Tony Robbins, The CEO Whisperer

“I owwwwwnnnnnn you!!!” As I snarl and holler at a woman more than a foot shorter than me while she points up and screams back, the awkwardness of the situation makes it hard for us to keep from laughing. But there’s something undeniably appealing about the experience: Unleashing so much raw energy, in however absurd a fashion, is seductive.

The setting for this mass act of catharsis is the third floor of the Moscone West exhibition space in downtown San Francisco. And the tech-savvy strivers who have filled the room on this Monday afternoon in October are all here for Dreamforce, the annual conference put on by software powerhouse Salesforce.com. In its 12th year, Dreamforce has grown from a small, sober customer event of 1,300 to the Lollapalooza of corporate gatherings.

Some 150,000 registered attendees wearing sky-blue credentials have invaded the city and are shuffling among some 1,400 sessions spread over the course of four days. Former Secretary of State Hillary Clinton, former Vice President Al Gore, media baroness Arianna Huffington, tech visionaries Marc Andreessen and Reid Hoffman, and musicians will.i.am and Neil Young all have featured roles in the four-day program.

On this opening afternoon of the conference, however, Salesforce CEO and co-founder Marc Benioff, 50, has given the big stage to one of his most important mentors: the bestselling self-help author and motivational speaker Tony Robbins.

“Very few people have had such a huge impact on me—my ability to be successful, my ability to give back,” Benioff tells the audience in his introduction. In fact, he says, it was Robbins who provided the leadership model that Benioff uses to set goals for Salesforce, one of the world’s largest software companies, with an expected $5 billion in sales this year and a market capitalization of $38 billion. “All of that came out of Tony’s work.”

crowd pleaser: Robbins revs up 6,000 attendees at Salesforce.com’s Dreamforce conference in San Francisco in October.Photo by Brian L. Frank—Getty Images for Fortune

For the past hour Benioff has been sitting in the front row and nodding his head enthusiastically as the almost larger-than-life Robbins—he’s six-seven, with hands the size of catcher’s mitts and a head that looks as if it were carved from granite—digs into the topic of “engagement.” Dressed in a black button-down shirt and dark jeans, he moves confidently on a round stage in the center of the crowd, projecting his trademark scratchy baritone through a headset mike. Robbins tells the crowd that he recently ran across a study that found that just 29% of employees in the U.S. are engaged in their work—and 24% are actively disengaged. (“That means they hate their jobs and they hate you!”) Such a notion is mind-boggling to the relentlessly energetic life coach, a happy workaholic who sleeps barely five hours a night and spends 200 days a year on the road in his never-ending quest to pull peak performance out of the underachieving masses.

It’s the responsibility of the people in the room to attack this engagement problem, he says. The best, most profitable companies are those in which employees are the most engaged. “You want to get someone engaged, you engage,” he exhorts. “That’s your job as a leader. You can’t maximize resources if you don’t have engagement.” And if you want to reach people, Robbins believes, one of the best ways to do so is to change your “state”—physically and emotionally. Which is why he has us standing and yelling.

“Does that feel better, yes or no?” he asks after the music stops. “If you feel better, do you make other people better or worse? If you feel better, do you perform better?”

Robbins, 54, has gone through his own professional change of state over the years. He burst onto the self-improvement scene nearly three decades ago with the publication in 1986 of his first bestseller, Unlimited Power: The New Science of Personal Achievement. His follow-up five years later, Awaken the Giant Within, was an even bigger success. But it was through the ever-expanding series of infomercials that many people first met him. Long-form TV ads for his 30-day programs to achieve personal growth ran 24 hours a day in different parts of the cable universe throughout the ’90s and beyond—lodging the life coach somewhere in the public consciousness between Ron Popeil and Dale Carnegie. You might remember him as the guy who has inspired thousands of people—including Oprah—to walk over burning coals. Others know Robbins as the guy, playing himself, who cast a spell on Jack Black in the movie Shallow Hal. He’s been called in to advise Bill Clinton during his impeachment ordeal, to work with athletes like Andre Agassi when they were off their game, and to help actor Hugh Jackman stay in the zone.

