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01 — Introduction

I'm a builder who started on stage.

I once taught a woman named Donna how to video-call her grandkids. The look on her face when it worked is something I still carry with me. That was my first startup: helping seniors learn to use technology.

I've been chasing that feeling ever since. Everything else is noise.

Ben Shapiro
02 — Journey

Stage to Startups to Strategy

My career started on stage. Seven years of musical theatre, TV, and film. None of it came from business school. It came from performing eight shows a week and learning that if you lose the audience in the first thirty seconds, you never get them back.

That background is the single most useful thing I carry into every client room. Executive presence, reading an audience, knowing how to tell a story that lands.

When I left performing, I went where I could see the impact directly. First: helping seniors learn to use technology (real people, real problems, faces lighting up when something finally clicked). Then: electric school buses, combining clean transportation with the most underserved riders in America.

Then came Tide Rock, a private equity firm where I became Director of AI. I deployed AI across the entire organization: operations, corporate development, HR, accounting. Every department had the same story: the technology worked, but the organization wasn't ready for it.

The gap was never the model. It was the strategy, the people, the change management. Seeing what was possible across every function of one firm made me realize how much opportunity existed across hundreds.

The thread across all of it: technology serving people who are underserved or overwhelmed. That thread led me to co-found Cadre AI.

03 — What I Did at Cadre

Hand the Work to AI. Know It Worked.

From December 2024 to September 2026 I was co-founder and Head of Product & AI Strategy at Cadre AI, an AI consulting firm and Anthropic partner. I led the front of most engagements: discovery, the roadmap, the price, and the handover to the team that built it.

The work kept coming back to one question. How do you hand real work to AI, and know it worked? For a research endowment, that meant holding six AI vendors, Claude included, to the same pass/fail gates. In a financial-aid tool, it meant every dollar figure came from fixed math, never the model. In my own testing, it meant writing down the expected result before every run.

I built with the tools I recommended. Claude skills, agent specs, prototypes, a knowledge system that checks its own facts. Some of it got used every day. Some of it never left the design doc. Both taught me something, and I write about both.

40+

AI Trainings Delivered

16

Organizations Trained

70+

Claude Skills Built

04 — How I Think

The Human Problem Behind Every AI Problem

Most AI consultants think transformation is a technology problem. I think it's a human behavior problem.

When a team resists a tool that clearly works, I'm not asking what's wrong with the rollout. I'm asking what feels threatening about it. Behavioral economics, psychological safety, loss aversion. These are the tools I use to figure out why an AI pilot succeeds in one department and dies in another.

And there's the Jevons Paradox: when AI makes execution cheaper, organizations don't do less. They do more. The efficiency gains create demand, not headcount reduction. Most transformation plans get this wrong.

I worked with a CTO who told his team he didn't think they needed consulting help. Smart people, good engineers. They'd figure it out. Two weeks into the engagement, he was bought in. The technology hadn't changed. The process had.

I should be honest about one thing. I'm a recovering perfectionist. For years I held everything to an impossibly high standard, and it cost me: missed deadlines, projects that stalled at the finish line. The biggest lesson I've learned as a co-founder is that 80% delivered beats 100% delayed. I still remind myself of that almost daily. It's made me a better builder. I'd rather ship something real this quarter than design the perfect system that never launches.

Outside of work, I build games. My brain needs to ship things that don't have a client attached. I still play music. And I think in systems whether I want to or not.

05 — What's Next

Looking for the Next Team

I'm looking for my next role. Ideally applied AI work: helping customers put AI into real workflows, and making sure it holds up. I'm also open to leading AI at a PE-backed company, where a lot of my client work lived.

Two things matter most to me. Work I believe in, and people better than me to learn from. If that sounds like your team, I'd love to hear from you.

What are you building?

Hiring for applied AI, building with it, or just want to compare notes? Tell me what you're working on.

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