Daniel Kottke was once a good friend of Steve Jobs. In college, the two friends experimented with LSD together, but as one of Apple’s earliest employees, Kottke’s friendship with Jobs crumbled when the tech visionary refused to give his friend any stock in the company.

In the early years when they were students at Reed College, Kottke and Jobs became good friends after discovering they both had read “Be Here Now,” a book about psychedelics and spirituality. They hung out and traveled together while regularly experimenting with LSD. Back then, they were just young college kids having fun and discovering who they were.

Jobs (left) portrayed by Ashton Kutcher and Kottke (left) portrayed by Lukas Haas

“There was a time when Steve and I hitchhiked out to the coast and camped out on the beach and got soaking wet. It wasn’t pleasant, but it was a happy memory. We were hitchhiking in the back of a pickup truck and he was playing his blues harp trying to be like Bob Dylan. He was never a super-talkative guy, but he had an open mind. We were interested in many of the same topics.”

Kottke admits that one of his biggest regrets is never having brought a camera to capture his adventures with Jobs. He recounts some of the good times he had with the late Apple co-founder:

“In 1975, Steve and I went up to the All One farm in Oregon — that’s where the apple orchard was. It was where the name ‘Apple’ came from. That’s when Steve was interested in the fruitarian diet, so Steve and I were fasting on apples, which was not that satisfying. [laughs]

“We had a good time [in India]. We were kind of like monks — taking third-class buses, shaving our heads. We were wearing Indian clothes, not American clothes, and we looked like a couple of Krishna devotees with backpacks just traveling around riding buses.”

While Jobs is widely regarded as a visionary, he could also be notoriously ruthless and calculating. According to Kottke, however, he had a good heart, at times.

“A bad thing that happened in India was when all my travel checks were stolen at a hotel. I had the numbers but I didn’t have the receipts. I completely freaked out because I had no money at all.

“Steve gave me all his money when he left — he left before I did. He gave me maybe only a hundred dollars. It was a generous thing to do. I was able to call the United States and call my father, who went to First National in New York and got me my refund for the travel checks.”

Jobs and Kottke remained good friends and lived together in Cupertino, where Kottke witnessed Jobs’ launch of Apple Computers. From there, the rift between the two men began to grow.

“When Apple was first starting, I was very hungry to learn more about computers so that I could contribute. Steve just didn’t tell me the most rudimentary stuff. I was asking questions and he was not interested in answering. It was frustrating to me. I find it hard to believe that he couldn’t just explain the basic thing about how a processor works. He was a guy who was always playing his cards close to his chest. Like knowledge was power — he didn’t need to tell you anymore than you needed to know.”

But the final nail in the coffin didn’t happen until 1979 when Kottke discovered he would receive no stock in the company, despite working at Apple early on as employee number 12. Kottke tried to talk to Jobs to no avail.

“In the summer of 1980, Apple was headed towards an IPO. I didn’t have any stock and I wanted to know what I should do to be on track to get some stock someday or whether he would just give me some. That was the time that Steve would just not talk to me — he just wouldn’t — and it was a very difficult time for me. I was actually applying at other companies. Since I didn’t have an electrical engineering degree, the only experience I had was out of Apple. Apple would not give me a road map for how to become an engineer without having a degree.”

By that time, Kottke had taught himself everything he knew about Apple Computers and was a technician at the company. According to Kottke, Rod Holt, founding VP/Engineering and employee number 5 at Apple, tried convincing Jobs to give him stock.

“Rod Holt went to Steve and said: ‘Your buddy Dan doesn’t have any stock. Why don’t we just give some stock to him and whatever you give him, I’ll match it.’

“Steve allegedly said: ‘Fine, I’ll give him zero.’

“However, no one ever told me that for 10 years. I never heard the story. Rod never told me. It was kind of bad on Rod’s part; he should have told me. Then it was a year after that that Rod gave me a hundred shares. Just as a token gesture, but I appreciated it. He should have just told me that Steve declined. That would have been useful to know.”

A year later, after the company’s IPO, Steve Wozniak was giving away $10 million of his shares to be split between a hundred engineers. Unfortunately, Kottke was a technician, not an engineer, which made him ineligible to receive those stock options.

“That’s when I felt really bad. There was just no remedy for it. So at the time it went public, there were a hundred millionaires and I was not on that boat. That was a very hard time for me.”

At the end of 1984, after working at Apple for eight years, Kottke left for a consulting company. A year later in 1985, Steve Wozniak gifted Kottke some shares.

“I was just very grateful for it. I don’t remember the exact number. It wasn’t a round dollar number or number of shares. It might have been worth $50,000 or something like that. However, I held onto it long after my accountants and advisors said, ‘Don’t.’ I knew many many people who blew through their stock options and then ran out of money when they were in ill health. I was very frugal and held onto it and it became worth a few million. Now I’ve lost it all.”

