The metagame: How WRITER’s Diego Lomanto reads the agentic future of marketing

Some people play the cards they’re dealt. They see what’s visible on the table and react to the moment.

Others play the player across the table. They read the subtle tells, calculate the invisible odds, and understand the psychology that truly drives the game. They know that the best decisions are made not with perfect information, but with a masterful read of the situation.

On this episode of Humans of AI, we talk to someone who literally went pro doing just that. Diego Lomanto, chief marketing officer at WRITER, once paid his way through grad school at the poker table. Now, he’s applying that same mastery of reading the game to the high-stakes world of AI.

Applying poker principles to marketing

What if the secret to mastering AI marketing has nothing to do with technology, but everything to do with a 150-year-old card game? Long before he was leading marketing at an AI company, Diego was mastering a different kind of strategic thinking at the poker table. He argues that poker is the perfect allegory for modern marketing — a delicate balance of hard math and human intuition, of quantitative analysis and qualitative storytelling.

“I actually think AI is forcing marketers to spend more time thinking about brand differentiation and personal relationships than ever before, and that’s what I’m seeing with the best of the best out there.”

In the episode, Diego shares the incredible story of how he paid his way through grad school by playing poker and how the experience sharpened his probabilistic thinking. He explains the concept of the “metagame” and how understanding the story your customers are telling themselves is the ultimate competitive advantage.

Embracing the paradox of AI marketing

What if the age of AI is actually forcing marketers to become more human, not less? Every marketer has heard the refrain, “do more with less.” The rise of generative — and now agentic — AI has turbocharged that pressure. Executives see splashy demos and ask the logical question: “Why can’t we just automate everything and cut budgets?” Diego believes this is a trap.

He argues that if every company uses the same AI tools to become faster and cheaper, the only true differentiator left is brand and human connection. Diego tells a powerful story about a major global retail brand that uses AI not to replace creativity, but to free their teams to focus more on it, fundamentally changing how they bring products to market.

Challenging the old way of working

How do you convince a team of experts, people who have honed their craft for 20 years, to fundamentally change the way they work? Diego says it requires a top-down mandate to challenge the status quo.

“You gotta force people, when they’re about to do things the old way, [to] stop and think, can AI do this? And if you can, make that investment in extra time to get it going for the first time.”

He reveals the one rule he forces his team at WRITER to follow before they can buy new software or start a new project — a rule that completely reframes their relationship with AI. It’s a simple but profound shift that forces everyone to stop doing things the “old way” and think like an AI-first organization.

Learning from technology’s “rhyming” history

Society will reshape itself around AI — that’s the unflinching conviction driving Diego’s long-term strategy. As a deep student of technology history, he argues that the fear and uncertainty surrounding AI aren’t new. Instead, they’re part of a predictable cycle that has played out with every major technological revolution, from the automobile to the internet.

“Society will reshape itself. Society will persist, society will survive. It’s just going to be in a different form than what we got used to.”

Diego explains why the only choice for professionals is to embrace the discomfort, learn from history’s rhyme, and adapt — or risk becoming a dinosaur in a world that has moved on without them.

To hear Diego’s full story and get his complete framework, listen to the full episode of Humans of AI on Apple Podcasts, Spotify, or watch the full video on YouTube.

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