30 Candid Stories and 20 Videos Covering Steve Jobs

 young Steve Jobs

Late last week, Steve Jobs announced that he was resigning from his position as CEO of Apple, no doubt a difficult choice for the man who created the company and helped pull it out of a major rut in the mid to late 90s. He’s still chairman of the board, so he has a lot of pull at Apple, and he is confident in Tim Cook’s abilities as a CEO, so we’re sure that all of that helped make the decision easier for him.

As he passes the torch, it’s time to take a look at the some of the coolest bits of his history as the CEO of Apple.

When many think about Steve Jobs, they think about the no-nonsense CEO who will squash you out the second you fall out of favor with him. Sure, he’s a notoriously tough businessman, but he’s also known as one of the most down-to-earth CEOs you will encounter. Here are a few stories taken from various sources around the internet of encounters with Steve Jobs.

Steve Jobs - Allen Paltrow

Image Credit: Allen Paltrow

1) Allen Paltrow, the 12-year-old who shaved an Apple logo into his head and sent it to Steve Jobs. Jobs invited him to the grand opening of the massive Apple Store in New York. Link

2) Steve Jobs is apparently very cool with his Silicon Valley neighbors racing RC cars in the parking lot near his private office:

My company ASTRO Studios started in the mid-’90s in downtown Palo Alto, where we shared a small private parking lot with Steve and his private office. In fact, our windows faced each other on this narrow tree-lined street. More than once Steve would be trying to park his stainless-steel Mercedes as our crew was finishing an RC car race on the back lot. He’d patiently wait for us to finish, then give us a look of “You boys have your fun; I’m changing the world,” or maybe it was a look of envy at our ability to just hang out and play. Tough to know for sure. (Link)


Here are a good bunch of stories coming from Gawker:

3) I used to work for apple for about 5 years. Quite often I would have to go to Cupertino for work stuff.

One time I was pulling out of the IL 1 parking lot ( 1 infinite loop) and this silver mercedes near swiped me as he pulled in. I slammed on my breaks and was like who the f*#k was that? The car next to me stops, rolls down his window, and says “Oops my bad, you okay?” (it was Steve Jobs) I sat there with my mouth open as he rolled his window back up and pulled in the handicap spot. The guy next to me goes “damn i wish he would’ve clocked us, imagine the settlement!”

4) Apparently, Steve Jobs is known for his in-car antics, which is…um, a bit wacky, to say the least:

I was working as a bagger at the Palo Alto Whole Foods in the summer of ’97 [he probably means ’98, when the iMac debuted in August]. I was shagging carts one afternoon when I saw this silver Mercedes parked in a handicapped spot. Steve Jobs was inside screaming at his car phone. This was right before the first iMac was unveiled and I’m pretty sure I could make out, “Not. Fucking.Blue. Enough!!!”


5) More Steve Jobs Driving:

A couple years ago, I had a networking-type breakfast with a friend of a friend who worked for Apple, in the main cafeteria on the company’s campus in Cupertino. After I’d finished my tasty chorizo omelet (Apple has an amazing omelet bar), my guy on the inside walked me back to my car.

We started saying our goodbyes, and I wasn’t really paying attention to where I was standing. Suddenly a silver Mercedes roadster-type car with no license plates came screaming around a bend and swerved ever so slightly to avoid me.

And my Apple guy said: “Do you know who that was who almost ran you over?”

It was an honor to have impeded your trip to your parking spot, Mr. Jobs.


6) This Security Guy Must Have Felt Like a Dope Afterward:

Not 100% sure if this is what you were looking for, but in 1998, the first year Macworld moved from the two convention centers in Boston to the Javits Center in New York City, I was walking around the lobby area trying to make my way back onto the convention floor. I was 13 at the time, playing with my 4 year old Newton 120 which my dad had given to me.

Now back in 1998 Steve Jobs wasn’t supposed to show up for the Keynote, he was going to do it via satellite, but much to my amazement however I see 10 feet in front of me, Steve Jobs.