Few if any self-improvement gurus are as familiar to Americans as Robbins, but somewhat more quietly over the years he has assumed a different role—as trusted adviser to corporate chieftains and captains of finance. He counts billionaires such as Virgin’s Richard Branson and gaming magnate Steve Wynn among his friends. His special gift, say admirers, is his ability to help successful people not only take their performance to the next level but also find personal fulfillment in the process. Robbins’ knack for combining pragmatic analysis with empathy has turned him into a modern-day consigliere to the C-suite. “He’s been a source of direction—a rebooter for me when I got off track,” says longtime Hollywood producer Peter Guber, the onetime CEO of Sony Pictures Entertainment and an owner of the Los Angeles Dodgers who first discovered Robbins through his tapes and then became a close friend. “I would call on him to look at what I was doing in my life. Was I being authentic?”

Getting “in state”: Moments before taking the stage at Dreamforce, Robbins does some trampoline training to get him energized for the three-hour program.Photo by Brian L. Frank—Getty Images for Fortune

Robbins remains a titan in the $10 billion self-improvement industry. His 25 multiday events this year will attract audiences of thousands who pay richly to learn his techniques for living a richer and fuller life. The average ticket to his six-day “Date With Destiny” program is $3,555. But he also devotes a significant portion of his time to working intensely with a small group of global power players—a Latin American industrialist, an Asian entrepreneur—who, he says, pay him seven-figure fees to coach them in their lives and careers. This group notably includes Paul Tudor Jones, founder of $13 billion hedge fund firm Tudor Investment Corp. and one of the world’s most acclaimed traders. Robbins has worked with Jones for 21 years, helping the investor keep his edge through wildly fluctuating markets. “Tony’s genius is his ability to deconstruct what drives certain behaviors,” says Jones.

One thing Robbins hasn’t done for more than two decades is publish a major new book. But that is about to change in November with Money: Master the Game, a 600-page tome that promises to give readers “7 Simple Steps to Financial Freedom” (see excerpt). The book, he says, was born out of a sense of moral outrage following the financial crisis of 2008. Watching the 2010 documentary Inside Job, he got angry that a handful of reckless financiers had tanked the markets and caused millions of less financially sophisticated people to suffer. “I was pissed,” says Robbins. And he wanted to do something about it. “I just started thinking, you know, I have access. That’s one unique thing I have. And I have the respect of a certain number of people, and I think I could enroll them in saying, ‘Look, you have understanding and advice that if we could get to the massive audience, they could make better decisions.’”

Leveraging his relationships with Jones and others, Robbins set out to interview 50 of the investing world’s elite and distill their lessons for the masses. He sat down with the likes of activist investing legend Carl Icahn, J.P. Morgan Asset Management’s Mary Callahan Erdoes, Vanguard founder Jack Bogle, Charles Schwab, and T. Boone Pickens—and included his Q&As with many in the book. He talked asset allocation with David Swensen, who runs Yale’s $24 billion pension fund, and grilled Ray Dalio, the founder of Bridgewater Associates, the world’s biggest hedge fund with $150 billion under management, on how to build a portfolio that will generate returns in any market environment.

The result is a mix of core practical advice—build a balanced portfolio, use low-cost index funds, and beware of brokers whose financial incentives aren’t aligned with yours—filtered through the Robbins regimen of empowerment. “How many people are going to tell you the system is rigged? That’s an old story,” he says. “How about we go to a new story called, ‘How do you use the system that exists instead of letting the system use you?’ Let’s focus on something you can do.”

Tony Robbins with Marc Benioff before the Salesforce.com’s Dreamforce conference in San Francisco in October.Photo by Brian L. Frank—Getty Images for Fortune

The book reveals a different side of a man dismissed by some as a purveyor of common-sense inspiration. Woven alongside classic Tony aphorisms (“Complexity is the enemy of execution”) is a passionate desire to explain—to solve the mystery of why so many people are set up to fail when it comes to their own financial management. Spend a few days with Robbins and it becomes clear that he isn’t just a hyperenergized salesman with a headset. Some of the most accomplished business and financial figures in the world deeply respect his ability to listen, process information, and translate it into positive results.

