Jour­nal­ists on the Left have always had prob­lems with insti­tu­tions. I’m not refer­ring here to these scribes’ hon­or­able muck­rak­ing pedi­grees, or their prin­ci­pled dis­trust of the nation­al secu­ri­ty state and the cor­po­rate board­room. Rather, they have trou­ble build­ing and sus­tain­ing viable media insti­tu­tions of their own in the broad­er mar­ket­place of ideas.

In a revealing account of Taibbi’s departure, a team of First Look journalists candidly noted that the start-up was hobbled at the outset by a “highly structured Silicon Valley corporate environment” riddled with “management-speak” and “a confounding array of rules, structures and systems imposed by Omidyar and other First Look managers.”

Hence, for exam­ple, the well doc­u­ment­ed strug­gles of cable pro­duc­ers at MSNBC, dat­ing back to the sec­ond Bush admin­is­tra­tion, to build a robust answer to Fox News’ suc­cess­ful monop­oly on right-wing news talk. MSNBC was turn­ing out slug­gish cov­er­age and suf­fer­ing declin­ing rat­ings even before the deba­cle of the 2014 midterms showed how faint­ly any pro­gres­sive mes­sage was get­ting through to the public.

And Air Amer­i­ca — the kin­dred bid to launch a pro­gres­sive brand in the heav­i­ly right-wing medi­um of talk radio — went bank­rupt in 2010, just as an enor­mous finan­cial cri­sis and a Demo­c­ra­t­ic sweep of Con­gress and the White House should have made left-lean­ing polit­i­cal jour­nal­ism more rel­e­vant than ever.

It’s hard, how­ev­er, to top the recent tra­vails of First Look Media, the fer­vid­ly hyped web pub­lish­ing empire fund­ed by Sil­i­con Val­ley bil­lion­aire Pierre Omid­yar, as a case study in how not to launch a pro­gres­sive media enterprise.

A poten­tial suit­or to pur­chase the Wash­ing­ton Post, Omid­yar instead decid­ed to spend $250 mil­lion to launch his own ring of web­sites and aggres­sive­ly sought top report­ing, blog­ging and edit­ing tal­ent, all of it decid­ed­ly left of cen­ter. Chief among his ear­ly recruits were Glenn Green­wald and Lau­ra Poitras, the team that had col­lab­o­rat­ed with NSA whistle­blow­er Edward Snow­den to reveal the true extent of the sur­veil­lance state’s spread. Omid­yar also brought on for­mer Rolling Stone inves­tiga­tive reporter Matt Taib­bi, who has sharply chron­i­cled the cor­rupt nexus between Wall Street and the Amer­i­can polit­i­cal estab­lish­ment, to run his own prop­er­ty under the First Look brand — a site called Rack­et devot­ed to muck­rak­ing and mis­chie­vous satire.

But before Taibbi’s project got off the ground, he left Omidyar’s start-up this Octo­ber amid hot­ly debat­ed (and shak­i­ly ver­i­fied) charges and coun­ter­charges, rang­ing from a pur­port­ed ide­o­log­i­cal muz­zling cam­paign mount­ed by Omid­yar to alle­ga­tions that Taib­bi may have been charged with sex dis­crim­i­na­tion in the Rack­et work­place. Today, First Look’s man­agers announced that they would no longer pur­sue Rack­et with­out Taib­bi and all of the employ­ees he had brought on would be let go.

How­ev­er, for all the fever­ish spec­u­la­tion sur­round­ing First Look‘s trou­bles, the most obvi­ous cul­prit is hid­ing in plain sight: the reliance on truck­loads of mon­ey from Sil­i­con Valley.

There’s a rea­son that the term ​“burn rate” was coined to describe the brief half-lives of tech start-ups — these fre­net­i­cal­ly over­man­aged oper­a­tions func­tion more as mon­u­ments to the hubris of the inno­va­tion econ­o­my than as proven mod­els of pro­duc­tiv­i­ty. Com­pound­ing this, the First Look fias­co clear­ly shows that a tech indus­try con­di­tioned for so long to scorn the out­mod­ed folk­ways of ​“print cul­ture” and ​“lega­cy media” (as the argot of Sil­i­con Val­ley has it) is large­ly clue­less about super­vis­ing the basic work of journalism.

In a reveal­ing account of Taibbi’s depar­ture, a team of First Look jour­nal­ists can­did­ly not­ed that the start-up was hob­bled at the out­set by a ​“high­ly struc­tured Sil­i­con Val­ley cor­po­rate envi­ron­ment” rid­dled with ​“man­age­ment-speak” and ​“a con­found­ing array of rules, struc­tures and sys­tems imposed by Omid­yar and oth­er First Look managers.”