I’m standing there watching the CEO of Apple and his 4-5 deep entourage yelling at the security guard. As I moved closer I heard one of the entourage say “This is Steve Jobs, he is the CEO of Apple Computer” to which the guard replied “He is not the CEO of the Javits Center, he needed a badge to enter.” So it seems in his last minute choice to go to Macworld, no one got Mr. Jobs an badge. Whoops.


7) On Parenting:

Many years ago, my family were hanging out at a park near downtown Palo Alto. My kids were running around like they were insane and soon we were joined by several others. As I am want to do, I turned into a monster and chased the kids bellowing at the top of my lungs and generally acting like the worlds largest 7 year old. One little girl went up to her dad and said ‘This is the best park ever! He’s so funny!’

Her dad was Steve Jobs.

He was warm, friendly and thanked me for running his kids ragged at the park. His wife was nice too.

My brush with awesomeness.


8) Steve Jobs’ amazing memory:

He met a friend of mine at some huge geek event, and two years later bumped into him at a different event, walked right up, stretched out his hand for a shake and said, “It’s Dave, right? From SFU?

9) On Cancer:

I don’t personally have a Steve Jobs sighting, but my friend did, probably about four years ago. She lives in downtown Palo Alto a few blocks away from University Avenue, same neighborhood as him. She was recovering from chemo (she has cancer) and was taking a walk with her husband near the house when they ran into a man who noticed her headscarf and asked her how her treatment was going. They discussed their respective cancer treatments for a while; after he’d moved on, her husband told her who she’d been talking to.


10) Larry Ellison and Steve Jobs talkin’ cars:

I am going to guess sometime in the summer of 1998, one afternoon my wife and I were driving down the street where Steve Jobs lives. As we drove towards Steve’s house, we noticed a silver car parked out front that looked like a Lamborghini or some other exotic car. Both of the passenger doors we raised up like scissors. One person was standing on the sidewalk by the passenger door; there was another standing in the street by the driver’s side door. Both were clearly admiring the car. As we got closer I recognized who the the driver was in the street — none other than Larry Ellison. I said to my wife, “Look, its Larry Ellison!” Then, as we passed by I recognized Steve standing there on the sidewalk and said, “Look, there is Steve Jobs, too!” It looked like Larry had dropped by Steve’s house to show off his new car. Only in Silicon Valley… (link)

11) Apple is a Team:

In 1999, I think right after the iMac came out in a range of colors, I happened to sit in on an internal meeting at Apple, one in a large theater filled with employees. Steve Jobs came out and the whole theater burst into applause, and the clapping went on for minutes, with people standing and cheering.  The success of the iMac was just becoming evident – the first act of Steve’s big return, leading from there to what Apple is now.

Steve let the applause go on for a little bit, then, with much effort, settled down the crowd. When things got quiet, the first thing he said was: “That’s an awful lot of applause considering that you guys are the ones who do all the work.”

Everyone leapt to their feet and applauded again for several minutes more, this time with Steve egging them on, applauding each other as a team. (link)


12) Steve the Gentleman:

One day, I was working late and left my office to get dinner at the cafeteria. When I stepped outside, I realized it had been the first time I had seen the sun all day, as it had been foggy that morning, and I had skipped lunch. I looked up at the sun and smiled, enjoying the feeling of it warming my face and arms, and I continued walking across the quad like this, face up at the sky, eyes closed, smiling.

I like to think that I’m not a chronically weird person, but I do have my moments.

Anyway, I knew the distance pretty well, so when I sensed that I was reaching the other side of the quad, I opened my eyes and looked down and Steve was holding the door for me, grinning to himself. I have no idea how long he had been holding it, though it was probably only a couple seconds, long enough to cause him to smile at my basking in the open air.