What does he give them that they can’t get elsewhere?

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Paul Tudor Jones was in a slump. It was 1993 and Jones, then 39, was already regarded as a full-fledged master of the hedge fund universe. His legend had been established when he correctly anticipated the market plunge in October 1987 and made huge profits when most of his peers lost a bundle. Jones earned his investors a 200% return that year. But six years later he was going through a “rough patch” that had hurt his confidence, and his friend Pat Riley, the Hall of Fame basketball coach who was then leading the New York Knicks, recommended that Jones reach out to Robbins. “Pat told me Tony would light a fire inside me, but in a very thoughtful and understanding way,” says Jones. The first thing Robbins had him do was get in the best physical shape of his life, because so much of winning is mental and attitudinal. “By controlling my body, which for me was an easy win, the path was then much easier to control my mind,” says Jones. “He was right.”

The next step was to delve into the secrets of Jones’s past success. Robbins helped Jones identify what made him profitable in his trading—the behaviors and circumstances under which he did best. “I had been a trader for more than 17 years,” says Jones. “But I really had no road map as to how I made money for my clients. I thought it was mostly instinctual, but it isn’t.” Working with Tony over the years, says Jones, has allowed him to get “clarity on where my ‘alpha’ or edge originates from, and that has helped both my longevity as a trader and peace of mind as a person.” Jones says his biggest challenge was overcoming a bad tendency to trade reactively and emotionally instead of developing a planned execution scheme with risk and reward propositions that are carefully thought through. Robbins helped him build a system. “I think that planning process alone has added 5% or more to my returns every year,” says Jones.

Over the two decades that Robbins has been working with Jones, the investor has made money every single year, including in 2008 when the U.S. stock market dropped nearly 40%. To maintain his edge, Robbins and Jones communicate daily. Jones sends Robbins a couple of paragraphs summarizing what happened that day in his trading. He also dictates a set of 12 to 15 criteria that he and Robbins measure together so that Robbins can monitor them. “I know the patterns,” says Robbins. “I know what to do to intercede so that we don’t run into a significant challenge. If we do, we can shut it down quickly if at all possible.”

Robbins says he establishes metrics for all his coaching clients—some more, some less. “It’s just like when I take over a business,” he says. “If you don’t measure, you don’t have a clue what you’re doing.” He has them track metrics of their psychological and emotional state. “I give them a set of qualitative measurements that they give me feedback on, so I get a sense of where they are psychologically,” he says. They also agree on certain key indicators to measure progress in their businesses. “Psychologically, I’ll measure a person’s weight every night,” says Robbins. “If this person starts gaining weight, if I see that something’s happening with them physically, I can see that something is happening emotionally. Within a few seconds, I can go, ‘Four pounds! What the hell happened over the weekend?’” For this level of personal guidance, Robbins charges Jones and his other elite clients $1 million a year, he says, plus a piece of the upside of their business. (Robbins says he has offered many times to stop charging Jones, but the trader insists on keeping the arrangement in place.) Of course, he gets compensated in other ways too. Going deep with Jones and other highly successful businesspeople is a powerful way to achieve what Robbins likes to call “mastery.”

Friends in high places: Clockwise from far right: Robbins with Salesforce.com’s Marc Benioff (left) and Virgin’s Richard Branson; taking a moment with hedge fund luminary and client Paul Tudor Jones; and solo, leading a seminar in 2000.Photos: Courtesy of Robbins Research International, Inc.

Multibillionaire Bridgewater Associates founder Dalio, who manages money exclusively for institutional clients, had some familiarity with Robbins before sitting down for an interview for his book. He had listened to a set of Robbins’ tapes years earlier. But he was captivated by Robbins’ ability to converse with him—what Robbins likes to call “pitching and catching”—at a high level. “I was blown away by him,” says Dalio. “He got the investment concepts we talk about better than many highly professional institutional investors who devote their lives to this subject. And he was able to convert it to a practical level. For me, it was really exciting.”

