The visionaries are here, laying out their visions. The senior vice presidents of “customer success” are presiding over presentations of their products, which don’t provide a service as much as a portal to a new world, the next world, the world in the empty space off the cutting edge, where one enters a blissful free fall and reaches a terminal velocity of innovation.

The wonks are also at this tech conference. Wonks from the East Coast, from Washington, that beacon of ineptitude and regulation and, worst of all, inertia.

Retired Gen. Stanley McChrystal is here, for a “fireside chat” with a Hewlett-Packard executive, comparing the challenges of conducting a war in Afghanistan to the challenges of “bringing together PC and printer groups” in a large corporation.

Super-lobbyist Heather Podesta is here, billed as “the insider’s insider,” telling attendees that their companies should be friends with their elected officials. “You’re like the shiny little object to a member of Congress,” she says, “because you’re the future.”

And Adrian Fenty is here. Adrian Fenty used to be the future — at least in the District of Columbia, where he was born and raised and served as neighborhood commissioner, city councilman and mayor.

As moderator for two sessions at the conference, Fenty introduces himself to attendees as “a new transplant to the West Coast” who has been “out here for the better part of a year.” His conference bio places him in the “visionary” category, as if the designation explains the last seven years of his whiplashed résumé: swept at age 35 into the mayor’s office on the promise of change, evicted from that office after one term of change that was too disruptive. More than half of District residents thought the city was moving in a favorable direction in the months leading up to the Democratic primary for mayor in 2010, and yet Fenty’s approval ratings tanked and focus groups found his leadership style offensive. That disparity — the gap between effect and affect — was his undoing. Fifty-four percent of Democratic voters went for his primary challenger Vincent Gray, nearly 30 years older.

Now, three years after being booted from the Wilson Building and 10 months after separating from his wife, the native son has gone into semi-self-exile from his home town. Fenty is seen around Washington now and then — chaperoning his twin sons as they train at the Junior Tennis Champions Center in College Park, getting a bite on 14th Street NW with former Obama speechwriter Jon Favreau, attending millionaire businessman Mark Ein’s glittery September wedding in Georgetown — but he is mostly gone.

Where exactly did he go?

The literal answer is Silicon Valley, where he’s fashioning a second act in a land that is more tolerant of brashness, of radical change at high speeds.

The vaguer answer, though, is somehow more fitting: Adrian Fenty has gone up into the cloud.

How green is the valley?

There have been only a handful of mayors of the District of Columbia, and all but one of them have remained rooted to their city after leaving office. Walter E. Washington, the first, became a partner in the D.C. office of a New York law firm. Sharon Pratt Kelly, the third, and Anthony Williams, the fifth, became and remain local consultants. Marion Barry, the second, later became the fourth and is the city councilman for Ward 8 through at least 2017, perhaps for eternity.

Last month Adrian Fenty, the sixth mayor of Washington, severed his last business tie with the city. He ended his two-year tenure as special counsel at the Dupont Circle law firm Bruce J. Klores & Associates and took a job with the Palo Alto, Calif., office of the law firm Perkins Coie, whose clients include the digital gods of the third millennium.

The sixth mayor’s new constituents — his employer’s clients, that is — are Facebook, Google, Microsoft, Twitter and (headed by Washington Post owner Jeff Bezos).

The firm, in its Sept. 24 announcement, called Fenty a “savvy strategist.” Indeed. The former wunderkind mayor has emerged from the other side of an embarrassing political defeat to become an adviser to wunderkinds.

This is Fenty the expat, who after his primary defeat said he would not run for office again, who has been romantically linked to billionaire Laurene Powell Jobs, widow of Apple co-founder Steve. He declined to be interviewed for this article. Conversations with Fenty’s friends, colleagues in Silicon Valley and former colleagues in D.C. paint a picture of his life today: Fenty 3.0, iterating up and out of his hometown.

“It puzzles me how someone who was purportedly so ardently committed to the city’s well-being could suddenly turn it off and have no public role at all in how we move forward,” e-mails Randy Speck, a Chevy Chase neighborhood commissioner who worked on and contributed to Fenty’s first mayoral campaign. “Maybe he feels rejected and has simply reciprocated.”