Those couple seconds probably cost Apple $1.4bn. (link)


13) Welcome to my Apple Store

Steve Jobs actually used to hide out in front of Apple Stores and watch. Employees thought he was gauging their performance. Actually, it turns out he wanted to see how consumers reacted to Apple products:

“We would find him hiding behind the bushes or around the corner outside, peering inside to see what was going on. We would go, ‘There’s Steve! Everybody play cool.’ We thought he was evaluating us. It was nerve-wracking.” (Link)


14) Steve Jobs in a Foul Mood:

One reporter met a young, rich Steve who had just launched the successful Apple Computer (long before it became known as Apple, Inc.) He was warned by the receptionist that Steve was in a foul mood. How foul was his mood? He apparently had a light-hearted exchange with the reporters (who planned to launch MacWorld magazine):

Steve turned to Andrew and asked, “What makes you think a dull PC guy like yourself can appreciate an elegant machine for artists like the Macintosh?”

“Well, Steve,” Andrew chuckled, “I didn’t used to be so dull. Before PC World, I edited the Whole Earth Catalog, and I’m still a Dead-Head.”

“Look,” I volunteered, “Andrew actually went to the Dead concert in Egypt and we were both at the US Festival–this IBM thing is just something we fell into and gosh, you can’t blame us, it’s been quite an amazing trip.”

“Oh, yeah, and I suppose you both dropped acid on your way to Cupertino this morning?”

We all laughed at Steve’s joke and Murray, a diminutive, purebred Irish guy complete with freckled face and sparkling eyes, spoke up for the first time, “Cut it out, Steve. These guys are cool. David and Andrew aren’t like the corporate suits we met from that other company.”

Steve shrugged, stood up and said, “OK, guys, follow me.” (Link)


15) Steve Jobs keeps his contacts close:

It was a hot August evening in 1998, and I was living in a little rented house in Toluca Lake, California. The phone rang, and I picked it up. “Hi Sky, it’s Steve Jobs.” After quickly getting over how he’d gotten my number, I asked him what was up. It turned out that one of EarthLink’s PR team had gotten a little overly excited and briefed a reporter on our new partnership in advance of the press release. Steve had gotten wind and politely asked me to reign them in. I told him I really appreciated the heads up, and I’d do that right away. Steve gave me his home number and told me to call him if I ever needed anything. This was a guy who had at least 10,000 employees at the time. (Link)


16) Steve Jobs is Not God:

One Sunday morning, January 6th, 2008 I was attending religious services when my cell phone vibrated. As discreetly as possible, I checked the phone and noticed that my phone said “Caller ID unknown”. I choose to ignore.

After services, as I was walking to my car with my family, I checked my cell phone messages. The message left was from Steve Jobs. “Vic, can you call me at home? I have something urgent to discuss” it said.

Before I even reached my car, I called Steve Jobs back. I was responsible for all mobile applications at Google, and in that role, had regular dealings with Steve. It was one of the perks of the job.

“Hey Steve – this is Vic”, I said. “I’m sorry I didn’t answer your call earlier. I was in religious services, and the caller ID said unknown, so I didn’t pick up”.

Steve laughed. He said, “Vic, unless the Caller ID said ‘GOD’, you should never pick up during services”. (Link)


17) While discussing the look of the original Macintosh, Steve Jobs had this exchange with a designer:

I went into my office and started to program, working on improving the code that drove the serial link between the Mac and Lisa, at Bud’s request. But I couldn’t help but overhear the passionate discussion taking place next door between Steve and James Ferris. For some reason, they were talking about cars.

“We need it to have a classic look, that won’t go out of style, like the Volkswagen Beetle”, I heard Steve tell James.

“No, that’s not right.”, James replied. “The lines should be voluptuous, like a Ferrari.”

“Not a Ferrari, that’s not right either”, Steve responded, apparently excited by the car comparison. “It should be more like a Porsche!” Not so coincidentally, in those days Steve was driving a Porsche 928.