For Dalio, who last year released a 30-minute animated video called How the Economic Machine Works, that ability to distill information is particularly compelling. “Sometimes people are wary of simplicity,” he says. “He’s able to see things in a simple but granular way. It’s a talent. I find that it’s a rare case that people have an ability to see things in a simple way and also appreciate the complexity of things. He’s blessed with a mind that allows him to see that way.” Elliot Weissbluth, the founder and CEO of Chicago-based HighTower Advisors, experienced much the same thing when Robbins reached out to him for help on the book project. “We’re both systems people,” says Weissbluth, who runs one of the largest independent registered investment advisers in the U.S., with $30 billion in assets, and wrote the foreword for Money: Master the Game. “He thinks about systems and how to take a system, unpack it, repack it, educate, train, and give people the tools to have a breakthrough.”

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Long before he had acquired those tools, Robbins was a scrawny kid trying to find order in a chaotic home life. He was born Anthony Mahavorick in Los Angeles, where his father was a parking garage attendant, but grew up in Azusa and Glendora, Calif., after his parents split when he was 7. His mother, an alcoholic and pill user whose father was a writer for Walt Disney and Hanna-Barbera, had a series of husbands—men whom Robbins refers to as his “fathers.” He especially connected with a former semi-pro baseball player named Jim Robbins, who legally adopted Tony.

His mother rarely left the house and could be abusive. Robbins, the eldest of three children, found himself searching for ways to manage the environment. “I had to become a practical psychologist to figure out how to protect my brother and sister and to protect myself,” he says. Robbins often did the grocery shopping, cooked meals, and persuaded the pharmacist to refill his mother’s prescriptions. Money was usually tight. So Robbins became a handyman too. A tinkerer by nature who liked to take apart radios for fun before age 10, he bought a cheap book called H.E.L.P.: Home Emergency Ladies’ Pal and used it as his bible for home repairs. In school he made friends by being a problem solver and pleaser. “I got addicted to making people light up,” he says. As a senior he was student body president.

In his last two years of high school, Robbins began a period of huge growth—both figuratively and literally. As a freshman he was unusually short, just five-one. Being small instilled in him a “ferocious intensity,” he says. “That’s what allows me to go in a room of 5,000 people and take it.” When he turned 16 he was still just five-seven. But over the next year he suddenly grew 10 inches. Robbins didn’t find out until he was in his thirties that the rapid growth had been due to a pituitary tumor in his brain. As Robbins tells the story, a Sikh cleric he met was the first one to warn him that he had a pituitary disturbance and should see a doctor. He brushed it off. But at his next physical the doctor told him that, indeed, he had a tumor and needed surgery or else his heart valves could expand fatally. After seeking multiple opinions, Robbins determined that the tumor had stabilized on its own. He’s been monitoring it for 20 years and says he’s perfectly healthy but with a bonus: an elevated level of human growth hormone. “I’ve got for free what some of those athletes are paying thousands for to get an edge,” he says.

As he was shooting up in height, Robbins began a concerted campaign to expand his mind. Looking for evidence that his biography would not limit his destiny, he dove into books. Robbins says he studied speed-reading and gave himself a goal of reading one book a day, gobbling up stories of great leaders as well as self-improvement literature. “I wanted stuff that was practical,” he says, “something I could use, that would touch something that mattered.” When he was 17 and a senior in high school, Robbins says, his mother chased him out of the house with a knife, and he never returned. He worked as a janitor and found a small apartment, but he dropped his dream of attending the University of Southern California to study sportswriting.

Shortly thereafter, Robbins landed a job with a motivational speaker named Jim Rohn, and his career in self-improvement was launched. The growing field of personal empowerment was a natural fit for an intelligent young man with a driving desire to lift himself beyond his origins. He pieced together his own approach to the topic. Packaged in phrases like Neuro-Linguistic Programming and Neuro-Associative Conditioning, the message boiled down to this: It’s possible to exert mind over matter, take control of your own destiny, and achieve your goals. It’s about changing the “story” you tell about yourself. That can be easier said than done. As Robbins observes, “I’ve had the privilege to be around some of the most successful people on the face of the earth, the best in the world at what they do. The one common denominator is hunger. So I can’t create that. But I can unleash it in people. I can trigger it.”