Kottke invested in a giant real estate project that went south. He had sold a property to new buyers who owed him $2 million, but the whole place burned down in a wildfire before money changed hands. Kottke had developed a passion for entrepreneurship over the years, but his streak of bad luck just wouldn’t seem to end.

“I was laid off my last big corporate job in 2001. I was a network engineer, vertical networks. I thought I had a whole new career as a network engineer but after 9/11 the whole telecom business tanked, long-term investment infrastructure all tanked.

“I was starting a company in 2002 to 2003. It was Cube Root; we made a digital clock that ended in disappointment. In 2005 I started another company called Lincoln Labs. We were going to make a scrolling message display. That was a disappointment not because it didn’t work — we couldn’t connect with the right market place. Nowadays you could do a Kickstarter and find out whether you have a market or not.

“In 2007 I was starting another company called Fast Movie. We were going to do online video hosting. So, I guess it wasn’t until 2007 — I was the CTO and the co-founder — and that’s when we were pitching VCs. That’s when I really started to feel like an entrepreneur. The other companies were much smaller scale, but Fast Movie didn’t get funded. That’s kind of what gave me the bug to be an entrepreneur.”

Currently, most of Kottke’s net worth is what’s left of his Apple stock portfolio and a house he owns in Palo Alto.

“I bought a rundown, three-bedroom house and converted it into a seven-bedroom house. I rent four rooms which used to pay my mortgage, but now that I’ve lost all my money, I’m actually in a big hole. I really have to get successful at something.

“I’ll be eternally grateful to Woz for just giving me some stock. That’s the thing that’s so great about Woz, the reason we wish somebody would make a movie about him someday. There was actually about half a dozen of us, more like eight people who did not get original stock options at Apple, people who were there right at the beginning. I was not the only one. I was the only one who actually worked in the garage, of course.”

Kottke recounts the last two times he interacted with Jobs. The first was a 15-minute phone call in 2009.

“He called me at 7 a.m. I was sound asleep. He apologized, but that was the only time he could talk. He just was calling on general principles, which I appreciated. We didn’t really talk about anything in particular. I think the reason he called is because Albert Hofmann, the inventor of LSD, had written to Steve asking for financial support for LSD research. Steve had talked about how helpful LSD was for him. So Albert Hoffmann, aged 101, writes to Steve asking him for money, and I offered to hand-deliver it. I didn’t end up hand-delivering it but I referred Rick Doblin [head of MAPS] to get Steve’s contact, and then he and Steve had some conversations, then Rick delivered the letter and Steve didn’t donate any money. But he was probably happy to get a handwritten letter from Albert Hoffmann. He was probably grateful for that.”



“I ran into him on April 3, 2010. It was the first day of the iPad and I didn’t want to wait in line, but it was my birthday. I wanted an iPad so I could put my sheet music on it and my song lyrics. So I just went to the Apple Store in Palo Alto and I’m standing there at the checkout and Steve just walks by, so I said ‘Hi.’ He stopped and we chatted for a few minutes. I didn’t realize there was a TV camera right behind me looking over my shoulder, so it was on the evening news, but that was very brief.”

To this day, Kottke doesn’t know the exact reason that Jobs started treating him so badly, but he has his theories.

“My latest theory now is, I had a memory that there was a girl that he met at a conference and she came to Cupertino and stayed with him for a while. I’m not clear on exactly when but the three of us hung out together and drove around. And at some point Steve had said he wasn’t going to continue dating her — she lived in Chicago. It’s not like she was going to move to California.

“Then, I had called her up one time and I went to visit her in Chicago. Nothing really happened. I never thought about it again. Now it occurs to me: I bet she contacted Steve and told him that I came to visit her and Steve got jealous. That’s entirely plausible because someone said, ‘Are you sure it isn’t something to do with a woman?’”

No matter what happened, Kottke still has positive thoughts on the late tech titan who was once his best friend.

“Although Steve caused very tangible suffering in my life, I’m really grateful for the product he’s created. Apple most certainly would have gone out of business if he hadn’t resurrected it. I never thought my story would see the light of day. And yet, I feel like as of now, between the Kutcher movie and ‘The Man In the Machine’ and this one now, it’s like, enough bashing this guy. We get it; he was an asshole. I think this message has been hammered home now. I think we can lighten up on Steve. It’s just unfortunate that Steve was not perfect; he had his flaws like many people have flaws.”

Last year, Kottke met Steve Jobs’ son Reed for the first time at an event. He recounts his experience as being “surreal.”

“Steve so often in his life, he was not a smiling guy. He would laugh but he was more often scowling. Reed is just a happy kid. He just had a smile on his face and he looks so much like his dad. It made me happy just to see this little version of Steve that was smiling. He’s a splitting image of his dad.”

Kottke, now 61, despite his streak of bad luck, continues to pursue success and is about to launch a smart home startup.