Interviews → Tom Williams Hired by Apple at 14. I interviewed him for his full story. Date: 2009-07

I was recently in Vancouver Canada for a week, considering moving there, when my friend Ariel Hyatt said, “You have to meet this amazing guy Tom Williams. He got hired by Apple when he was only 14. I think the company had to, like, legally adopt him to do it. He’s a go-getter like you. Plus his wife, Jessie is an awesome country artist.”

I met Tom for dinner, loved his story, and wanted to share it with everyone.

Especially in this environment of 10%-25% unemployment, his story and philosophy have some inspiring lessons about how to get a job or make huge deals despite a lack of experience.

So I recorded a phone call and let him tell his tale in his own words:

My mom calls this story my elaborate form of running away from home, except it doesn’t have a stick and a kerchief with it.

I grew up in a very normal, middle class family in Victoria. Very, very happy. But I wasn’t a very good student in school. In fact I was a very rebellious learner. I didn’t even take pen and paper to class. I would interrupt my teachers. I would question what they were teaching us. Every parent-teacher interview was focused on having Tom be less disruptive, and a little bit more conformist.

And at the same time, my parents, in the summer break between 6th and 7th grade, announced that they were getting separated. That really just devastated me. Even though my parents were dealing with that relatively amicably, I was very distraught and quite upset.

I then realized I was quite powerless, and the solution was to find my own income.

I started out selling chocolate bars and quickly noticed I was the top seller in school. However, I only got a Nintendo even though I sold about $2,000 worth of chocolate-covered almonds.

I realized I was getting kind of gypped, so I negotiated to be the direct retailer of this wholesale chocolate bar operation, basically usurping the school. I had my dollar of chocolate and they had theirs. My dad had to vouch that I wouldn’t just eat the inventory.

That summer I sold several thousand dollars worth of chocolate bars. This was not some passive kid sitting outside the store, eyes down, hoping somebody would take pity. I was literally walking backwards, chocolate bar in hand. As somebody would walk by me, I’d peddle my very refined spiel about how these chocolate bars were the world’s best thing. They were actually called World’s Best Chocolate, from which I derived my sales pitch.

As a child I was horrible with math, even with the rudimentary. In fact, I had to go to summer school once. However, I understood when I was being taken advantage of and when I was in control.

With my first lemonade stand I realized I’d have to actually spend money on Kool-Aid. This meant I’d have to spend the entire day selling at five or ten cents, (which was the competitive going rate back then), or I’d have to either steal the Kool-Aid pack, or figure out some way around this huge cost liability.

I managed to put up my sign in the local store, without help from my parents. They were academics and bureaucrats, not in any way entrepreneurial. For me, this thinking about what was a bad deal or a good deal was instinctive. I was hard-wired from day one, always trying to make good deals.

I always relied on my own instincts. I knew that if I wanted to get something done, I had to do it. Nobody else was going to do it for me. Nobody else was going to support me. I didn’t expect to be supported. I just knew I had to do it if I wanted to do it. That’s how I lived every aspect of my life.

Even when I was interested in bird-watching, I had a newsletter and charged a subscription to family and friends. I was always constantly thinking about how to make money and generate revenue.

Using the proceeds of the chocolate bar sales, I rented an office in the same building as the local sales office for Apple in Victoria. I would go to my office after school, not really having much to do but trying to build edutainment software on CD-ROM. I even had an outsourced receptionist service.

This was the stepping stone. It was clear to me that I wanted to try and short circuit life’s path. I didn’t want to stay in school until the 12th grade or at home. I wanted to live on my own and be free.

I read John Sculley’s biography, who was Apple’s CEO at the time, and my hero. As other kids had sports stars or actors, he was my hero. I wanted to be him or be like him.

So I started calling Apple in the 7th grade. Every single morning, at about 8:00 am before I went to school, I would call up the main Apple switchboard number, and ask for John Sculley’s office, and they would put me to his assistant.

Every single morning I’d be talking to Jerry, his assistant, and would start for the first few weeks with just my standard pitch. I was taking the business development angle. I’m the CEO of my own company, which was called Desert Island Software, and he’s the CEO of his company. Let’s have two CEOs talk to each other about how we can work together.

For the first few weeks I’m sure Jerry thought that it was some kind of a prank or weirdo. Eventually I started to be less reliant on the pitch and say, “Hi, Jerry, how are you?” This is the gatekeeper to somebody that is receiving a lot of unsolicited phone calls. I think instinctively I realized that by building a relationship with Jerry, I was building a relationship with the gatekeeper. If they like you and support you, that’s really helpful.

