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To think they can change 4 page

prouder of,” he said. “I still think it was incredible.”

One night Wozniak drove down from Berkeley to Jobs’s house to try it. They attempted to call

Wozniak’s uncle in Los Angeles, but they got a wrong number. It didn’t matter; their device had

worked. “Hi! We’re calling you for free! We’re calling you for free!” Wozniak shouted. The

person on the other end was confused and annoyed. Jobs chimed in, “We’re calling from

California! From California! With a Blue Box.” This probably baffled the man even more, since

he was also in California.

At first the Blue Box was used for fun and pranks. The most daring of these was when they

called the Vatican and Wozniak pretended to be Henry Kissinger wanting to speak to the pope.

“Ve are at de summit meeting in Moscow, and ve need to talk to de pope,”

Woz intoned. He was told that it was 5:30 a.m. and the pope was sleeping. When he called

back, he got a bishop who was supposed to serve as the translator. But they never actually got the

pope on the line. “They realized that Woz wasn’t Henry Kissinger,” Jobs recalled. “We were at a

public phone booth.”

It was then that they reached an important milestone, one that would establish a pattern in their

partnerships: Jobs came up with the idea that the Blue Box could be more than merely a hobby;

they could build and sell them. “I got together the rest of the components, like the casing and

power supply and keypads, and figured out how we could price it,” Jobs said, foreshadowing roles

he would play when they founded Apple. The finished product was about the size of two decks of

playing cards. The parts cost about $40, and Jobs decided they should sell it for $150.

Following the lead of other phone phreaks such as Captain Crunch, they gave themselves

handles. Wozniak became “Berkeley Blue,” Jobs was “Oaf Tobark.” They took the device to

college dorms and gave demonstrations by attaching it to a phone and speaker. While the potential

customers watched, they would call the Ritz in London or a dial-a-joke service in Australia. “We

made a hundred or so Blue Boxes and sold almost all of them,” Jobs recalled.

The fun and profits came to an end at a Sunnyvale pizza parlor. Jobs and Wozniak were about

to drive to Berkeley with a Blue Box they had just finished making. Jobs needed money and was

eager to sell, so he pitched the device to some guys at the next table. They were interested, so Jobs

went to a phone booth and demonstrated it with a call to Chicago. The prospects said they had to

go to their car for money. “So we walk over to the car, Woz and me, and I’ve got the Blue Box in

my hand, and the guy gets in, reaches under the seat, and he pulls out a gun,” Jobs recounted. He

had never been that close to a gun, and he was terrified. “So he’s pointing the gun right at my

stomach, and he says, ‘Hand it over, brother.’ My mind raced. There was the car door here, and I

thought maybe I could slam it on his legs and we could run, but there was this high probability



that he would shoot me. So I slowly handed it to him, very carefully.” It was a weird sort of

robbery. The guy who took the Blue Box actually gave Jobs a phone number

and said he would try to pay for it if it worked. When Jobs later called the number, the guy said

he couldn’t figure out how to use it. So Jobs, in his felicitous way, convinced the guy to meet him

and Wozniak at a public place. But they ended up deciding not to have another encounter with the

gunman, even on the off chance they could get their $150.

The partnership paved the way for what would be a bigger adventure together. “If it hadn’t

been for the Blue Boxes, there wouldn’t have been an Apple,” Jobs later reflected. “I’m 100%

sure of that. Woz and I learned how to work together, and we gained the confidence that we could

solve technical problems and actually put something into production.” They had created a device

with a little circuit board that could control billions of dollars’ worth of infrastructure. “You

cannot believe how much confidence that gave us.” Woz came to the same conclusion: “It was

probably a bad idea selling them, but it gave us a taste of what we could do with my engineering

skills and his vision.” The Blue Box adventure established a template for a partnership that would

soon be born. Wozniak would be the gentle wizard coming up with a neat invention that he would

have been happy just to give away, and Jobs would figure out how to make it user-friendly, put it

together in a package, market it, and make a few bucks.