I thought it was kind of pompous to compare computers with sports cars, even metaphorically. But I was impressed with Steve’s passion for elegance in the industrial design and his powers of discrimination continually amazed me as the design took shape. (link)

18) Dinner’s on me:

A long, long time ago when Apple was still a tiny company and folks were assembling PC boards by hand just to see if the thing worked, the team was wondering if they should continue through the late hours or call it a weekend. In came Steve:

“Hey, I heard that the PC boards finally arrived. Are they going to work? When will you have one working?”

Burrell explained that the boards had just arrived, and that it would take at least a couple of hours to assemble one, so they were thinking about whether to start tomorrow morning or wait until Monday.

“Monday? Are you kidding?”, replied Steve, “It’s your PC board, Burrell, don’t you want to see if it works tonight? I’ll tell you what, if you can get it to work this evening, I’ll take you and anyone else who sticks around out for Pineapple Pizza.”

Steve knew that Pineapple Pizzas had recently replaced Bulgarian Beef as Burrell’s current food obsession (which, as a staunch vegetarian, he thought was a positive development) and that Burrell wanted a Pineapple Pizza pretty much every chance he could get. Burrell looked at Brian Howard and shrugged. “OK, we may as well give it a shot now. But I don’t think we’ll be able to get it working before the restaurants close.”  (link)


19) Steve Saves Bruce:

Apple had a bright young GUI designer by the name of Bruce Horn. He’d been programming graphic user interfaces since the age of 14, and joined Apple at 21. All was great with Bruce, except for one problem. The kid did not play well with authority. After an argument with Bob Belleville when designing the Mac’s GUI, Belleville decided he would fire Bruce. Andy Hertzfeld argued with Belleville saying that Bruce had to stay as dropping him would set the company back months:

“You can’t fire Bruce!”, stating something that I thought was obvious. “He’s doing really important work for us, and losing him would set us back months.”

“Keeping him will set us back even more, because he’s a trouble maker, and he’ll cause more trouble in the future.”

But I was adamant, defending Bruce until Bob got frustrated with me. “Well, Andy, I am very disappointed in you. I thought you had more sense than that.” I walked out of his office not knowing what was going to happen.

Later that day, when Steve Jobs came by for his usual early evening visit, I told him what transpired and repeated how bad it would be if we lost Bruce. I don’t know what Steve eventually said to Bob, but he apparently dropped his plan to fire Bruce since he never mentioned it again. But I never thought of Bob the same way after that, and I think that was when he started to have problems with me as well. (link)


20) I’m in Charge

Steve and some others walked into one of the buildings around Apple HQ. One particular building, the Bandley 4 building had an alarm installed on the back door. Sometimes, someone would leave through the back door and set off the horribly annoying alarm. Here’s what happened:

It went on for at least three minutes before Steve yelled out, “Can’t someone figure out how to stop that thing?”

I saw a chance to vanquish my nemesis. “Are we allowed to damage it to get it to stop?”, I asked him.

“Yes, do anything you want, I don’t care if you break it,” he replied, holding his hands over his ears. “Just get the damn thing to stop!”

Bruce Horn and I ran over to the nearby hardware lab and picked up every tool we could find. I got a hammer and screwdriver, and proceeded to pound the screwdriver into the center of the alarm, driving a stake through the demon’s heart. The screwdriver went all the way through to the other side, but the alarm kept sounding.

Finally, Bruce took over and gave the screwdriver a mighty twist, and the whole thing flew apart into a half dozen pieces and fell to the ground. The horrible noise finally stopped.

At that very moment, a grizzled security guard entered the back door, just in time to see us cheering as the wrecked alarm finally gave up the ghost. He looked at us, our tools of destruction still in our guilty hands, and said, “You guys are in big trouble!!! Who is in charge here? You better show me your badge.”

Steve stepped forward and handed the guard his badge. “I’ll take responsibility for this”, he told him.