Here I was, literally for about a year and a half, calling every single morning. The relationship obviously evolved to “Hey Jerry, what’s going on with you?” and “Oh, you know, school’s tough this week Tom‚” blah blah blah.

In a parallel track, because I had rented this office, I was developing a relationship with the two local sales guys who at this point had taken an interest in me and who I would stop in on every single day. They wrote e-mails, which somehow came in to Cupertino. I think it was just a benevolent gesture. Here was this kind of young, highly enthusiastic, but different than just a Mac fanatic guy that was trying to build a software company.

They were able to get me forwarded all the way up, back into John’s office, Jerry and some other support staff. There was now this loop of several people interested in helping me out and seeing my dream.

My dream was to meet John for five minutes, and then I just meet him, and pitch him in person. I knew that If I was granted five minutes, I was going to be able to extend that into half hour, and that half hour would dictate or drive what would happen next.

Through many, many people’s generosity at Apple, they had arranged to give me a free pass to the Worldwide Developers Conference, which I think the ticket price was about $1,500 for the whole week.

Because of the divorce, my mom and I were quite poor. We had to actually borrow money from my grandmother, (it always makes me verklempt to remember her generosity), to fly my mom and I down, May 1993.

In fact the conference registration began on Sunday, which was May 15th. I remember the date because it was Mother’s Day, and my mom was thinking we’d have a nice day to kind of celebrate it. We went to one of the hotels near the convention center in San Jose, and I scarfed down my breakfast because I wanted to get my registration at Apple done right away.

There I was, registered, and greeted well. People were like, “Oh, well, we’re expecting only one tiny kid from Canada at the conference.” They were expecting me, and John’s PR person said, “Okay, first thing in the morning, be here 7:30, bright and early, and before he begins his keynote, you’ll have your five minutes.”

For me, this was the night before being able to walk on to the stadium and toss out the first pitch. It was the pinnacle dream moment. I couldn’t sleep, my mind was racing with how I would spend these first five minutes to make an impression on him. I knew from his books that he was a concept guy, and loved being able to come up with new ideas on the spot, new ways of positioning things.

I knew the rumors of what technologies were being introduced at the conference and what he was speaking at in the keynote. I was really studying those technologies to come up with my own spin.

At the time it was actually the Newton that was being announced at the conference. It commercially failed later, but was successful from an innovation perspective.

I had my own business cards that said, Tom Williams, CEO, Desert Island Software. I met him and pitched him. I said, “Here’s what I kind of think of the Newton....” I barfed out five minutes of stuff that I thought might be impressive to him. That five minutes extended into a full half hour - up until minutes before he was being pulled away to give the keynote.

At the end we exchanged business cards. He had two business cards, one that said “Chief Listener” and one that said “CEO”. He gave me his CEO card because he was out of the other. We promised to keep in touch.

At the conference, I was given VIP access. I sat with all the vice presidents. I was one of the first guys outside of Apple to actually be able to play with the Newton. I was anointed as an interesting guy, and I met every vice president at the company that was there that week.

Three months after the conference, John left Apple. He was booted out in a boardroom coup, and then he went into a company called Spectrum. He stayed there very shortly. It was a bit of a bad story.

As a consequence of leaving Apple, John actually had time to call me. I remember the first phone call. I’d left my office, because my cash was running out from my chocolate bar sales. At this time, I’d left my office, and had my office in my bedroom in Victoria. The phone was ringing in the upstairs bedroom. I was downstairs and could hear it ringing. I raced up, and it was John on the phone.

Because of networking deep at Worldwide Developers Conference that year, other executives at Apple and the engineering team on the QuickTime products team had organized to get me back to the conference, but this time as a speaker.

I was demonstrating a use of the QuickTime conferencing API that a developer friend of mine and I had mocked up. In the QuickTime conferencing API you could build any interface on top of the basic function of video conferencing. We built up this Star Trek-like communications interface. It was visually appealing, met the geek quotient, and I was there to demo that.

Because of that demo, my brain, and Apple being a corporate culture, which at the time was kind of the dark era of Apple, I was getting hired.

We were just at the end of this first era of human capital and innovation, and so the people that were most respected on the campus were of course the engineers. The engineers didn’t matter or care what you looked like, or what your educational background was. You proved your mettle with them simply by virtue of interacting with them on the spot - what your brain was like in those conversations.

Even though I was a marketing guy, it was the engineering team, that on a Wednesday of WWDC, in 1994, had offered me a job. They said, “We want you to come work with us!”

