first great Internet rocket ship, when it went public on Aug. 9, 1995.

With the first consumer-friendly browser software, which made the Web easily understandable to the masses, Netscape was at the red-hot center of the nascent digital revolution.

“Wall Street went bonkers,” said one news reporter about the IPO, and the craziness did not stop for quite a while.

Rising to insane levels, the stock was ground zero of the Internet gold rush too, despite the fact that it had no profits to speak of.

But it did have a 23-year-old co-founder and tech wunderkind in Marc Andreessen, and a growth trajectory that was astounding.

If you think it sounds somewhat similar to Facebook today–where Currie will now help out as temporary financial adviser after the social-networking site parted ways with its CFO, Gideon Yu, yesterday, following mutual disagreements and announced a search for a replacement–you are correct.

In that job, the 53-year-old Currie will be helping Facebook CEO and founder Mark Zuckerberg, 24, navigate–albeit temporarily–through some stormy economics seas on a journey that will hopefully end in an initial public offering.

The search for a new CFO will also involve Currie, obviously, and will be conducted by Jim Citrin of Spencer Stuart.

But until a new CFO is in place, Facebook’s quest still entails sorting out a substantive advertising monetization strategy while also keeping up its speedy growth rates and managing the high costs that mount with its popularity.

That certainly was Netscape’s major challenge, which it never met successfully and which was made worse by intense attacks from Microsoft (MSFT) on Netscape’s core browser business.

That eventually led to the antitrust trial against the software giant, even as Netscape saw its star fall dramatically.

It was sold to AOL in 1998 for $4 billion, a shadow of its bubble valuation, and is now more of a footnote than an ongoing tech product (although the now-popular Mozilla browser is a direct descendant of Netscape).

In fact, in 2008, Time Warner (TWX) online unit AOL dropped its support for the Netscape browser and said it was no longer releasing new versions.

Still, a lot of former Netscape execs now hold other key jobs in the Web space.

Its investor relations exec, Quincy Smith, now heads up the digital arm of CBS (CBS), for example.

And Andreessen has started a number of companies and has transformed himself into an kind of elder statesman of Silicon Valley of late, as well as a newly minted venture investor.

Andreessen, many sources said, was a shadow influence on Zuckerberg’s decisions related to Yu, with whom relations had gotten tense, and to bring in Currie (pictured here).

Currie is certainly a great choice, in terms of the close-knit tech sector’s respect and experience.

Currie is also unusually tall, aggressively avuncular and laid-back, loves Elvis and enjoys pranking reporters like BoomTown. (Case in point: He once tried to spread the rumor that I am short due to a medical condition.)

Now the president of Currie Capital, a private investment firm, he had previously worked at General Atlantic in private equity.

After Netscape, he was a partner and co-founder of the Barksdale Group, an early-stage venture capital firm.

Before Netscape, he was CFO of McCaw Cellular Communications and also worked at Morgan Stanley (MS).

Currie is also board-happy, serving as a director of a variety of tech firms, private and public. They have included CNET Networks, Critical Path, Clearwire (CLWR), Safeco, Ofoto, Tellme Networks and Zantaz, as well as Sun Microsystems (JAVA).

He has an MBA from Stanford University and went to Williams College.

Here is the video interview I did with Currie and others at an event to support his friend and former Netscape exec Mike Homer, who recently died of Creutzfeldt-Jakob disease (Currie is at the 2:16-minute mark):

(Image of Netscape IPO T-shirt courtesy of intothefuzz on Flickr.)

In a back-to-the-future move, former Netscape CFO Peter Currie will be the key adviser to Facebook about financial matters, until a new CFO is found, sources said.

The temporary move puts a well-known and well-liked Silicon Valley figure in place at the company at what is surely a tumultuous moment. Currie has most recently been a venture investor.

Today, Facebook parted ways with its CFO, Gideon Yu, saying it was prepping for an eventual IPO.

But others sources at the company said Yu and Facebook CEO and founder Mark Zuckerberg had had intensifying differences in recent weeks over a range of issues.

In Currie, Zuckerberg gets a seasoned tech exec, with deep ties in the sector. He serves on the board of Sun Microsystems (JAVA), one of many such seats he has held at tech companies.

And, perhaps most significant of all, Currie is very close with Facebook board member and Netscape Communications co-founder Marc Andreessen. Sources said Andreessen was also influential in the decision related to Yu leaving his job.