CHAPTER THREE

THE DROPOUT

Turn On, Tune In . . .

Chrisann Brennan

Toward the end of his senior year at Homestead, in the spring of 1972, Jobs started going out with

a girl named Chrisann Brennan, who was about his age but still a junior. With her light brown

hair, green eyes, high cheekbones, and fragile aura, she was very attractive. She was also enduring

the breakup of her parents’ marriage, which made her vulnerable. “We worked together on an

animated movie, then started going out, and she became my first real girlfriend,” Jobs recalled. As

Brennan later said, “Steve was kind of crazy. That’s why I was attracted to him.”

Jobs’s craziness was of the cultivated sort. He had begun his lifelong experiments with

compulsive diets, eating only fruits and vegetables, so he was as lean and tight as a whippet. He

learned to stare at people without blinking, and he perfected long silences punctuated by staccato

bursts of fast talking. This odd mix of intensity and aloofness, combined with his shoulder-length

hair and scraggly beard, gave him the aura of a crazed shaman. He oscillated between charismatic

and creepy. “He shuffled around and looked half-mad,” recalled Brennan. “He had a lot of angst.

It was like a big darkness around him.”

Jobs had begun to drop acid by then, and he turned Brennan on to it as well, in a wheat field

just outside Sunnyvale. “It was great,” he recalled. “I had been listening to a lot of Bach. All of a

sudden the wheat field was playing Bach. It was the most wonderful feeling of my life up to that

point. I felt like the conductor of this symphony with Bach coming through the wheat.”

That summer of 1972, after his graduation, he and Brennan moved to a cabin in the hills above

Los Altos. “I’m going to go live in a cabin with Chrisann,” he announced to his parents one day.

His father was furious. “No you’re not,” he said. “Over my dead body.” They had recently fought

about marijuana, and once again the younger Jobs was willful. He just said good-bye and walked

out.

Brennan spent a lot of her time that summer painting; she was talented, and she did a picture of

a clown for Jobs that he kept on the wall. Jobs wrote poetry and played guitar. He could be

brutally cold and rude to her at times, but he was also entrancing and able to impose his will. “He

was an enlightened being who was cruel,” she recalled. “That’s a strange combination.”

Midway through the summer, Jobs was almost killed when his red Fiat caught fire. He was

driving on Skyline Boulevard in the Santa Cruz Mountains with a high school friend, Tim Brown,

who looked back, saw flames coming from the engine, and casually said to Jobs, “Pull over, your

car is on fire.” Jobs did. His father, despite their arguments, drove out to the hills to tow the Fiat

home.

In order to find a way to make money for a new car, Jobs got Wozniak to drive him to De Anza

College to look on the help-wanted bulletin board. They discovered that the Westgate Shopping

Center in San Jose was seeking college students who could dress up in costumes and amuse the

kids. So for $3 an hour, Jobs, Wozniak, and Brennan donned heavy full-body costumes and

headgear to play Alice in Wonderland, the Mad Hatter, and the White Rabbit. Wozniak, in his

earnest and sweet way, found it fun. “I said, ‘I want to do it, it’s my chance, because I love

children.’ I think Steve looked at it as a lousy job, but I looked at it as a fun adventure.” Jobs did

indeed find it a pain. “It was hot, the costumes were heavy, and after a while I felt like I wanted to

smack some of the kids.” Patience was never one of his virtues.

Reed College

Seventeen years earlier, Jobs’s parents had made a pledge when they adopted him: He would go to

college. So they had worked hard and saved dutifully for his college fund, which was modest but

adequate by the time he graduated. But Jobs, becoming ever more willful, did not make it easy. At

first he toyed with not going to college at all. “I think I might have headed to New York if I didn’t

go to college,” he recalled, musing on how different his world—and perhaps all of ours—might

have been if he had chosen that path. When his parents pushed him to go to college, he responded

in a passive-aggressive way. He did not consider state schools, such as Berkeley, where Woz then

was, despite the fact that they were more affordable. Nor did he look at Stanford, just up the road

and likely to offer a scholarship. “The kids who went to Stanford, they already knew what they

wanted to do,” he said. “They weren’t really artistic. I wanted something that was more artistic

and interesting.”