A better word is “disenchanted,” according to Fenty’s lifelong friend and former D.C. attorney general Peter Nickles, who had lunch with Fenty over the summer in the District. Nickles makes note of Fenty’s “prior life” and “new life,” and how the ex-mayor doesn’t keep up with local politics anymore.

“I think he was disappointed enough in the political process that he probably didn’t feel he needed to spend a lot of time following events,” Nickles says. “I think he was going through these issues with his wife and his family, and also determining the perennial question you ask when you get out of college, when you finish your first job, when you retire: ‘What do I wanna do with the rest of my life?’ And he had a lot of opportunities.”

In the seven months after he left office in January 2011, Fenty booked five gigs that signaled his transition from public official to private guru: an “outside adviser” to both a Philadelphia accounting firm and foreign-language software publisher Rosetta Stone, a “strategic adviser” on government matters to the Herndon office of information-technology consultancy Capgemini, special counsel at his friend and fundraiser Bruce Klores’s law firm, and an “advisory board member” at Georgetown’s EverFi, an education technology company.

His value? Connections. Klores’s firm had a long-standing case involving the State Department, which was giving its lawyers the runaround, Klores says, until Fenty was dispatched “to talk the language from one person in government to another to get them to understand the bigger picture of the case.”

Fenty connected EverFi directly to government officials with whom he’d previously networked, helping the company transition its business from small markets such as the Mississippi Delta to school systems in major cities. Access is invaluable, says EverFi’s president and founder, Tom Davidson, and Fenty delivered it.

“You can’t throw a cat in this town without hitting a former politician trying to get involved with technology companies,” Davidson says. Fenty has been welcomed with open arms out West because “Silicon Valley is targeting these intractable social issues in a way that it never really has before.”

Fenty’s issue is education, and it has carried him to California. Within days of leaving office in 2011, Fenty branded himself as “a national leader in the area of urban education reform” when he joined the roster of celebrity speakers at the Greater Talent Network. He met Laurene Powell Jobs that year at an education conference in Houston, joined the board of her education nonprofit in February 2012 and met investor Marc Andreessen, a Netscape co-founder, at one of its events. That September, Fenty became a “special adviser” to his hotshot venture capital firm, Andreessen Horowitz, which manages a multibillion-dollar fund from its headquarters in Menlo Park.

Perkins Coie partner Buddy Arnheim had a casual lunch with Fenty in California around that time at the suggestion of John Devaney, a partner in the firm’s D.C. office, where Fenty’s wife, Michelle, used to work. As of last month, Fenty had an office two doors down from Arnheim at the Palo Alto office, a 10-minute drive from Andreessen Horowitz.

He spends about three days a week as counsel in Perkins Coie’s Emerging Companies & Venture Capital practice, where his business-development portfolio is likely to eventually consist of a couple dozen start-ups and a handful of institutional investors. The balance of his week is spent on Andreessen Horowitz and weekend visits to the District, where his teen sons reside with his parents, Phil and Jan Fenty. Michelle Fenty’s job as the Inter-American Development Bank’s representative in Trinidad and Tobago is based in its capital of Port-au-Spain; their 4-year-old daughter, Aerin, stays with her.

Adrian Fenty told the Silicon Beat blog last month that he’s living in Palo Alto with a friend whom he’s known “for a long time.” Fenty isn’t talking about his personal life, though it has popped into the news this year in January when he separated from Michelle and in August when The Post revealed his “budding romance” with one of the richest women on the planet.

His most recent interaction with the District was a small one. During the first week of October, he set up a crowdfunding Web page to raise money for Capitol Police officers who were working unpaid during the government shutdown. His introduction on the page began “Beloved D.C. family,” then mentioned how he spends “some time in California” and described the usefulness of “group action tech” and the funding platform Crowdtilt.

Crowdtilt is a San Francisco start-up that is funded in part by Andreessen Horowitz.

Trying to do good while hawking a product.

