One might make the argument that of all the Wall Street personalities who made names for themselves in the internet boom of the late 1990s and in the bust that soon followed, Morgan Stanley’s Mary Meeker was the most important.

Sure, she isn’t as widely known in the mainstream as former Credit Suisse First Boston investment banker Frank Quattrone or former CIBC Oppenheimer and Merrill Lynch analyst Henry Blodget, who found themselves in the spotlight due to legal action that was taken against them in regards to their behavior‘ during the boom.

But despite the fact that Meeker never found the infamy of Quattrone and Blodget, the woman dubbed the Queen of the Net‘ by Barron’s in 1998 was just as much a player in the world of technology investments. And she still is.

Last week, I came across an old Fortune article from 2001 describing Meeker’s story. It sure is an intriguing one.

After rising to Wall Street fame during the .com boom and pocketing $15mn in compensation in 1999 alone, Meeker and her rosy ratings found themselves defeated by the unstoppable forces of the market.

Amazingly, following the crash, Meeker refused to downgrade most of the companies she was following and maintained positive ratings on many of them. Some fell as much as 97% from their highs yet she still, for whatever reason, decided to ignore reality.

But Meeker’s folly was not so much that she made mistakes or was simply a poor analyst, it was that Meeker hadn’t been playing the role of Wall Street analyst at all.

As Fortune observed in 2001:

“But Meeker’s refusal to downgrade her stocks is only a small piece of a bigger story. This larger story is about how a smart, hard-working analyst became a big part of the world she covered. Meeker came to see herself not merely as an analyst but as a player–a power broker, a dealmaker, a force to be reckoned with. She was a true Internet insider–and other Internet insiders, most of whom were her friends, shared this exalted view of her.”

Prominent venture capitalist John Doerr went so far as to call Meeker a ‘service provider’ and stated point blank, “I don’t think of Mary as an analyst.”

As I took a walk down memory lane courtesty of Fortune’s article, I couldn’t help but note a parallel between some of the tech blogosphere’s most prominent personalities and Mary Meeker.

As Meeker did, many of the tech blogosphere’s A-listers find themselves in an awkward position. They have assumed the roles of journalists yet at the same time, they are insiders in the very industries their readers turn to them to cover.

Some are consummate Silicon Valley insiders‘ who wheel, deal and have make investments in the types of companies they cover. Others work for companies in the industry and have obligations to their employers that could conceivably (at times) conflict with their informal obligations to the readers. Most count friends and personal associates amongst those whose companies could be impacted by their writing.

I’ve discussed conflicts of interest in the blogosphere in some depth already and don’t want to rehash the same points I’ve already made.

But reading an old Fortune article on Meeker caused me to look at the issue of conflict with a slightly different perspective.

Meeker’s story demonstrates the pitfalls of not knowing who you are, of trying to walk the thin line that exist when dual roles find themselves in conflict with each other and of compromising the key values that are crucial to doing your primary job properly.

As Fortune wrote:

“In responding now to criticism that she let investors down, Meeker refuses to admit–or even see–how compromised she is. She defends herself in part by saying she feels protective toward the phenomenon she helped launch–and especially toward the dozens of companies she helped Morgan Stanley take public: ‘There is something compelling about…playing an important role in something that will never happen again….I feel a–‘stewardship’ is a strong word–but I feel a keen sense of responsibility.’ She adds, ‘If you take a company public and you are really aggressive on the downside, it can be devastating.’ Of course, if you’re not aggressive on the downside, it can be devastating for investors. But that was never a Meeker priority.”

Clearly, Meeker, forgetting that she was really an analyst, also forgot that she was supposed to be a steward for the interests of investors who based investment decisions on her reports. Analysts are not supposed to be stewards for the companies they cover.

Yet because Meeker placed herself in a position that compromised her ability to see the forest from the trees, she did apparently see herself as steward for many of the companies she was involved with.

Although Meeker is still around, she’s a little less excitable (perhaps because Morgan Stanley isn’t taking a whole lot of tech companies public these days). Her interesting presentation at the recent Web 2.0 Summit is noticeably free of the type of hype she promoted during Bubble 1.0.