Instead he insisted on applying only to Reed College, a private liberal arts school in Portland,

Oregon, that was one of the most expensive in the nation. He was visiting Woz at Berkeley when

his father called to say an acceptance letter had arrived from Reed, and he tried to talk Steve out of

going there. So did his mother. It was far more than they could afford, they said. But their son

responded with an ultimatum: If he couldn’t go to Reed, he wouldn’t go anywhere. They relented,

as usual.

Reed had only one thousand students, half the number at Homestead High. It was known for its

free-spirited hippie lifestyle, which combined somewhat uneasily with its rigorous academic

standards and core curriculum. Five years earlier Timothy Leary, the guru of psychedelic

enlightenment, had sat cross-legged at the Reed College commons while on his League for

Spiritual Discovery (LSD) college tour, during which he exhorted his listeners, “Like every great

religion of the past we seek to find the divinity within. . . . These ancient goals we define in the

metaphor of the present—turn on, tune in, drop out.” Many of Reed’s students took all three of

those injunctions seriously; the dropout rate during the 1970s was more than one-third.

When it came time for Jobs to matriculate in the fall of 1972, his parents drove him up to

Portland, but in another small act of rebellion he refused to let them come on campus. In fact he

refrained from even saying good-bye or thanks. He recounted the moment later with

uncharacteristic regret:

It’s one of the things in life I really feel ashamed about. I was not very sensitive, and I hurt their

feelings. I shouldn’t have. They had done so much to make sure I could go there, but I just didn’t want

them around. I didn’t want anyone to know I had parents. I wanted to be like an orphan who had

bummed around the country on trains and just arrived out of nowhere, with no roots, no connections, no

background.

In late 1972, there was a fundamental shift happening in American campus life. The nation’s

involvement in the Vietnam War, and the draft that accompanied it, was winding down. Political

activism at colleges receded and in many late-night dorm conversations was replaced by an

interest in pathways to personal fulfillment. Jobs found himself deeply influenced by a variety of

books on spirituality and enlightenment, most notably Be Here Now, a guide to meditation and the

wonders of psychedelic drugs by Baba Ram Dass, born Richard Alpert. “It was profound,” Jobs

said. “It transformed me and many of my friends.”

The closest of those friends was another wispy-bearded freshman named Daniel Kottke, who

met Jobs a week after they arrived at Reed and shared his interest in Zen, Dylan, and acid. Kottke,

from a wealthy New York suburb, was smart but low-octane, with a sweet flower-child demeanor

made even mellower by his interest in Buddhism. That spiritual quest had caused him to eschew

material possessions, but he was nonetheless impressed by Jobs’s tape deck. “Steve had a TEAC

reel-to-reel and massive quantities of Dylan bootlegs,” Kottke recalled. “He was both really cool

and high-tech.”

Jobs started spending much of his time with Kottke and his girlfriend, Elizabeth Holmes, even

after he insulted her at their first meeting

by grilling her about how much money it would take to get her to have sex with another man.

They hitchhiked to the coast together, engaged in the typical dorm raps about the meaning of life,

attended the love festivals at the local Hare Krishna temple, and went to the Zen center for free

vegetarian meals. “It was a lot of fun,” said Kottke, “but also philosophical, and we took Zen very

seriously.”

Jobs began sharing with Kottke other books, including Zen Mind, Beginner’s Mind by Shunryu

Suzuki, Autobiography of a Yogi by Paramahansa Yogananda, and Cutting Through Spiritual

Materialism by Chögyam Trungpa. They created a meditation room in the attic crawl space above

Elizabeth Holmes’s room and fixed it up with Indian prints, a dhurrie rug, candles, incense, and

meditation cushions. “There was a hatch in the ceiling leading to an attic which had a huge

amount of space,” Jobs said. “We took psychedelic drugs there sometimes, but mainly we just

meditated.”

