Ryan Blair's rag-to-riches story is no marketing shtick. He may have dubbed one of the chapters of his New York Times bestselling book, "my philosophies from the jail cell to the boardroom," but Blair's childhood isn't naturally packaged into slogans. And the things he learned on the streets of Los Angeles, and from two stints in juvenile detention, did help him build a series of successful startups, the latest of which took in $231 million in sales last year.

Growing up, Blair idolized gang culture, he told AOL Jobs. His older sister was a gang member, selling the weed his father grew. After his father abandoned the family when Blair was 13, and his mother started drinking, he needed money. Initiated into a gang with a brutal beating that left him with a mouthful of broken teeth, he started peddling stolen car stereos, and learned the first principle of business: "Buy low, sell high."

"The roots of my entrepreneurial mindset lie in seeing the entrepreneurial work of poverty," Blair says. "The working, hustling rich and the working, hustling poor are the same species, except one plays by society's rules. Or makes them, some would say."

Blair bulked up. He was 260 pounds at his peak, his body a patchwork of gang tattoos. The more intimidating he appeared, the less he would have to fight. "When you're 15 and you see someone get murdered," he says, "survival becomes your goal."

That idea, in a somewhat modified form, is true in the business world too. Success depends on the ability to adapt to your surroundings and provoke the reaction you want. "Every board member creates his signature, a signature of his insecurities overcome," he says. "A combination of old-fashioned DNA, anthropology, culture, ambition and aspiration."

Blair's "signature" is, of course, his past -- a past that he finally put behind him during his second stint in juvenile detention. His first came when he was 14, after he attempted to rob a restaurant but set off a silent alarm when he threw a rock through the window.

Gangsters, he now contends, are "entrepreneurs who steal from other entrepreneurs." The best thing small-business owners can do, he thinks, is to "educate the local hoodlums" in legitimate business skills -- "as a form of insurance." That's exactly what Blair now does with his foundation.

Blair was locked up for the second time at age 16, for a strong-arm robbery and battery. He says that he was beaten up on the first day, the last time around, so he decided to go on the offensive. As he puts it in his book, "If you let someone take your milk the first day, they'll start taking it every day." Blair incited a riot.

Over the next 30 days, most of it spent in solitary confinement, some thoughts gnawed at Blair. Mainly the fact that, at the judge's whim, he could be spending the next four years of his life behind bars.

He read his first, and only, work of fiction at this time, Stephen King's "Firestarter," sounding out the syllables phonetically and listening to them bounce off the walls. Today, Blair has read over 1,000 books and remembers most of what he reads, a remarkable feat for a dyslexic high school dropout. He says that it's because he doesn't read visually, but auditorily, thanks to that excruciating month he spent with nothing but his own voice.

Blair wrote a letter to the judge, with some spelling assistance, begging for leniency. "You should be writing in college," the judge replied, "not in prison."

When Blair was released, he found his mother's home ransacked -- his fellow gang members assumed that he'd become a "rat." Blair decided to begin the long, delicate and sometimes life-threatening process of leaving his gang. He got a job picking up the cans dropped off for recycling, meeting what he calls the "lowest form of life": the crackheads clutching at nickels for the next hit, the drunk who turns in his beer cans just to scrape together enough cash for the next 12-pack.

Nothing spurred Blair upward faster than staring into the eyes of the bottom. He worked almost every waking hour of the day, seven days a week, and still does. His mother started dating a new guy, a successful real estate entrepreneur, who moved them out of their crummy neighborhood, let Blair drive around in his Cadillac Allante, and hired him to do odd jobs. Blair suddenly appreciated the connection between wealth and hard work.

Soon he got a job at another company, answering phones, but impressed the higher-ups when he covered a shift at the data center. Computers had always been a passion of his. After all, he says, he'd "liberated a bunch."

Within three years, Blair became vice president. His starting salary had been $6 an hour. His new salary was $100,000 per annum. The next year, he founded his own 24-hour computer repair company, at age 21. Blair claims that this rapid rise came thanks to his ability to "hustle" and his "nothing-to-lose attitude," but no doubt his charisma helped too. Blair has the charm of a practiced motivational speaker -- which he is.

Blair claims that he "sees the world as a technologist." His current company may not seem so technical: ViSalus is a weight-loss and fitness program. But it's based on the idea of challenges; people set their goal, and get prizes for completing it. It "game-ifies" weight loss, like the many websites that keep people coming back through badges and give-aways, and anything that will tickle the brain's reward center. Blair approached his book similarly, making the chapters short enough to give his readers a regular jolt of accomplishment.

He's approached himself the same way too. "I've trained myself to be addicted to business," he says. And that's what drives him, not some misty sense of a legacy. He's requested that his foundation be wound down within 10 years of his death, along with the 90 percent of his assets that he's dedicated to it.

In 2004, Steven Levitt said that being in a gang is "perhaps the worst job in all of America." In 2012, Blair says, "it's one of the only jobs." Kids are increasingly turning to gang culture for money and meaning. Blair hopes to prove to them that they have the skills to get a lot more money and a lot more meaning, if they play by society's rules.

You can read the first chapter of Ryan's book, "Nothing to Lose, Everything To Gain: How I Went From Gang Member to Multimillionaire Entrepreneur," for free here.