“Tony’s genius is his ability to deconstruct what drives certain behaviors,” says hedge fund billionaire and client Paul Tudor Jones.”

In 1984, Robbins became a family man in a hurry at age 24 when he married his first wife, Becky. She already had three kids from two previous marriages. And the same year he had a child with a past girlfriend. That son, Jairek Robbins, is now a motivational speaker and performance coach like his dad. In 2001, Robbins and Becky finalized a divorce, and later that year Robbins married Sage, whom he met when she was working at one of his seminars.

Robbins sometimes doesn’t seem totally comfortable with his empowerment origins. He will frequently toss off a comment like, “I don’t believe in a bunch of self-improvement bullshit.” Raise the subject of his infomercial past or teaching people to fire-walk, and he bristles a bit. But decades of assessing people has imbued him with an inherent self-confidence. “I know that I’m inferior to everybody in some way,” he says. “You may be a better singer than I am or more centered in some ways. But I also know that I’m superior to you in something else. I know how to create a process to achieve things, and I never, ever give up. That makes us equal.”

a rare moment at home: Robbins and his wife, Sage, at their home near Palm Beach. The two are on the road 200 days a year.Photo by Martin Schoeller for Fortune

This self-assurance serves him well in dealing with powerful people. In the mid-1990s, for instance, Guber was ready to give up his job at Sony, but he was struggling to let go of the status and the responsibility. He turned frequently to Robbins for advice, and Robbins guided Guber with questions. “He would say, ‘What are you looking at?’ ” says Guber. “He allowed me to gauge the value proposition of staying and going, and to do it myself. He put me in charge of the process. I don’t think I would have trusted anybody who said to me, ‘You should leave. You should stay.’ I used to call him, ‘So what do I do? What do you think?’ And he never, ever told me what to do. That was his secret.”

To Guber, Robbins’ message was both simple and authentic: “He said, ‘Be in charge of your life. You’re going to have reward and risk wherever you are, but be authentic to what you want to be and what you want to do. Don’t be worrying about what somebody thinks about you. Don’t flatter yourself. They’re really not thinking about you.’ And that’s true.”

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With my eyes closed and my hands palm up, I’m trying hard to stay focused on feelings of gratitude when I feel Robbins’ massive hands gripping my skull. We’re in the meditation room in his oceanfront house in Palm Beach. It’s a perfectly Zen setting. The only light comes from the 30 white candles burning on two hanging trays and a credenza. Indian music is pulsing through the sound system.

Robbins bought the house a year and a half ago for $24.75 million when he got fed up with state income taxes in California and decided to make Florida his main base. He still has a home in Palm Springs, another in Sun Valley, Idaho, and one in British Columbia, Canada, in the small town outside Vancouver where his wife, Sage, grew up. Then there’s the Namale Resort and Spa he owns in Fiji, which he says is his favorite place in the world—not just because of its inherent beauty but also because of the inherently positive outlook of its people. The Robbinses have only recently finished mostly renovating the Palm Beach house—not counting the guesthouse they’re building on the property. There is a 165,000-gallon infinity pool, and the master bedroom has a balcony that overlooks the Atlantic. “I’m a freak for the ocean,” says Robbins. “It energizes me.”