Jobs’s engagement with Eastern spirituality, and especially Zen Buddhism, was not just some

passing fancy or youthful dabbling. He embraced it with his typical intensity, and it became

deeply ingrained in his personality. “Steve is very much Zen,” said Kottke. “It was a deep

influence. You see it in his whole approach of stark, minimalist aesthetics, intense focus.” Jobs

also became deeply influenced by the emphasis that Buddhism places on intuition. “I began to

realize that an intuitive understanding and consciousness was more significant than abstract

thinking and intellectual logical analysis,” he later said. His intensity, however, made it difficult

for him to achieve inner peace; his Zen awareness was not accompanied by an excess of calm,

peace of mind, or interpersonal mellowness.

He and Kottke enjoyed playing a nineteenth-century German variant of chess called Kriegspiel,

in which the players sit back-to-back; each has his own board and pieces and cannot see those of

his opponent. A moderator informs them if a move they want to make is legal or illegal, and they

have to try to figure out where their opponent’s pieces are. “The wildest game I played with them

was during a lashing rainstorm sitting by the fireside,” recalled Holmes, who served as moderator.

“They were tripping on acid. They were moving so fast I could barely keep up with them.”

Another book that deeply influenced Jobs during his freshman year was Diet for a Small Planet

by Frances Moore Lappé, which extolled the personal and planetary benefits of vegetarianism.

“That’s when I swore off meat pretty much for good,” he recalled. But the book also reinforced

his tendency to embrace extreme diets, which included purges, fasts, or eating only one or two

foods, such as carrots or apples, for weeks on end.

Jobs and Kottke became serious vegetarians during their freshman year. “Steve got into it even

more than I did,” said Kottke. “He was living off Roman Meal cereal.” They would go shopping at

a farmers’ co-op, where Jobs would buy a box of cereal, which would last a week, and other bulk

health food. “He would buy flats of dates and almonds and lots of carrots, and he got a Champion

juicer and we’d make carrot juice and carrot salads. There is a story about Steve turning orange

from eating so many carrots, and there is some truth to that.” Friends remember him having, at

times, a sunset-like orange hue.

Jobs’s dietary habits became even more obsessive when he read Mucusless Diet Healing

System by Arnold Ehret, an early twentieth-century German-born nutrition fanatic. He believed in

eating nothing but fruits and starchless vegetables, which he said prevented the body from forming

harmful mucus, and he advocated cleansing the body regularly through prolonged fasts. That

meant the end of even Roman Meal cereal—or any bread, grains, or milk. Jobs began warning

friends of the mucus dangers lurking in their bagels. “I got into it in my typical nutso way,” he

said. At one point he and Kottke went for an entire week eating only apples, and then Jobs began

to try even purer fasts. He started with two-day fasts, and eventually tried to stretch them to a

week or more, breaking them carefully with large amounts of water and leafy vegetables. “After a

week you start to feel fantastic,” he said. “You get a ton of vitality from not having to digest all

this food. I was in great shape. I felt I could get up and walk to San Francisco anytime I wanted.”

Vegetarianism and Zen Buddhism, meditation and spirituality, acid and rock—Jobs rolled

together, in an amped-up way, the multiple impulses that were hallmarks of the enlightenmentseeking

campus subculture of the era. And even though he barely indulged it at Reed, there

was still an undercurrent of electronic geekiness in his soul that would someday combine

surprisingly well with the rest of the mix.

Robert Friedland

In order to raise some cash one day, Jobs decided to sell his IBM Selectric typewriter. He walked

into the room of the student who had offered to buy it only to discover that he was having sex with

his girlfriend. Jobs started to leave, but the student invited him to take a seat and wait while they

finished. “I thought, ‘This is kind of far out,’” Jobs later recalled. And thus began his relationship

with Robert Friedland, one of the few people in Jobs’s life who were able to mesmerize him. He

adopted some of Friedland’s charismatic traits and for a few years treated him almost like a

guru—until he began to see him as a charlatan.

