Darren KimuraChairman & CEO of AISquared

Born and raised in Hilo on the Big Island of Hawai‘i, I learned early that resources were not unlimited. Almost everything arrived by ship, usually through O‘ahu first, before making its way to the outer islands. Things were expensive, supply was limited, and you learned to make do with what you had.

That environment shaped me.

If something broke, we fixed it. If we lacked a resource, we found another way. That taught me to understand problems at a fundamental level, and to approach problems from first principles rather than simply accept assumptions because when you're working with scarce resources, you only have one shot to get it right. 

It also taught me the value of community. No meaningful progress happens alone. Everyone has a role to play, and leadership is about understanding people's strengths, aligning them around a shared goal, and communicating clearly enough to help them do their best work.

Those lessons became the foundation of my career.

As a cub scout and boy scout, I sold Makahiki tickets by walking all the streets of Hilo, going door to door.  I did the same with my first company, going door-to-door of businesses, cold-called from lists.  I financed the business with credit card applications I picked up from the gym.  I used my surfboard as my first desk on the trunk of my Chevy Blazer where I wrote my proposals. At the time, my friends thought I was crazy for choosing to work 17-hour days.

The lessons from that period still guide me: stay close to the customer, move with urgency, build with discipline, and never confuse vision with execution. 

Every company I have built started from the same place: a real problem, a scrappy beginning, and an obsession with building the right product for the right market.

Follow your Passion – Crazy to Visionary: Darren Kimura – Page 46

In The Greater Good: Life Lessons from Hawai‘i’s Leaders by Evan and Kari Leong, my chapter is titled “Follow Your Passion, Crazy to Visionary: Darren Kimura.” The title captured something I have seen repeatedly in entrepreneurship: many bold ideas are dismissed as crazy before they are recognized as visionary.

The difference is not rhetoric. It is time, execution, discipline, focus, and the ability to turn conviction into something that creates real value for customers.

Today, I am focused on artificial intelligence and the practical challenge of deploying it safely, responsibly, and effectively inside real organizations. I speak frequently on AI strategy, governance, and enterprise deployment, and serve as a regular AI contributor on ABC Mornings Live Bay Area. At Claremont Graduate University, I developed the Claremont AI Controls Framework, a structured approach to helping large organizations deploy AI more reliably, responsibly, and at scale.

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