As any vet­er­an of the ter­mi­nal­ly self-infat­u­at­ed tech world can tes­ti­fy, a start-up ethos usu­al­ly means a very long string of con­fer­ence calls and navel-gaz­ing man­age­r­i­al mono­logues. And a num­ber of First Look­ers told me that the media side of things endured a sus­tained bout of neglect as man­age­ment talk metastasized.

At First Look, ​“strat­e­gy meet­ings are always more impor­tant than actu­al­ly pro­duc­ing things,” says one of the jour­nal­ists still hop­ing to weath­er the storm at the com­pa­ny. These con­fabs tend to per­pet­u­ate them­selves in all bureau­crat­ic work envi­ron­ments, but at an osten­si­ble jour­nal­is­tic endeav­or — which is, after all, tasked with nim­bly break­ing news and mov­ing just as quick­ly on to the next big sto­ry — they can become lethal­ly coun­ter­pro­duc­tive. Anoth­er source at the com­pa­ny says the dis­con­nect goes much deep­er than a sim­ple aver­sion to pro­duc­tive activ­i­ty. Com­pa­ny man­agers ​“are afraid of us, they don’t like us, they grav­i­tate toward the peo­ple who can engage in their weird management-speak.”

Omid­yar him­self exert­ed heavy-breath­ing over­sight of every­thing from the roll­out sched­ules and social-media strate­gies of First Look sites to indi­vid­ual reporters’ trav­el expense state­ments. Taib­bi and John Cook, his coun­ter­part at First Look’s dai­ly site The Inter­cept, ​“chafed at what they regard­ed as oner­ous intru­sions into their hir­ing author­i­ty,” the First Look team not­ed. Cook lat­er made his dis­plea­sure all too clear by leav­ing First Look in Novem­ber and return­ing to his for­mer home of Gawk­er Media (though in a post for First Look and sev­er­al tweets, Cook said that work­ing at First Look ​“was incred­i­bly sat­is­fy­ing professionally”).

Indeed, in the company’s bare­ly year-long exis­tence, sev­er­al edi­to­r­i­al lead­ers have fall­en in and out of favor with Omid­yar, each try­ing his best to car­ry out the founder’s gnom­ic dic­tates. The newest bear­er of Omidyar’s good graces is John Tem­ple, who ran an ear­ly jour­nal­ism start-up for him in Hawaii.

On con­fer­ence calls, staffers would ​“bet among our­selves how soon it would be until Pierre described him­self as a ​‘tech­nol­o­gist,’ “ anoth­er First Look employ­ee reports. ​“It was always less than three minutes.”

But ​“the thing is, Pierre became a bil­lion­aire in 1997 – 98,” the same employ­ee says. ​“He’s ensconced in a Web 1.0 bub­ble. He hasn’t heard any of the stuff we’ve been dis­cussing all that time. … So he’ll look up at us at a meet­ing and say some­thing like ​‘Hey, have you guys heard of Vice Media?’ “

The odd thing about the First Look man­age­ment team, though, is that they aren’t real­ly all that tech-savvy, sources say.

One employ­ee recounts a glitch that was extreme­ly dam­ag­ing for work­er morale, which hap­pened on ​“on our hor­ri­ble [intranet] thing Asana, which is named after a yoga pose, that we all have to use because Pierre declared that email is over. It’s a Face­book wall, basi­cal­ly, and they post­ed all our salaries on it for three hours. So we all know how much every­one makes.” Not sur­pris­ing­ly, some of the most lav­ish­ly reward­ed man­agers on the list were also some of the least revered com­pa­ny officials.

With the real­i­ties of com­pa­ny pow­er laid so embar­rass­ing­ly bare, the company’s seem­ing­ly incur­able addic­tion to meet­ing-speak took on an increas­ing­ly hol­low ring, sources say. ​“For all their talk about ​‘iter­at­ing,’ ​‘blue sky,’ and the rest, they’re not inter­est­ed in any of the dif­fi­cult stuff of lead­er­ship. They’re into the most pet­ty, shit­ty trans­ac­tion­al issues — like Kevin Spacey in a Glen­gar­ry Glen Ross way,” an employ­ee says.

When this con­flict-averse crew of man­agers does pick a fight, the stakes are unbe­liev­ably low, sources say. ​“We get dumb, lengthy fights over whether or not we need phones. In Sil­i­con Val­ley, work­ers use their cell phones to per­form all work that neces­si­tates phone use, so why can’t we?” one First Look­er reports. (Any­one with the faintest acquain­tance with the actu­al work of jour­nal­ism knows that land­lines are far and away the best means of reli­ably record­ing inter­views with sources, even in our mirac­u­lous dig­i­tal age.)

