The amazing gift Steve Jobs gave a lost boy


I was 17 when my father died, and the only moments of peace in the months that followed were in the few seconds after waking up, before my synapses started firing. That twilight between my dream state and the reality of my day. But when my first thought finally formed each morning, it was inevitably, “something is wrong.” Then the fog cleared and I remembered my father was gone. And in an instant, the heaviness in my heart returned, my spirit shrank, and the physical weight of my emotional grief climbed on my back like a giant gorilla.

It’s how I felt again, the day after Steve Jobs died.

While the world lost a charismatic visionary, I lost something far more personal. Steve had been my hero since I was 15 years old. In my career as a Mac consultant, and later editor, publisher, and TV writer, he was my True North. On the day I heard the news, even more than grief and sadness, I felt derailed and set adrift.

Every teen feels the world revolves around them, but growing up in Silicon Valley in the 80s, it actually did. For me, the best of America was California, the best of California was the Bay Area, and the best of the Bay Area was the Silicon Valley where I lived — the epicenter of an industry that was transforming the world.

I was naturally drawn to technology, and I was one of the geeks who’d spend every lunch hour in high school shackled to an Apple II writing code in Basic. Writing programs that always returned a predictable result was so powerful to me. The computer was never wrong. Even when I was certain I had done everything correctly, if the computer returned an unexpected result, it was always due to user error.


The code objectively reflected the user’s thinking process, and thus revealed any flaws. Ultimately that meant the solution to every problem was within me — to get a different result I had to alter the program or change my approach, which is an ideal metaphor for all of life’s problems. For me the computer came to represent objective truth, which is probably why unlike my parents’ generation, I tend to trust computers over people. Through programming I learned not only critical thinking, but also the power and precision of language. It’s probably why I’m a writer today.

My father owned an electric typewriter rental company, and I used to help him on his delivery runs. He’d pack his giant Cadillac up with a selection of IBM Selectrics, and I’d accompany him around to different offices where I’d lug the typewriters in while he flirted with the secretaries. His gift was humor — a talent he’d use to charm these girls into ordering just about anything he wanted to sell them.

But dad’s whole business was built on a technology that was about to get stomped on by the PC, and more directly, the LaserWriter. It may have just been a generational thing, but he was perfectly happy running his analog business. While I valued my dad’s humor and ability to connect with people, I was starved for a young role model I could emulate, who understood computers and the future that Silicon Valley was creating.

When Steve Jobs burst onto the scene, he was handsome, charismatic, and confident, and embodied everything the Bay Area was about. He was sex, drugs, and rock and roll, and he resonated with me immediately. I grew up in Los Altos, less than 2 miles from Steve’s infamous garage on Crist Drive, so Steve’s story naturally became my own blueprint for what was possible as an entrepreneur. Steve and I lived in the same hood so I considered him my tribal leader, and tasked myself with learning everything I could about the man and the company he was creating.

I once delivered a typewriter to an office which had a just-released LISA computer — the precursor to the Macintosh. When the owner saw me stop in my tracks, typewriter in hand, to stare at the LISA, he tried to impress his secretaries by explaining to me “This is a LISA — it was named after Steve Jobs’ daughter.” I shot back “It’s also an acronym for Local Integrated Software Architecture. Where do you want this?”

An old man thinks he knows more about an Apple computer than me? Please.

At the time, I was also a closeted teenager, and I had done what so many gay kids of that era did to distract the world from our developing sexual identities: I became an overachieving “Golden Boy.” I kept my hardworking single mom happy by cleaning the house and having wine and cheese waiting for her when she got home from work. I related to adults better than with other kids, and bonded with my mom’s friends – who often confided in me with their marriage problems. I helped dad with his business, taught myself computer programming, and set a school record for the 50-yard dash. I took AP classes in high school during the day while taking classes in French and Accounting at a community college at night. I was the youngest member of a local dance company, and was even dating (albeit platonically) the head cheerleader. Like a good Golden Boy, I had all my plates spinning solidly in the air.

When my father died suddenly of a heart attack, all the plates came crashing down.

His death cracked me wide open and left me lost and scrambling. I didn’t know who I was or how to move forward. Without my father’s guidance, and still rejecting my true self, I needed that tribal leader more than ever. Steve Jobs became my superman, and a model for the kind of man I could be moving forward.

I’ll never forget the first time I saw a Macintosh. It was the first consumer level computer with a graphical user interface (GUI), and there was an application called MacPaint, which let you fill a square with a pattern like stripes or bricks, and select different tools like a paintbrush or spray paint can. Once I created a wall of bricks and wrote my name in spray paint to emulate graffiti, something clicked. It wasn’t what the technology could do, it was what I could do with the technology. Digitally manipulating graphics is trivial now of course, but 32 years ago, it was a revelation.

That first Mac experience was also the first time I uttered the two words that became my mantra around every new Apple product: “Must. Have.”

The Mac was $2,500 – and this was in 1984. I had no idea what programs came with it, if any, but as a non-artist I could create a graffiti wall in seconds and that’s all it took. The technology made me an artist. That was the magic of Steve’s vision. It wasn’t about the computer, it was about what technology could do for regular people — which is why his vision for the Mac was “a computer for the rest of us.”

The first time I performed with the dance company on stage was at the age of 15 at Flint Center – the same stage where Steve announced the Macintosh. For the next 30 years, I continued to follow in Steve’s tailwind as he journeyed from Apple to NeXt to Pixar and back to Apple, transforming industries with products like the iMac, iPod, iPhone, and iPad. I made my living as an Apple consultant off and on for 20+ years, and explored veganism, meditation, Zen Buddhism, and calligraphy solely because Steve did. In 1998 my partner Sam and I created a successful magazine for gay men who didn’t feel represented by gay media. The magazine took off when in a nod to Steve we added the tagline, “the magazine for the rest of us.”

I never missed a single one of Steve’s Apple keynotes, and I’ve waited in line for every new Apple product since the first iPod. In 2013 when I was a writer/producer for Ellen Degeneres, the first monologue I wrote for Ellen that made it to air was about the release of the latest iPhone. Suffice it to say, Steve’s influence on my life has been significant.

One of the things I admired most about the man was his obsession with design. Steve knew that design could function as a key to unlock understanding. Remote controls are inherently confusing because there are too many buttons – so simplify, simplify, simplify, and you’re left with a 5-button Apple TV remote. Keep refining the design of a smart phone and you’ll get an iPhone with a single button. That same design rigor created a complex tablet computer that even a 2-year old can intuitively use (if you’ve seen a child with an iPhone or iPad you know what I mean).

I’ve learned that writing functions in the exact same way – it’s the other side of the design coin. With careful thought and precision, you can design a reader’s emotional experience simply by writing down words and phrases in a specific sequence. The right sequence can evoke laughter, tears, understanding, and connection. Writing and design are both tools for transformation — programming languages with the power to change the world.

Steve understood this — it was the kind of magic he orchestrated on a daily basis. And sometimes we don’t know the magic we’re capable of creating ourselves until we see it in someone else.

It’s been 5 years since the world lost Steve Jobs, and since today is his birthday I wanted to say thank you, Steve — for the endless moments of beauty, magic and inspiration you brought and continue to bring to my life. You were a bright light in a dark time for this young boy, and it was an honor to have been a part of your tribe.

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