The story
I am slightly uncomfortable on purpose. Not because I’m reckless — because I’ve learned that the edge of comfort is exactly where growth lives. Every meaningful thing in my life has started there.
How I think
“I ask questions that better frame the question. I identify variables that may not have been considered. I listen and synthesize — such that you can progress in your own internal thinking.”
Most people think advisors are valuable because of what they know. I’ve come to believe the most useful thing an advisor can do is change the shape of the question. Not provide the answer — change what you’re asking.
I’ve been doing this my whole life. Long before anyone paid me for it. With close friends navigating impossible decisions. With family systems that needed reframing, not fixing. With leaders who had all the information they needed but couldn’t see the variable that was blocking them.
It’s not a methodology. It’s a way of paying attention. And it took decades of living fully — in uniform, on race courses, on summits, in boardrooms, and across cultures — to develop the depth to do it well.
01
“Every problem has a unique set of variables — some visible, some undiscovered. The ones that stay hidden are usually the ones that matter most.”
02
“Listening and agreeing are essential for trust. Agreeing doesn’t mean acceptance — it means understanding.”
03
“Emotions matter and can make decision making difficult. Everyone has them. Moving them to the side and looking at the true variables — that’s a skill.”
04
“The photocopier problem: the more copies we make, the slight variations bring us further from the original. Most organizations are running on a copy of a copy.”
The life behind the work
I don’t separate my professional life from my personal one. Everything I’ve done outside the office has made me better inside it.
Endurance
Long commitments with uncertain outcomes are how I operate best. You train for months toward a finish line you can’t fully see. You learn to be comfortable being uncomfortable. That’s not athletic training — that’s a philosophy. I bring it to every engagement I take on.
Courage
On stage. Completely vulnerable. A year of discipline visible in a single moment of judgment. Most people think endurance sports require the most courage — but standing under bright lights having worked your body for a year, that’s a different kind of brave. Long goals. Great outcomes.
Adventure
Some dreams don’t die — they just wait. I’ve been working toward a pilot’s license for years not because it’s practical, but because some aspirations are worth maintaining regardless of timeline. I believe in chasing the thing, not just the credential.
Service
I coach a youth swim team because teaching someone to move through something they’re afraid of — water, in this case — is one of the most satisfying things I’ve found. I’ve also traveled to Haiti to help build homes for an orphanage. Service isn’t a resume line. It’s what you do when nobody’s watching.
Story
My mother never met her father. He left behind a diary written in 1946 at the height of the Chinese Civil War — a love story, a window into a world that no longer exists. I’m helping her publish it. The stories people never told are often the most important ones. I believe in finishing what someone else started.
Family
I believe children should see the world before they’re told what to think about it. One annual trip with close friends keeps me sharp and connected. One with my family ensures my kids grow up knowing the world is bigger than their neighborhood. It’s not a tradition — it’s a curriculum.
The career — in brief
My career in technology started hands-on — learning systems by working inside them, absorbing expertise from the people who built them, and replicating what worked. I was a button-clicker first. That foundation matters. It means that when I sit across from a technical team, I’m not performing fluency. I’ve lived it.
Over twenty years that hands-on experience grew into something different — the ability to translate. To take complex technical realities and render them into language that boards, executives, and investors can act on. To sit in a room full of competing agendas and find the one question that moves everyone forward.
I served as CIO for a subsidiary of the $2.5B UMass Memorial Health system. I led patient and population health technology for $2.1B Baystate Health — one of New England’s largest health systems. I’ve served as an elected Trustee and Board Member for Country Bank since 2016, advising its Risk and Audit Committees on technology risk and digital strategy. I’m currently VP of Customer Success and a personal investor at Psympl, an enterprise AI startup.
“The technology career gave me credibility to get in the room. What happens once I’m there has nothing to do with technology.”
The work I’m most proud of came from a problem that had nothing to do with technology and everything to do with human nature. A Medicare Accountable Care Organization — nine independent health systems, nine CEOs, nine CIOs, each with their own budgets, their own boards, and a long history of competing for the same patients. We were asked to share data in real time across organizations that had no shared authority, no shared infrastructure, and no particular reason to trust each other. The financial incentive was real, but so was the risk. One wrong move and a competing institution had access to something they shouldn’t.
The technology we built to solve that problem is now patent-protected. Co-inventor of a U.S. patent — No. 12,080,430 B1, Care Plan Management — a distributed care coordination architecture that enabled nine organizations to share what they needed to share — and nothing more — in real time, across systems that had never spoken to each other. But the architecture wasn’t the hard part. The hard part was building a governance model where every institution could see their self-interest inside the shared framework. That’s the work I find most interesting. Not the technology. The conditions that make the technology possible.
I’m a doctoral candidate in Engineering Management. I hold a Bank Director Certification from BankDirector, a CPXP certification, and Six Sigma credentials. I was named to BusinessWest’s 40 Under 40 in 2016. I served in the Air Force and am a veteran of Operation Enduring Freedom.
None of that is why people call me. They call because I help them see something they couldn’t see on their own — and leave the conversation knowing exactly what to do next.
The world
I was born in Japan and left when I was two. I’ve spent the years since trying to get back to that feeling of being somewhere completely new — and finding that the world makes more sense the more of it you’ve seen.
Every year I try to travel once with close friends and once with my family — so my children can experience the world before they’re told what to think about it. The world is the curriculum. The passport is the proof of work.
For the record
Education
Certifications
Recognition
Innovation
Service
Ready?
No pitch. No intake form. Just the conversation that should have happened first.
Start the conversationI read every message personally. You’ll hear from me within 24 hours.