At the same time my school year was ending, and John and his wife were doing a CD-ROM multimedia startup of their own in San Francisco, where his son lived. At this point John had become a regular mentor. I’d asked him to join my board of advisors to Desert Island Software, and he agreed. He even sent me a letter that I had framed, acknowledging his acceptance to the advisory board. My mom was comfortable with me coming down to live with his son and daughter-in-law for the summer to get some work experience.

At the same time, I was doing work experience, and going down to Cupertino once in a while trying to figure out, over the course of the summer, how I could take this invitation of work with them - become hired by them even though it was infringing upon child labor laws and immigration issues and so on. What they eventually figured out was that if I was a consultant contracted by Apple through a Canadian company, the Canadian company would be responsible for any issues.

They were able to put the blame or liability elsewhere. Now the problem was I couldn’t even be a director of my own company because I was under 18.

My mom, was reluctantly, very supportive of me but always worried about the downsides to my stability, childhood, and all the motherly things that one would be concerned about.

I’d convinced her to at least start the company, that was back in the Desert Island Software days. We had the company established, and literally a week before I was to go back home and start the 9th grade, the team said, “Hey, we figured this out. Want to sign the contract?”

I called my mom on a Monday, and said, “Mom, I’m starting work with Apple on Thursday, and I’m not coming home.” It was a very hard thing for my mom, you know: the baby son, and California, whatever. My mom, knowing how stubborn I was, and all these external factors at play, agreed. She allowed me to do this even though she was very, very concerned that I had negotiated my own contract.

I was later told that she came down and negotiated a different kind of contract, which was to say, “Hey, you know, guys, you are going to be responsible for my child, not only in terms of his physical welfare, but his spiritual and emotional welfare.”

I was a cellist at the time and had a bunch of other interests, and she just wanted to make sure that I maintained a childhood and a sense of balance in my life.

It was such an amazing corporate culture at Apple. There was a lot of people that were looking out for me, and of course, especially given what I was doing there. There was a lot of opportunity to kind of be a young rebellious teen, and I did some of that, but generally I had a really great group of people around me.

I remember there was a beer bash, when we did a alpha or beta launch of a software product. There would be a beer bash on campus, and I remember having a beer, and some HR person getting completely freaked out. There was a bunch of that kind of stuff.

However, I wasn’t the youngest. It was Chris Espinosa, who was actually employee number eight at Apple. Because I was never an employee, I was a contractor, I’m the youngest ever contractor I know through Apple. Chris was youngest ever employee, and actually beat me by I think a year or so. Chris actually has the title and will always likely carry that title.

I was hired in QuickTime products group, and I was savvy technically. I was able to comprehend at lower levels the technical concepts, but was a very bad, almost completely dysfunctional, programmer.

The team thought, “What do we make of this guy? What do we do with this guy?” I was put into an evangelist role. It wasn’t planned. They didn’t say, “Oh, Tom would be great at this.” They just thought I would be a great guy to have around. We kind of had to figure out what my role was.

With QuickTime, we were really trying to build a platform, a media platform, as a consequence of some of the technical portions of later versions of QuickTime. At the time there was a new standard called CD-plus, and CD-ROM, in the music industry. CD-plus was a totally different form of manufacturing a CD. You had a data layer, and you had a audio layer on one CD. The idea was to use QuickTime to demonstrate how we could create interactive content for artists that would increase engagements around the music on a CD-ROM.

This was 1995, and the internet was becoming more and more popular. It was coming out of the academic world and in the fringe technology world. Not so much in any way the mainstream, but becoming more and more, “What can we do with this?, How can we use it?”, etc.

Really our vision for how QuickTime and this online music stuff could interact, was that we could have individual files that would contain the music, but also contain very, very simple data structure describing the song. Being able to use an application which would then be able to look up that data and bring other relevant content in the form of commercial links. Links out to the web, that would allow for greater music discovery, but also allow for the tracking of how that music is explored, and how that fan engages with that particular track.

What we were tasked with was not only coming up with some prototypes about how that would manifest, and we’d pitch differently to artists and labels, but ultimately, I was kind of out there evangelizing to the music community.

I remember hanging out with Radiohead backstage at a show they did in San Francisco in 1995. Tom was already designing his album covers using Photoshop on a Mac. We had a tremendous number of artists who were already Mac users. We were trying to explain, “Hey, there’s this new stuff coming!”

In New York, we were part of the New York Music Festival, wiring up 13 clubs. There were 270 bands playing over seven days, and we were live streaming the venues to anybody on the web. On the crappiest of connections - probably four-frames-per-minute, with the worst 8 kHz mono sound quality.

The way that I approached my work in reaching out to the music business was the same approach that I took with Sculley. We are all people, regardless of title, whatever. We were all completely equal and it was all about being likeable and liked.