Personally, I’m one who forgives but never forgets. In my opinion, Meeker and the other compromised Wall Streeters who forgot who they were and who they were supposed to be answering to lost credibility that can never be fully regained.

As the current economic downturn has dampened the euphoria in Silicon Valley, especially amongst Web 2.0 startups lacking viable business models, it’s hard not to notice a similar dynamic developing in the blogosphere.

Some prominent tech bloggers, for instance, who do deserve credit for chronicling the rise of Web 2.0 and who I have no doubt are truly passionate about technology and the internet, now find themselves in positions where some of their posts over the past several years are, in hindsight, far too frothy to reconcile with some of their recent, more down-to-earth posts.

Case in point: one of the most visible cheerleaders for the Web 2.0 ‘movement‘ who I will not name (names are not important).

In January 2007, he argued that Web 2.0 companies could become sustainable businesses, that too much money wans’t chasing too few good ideas, that “The Network Effect is still the most powerful force driving Internet success today” and that in the world of startups and venture capital, “Assets are allocated efficiently, and everything works out fine in the aggregate.

Flash forward to today. The vast majority of Web 2.0 companies haven’t become sustainable businesses, it’s now obvious that too much money has been chasing too few good ideas, revenue once again trumps network effects‘ (as well as users‘ and pageviews‘) and VCs are not only challenged by troubled portfolio companies that were being run by drunken sailors but also by the troubled dynamic that now exists in their industry.

It seemed that the blogger in question may have realized what was coming. By May 2007, he seemed to be having second thoughts. The “$3 – $8 million Series A round experiments” that were okay January 2007 were now bothering him, as were the growing number of parties and the startups that didn’t make sense. Perhaps he truly recognized that this was unsustainable. Perhaps, as his post hints, he also longed for the simpler days when startups were launched at small parties at his house.

Whatever the case, his Web 2.0 hyping continued on. Parties he threw filled with entrepreneurs more interested in money than innvoation (as well as the distracting “hot PR chicks” he apparently didn’t like) only grew bigger. In September of this year, a business-oriented Twitter clone created by a company that was his sponsor and run by a former PayPal exeuctive won top prize at a conference he put on that by the way, had no shortage of bubbly after-parties.
Little more than a month later, on October 10, 2008, this blogger declared his beloved Web 2.0 dead and criticized a group of young Web 2.0 insiders who partied like it was 1999 at a mansion in Cyprus while the US stock market crumbled.

Sound confusing? Much of the contradictions in this blogger’s statements are illogical until you consider that this blogger is a Silicon Valley powerbroker whose involvement in the Web 2.0 phenomenon went far beyond that of intrepid reporter.‘ His flip-flopping makes complete sense when one recognizes that his perspective could never have been one of objectivity.

That much of the unbridled hype that he not only bought into but helped promote has proven to be unjustified now makes it difficult to overlook the obvious credibility issues he and other individuals who played the roles of both insiders and New Media journalists have created for themselves. In short, for those who were paying attention, it’s hard to take many of these people seriously.

To be fair, we all make mistakes. It’s easy to overestimate the prospects of a company or industry. Predicting the future is difficult to say the least. And the lure of some modicum of fame and fortune is always hard to resist. After all, who wants to be an ‘analyst‘ or ‘blogger‘? Being an industry insider – a mover and shaker – is far sexier.

Yet a reasonable firewall should placed between those who report on an industry and those who live‘ it.

Mary Meeker had to learn that lesson the hard way. Her villification after Bubble 1.0 burst couldn’t have been fun. But such villification could have been avoided if she had maintained a firewall between her real job and the activities that earned her the title of ‘Queen of the Net.’

Just as the bursting of the .com bubble evidenced the fact that Wall Street analysts did a disservice to themselves and their true constituents by becoming industry insiders, I can’t help but wonder whether, in some years’ time, we might say the same thing about some of today’s tech bloggers who seem to suffer from an identity crisis of their own.