That is Silicon Valley in 2013.

This is Adrian Fenty, private citizen.


Malcolm Gladwell takes the stage in a cavernous underground ballroom of the Union Square Hilton in San Francisco. Haloed by his frizz of hair, the author preaches to thousands of listeners about “social risk-taking,” about how disruptive ideas upset people, about how all successful entrepreneurs and innovators possess at least two shared traits:

1. A sense of urgency.

2. A disagreeable attitude, wherein “disagreeable” means “someone who does not require the approval of others to go forward.”

Gladwell might be describing Adrian Fenty, whose supporters and critics point to his go-go-go attitude as a distinguishing characteristic. Fenty is also at this BoxWorks 2013 tech conference as a moderator and bold-faced name — partly because he is a “visionary” and partly because Box, the file-sharing and cloud-computing company presenting the conference, is also part of Andreessen Horowitz’s portfolio.

You might also say he’s here because of two women: Michelle Rhee, whom he was smart (or reckless?) enough to hire as chancellor of schools and who elevated his own profile, and Laurene Powell Jobs, whom he was lucky (or smart?) enough to meet and befriend.

The Silicon Valley cliche is thriving here at BoxWorks, with innovator-disrupters paying at least $800 for the privilege of mingling with people who are so forward-thinking that they’re practically doing somersaults down the Hilton’s escalators to the frenetic Partner Pavilion, where sponsors court potential investors and customers with tag lines such as “trust in the cloud” and “get collaboration in context.”

This is Fenty’s world now. Forty-five minutes after Gladwell wraps up his keynote, Fenty and California’s lieutenant governor are sitting next to each other in white leather seats as featured speakers in a smaller adjoining ballroom. Each wears a charcoal suit with a blinding-white dress shirt. Gavin Newsom is polished, poised, charming, without a word or hair out of place. Fenty is slouched. His speech has a slight slur, as it always has, that is partially excused by his surferlike demeanor. It’s obvious which one of these ex-mayors still holds elected office.

Their conversation is titled “Revolutionizing Democracy in the Digital Age.”

“I’m representing the East Coast,” Fenty says during his introduction. “You’re representing the West Coast.”

“What do they say?” Newsom replies. “You go to the East Coast to join something. You come to the West Coast to start something.”

Halfway through the conversation, Newsom draws a line from Gladwell’s keynote speech to Fenty, saying that being indifferent to one’s constituency is sometimes an essential part of leadership.

“You, Adrian, are an example of this — doing audacious things,” Newsom says, referring to Fenty’s 2007 school takeover, which installed Rhee, who closed dozens of schools, fired hundreds of teachers for underperformance and set in motion the backlash that would end his political career. “You paid a political price by not getting reelected,” Newsom adds, “but we are all beneficiaries of the principles you stood for.”

The ex-mayors carp about the “constraints of formal authority,” about taking hits for taking a stand, and this rhetoric blends in with Box’s conference slogan, which seems both idealistic and somehow threatening: “There’s no end to possible.” Fenty closes his chat by declaring that Box is “a product that works,” reminding everyone that this conference is ultimately a commercial.

The feeling here (and everywhere in Silicon Valley, really) is that government is a major drag unless you know how to work it. And people like Adrian Fenty know how to work it, or at least work around it.

Fenty, says Buddy Arnheim of Perkins Coie, will be a sounding board for companies that must negotiate new challenges as the government catches up to technology on issues ranging from privacy to cross-border development. And his simultaneous association with Andreessen Horowitz makes him a “truly unique” player in Silicon Valley.

When approached by this reporter after his chat with Newsom, Fenty is amiable but puzzled that anyone would be interested in the life of an “ex-politician.” He then moves on to quick conversations with young tech wonks who want to pick his brain about education reform (the documentary “Waiting for ‘Superman,’ ” featuring Rhee, comes up) and immigration policy (he’s frustrated with the “typical Washington” meekness of Democrats) and his life in California (he’s having “a ton of fun”).

And he does things that he was criticized for not doing in the latter years of his mayorship.