What was happening before I joined Apple was that there had been several kind of high profile attempts at creating what the press referred to as, “Sili-wood” which was Hollywood and Silicon Valley coming together to create these massive studio-produced CD-ROM projects.

The industry observers were saying that the two cultures were clashing. The Silicon Valley types were saying, “Well this is how we try to impose their methodologies and their approach to business on Hollywood.” and vice versa.

Whereas I was just this happy kid that was very excited about the technologies I was working on. Just being at Apple was my dream job. That enthusiasm and passion was disarming, and the fact that I was a kid.

Literally every single meeting for the first year, any new meeting, everybody would start looking for the hidden camera. Looking at each other for either whose kid this was, or who put up this joke. Then the meeting would start, and again people would still be kind of chuckling. Then five minutes in, as a consequence of what I was saying, and how I was saying it, they realized that this was this freakish but nevertheless real scenario of this kid being at Apple.

The music industry had the exact same attitude about people. They didn’t care what package or experience you came in. If you could play your part, that’s all that was required for acceptance.

That was the exact same culture that got me in at Apple. Here I was living in this convergence of those two communities, which really worked for me. I was doing really high concept stuff.

I had approached Bill Bottrell, a very famous engineer and studio guy, who had also gotten quite critically acclaimed as a producer. He had produced Sheryl Crow’s first album, “Tuesday Night Music Club”, and that album title was no coincidence. In her studio in Pasadena, he was organizing a Tuesday night jam session of friends and musicians that he knew.

Our idea was to wire up the studio so that the outside world could see what was going on and allow outsiders to contribute song ideas and lyrics into the studio. Then if those songs got cut, you would basically, by virtue of membership, be a contributor. You would sign up to get an audio CD compilation, of all the songs that had gotten cut, but you would get a pre-negotiated small kind of cut from the song that you had gotten cut if you were contacted had come in.

If you fast forwarded to 2009, and user-generated media contributions, collaboration online, I mean this is 1995, we just didn’t have the bandwidth to do it. We didn’t have a user base to do it. Even though Bill was tremendously excited about it, and so was a pretty high level executive within Apple, the concept worked up several layers above me to our vice president’s level, what they were looking for was really more.

They looked at our music stuff as more traditionally corporate sponsorship stuff. So the lens was exposure in the music industry, exposure to consumers, without going into too much of Apple’s history, you could argue that music was part of the brand DNA of Apple from the very beginning.

Even though Jobs was gone, it was always seen more as, “Hey, if we can do high visible stuff, get musicians endorsing what we’re doing.” Remember the, “Think Different” campaign.

The actual technical business rationale of our unit was that 90% of the music industry, we had 90% share of, of computers in studios and musicians from a pure market analysis perspective, the other ten was analog, and those were the guys that weren’t moving. If we could create high concept stuff, be seen as real supporters of the industry, perhaps we could move the dial, one, two percent, into that other 10%.

Remember it was Mac platform only that was hosting Pro Tools, Digidesign, and all that stuff. There was a kind of corporate culture that we were in. This was illustrative of the disconnect of the time that I was at Apple, which was under our CEO Michael Spindler, at the time.

I left before Gil Amelio came in. Spindler and Amelio were arguably two of the worst CEOs Apple ever had. Well, there’s only been four. This was an indicator of their “let’s sell more boxes” mentality, so our music stuff was in the rationale of, “Let’s sell, let’s move the dial on those analog guys.”

The reality of it, is those analog guys were analog for a reason, and they likely wouldn’t be switching because of our sponsorship of Woodstock 2.

Nevertheless, that was the mentality. Whereas internally, as we moved down from the VP into the operating dynamics of our unit, it was just keeping that culture that Apple was famous for. The culture of early innovation, concept, reaching out to innovators, and empowering them through our ideas.

There was that corporate culture disconnect that was very reflective to the whole company.

With the studio deal, even though there was high levels of support, it came down to negotiating a legal contract. The legal issues that an entertainment lawyer brought to a contract, and what our Fortune 500 Silicon Valley lawyers brought, were two very, very different contract legalities.

Even though there was cultural similarity, from a legal perspective, they were so different. It was the legal cultures that were the big issue in allowing us to do deals. As a result, we did a lot of sponsorship deals.

My business card and the title on my office read, “Tom Williams, The Kid”. That was the brand that was created for me, which I quickly embraced, and owned as my own.

I left Apple as my parents were actually going through the divorce proceedings. My father didn’t want to pay child support because on paper I was making more money than he was. I had no concept of money, and was spending more than I was making.