Robbins discovered meditation eight years ago when he was searching for something that would alleviate Sage’s extreme motion sickness, an affliction she had struggled with since childhood. “Here I am, Mr. Solutions for everybody else, and I couldn’t figure this out,” says Robbins. Then he heard from a friend who had traveled to the Oneness University, a meditation center in the state of Andhra Pradesh in India. The guru there had a technique that could slow the activity in a person’s parietal lobes, the part of the brain that controls motion. Robbins thought it might help Sage. He began looking for someone in the U.S. who could instruct them in the technique. And that’s how he met Rick Allen, the drummer of rock band Def Leppard, who had turned to meditation years earlier to help deal with the trauma of losing his left arm in a car accident in the 1980s. Allen came to the Robbinses’ house in California and led them in a session. Not long after, Robbins and his wife made their own trip to the Oneness University for several days of intensive study—and virtually nothing else. Robbins was soon going stir-crazy. “I’m thinking, ‘This is bullshit,’” he says. “Is this really going to do anything?” But eventually the guru took them for a ride in a car, and for the first time she could remember, Sage didn’t feel sick. She has been largely cured ever since.

As Robbins’ hands wrap over my skull, he delivers the Oneness “blessing,” or deeksha, which is said to initiate a neurobiological change in the brain. Robbins says he doesn’t engage in full-on meditation on a daily basis. But he has incorporated elements of the ritual into his routine—a process he calls “priming.” He takes 10 to 20 minutes a day to put himself in a positive state of mind. First he does a physical and breathing routine to change his state, and then he focuses on one emotion. “I prime gratitude, because of all the human emotions, you can’t be angry and grateful simultaneously,” says Robbins. He likes to finish by focusing on three goals he wants to accomplish.

Finding his center: As part of his daily routine, Robbins takes a few moments to “prime” gratitude and reject negativity.Photo by Martin Schoeller for Fortune

For Robbins, the priming is a counterweight to a schedule of seminars that is grueling. “I designed these programs when I was a crazy young guy of 24,” he says. “Now I’m 54.” In a four-day event, Robbins says, he will cover the equivalent of an ultramarathon over 52 hours of seminar time—and he’s in the spotlight, talking, almost nonstop. To recover, he has long been a proponent of “cold plunges” into an ice bath. And more recently he has begun using a cryotherapy machine, which exposes the body to –220° F for three minutes to reduce inflammation. He’s also fastidious about his diet. Robbins doesn’t drink alcohol or caffeine, or eat red meat or chicken.

In addition to his core work as a strategist, these days Robbins presides over a diverse portfolio of businesses—but the size of that portfolio is not easy to derive. In an appendix to his new book, he describes the Anthony Robbins Cos. as having “combined revenue exceeding $5 billion a year.” For a single company filing financial statements with a government agency, that would be enough to qualify for the Fortune 500. (United Rentals, No. 500 on the 2014 list, had $4.95 billion in revenue last year.) But none of his companies are publicly traded. And Robbins is cagey about divulging specifics or discussing his net worth, though his life of lavish homes and chartered Gulfstream jets suggests that he’s living on a par with some of the power players he advises. Robbins says that he’s started more than a dozen companies and owns a piece in another dozen or so more. The range goes from CloudCoaching International, a holding company that owns businesses focused on “corporate improvement” and has clients like Dell and Ingersoll Rand, to Unlimited Tomorrow, which is working on “exoskeletons” that could someday allow paralyzed people to walk again.

Soon Robbins will be a professional sports team owner too. In late October he joined his friend Guber as part of a group—including Magic Johnson, Mia Hamm, and several other investors—paying $100 million for the rights to launch a new Major League Soccer franchise in Los Angeles. The team will start playing in 2017 in a privately funded new stadium.

To support him in his varied activities, Robbins has a team of six assistants who are on call pretty much 24/7. They do everything from sorting, coding, and summarizing his emails to brainstorming material and creating the circular “mind maps” he likes to study as a visual outline for his seminars. The actual sequence is improvised as he goes (see “Robbins’ Rules: How to Give a Presentation, below”).

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Robbins’ Rules: How to Give a Presentation
Five tips for engaging a crowd like Tony.

1 DO YOUR HOMEWORK

“My first thing in preparing for a presentation,” says Robbins, “is you’ve got to know your audience and what their deepest needs are, their deepest desires, and their deepest concerns. That’s more important than anything else. You have to carve your message and really make sure that it’s going to hit the mark for who you’re speaking with. So I usually do quite a bit of homework in advance, and I have a team of people who also do homework. You can’t add value until you know their needs.”

