At first glance, Brian Robertson doesn't seem like the most obvious candidate to be a management guru.

He's a high school dropout who taught himself how to code. He went from running the small software business he founded in 2001 to now running an even smaller, 13-person software maker and consultancy firm. He's never run a large company.

And yet Robertson has acquired many of the hallmarks that usually come with leadership-guru status. He's got a trademarked philosophy--it's called holacracy. He's penned a book on the subject. He's done TED Talks.

Most notably, he's gathered a circle of high-profile devotees who speak, with passion, about Robertson's vision of replacing traditional hierarchies with self-managing teams. He--and by extension, they--are convinced they have discovered the holy grail of management theory and organizational efficiency.

Zappos CEO Tony Hsieh is one of them. Getting Things Done (GTD) author David Allen is another. 

"I heard him speak, I thought, 'Holy Jesus, he's laying it out. What GTD is for an individual person, holacracy is for an organization.' I knew it could work if it was, in practice, as bulletproof as it sounded cognitively," Allen says.

Today, Robertson's company, HolacracyOne (H1), counts not only Allen and Hsieh as client-converts, but also Twitter co-founder Evan Williams, whose Medium blogging platform is implementing the system. Divisions of Dannon and Starwood are also aboard.

All this from a $3 million company in Spring City, Pennsylvania, that's pitching a theory of corporate governance that isn't even a completely original idea. 

And yet, Robertson's brand of flattened hierarchies is probably the hottest thing to happen to the dusty subject of organizational structure in years. Here's an inside look at the man behind the upstart management movement.

Just Another Dropout Entrepreneur.

"School was--I loved it, but not in the way the school intended me to love it," says Robertson, 36, who is married but does not have children. "I was always challenging the social system of it."

For example, Robertson says he would often sit in class and openly read a book, irrespective of what the teacher was teaching. "I didn't hide it," he says. More often than not, he was reading about software development, a hobby of his from the age of 6.

His earliest entrepreneurial experiences came when he was a teenager in Hackensack, New Jersey. At 13, he taught programming online for a few hours a week. This was, of course, the era of the infamous New Yorker cartoon in which a dog says: "On the Internet, nobody knows you're a dog." Likewise, no one paying $25 an hour for Robertson's online coding lessons knew he was 13.

At 17, Robertson says, he dropped out of high school and talked his way into a technical college. One year later, he left to become a full-time employee at Exton, Pennsylvania-based Analytical Graphics, Inc. (AGI), a two-time Inc. 500 company in the late 1990s.

This was one of Robertson's formative experiences, when it came to thinking about organizational structure. He was a teen accustomed to doing things when and how he wanted. Now he was out of school, in the real world, ostensibly a more suitable setting for a self-starter. And yet, even at a nimble fast-growth company like AGI, the decision-making structure tried his patience. He stayed for three years.

"But I realized that the only way I was going to have the freedom to respond to every tension I sensed would be to drop out of the system completely and start my own company," he writes in his 2015 book, Holacracy: The New Management System for a Rapidly Changing World.

Shaking Off the Shackles of Leadership.

And so, in 2001, Robertson founded Ternary Software, which provided custom development services to high-tech startups. He quickly realized that even for founder-owners--those who sit atop organizational structures--there were bottlenecks galore. Seemingly every decision the company made crossed his desk. There's a reason Robertson, to this day, calls himself "a recovering CEO."

Indeed, for many founder-CEOs who have become holacracy converts, the system's voluminous regulations for how to self-organize (spelled out in an oft-revised constitution) are actually freeing--and the trials of transition are well worth it.

Brian Robertson delivering his holacracy message at a Zappos "All Hands" meeting in Las Vegas in 2014.

Here's how it works, in brief. Instead of a job title--whether you're the CEO or an intern--each job is defined by a number of roles, which anyone in the organization can see. For example, at Zappos, one employee's roles include "Holacracy Implementation," "Diversity," and "Uncaptured Work." The roles are grouped into organizing units called circles, which are essentially stand-ins for departments. A large company might have a large marketing circle, with smaller circles (say, social media and press relations) operating within the larger one. Employees called "links" serve as liaisons between the smaller and larger circles.

Each role has spelled-out responsibilities and decision-making authorities. This feature is designed to prevent the bottlenecks that occur when every little decision gets kicked upstairs to executives. In holacracies, everyone knows which team members are empowered to make which decisions. The person formerly known as the CEO can feasibly tell the employees seeking his sign-off, "That's not my job."

"It instantly relieved 60 tons of pressure off my shoulders," says Allen. "I always said to myself, 'Wouldn't it be nice if this organization could run without a CEO,'" he says. Now it does. "Most people's perception is that [holacracy] is just willy-nilly, distributed authority," he adds. "But it's quite dictatorial. It's just everyone agrees: 'This is your area, dude.'" 

Packaging the Holacracy Brand.

Mind you, the system Allen would begin to implement in 2010 has come a long way from the structures Robertson began to experiment with to cure bottlenecks and free up his own time at Ternary Software in 2001. Robertson's history of the system, including the 2007 founding of H1 and the many iterations of the constitution, cites multiple sources and influences, including GTD and sociocracy. (Some members of the sociocracy community believe Robertson does not credit sociocracy's architects nearly enough. They are especially critical of his attempt, in 2007, to patent some of sociocracy's longstanding tenets, which Robertson now calls a "horrible, horrible mistake.") 