The guard scrutinized Steve’s badge. He looked at Steve, then back at the badge a few times. Finally, he shrugged his shoulders, picked up the pieces of the broken alarm, and walked away, without saying another word.  (link)

21) “Don’t worry, the Mac team is doing to nab you!”

One programmer had impressed Steve Jobs with a chess game called Alice. Jobs made sure that person was on the Mac team:

Steve Jobs didn’t play Alice very much, but he was duly impressed by the obvious programming skill it took to create it. “Who is this Capps guy? Why is he working on the Lisa?”, he said as soon as he saw the program, mentioning Lisa with a hint of disdain. “We’ve got to get him onto the Mac team!”

But the Lisa was still months away from shipping, and Capps was needed to finish the printing software, so Steve wasn’t able to effect the transfer. One weekend Capps ran into Steve Jobs in Los Gatos and was told, “Don’t worry, the Mac team is going to nab you!” Finally, a compromise was reached, that allowed Capps to transfer over in January 1983 after the first release of the Lisa was completed. (Link)


22) Steve Understands Going Against the Rules:

Apple as working on a disc drive for their computer, it was called the Twiggy. It wasn’t going well, and Apple caught wind of Sony’s 3.5-inch drives. Steve was impressed and told his team that he wanted to create his own drive rather than strike a deal with Sony. However, the computer was set to ship in 7 months. Not nearly enough time to develop and ship a drive. Bob Belleville and George Crow decided to work with Sony on the disc drive for the Mac in secret while going along with Jobs’ plans. Here’s what happened. One day, Sony sent over a young engineer named Hide Kamoto. He had to work with Apple engineers without being spotted:

George knew that Steve would wonder who Kamoto-san was if he saw him. Thinking quickly, he immediately tapped Kamoto-san on his shoulder, and spoke hurriedly, pointing at the nearby janitorial closet. “Dozo, quick, hide in this closet. Please! Now!”

Kamoto-san looked confused but he got up from his seat and hurried into the dark janitorial closet. He had to stay there for five minutes or so until Steve departed and the coast was clear.

George and Larry apologized to Kamoto-san for their unusual request. “No problem. “, he replied, “But American business practices, they are very strange. Very strange.”

As predicted, a few weeks later the Alps team came back with an eighteen month estimate for getting their drive into production, and we had to abandon the project. When Bob Belleville revealed that he and George had kept the Sony alternative alive, Steve swallowed his pride and thanked them for disobeying him and doing the right thing. The Sony drives eventually worked out great, and it’s hard to imagine what the Mac would have been like without them today.



23) You’re full of sh*t

Steve spoke with Stanford professor of computer science Don Knuth. Jobs arranged for a lunchtime lecture for the Mac team. Knuth is said to have written at least a dozen books at this time. Huge, huge books. Here’s what happened when he and Steve met:

I was sitting in Steve’s office when Lynn Takahashi, Steve’s assistant, announced Knuth’s arrival. Steve bounced out of his chair, bounded over to the door and extended a welcoming hand.

“It’s a pleasure to meet you, Professor Knuth,” Steve said. “I’ve read all of your books.”

“You’re full of shit,” Knuth responded. (link)



24) You’re sharp. I like that.

Steve Jobs is known for his sharpness and ability to think on his feet. When meeting someone else who shares that, Jobs seems to appreciate it. Here’s a funny little story about that. Perhaps Jobs appreciated his”I ain’t taking crap from anyone” attitude and witty comeback:

[I’m a] former employee. He likes to make surprise visits to the New York stores and has been know to frown upon employees who boast and get all fan boy at him.

Also a BIG no no is smoking outside in uniform. Its is company policy but often overlooked. He has been known to crack the whip on people because of it. After the Upper West Side location opened he made one of his famous visits and catches an older employee smoking outside with his uniform on (under a jacket mind you) and asks him “You work here?” to which the employee responds “More than you do…” Jobs chuckled, and shook his hand and walked away leaving his job intact… (link)


There are also a few letters from Steve. Which we ran a feature on several months back.

