There’s a familiar executive reflex when AI shows up: buy the tools, hire the experts, ship the pilots, call it transformation. And sure, you should do those things. But there’s a quieter truth most leadership teams are bumping into right now.

As artificial intelligence reshapes every system of work, the advantage that actually compounds is no longer technological. It’s human.

Because AI doesn’t just automate tasks. It mediates relationships. It changes how decisions get made, how influence moves through organizations, how trust is built (or quietly eroded), and how culture holds when the old signals of competence and value start to blur. When machines can draft the memo, run the analysis, and propose the strategy, what’s left as distinctly “leadership” is judgment, character, and the ability to create alignment among real people.

That’s the premise of A.I. + Me, a highly curated executive retreat for a small group of leaders, hosted along the Santa Cruz coastline, designed to create the kind of clarity that does not happen in boardrooms. The retreat blends high-level dialogue, reflective practices in nature, and intimate dining by a Michelin-starred chef. The point is not luxury for luxury’s sake. It’s leverage: the conditions that allow leaders to think differently, speak honestly, and return with language and frameworks that travel.

You’ll be guided by Steve Fortunato (founder/CEO of Hospitality Collaborative and author of The Urgent Recovery of Hospitality) and Sasha Strauss (brand strategist and founder of Innovation Protocol), two facilitators who come at the same problem from complementary angles: relationship strategy and identity-based influence.

Dates: February 24-27
Investment: $6,250 per person, or $25,000 for a team of four

If your executive team is serious about leading people, not just systems, in the age of AI, request an invitation.

Learn more

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