He shakes hands.

He poses for photos.

He mingles and lingers, smiley and easygoing and generous with his time.

Then he slips into the other ballroom to watch software executives talk about the “Future of Cloud.”

Real power

The cloud, of course, is where all our stuff is, or is going. It is, in some ways, the Internet itself, or the parts of the Internet where we put content so it can be shared, stored or edited across the space-time continuum. Government is also headed there.

In this prior life, Fenty was known for being hard-wired to his BlackBerry, for responding directly to constituent e-mails within hours. His most substantial overture to the District’s nascent start-up scene was made by his chief technology officer, Vivek Kundra, who helped organize a 2008 contest called Apps for Democracy, which reportedly cost the city $50,000 and garnered 47 civic-minded Web applications valued at $2.6 million — all in the name of making government data and services more accessible to citizens.

But the hands-on vigor for technology he’s demonstrating out West was not very visible during his four years leading the District, says Peter Corbett, founder and chief executive of iStrategyLabs, the Dupont Circle digital agency that helped jump-start the District’s tech scene six years ago with a series of meet-ups for entrepreneurs.

“I never once saw him at a single meet-up or shaking the hand of an entrepreneur, which is a dramatic contrast to [Vincent] Gray,” Corbett says.

Granted, Gray assumed office with a richer, more rooted start-up community on his hands than Fenty had at the start of his own term, says Michael Mayernick, the D.C.-based co-founder of Spinnakr, a Web-site data analysis start-up. Mayernick met with Fenty over the summer in the Palo Alto office of Andreessen Horowitz, which invested in Spinnakr in June. Fenty seemed genuinely hungry to learn about the business and fascinated by tech in general, Mayernick says.

“It was clear when I chatted with him,” Mayernick says, “that he saw an alignment between himself and entrepreneurs, in the style of disruption: ‘I’m going to look at things as they are, and I’m going to do the best thing without regard to institutional inertia.’ ”

Disruption is what he left behind in the District, according to a broad e-mail sampling of community activists and current and former neighborhood commissioners who have either fond, combative or mixed feelings toward Fenty. There are, of course, the bike lanes — bane or boon, they are visible to the entire city in a way that school reform is not. There is Police Chief Cathy Lanier, a Fenty appointee who shook up the ranks and remains in charge of a respected department that has chipped away at crime. There is rampant development, begun by predecessor Anthony Williams and broadened by Fenty under the banner of “smart growth,” even when individual neighborhoods rallied against its potential impact. There was somehow both a heightened responsiveness on the part of government agencies and an arrogant dismissal of the concerns of the District’s African American population, commissioners say.

Fenty moved fast. Fenty moved too fast. Depends on whom you ask.

“My residents of 7C most definitely miss that level of urgency,” if not Fenty’s “abrasive” personality, says commissioner Greg Stewart, who represents the Ward 7 neighborhoods of Capitol View and Richardson Dwellings.

Peter Nickles, who in his role as attorney general was criticized for being as antagonistic as Fenty, recalls that on many issues the Fenty administration tackled — from schools to slumlords, from unpermitted used-car lots to pornography on city employees’ computers — they were met by entrenched interests that resisted their progressive vision.

When the organized opposition won the 2010 primary for Gray, Nickles says, “it was like Peggy Lee in that song ‘Is That All There Is?’ It was right back to where it was: same old, same old. Maybe that’s what politics is.”

Quite simply, “Fenty didn’t understand that it’s a popularity contest at the end of the day,” says Ward 4 neighborhood commissioner Martha Mitchell, who campaigned for Gray in 2010. “Folks don’t vote for candidates that they don’t like.” She adds, “Staying power is the real power.”

Or maybe going power is.

Maybe politics is the same old, same old, and government’s default setting is inertia, and the real innovation is getting out of it, into the private sector, where government experience is a hot commodity, where there is less anguish and a different kind of power. Up there, in the cloud, you’re beholden to like-minded investors and your own ideals, not half a million citizens with half a million concerns.

Where did Adrian Fenty go?

To a better place, it sounds like, for him.