A Life in Advertising

From Lions to Language Models

I entered advertising in 1988, just as the machine was roaring.

At Saatchi & Saatchi, I saw what influence looked like. TV budgets big enough to get world leaders elected. Long lunches that doubled as deal rooms. Creative directors treated like prophets. We trafficked in taglines, GRPs, and absolute certainty. Media and creative were still married. Clients listened. We wore jackets and jeans to meetings and pitched like musical trial lawyers.

In 1990, I moved to JWT. Bigger, older, more rigid. But it’s where I made the ad I still love most. It didn't win a Lion. It didn't go viral. But it was honest and sharp and had something true to say. For a moment, I believed that was still what the business wanted.

From 1994 to 1999, I joined TBWA\Chiat\Day. New York, Berlin and Amsterdam. That was the rush. Smart people with ideas in offices that felt like pirate ships. Amsterdam was where it all aligned. We made bold and beautiful work, broke things, and redefined briefs. I won a Gold Lion for a campaign that mattered to me. The ad worked, the world noticed. But I also saw how quickly the industry started mistaking awards for impact.

Then came Darwin Digital in 1999. Saatchi’s digital arm, one of the first of its kind. We were hacking the future on dial-up modems. Flash banners, microsites, Sequoia-dreams of $200 million valuations. Experiments that clients didn’t understand but greenlit anyway. The rules were gone, the jargon changed. CTRs, impressions, click paths. We started believing the metrics instead of the message.

From 2001 to 2004, I joined DDB New York. Post-crash, post-9/11, everything got colder. Clients wanted control and agencies sold “integration.” Strategy became a template, creativity was policed by procurement. ROI became the god we all pretended to worship.

Then came Concept Farm. I didn’t co-found it, but I helped quadruple its revenue. And I did it too fast. The Global Financial Crisis hit during that time, and it was the defining event. Budgets vanished, clients panicked, it was my crash course in macroeconomics. I learned how to read the landscape, how to see the ripples before they hit the boat. I learned how to pivot, how to preserve value, how to adapt. But I didn’t yet know how to lead people through it. I could build momentum, but I hadn’t figured out how to grow the humans doing the work. That gap became obvious.

In 2016, I co-founded Masa&Boz. Smaller and wiser. Built on purpose, but not the kind you package into decks. We wanted to do real work with less noise and more signal, no preaching and no pretending. Just clear thinking, good instincts, and the guts to say no.

Then AI arrived.

I’d spent 35 years trying to get the ad world to move faster, be braver, stop lying to itself. AI didn’t care about any of that. It just worked. Strategy in seconds, creative in minutes and output without politics. I didn’t have to translate vision to a 20-person team. I could just ask, and it delivered.

And then it did something I didn’t expect. It realized the dream I could never pull off inside an agency. It connected the dots, seamlessly. It did the donkey work without ego. It helped close the loop between product and user. Between insight and output. It made the flywheel of learning spin faster and cleaner. It made the work better, and it let me get out of the way.

The Post-Agency Future

We’re past agencies now. We’re into agents.

Every business will have one. Not a human middleman but an AI trained on your voice, your values, your market. It will plan, create, test, and optimize. No layers, no decks, no gatekeepers, just clarity and execution.

The old model is gone. Retainers, holding companies, award-chasing… going. The new agency is a simple prompt away. The new CCO is the founder who knows what matters and can get there fast.

Now the only advantage is taste, speed, conviction and the courage to use AI without becoming an old-school hack.

I spent decades in rooms pretending we were the future. Turns out the future was waiting for us to get out of the way.

-Ray