Initially, Robertson experimented with any and all organizational structures and practices that could potentially limit or alleviate bottlenecks. The experimentation was arduous. Rules changed constantly, which is, of course, hardly the best recipe for organizational stability. For example, there was a yearlong period in which Ternary went through five different salary systems.

Like any attempt to apply theories in practice, there were burns from a baptism by fire. For example, when Ternary reached 12 employees in 2004, it tried to create a mission statement by consensus. The meeting lasted two days, resolving nothing, save for the notion of finding a democratic way to run the company. "But Mr. Robertson persevered, guided by two out-of-print books about a Dutch management technique called 'sociocracy' or 'dynamic governance,'" notes a Wall Street Journal story from April 2007. "He has dubbed Ternary's system 'holacracy' and has begun marketing it as a managing style."

Indeed, by 2007, Ternary had grown to 19 people, all of whom had roles and were grouped in linked circles. Robertson, at that point, was still called the CEO but had "little typical CEO authority," notes the Journal

Buoyed by the PR in the Journal, Robertson formed HolacracyOne with the mission of packaging the system Ternary had evolved for use in other companies. In 2009, HolacracyOne published its first constitution, refining it year after year. Over time, many of its initial legalese-sounding regulations were replaced with the simpler wording you might find in GTD. "Now it's more like a rule book to a sport than a legal document," says Robertson.

Robertson says the company currently has ongoing consulting-plus-software relationships with three-dozen companies. But the overall number of customers is about "10 times that," he says, if you count all the companies who've paid for H1 training or a workshop. The weeklong seminars--detailed sessions explaining the system's voluminous rules--cost $4,000 a seat. GlassFrog, the software program H1 created to record and streamline communication among roles and circles, costs $500 a month. In-depth consulting, which keeps H1 on retainer at all times during your thorny transition, starts at $50,000.

It's Not Easy Being Teal.

Leaving aside the tangled tale of its roots, holacracy is now part of most high-concept conversations about management theory. Frederic Laloux, a former McKinsey consultant, believes holacracy is part of a massive paradigm shift. In his seminal 2014 book on the intersection of management, culture, and social systems, Reinventing Organizations, Laloux cites holacracy as one example of the "teal" or no-manager structures that he believes are the next wave of how all organizations--businesses, schools, nonprofits, governments--will operate.

Brian Robertson and Frederic Laloux discuss alternative organizational structures.

Laloux chose "teal" as the color to represent the next paradigm as a way of indicating a clear next step beyond today's "green" organizations, which embrace corporate social responsibility and behave with an eye on not only their investors and customers but also other stakeholders, such as their employees, their suppliers, and their local communities.

A teal organization has the social conscience of a green one, and adds to it principles of self-management. It's difficult boiling Laloux's all-encompassing treatise down to a sentence, but if you had to, the crux would be this: As the world grows more democratic and pluralistic, so too must organizational models.

Hsieh himself had a Skype call with Laloux for advice before drafting his now-immortal 4,700-word email to Zappos employees in March, offering buyout terms to those who wanted no part of holacracy. The transition to holacracy has been rough--210 employees (or 14 percent of the company) took the buyouts and left.

No Bosses--and That's an Order.

The essential irony of many teal organizations is that it's often the boss who is spearheading the new-agey change to so-called bosslessness.

And if humans are acting human, then the boss--who is often the owner--will continue to have clout. In the The New York Times's recent update on the Zappos transition, the reporter describes a scene in which Hsieh twice asks John Bunch, who is leading the company's holacracy initiative, to look into a new task-management system. Bunch, who initially says he is too busy, finally relents. "Zappos may not have a hierarchy, but it was clear who was in charge," writes the Times. (Bunch, by the way, tells Inc. he takes issue with this characterization and claims he has since decided not to take on the task.)

Robertson, for his part, does not have a problem with any leader who dictatorially decrees that his or her organization will become a holacracy. "How else will it happen?" he asks. "That is the simplest, cleanest path forward. Doing anything else is fighting reality. The reality is, CEOs hold power.... So the simplest way is for the CEO to say, 'I'm ceding it to a constitutional process.' How do you get that from the bottom up?" 

That's one way to look at it. In other teal systems, though, there's a sense that implementation should be democratic. Daniel Mezick, an Agile business consultant who has praised Hsieh and Zappos for bringing mainstream attention to sociocratic structures, has blogged that Hsieh erred by using too much "coercion," too much "self-organize or quit," in his approach. John Buck, a certified sociocratic organizational consultant, agrees. While he lauds how Robertson has marketed holacracy, he believes Robertson's acceptance of top-down implementation "absolutely doesn't work." Instead, he says, "you have to go in in small steps."

Robertson believes he knows better. And he's not afraid to say it, even if it means challenging the conventional wisdom. He openly confesses to being "an arrogant prick," someone who can hold a microphone at a Zappos "All Hands" meeting and admit to struggling with one of Zappos's 10 core values: "Be humble." He's fond of the Frank Lloyd Wright quote: "Early in life, I had to choose between honest arrogance and hypocritical humility. I chose the former and have seen no reason to change."

Robertson may have seen no reason to change his personality. But as his numerous changes to the holacracy constitution point out, he's unabashed about changing the system, when he needs to. 

It's gotten him this far.