Friedland was four years older than Jobs, but still an undergraduate. The son of an Auschwitz

survivor who became a prosperous Chicago architect, he had originally gone to Bowdoin, a liberal

arts college in Maine. But while a sophomore, he was arrested for possession of 24,000 tablets of

LSD worth $125,000. The local newspaper pictured him with shoulder-length wavy blond hair

smiling at the photographers as he was led away. He was sentenced to two years at a federal

prison in Virginia, from which he was paroled in 1972. That fall he headed off to Reed, where he

immediately ran for student body president, saying that he needed to clear his name from the

“miscarriage of justice” he had suffered. He won.

Friedland had heard Baba Ram Dass, the author of Be Here Now, give a speech in Boston, and

like Jobs and Kottke had gotten deeply into Eastern spirituality. During the summer of 1973, he

traveled to India to meet Ram Dass’s Hindu guru, Neem Karoli Baba, famously known to his

many followers as Maharaj-ji. When he returned that fall, Friedland had taken a spiritual name

and walked around in sandals and flowing Indian robes. He had a room off campus, above a

garage, and Jobs would go there many afternoons to seek him out. He was entranced by the

apparent intensity of Friedland’s conviction that a state of enlightenment truly existed and could

be attained. “He turned me on to a different level of consciousness,” Jobs said.

Friedland found Jobs fascinating as well. “He was always walking around barefoot,” he later

told a reporter. “The thing that struck me was his intensity. Whatever he was interested in he

would generally carry to an irrational extreme.” Jobs had honed his trick of using stares and

silences to master other people. “One of his numbers was to stare at the person he was talking to.

He would stare into their fucking eyeballs, ask some question, and would want a response without

the other person averting their eyes.”

According to Kottke, some of Jobs’s personality traits—including a few that lasted throughout

his career—were borrowed from Friedland. “Friedland taught Steve the reality distortion field,”

said Kottke. “He was charismatic and a bit of a con man and could bend situations to his very

strong will. He was mercurial, sure of himself, a little dictatorial. Steve admired that, and he

became more like that after spending time with Robert.”

Jobs also absorbed how Friedland made himself the center of attention. “Robert was very much

an outgoing, charismatic guy, a real salesman,” Kottke recalled. “When I first met Steve he was

shy and self-effacing, a very private guy. I think Robert taught him a lot about selling, about

coming out of his shell, of opening up and taking charge of a situation.” Friedland projected a high

-wattage aura. “He would walk into a room and you would instantly notice him. Steve was the

absolute opposite when he came to Reed. After he spent time with Robert, some of it started to rub

off.”

On Sunday evenings Jobs and Friedland would go to the Hare Krishna temple on the western

edge of Portland, often with Kottke and Holmes in tow. They would dance and sing songs at the

top of their lungs. “We would work ourselves into an ecstatic frenzy,” Holmes recalled. “Robert

would go insane and dance like crazy. Steve was more subdued, as if he was embarrassed to let

loose.” Then they would be treated to paper plates piled high with vegetarian food.

Friedland had stewardship of a 220-acre apple farm, about forty miles southwest of Portland,

that was owned by an eccentric millionaire uncle from Switzerland named Marcel Müller. After

Friedland

became involved with Eastern spirituality, he turned it into a commune called the All One

Farm, and Jobs would spend weekends there with Kottke, Holmes, and like-minded seekers of

enlightenment. The farm had a main house, a large barn, and a garden shed, where Kottke and

Holmes slept. Jobs took on the task of pruning the Gravenstein apple trees. “Steve ran the apple

orchard,” said Friedland. “We were in the organic cider business. Steve’s job was to lead a crew of

freaks to prune the orchard and whip it back into shape.”

Monks and disciples from the Hare Krishna temple would come and prepare vegetarian feasts

redolent of cumin, coriander, and turmeric. “Steve would be starving when he arrived, and he

would stuff himself,” Holmes recalled. “Then he would go and purge. For years I thought he was

bulimic. It was very upsetting, because we had gone to all that trouble of creating these feasts, and

he couldn’t hold it down.”