2 RESPECT YOUR AUDIENCE

“It’s not enough just to know your audience. You’ve got to honestly respect them too. You can’t influence someone you’re judging. So when I sit down and do the slides, I think, ‘Who’s in this audience? What do I respect about them? What do I appreciate about them?’ That gives me a connection with them that I—and they­—can feel.”

3 GO DEEP QUICKLY

“The next question is to ask, ‘How am I going to engage them from the very beginning—to quickly get to what matters to them?’ And to engage other people, you’ve got to be engaged. One way to engage is with shock. Or entertainment. But I think, ‘Let’s engage with the truth. Let’s go for what’s real and raw.’”

4 KNOW YOUR OUTCOME

“You need an outline of what you want to do, but the key is to know your outcome. I pick outcomes that I’m passionate about. I don’t think anyone should ever speak about anything they’re not passionate about. If you’re not passionate about something, no one else is going to be, and you’re wasting everyone’s time.”

5 EMBRACE SPONTANEITY

“Some people clearly need a sequence in their presentation to be able to function, and I understand that. But you also have to be able to flex so that you can be real and in the moment. People are starving for spontaneity. Everybody’s sick of watching somebody do a PowerPoint. I mean, it’s just absurd.”

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To be sure, there’s a theme that runs through the Robbins business empire, the book sales and seminars, the road warrior lifestyle that has him on a plane roughly every four days, even his philanthropy—he’s donating all the earnings from the book’s sale to feeding the hungry and has pledged over the next 12 months to serving at least 50 million meals to people in need through a partnership with the nonprofit Feeding America. Everything the man does is outsize, as if cast from the same mold that shaped his 6-foot-7, 285-pound frame. He is so comfortably larger than life that when his eyes water with suddenly intense emotion—as they frequently do—it is hard not to want to feel along with him.

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The day before his keynote seminar at Dreamforce, Robbins and I visit Benioff at the elegant row house in the Pacific Heights neighborhood of San Francisco where the Salesforce CEO used to live and that he now uses as a home office. Robbins greets his friend with a kiss on the cheek, and we sit down to talk around the dining room table. Benioff discovered Robbins through his tapes two decades ago when he was a fast-rising executive at software giant Oracle, and then began attending seminars. Eventually they got to know each other. But he was a fan before he was friends with Robbins. And he still seems a bit in awe of his mentor, as if he’s in the presence of a childhood sports hero. “It’s just surreal that he’s here,” he says, blushing and looking down.

When he was at Oracle, Benioff borrowed a system that Robbins calls RPM (or Rapid Planning Method) and adapted his own version he calls V2MOM (Vision, Values, Methods, Obstacles, and Measures) as his management model. Eventually he used it as the template for founding Salesforce.com. He wrote out the first Salesforce V2MOM on an American Express envelope. “Tony says, ‘The quality of your life is the quality of our questions,’” says Benioff. “But also the quality of your leadership is the quality of your questions. And if you can get your employees to also learn how to constantly answer those questions, you can get this mass alignment.” Benioff and his executive team use the process every year to set the company’s goals. Now, says Benioff, he is teaching the system to Brian Chesky, the founder of Airbnb.

Asked to explain Robbins’ long-lasting influence on his life, Benioff turns reflective. “So I was a young VP at Oracle, like 24 years old, making a lot of money and working for, you know, a crazy person,” he says. “And it was just really intense and surreal and scary.” Benioff had gone to the University of Southern California and gotten a degree in entrepreneurship. They taught him marketing. They taught him about organizational development, accounting, various business things. And then he went to work. Even after all that, “you don’t really have tools for leadership,” he says. “And that’s what Tony gave me.”

This story appears in the November 17, 2014 issue of Fortune.

An earlier version of this story incorrectly included Warren Buffett in a list of prominent investors with whom Robbins “sat down” for interviews for his book Money: Master the Game. The book includes a chapter devoted to Buffett, but Buffett declined Robbins’ request for an interview.