And once more, the source reports, the con­trast with the company’s actu­al­ly exist­ing jour­nal­is­tic needs was ter­ri­fy­ing­ly vivid: ​“We start bar­rel­ing toward launch with­out the com­pa­ny hav­ing actu­al­ly hired any­one to do visu­al and graph­ic work besides our one poor pho­to edi­tor with no illus­tra­tion experience.”

Even on the rare occa­sion when the company’s lead­ers try to break form, the quo­tient of off-putting self-drama­ti­za­tion is so high, employ­ees say, that the over­tures are empty.

“At one of these ​‘all hands’ gath­er­ings we had — these com­pa­ny-wide meet­ings where the five skulls who run the place talk at us, [one senior fig­ure] gets up at the end and says, ​‘Is there any­one who’s not a white man who would like to talk?’ ” This employ­ee — one of the hand­ful of non-dude com­pa­ny hires — describes her quite ratio­nal stunned silence: ​“I’m like, ​‘Well, I don’t want to now—you’ve pret­ty much tak­en that space, haven’t you?’ ”

To put things mild­ly, these are not the kinds of prac­tices and insti­tu­tion­al rou­tines that make for fear­less inde­pen­dent jour­nal­ism. Edi­tors and reporters can’t glee­ful­ly tar­get the cor­po­rate titans of the Amer­i­can scene, as Taib­bi and Cook were charged to do, with one of them perched over their shoul­ders, insist­ing on vogu­ish pat­terns of tele­phone usage and cross-tab­u­lat­ing what they’ve spent on taxis and meals with sources.

Taibbi’s first big exposé report­ed dur­ing his First Look tenure bears elo­quent tes­ti­mo­ny to this point. He scored a block­buster inter­view with JP Mor­gan Chase whistle­blow­er Alayne Fleis­chmann, whose poten­tial to give damn­ing tes­ti­mo­ny against the bank in fed­er­al court was being used by the Jus­tice Depart­ment in set­tle­ment negotiations.

But First Look’s pro­ce­dur­al inani­ty left Rack­et in lim­bo for months and, even­tu­al­ly short-cir­cuit­ed Taibbi’s future at the com­pa­ny. (He placed the sto­ry at Rolling Stone.)

The more the Omid­yar saga unspools, the less sur­pris­ing it all looks. Decades into the infor­ma­tion age, the cul­ture of Sil­i­con Val­ley and the tra­di­tions of inves­tiga­tive report­ing still make for an awk­ward fit. The tech industry’s obses­sions with dig­i­tal gad­getry and vac­u­ous inno­va­tion-speak are noto­ri­ous­ly resis­tant to basic jour­nal­is­tic val­ues such as skep­ti­cal inquiry. One need only wit­ness the geyser of hosan­nahs that attends a new iPhone release (no mat­ter how bug­gy it turns out to be), or the insu­lar wit­less­ness of your aver­age TED talk to real­ize that the tech indus­try prefers its media cov­er­age with­out crit­i­cal think­ing or inde­pen­dent judgment.

And the core ten­sions involved in the clash of these two cul­tures are by no means con­fined to First Look: After an exec­u­tive of the bal­ly­hooed ride-shar­ing start-up Uber oafish­ly indi­cat­ed that he wouldn’t mind ini­ti­at­ing pri­vate sur­veil­lance cam­paigns against crit­i­cal reporters, a for­mer col­league of his just as oafish­ly took to the Huff­in­g­ton Post to declare the whole thing an overblown non-issue. The prob­lem, she explained, was that the offend­ing reporter who’d dared to ques­tion Uber’s lead­er­ship class, BuzzFeed’s Ben Smith, had regret­tably elect­ed to ​“change the tenor of an oth­er­wise enjoy­able din­ner.” One could almost hear the con­temp­tu­ous sniff of an aggriev­ed Haps­burg monarch.

It’s clear, against this harsh­ly polar­ized cul­tur­al back­drop, that the recent spate of dra­mat­ic exits from First Look was a long time com­ing — just as it seems like that there will be more to come. The First Look team is sad­ly com­ing to real­ize that the company’s work envi­ron­ment is far more like­ly to con­jure the final reel of The Caine Mutiny than All the President’s Men.

“Even­tu­al­ly First Look Media will just be Pierre’s Sec­ond Life avatar wan­der­ing around an open-space office plan,” one employ­ee says. For all the evi­dent data-hew­ing genius of fig­ures such as Omid­yar, the wiz­ards at the helm of First Look have evi­dent­ly over­looked one of the ear­li­est cre­dos of the per­son­al com­put­ing rev­o­lu­tion: Garbage in, garbage out.

A con­densed ver­sion of this sto­ry ran in the Jan­u­ary issue of In These Times.