Born on the bay. Raised on the beach. Living on a mountain.

I was a kid writing text adventures in BASIC on a TRS-80, thrilled to have the machines doing my bidding.

Then I swerved. I picked human languages over computer ones (Latin, French, Spanish, Italian) and read the dictionary for fun.

The machines came back around in San Francisco. Around 2012 I saw early neural-network work in a lab, right around the AlexNet breakthrough, and I've tracked it ever since. When ChatGPT launched on GPT-3.5 in November 2022, it took me about a week and a half to know what BrandMultiplier would be.

Now I spend my days wrestling with the machines again, with a human deciding every line that ships. My kids find the phrase "wrestling with the machines" hilarious. They're not wrong.

I was born in Tiburon, on the bay. I grew up a beach kid, a mediocre surfer in Cocoa Beach next to kids who'd been riding waves in the womb.

My favorite conditions were pure glass. College summers, I told scripted jokes from the bow of the Davy Crockett Explorer Canoes at the Magic Kingdom. Then came more than two decades in California: Windansea in La Jolla, my happy place, and a decade in San Francisco, back on the bay.

Then I fell in love with a woman from Aspen, and we decided to build a family here. So now I'm a water person living on a mountain, which is about as fish-out-of-water as it gets. I've adapted. I wing-foil, paddleboard, and take 39-degree cold plunges.

When the kids are grown, I suspect the water wins.

An agency owner tracked me down at the restaurant where I waited tables and offered me a job as a copywriter. I'd never heard the word.

Within weeks I was writing for the agency's two biggest clients, Disney and Hard Rock Cafe. They left me with a question I still haven't put down: what makes people love a brand for generations? What kind of black magic is going on there?

I chased it in-house at Hard Rock, where I produced the first Hard Rock Cafe International website. At Fantasy in San Francisco I wrote for Google, Sony and Samsung, including the messaging for Google's Project Re:Brief (the project took a Cannes Cyber Lion). Inside big agencies I led creative for Intel, Microsoft, Nike and Apple. At Accenture Interactive I led a pitch studio; across twelve months, the pursuits we built brought in more than $1B in new business. And at my own shop, ChrisRubinCreativ, I chased it across 65+ engagements with challenger brands.

In the late '90s a global consultancy hired me into its San Francisco office, and when the dot-com bubble burst, the office closed and I walked out with a severance check. What came next was La Jolla, where I built, managed and mentored a creative team from the ground up.

Now I answer the question for founders, at BrandMultiplier. Turns out the black magic can be taught.

How I work: care and conviction.

• Win the room before you show the work. Once creative is on the table, anyone can kill it with "I don't like that word." So the hard conversations come first.
• Lead from support. Servant leadership, unblock and elevate. I start by listening.
• A standard only counts when people who aren't you can hit it. I'd rather a writer argue me out of a line than wait for me to fix it.
• Persuasion is the wrong goal. Give the best information to the people who stand to benefit most, then trust them to decide.
• Put a number on it. A brand argument without one gets cut in the first hard quarter.

I filled spiral notebooks with stories as a kid. The job I'd never heard of turned out to be the one I was built for.

At Fantasy, a famous design agency with no writer in-house, I was the go-to for anything language-related by my second month. Over the next 18 months we launched nine case studies, and with no sales team, they became the agency's main source of new business ($5M+/year).

I've written 1,000+ words a day for 10+ years. The habit runs on two rules: Seinfeld's "don't break the chain" and Pressfield's "just show up and do the work." I write for the flow, the place where time disappears, and for what comes after it. I call that the after-joy.

I also keep a commonplace book. The line on the wall this month: "Every word is optional until it proves to be essential." (Verlyn Klinkenborg)

My grandfather, GrandJoe, was my mother's father and the greatest man I've ever known.

He was a Duke Law graduate with his own practice in the South, raising two girls, when he had a vision. He went back to school for a doctorate in theology and spent the rest of his life as a Presbyterian minister: tending the sick, caring for his congregation, preaching on Sundays. He was an excellent golfer, too.

My grandmother, Rodie, was a classically trained pianist with a sweetness to match his, and she led the choir in their church. On Sundays he had the pulpit; she had the choir loft.

GrandJoe's whole teaching was lovingkindness. And he told me, very young, to gather all the information first, then make my own choices. No dogma.

I've spent about 20 years with Boys to Men, mentoring boys and young men. I set out to bring it to San Francisco, got a Bay Area chapter going a couple of years later, led it, and handed it off when I moved to Aspen. I also ran my own creativity and critical-thinking program through Junior Achievement in two San Francisco high schools, and mentored in a middle-school program in the city.

These days I've been coaching my son's flag-football team, the 49ers. We built the team on three Hs: hustle, hunger, and heart. Triple H. Four championships in five years. My favorite game: we fell behind 12–0, scored 48 straight and won 48–12.

My wife is a psychoanalyst. On our first date we ended up deep in Carl Jung, which is part of why Jungian archetypes run all the way through my work. Home is Aspen, with her, the twins, the dog, the cat in charge, and a tortoise named Timmy.