Jobs was also beginning to have a little trouble stomaching Friedland’s cult leader style.

“Perhaps he saw a little bit too much of Robert in himself,” said Kottke. Although the commune

was supposed to be a refuge from materialism, Friedland began operating it more as a business;

his followers were told to chop and sell firewood, make apple presses and wood stoves, and

engage in other commercial endeavors for which they were not paid. One night Jobs slept under

the table in the kitchen and was amused to notice that people kept coming in and stealing each

other’s food from the refrigerator. Communal economics were not for him. “It started to get very

materialistic,” Jobs recalled. “Everybody got the idea they were working very hard for Robert’s

farm, and one by one they started to leave. I got pretty sick of it.”

Many years later, after Friedland had become a billionaire copper and gold mining executive—

working out of Vancouver, Singapore, and Mongolia—I met him for drinks in New York. That

evening I emailed Jobs and mentioned my encounter. He telephoned me from California within an

hour and warned me against listening to Friedland. He said that when Friedland was in trouble

because of environmental abuses committed by some of his mines, he had tried to contact Jobs to

intervene with Bill Clinton, but Jobs had not responded. “Robert always portrayed himself as a

spiritual person, but he crossed the line from

being charismatic to being a con man,” Jobs said. “It was a strange thing to have one of the

spiritual people in your young life turn out to be, symbolically and in reality, a gold miner.”

. . . Drop Out

Jobs quickly became bored with college. He liked being at Reed, just not taking the required

classes. In fact he was surprised when he found out that, for all of its hippie aura, there were strict

course requirements. When Wozniak came to visit, Jobs waved his schedule at him and

complained, “They are making me take all these courses.” Woz replied, “Yes, that’s what they do

in college.” Jobs refused to go to the classes he was assigned and instead went to the ones he

wanted, such as a dance class where he could enjoy both the creativity and the chance to meet

girls. “I would never have refused to take the courses you were supposed to, that’s a difference in

our personality,” Wozniak marveled.

Jobs also began to feel guilty, he later said, about spending so much of his parents’ money on

an education that did not seem worthwhile. “All of my working-class parents’ savings were being

spent on my college tuition,” he recounted in a famous commencement address at Stanford. “I had

no idea what I wanted to do with my life and no idea how college was going to help me figure it

out. And here I was spending all of the money my parents had saved their entire life. So I decided

to drop out and trust that it would all work out okay.”

He didn’t actually want to leave Reed; he just wanted to quit paying tuition and taking classes

that didn’t interest him. Remarkably, Reed tolerated that. “He had a very inquiring mind that was

enormously attractive,” said the dean of students, Jack Dudman. “He refused to accept

automatically received truths, and he wanted to examine everything himself.” Dudman allowed

Jobs to audit classes and stay with friends in the dorms even after he stopped paying tuition.

“The minute I dropped out I could stop taking the required classes that didn’t interest me, and

begin dropping in on the ones that looked interesting,” he said. Among them was a calligraphy

class that appealed to him after he saw posters on campus that were beautifully drawn. “I learned

about serif and sans serif typefaces, about varying the amount of space between different letter

combinations, about what makes great typography great. It was beautiful, historical, artistically

subtle in a way that science can’t capture, and I found it fascinating.”

It was yet another example of Jobs consciously positioning himself at the intersection of the

arts and technology. In all of his products, technology would be married to great design, elegance,

human touches, and even romance. He would be in the fore of pushing friendly graphical user

interfaces. The calligraphy course would become iconic in that regard. “If I had never dropped in

on that single course in college, the Mac would have never had multiple typefaces or

proportionally spaced fonts. And since Windows just copied the Mac, it’s likely that no personal

computer would have them.”

In the meantime Jobs eked out a bohemian existence on the fringes of Reed. He went barefoot

most of the time, wearing sandals when it snowed. Elizabeth Holmes made meals for him, trying

to keep up with his obsessive diets. He returned soda bottles for spare change, continued his treks

to the free Sunday dinners at the Hare Krishna temple, and wore a down jacket in the heatless


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