25) I don’t like the new iTunes Logo


Enjoyed the presentation today. But, this new iTunes logo really sucks. You’re taking 10+ years of instant product recognition and replacing it with an unknown. Let’s both cross our fingers on this.


We disagree.

Sent from my iPhone


26) Wireless sync coming soon

Do you think you will ever allow syncing iPhone to Mac over wifi?


Yep, someday. 

27)  Newsweek is Completely Wrong

Mr Jobs,

Newsweek just ran an “obituary” for the Mac, saying the Mac has been “relegated to the steaming dung heap of the past.”

I hope he’s wrong, I believe and hope that the Mac will remain a vibrant, vital part of Apple’s future and one of its (admittedly many) product lines.

So, as you view it, does the Mac have a long and important history ahead of it?


What did Steve have to say?

Completely wrong. Just wait.


28) Don’t Believe Everything You Read

Good Morning, Mr. Jobs:

As a release-day purchaser of an iPad, I was elated when you revealed iOS 4.2 would support AirPrint. Now comes reports AirPrint support has been pulled from 4.2. Between announcements/assurances of the white iPhone, and now the pulling of AirPrint, is Apple going to lose credibility and become known for announcing ‚ ‘vaporware’?


AirPrint has not been pulled. Don’t believe everything you read.


29) Jobs Respects Adobe

Do you hate Adobe and their products (Photoshop, Illustrator, etc) or do you just hate their view on Flash?


I respect and admire Adobe. We just chose to not have Flash on our devices.

Sent from my iPhone

30) And Finally, Steve Jobs on why he came back to Apple:

“When I was trying to decide whether to come back to Apple or not I struggled. I talked to a lot of people and got a lot of opinions. And then there I was, late one night, struggling with this and I called up a friend of mine at 2am. I said, ‘should I come back, should I not?’ and the friend replied, ‘Steve, look. I don’t give a f–k about Apple. Just make up your mind’ and hung up. And it was in that moment that I realized I truly cared about Apple.” (Link)


1) Steve Jobs saying computers are like “a Bicycle for our minds.”

2) Steve Announces the Apple Store

3) Apple Doesn’t Ship Junk

4) The Return of Jobs

5) Meet the iBook

6) We are calling it iPhone

7) The iPad is announced

8) Steve Jobs and Bill Gates Interview

9) Say Hello to the Original Macintosh

10) How Apple’s Computer Joined the Consumer Market

11) Stanford Commencement Address

12) Cupertino City Council Meeting: Steve Jobs Pitches New HQ

13) Steve Jobs is a man not shaken when challenged

14) Steve Jobs on the importance of knowing when to say “No”

15) Welcome the original iPod

16) Young Steve Jobs Preparing for a very early TV appearance

17) Steve Jobs Knows How to Present, Even After a Leak he cracks a joke.

18) iPhone 4 Demo Goes Not Totally as Planned.
What’s interesting about this particular video is that Jobs was able to turn it around and explain that there were over 500 wifi networks operating at once, causing issues. What was interesting was Jobs’ ability to spin what could have been totally negative into a statement on how many (likely media needing a wifi connection) were at the event covering the new iPhone.

19) Steve Jobs isn’t afraid to admit a mistake

20) Steve Jobs on Microsoft (sorry, audio/video is off-sync. Still interesting viewing)



Helping Lead Technology Through the Ages

Steve Jobs will remain on the board, for as long as he possibly can. He truly loves Apple and everything they stand for. Stepping down from his position as CEO had to be a tough choice, but he knows that Apple is in good hands. I truly seems that Steve puts Apple before he puts himself, as his letter said, “I have always said if there ever came a day when I could no longer meet my duties and expectations as Apple’s CEO, I would be the first to let you know. Unfortunately, that day has come.”

Still, Apple is continuing on and we look forward to seeing what they bring in the future.

About 8bitjay

Google + Profile