Because of the unique nature of our story, it ran in our local paper and it was syndicated very, very quickly across the country. The Canadian media got interested in doing a story on me. CBC National which was the prime-time national news hour in Canada, came calling to me in California to do an interview for a documentary.

I negotiated, and by this time had some ink on me: The Christian Science Monitor, the New York Post, A Current Affair. I had a bunch of media, and was hanging out with musicians. I very quickly understood the importance of having control over your own brand. This was not done with the Apple PR people, but directly between me and the CBC folks.

That documentary created brand awareness for “The Kid” in Canada, and as a consequence, I had a number of job offers.

Before the documentary even started, several of our new media guys got themselves hired by Microsoft. Microsoft has been involved quite heavily in promoting their own music stuff, though Apple was far better at achieving the high profile marketing wins.

Microsoft’s corporate culture was far different than Apple. Even though they had way more money to spend, and they got The Rolling Stones‚ “Start Me Up” for Windows, they could buy their way only so far. I’d done an interview with Microsoft, as several of the guys I knew from Apple were keen on getting me into there.

By this time, the documentary ran and there was a lot of job offers, one of which I ended up taking back in Vancouver.

That was the launch of the brand “The Kid”, which became, for better or worse, part of my public persona, quite successfully for the next ten years of my life.

During the ten years, it was the same notion of: build the relationship, success requires a persistent misreading of the odds, have access to anyone that was famous or at a certain level. The notion that I didn’t or wasn’t able to have access to that didn’t exist.

There was no psychological intimidation because I always had that level of confidence, or maybe it was just pure arrogance. It’s either a supreme level of confidence or truly seeing everybody, myself included, as just peers of everybody else.

All this title was a function of luck, it didn’t really imply any kind of specialness that I or anybody else didn’t have. Hold the relationship, be friendly, be likeable, and good things come from that.

I remember working as a technology analyst for this really crappy investment retail brokerage house in Canada. Not that I’m insulting the Canadian technology community in the mid-late 90s, but I wanted to go after the same deals that the white investment banks were going after.

There was a company called Invention Machine in Boston that had a bunch of big venture capital money put into it, and were contemplating an IPO. They needed a few million bucks raised privately before going out IPO, and this was the kind of thing that I did.

I knew that the CEO was a smoker, as we met at a conference in the past where we talked about cigars. There’s a comic aspect to this. An 18-year-old talking about his love of cigars to a 50-year-old. Seems so silly and ludicrous now that I can look back on it.

Nevertheless, I literally bought a box of cigars and sent it to him a week before I was to meet with him. I wined and dined him. The night before I was to meet with his board, which included guys from these New York investment banks, and venture capital funds, I convinced him to give me the opportunity to do a private equity round for the company. We shook hands, but he said it’s ultimately up to the board.

This very, very powerful board was like, “This is a joke! Why should we do it with you?” I said “Well I’ll get it done in a week.” They said, “Everybody says that and nobody does it.” I said, “So then you got no liability if I can’t get it done.” He said, “Well I guess you got me there.”

This was a Tuesday. Wednesday I flew to Toronto, met with a mutual fund there. By Thursday we had a term sheet. By Friday they got down there, and the deal closed on a following Wednesday. The commitment was there, pretty much right away. I gained the respect of that team and board.

My favorite quote is from author and management consultant Tom Peters, “Success requires a persistent misreading of the odds.” That’s exactly what that was. I didn’t know that quote when I did it, but it fit very well to describing part of my attitude and approach to this stuff.

It was about relationships, first and foremost. If people like you, they want you to succeed. If they want you to, they will help you succeed. It has to be genuine.

A lot of people approach their relationship-making as mercenary transactions. As much as you appear very genuine they can see your endgame. Take the time.

Earlier this week, I was traveling back home with my Mom and we agreed to take a particular ferry home, which would allow me about fifteen minutes of face time with a friend and mentor of mine.

She said: “Why bother if it’s just fifteen minutes?” I said, “Well, because it’s face time, and that fifteen minutes should be spent building and strengthening the relationship.”

What can you accomplish in fifteen minutes? Nothing other than strengthening the relationship.

Recognize that by being useful and good to others, you will eventually build a very strong team of supporters. They’ll lift you up to new heights and protect you. If you falter they will be there to bring you back up and support you.

I think it’s one of the most overlooked components of business. Simply, we’re always able to say that at the end of the day, all you have is your friends.

But, if your friends are your friends, and they happen to be in business, and are helpful to your business, then all that much better, because those people will be there to support you.

Pithy aphorism? Probably. Absolutely true? 100%.

© 2009 Derek Sivers