I spent twenty years moving things. Packages, freight, entire supply chains — I negotiated billion-dollar air cargo deals, built systems that tracked millions of shipments and flagged problems before they became expensive. I founded Amazon Air. I ran e-commerce transportation at Walmart. I built a supply chain startup called Pandion and scaled it beyond $50 million in annual revenue.
And then my family got a medical bill, and I couldn't figure out if it was right.
That's the moment that won't leave me. Not because the bill was catastrophic — it wasn't. But because I'm someone who spent his career as a procurement specialist negotiating some of the most complex deals in the industry, building automated audit systems that caught discrepancies across millions of transactions — and when I sat down with an Explanation of Benefits from our insurance company, I couldn't make sense of it. The codes didn't match. The math was off. The document that's supposed to make the process transparent was damn near unreadable.
If I can't figure this out, who can?
I need to back up, because the path from "supply chain guy" to "healthcare startup founder" isn't as strange as it sounds.
I went to The Citadel — four years of military college in Charleston. Then the Marine Corps. The military teaches you a lot of things, but the one that stuck hardest was simple: when you see a problem and you have the skills to fix it, you fix it. You don't wait for someone else. You don't study it for another quarter. You act.
After the Marines, I spent a couple decades at manufacturers and retailers, culminating at Amazon and Walmart. I started Amazon Air — the air cargo network. At Walmart, I ran their e-commerce transportation operation. Big teams, big budgets, genuinely impressive scale. But I'd be lying if I said any of it kept me up at night because I believed in it. I was making massive companies slightly more efficient and their executives slightly wealthier. That's fine work. It's just not the kind of thing you tell your grandkids about.
So I started Pandion. My own venture-backed small parcel transportation company. We grew fast, served real businesses, built something I was proud of with some phenomenal people. An investor once told me during a practice pitch: "You sound like an expert, not someone who wants to be rich." I took it as a compliment. It wasn't meant as one.
And then, for a lot of reasons I've spent a long time thinking about, Pandion didn't make it. Some of that was market timing and bad luck. A lot of it was my mistakes — wrong hires, scaling too aggressively, not raising enough capital at the right moment, underinvesting in marketing, you name it — I screwed it up. I've sat with those failures honestly. They shook me in ways I didn't expect.
When Pandion closed, I took care of my employees first. Made sure people landed on their feet. It's just what you do. Or at least what I think you do. And then I spent months processing what had happened, a lot of it standing in a river with a fly rod, breaking down what went wrong and what I'd do differently.
Here's where healthcare enters the picture.
During the Pandion years, I was more stressed than I might have realized at the time. Bad diet, too little exercise, not enough sleep, no balance. The company was consuming me. In the spring of 2025, I ended up in the ER with chest pain. A few tests later, I had emergency heart surgery. Things turned out ok and are much better now, but the scare was real.
Apparently I had been silently ill for a year or so. My wife put it plainly: "Your choices nearly killed you." Not the company — my choices about how I dealt with the pressure. She was right.
So I got healthy. Fixed the diet, fixed the sleep, fixed the habits. And I started thinking about what I actually wanted to do next. Not what would make the most money — what would matter.
I looked at the biggest problems I could find. Climate change. Energy. Healthcare. I kept coming back to healthcare. The largest industry in the country — nearly 20% of GDP — and one that treats its customers like shit. An industry whose primary communication tool, in 2025, is still the fax machine. I didn't have domain expertise, but I was living the problem. My family's medical bills were a mess. Our insurance was processing claims months late. Providers were billing incorrectly. And every time I tried to get something fixed, I hit a wall of hold music, transferred calls, and form letters.
Then one of my kids had surgery, and the claim got disputed by our insurer. I dove into the details. What I found wasn't a one-off mistake — it was a system operating exactly the way it's designed to. The insurance company was sitting on claims. Our EOBs were wrong because earlier claims hadn't been processed yet. We paid bills we shouldn't have, because that's what normal people do when a bill shows up — you pay the damn thing. And then we had to fight to claw the money back from providers and our insurance company who were suddenly very difficult to reach.
That slow, quiet game — delayed processing, cascading errors, complexity that grinds you down until you stop fighting — that's not a bug. That's the business model. The system doesn't screw you with one dramatic denial. It screws you with a hundred small ones until you give up. And once you see it, you can't unsee it.
I realized something that should have been obvious sooner: healthcare administration and supply chain have the same DNA.
Both are process-heavy industries running on infrastructure from the 1980s. Both have convoluted workflows, legacy technology, and incumbents who benefit from the mess staying messy. The pattern-recognition and automation I'd spent two decades building — tracking shipments, flagging anomalies, catching errors before they compound — transfers directly to medical billing. It's the same damn problem with different paperwork.
The difference is the buyer. In supply chain, I sold to procurement executives making rational purchasing decisions. In healthcare, the "buyer" is a patient who just got out of surgery and is staring at a bill they can't understand while managing pain medication and follow-up appointments. The process complexity is comparable. The human experience around it is fundamentally different — and fundamentally worse.
Hospitals and insurance companies have armies of engineers building software to maximize what you pay. Revenue cycle management is a multi-billion dollar industry — and every dollar of that revenue comes from one place: your pocket. Billing coders, claims adjusters, collections agencies — they all exist to extract every possible dollar from patients. Every one of those tools is optimized for the provider or the payer.
Not a single one is built for you. Think about that for a second. Billions of dollars in software and Artificial Intelligence, and none of it is on your side. Until now.
That's what Kupu is. The system that should have existed for decades, built for the person who actually gets the bill.
Kupu analyzes your medical bills and Explanations of Benefits for errors — overcharges, duplicate charges, unbundling violations, balance billing problems, and more. When it finds something wrong, it helps you understand what happened in plain language and generates the documentation you need to dispute it. The right language, the right codes, the right regulatory citations. Kupu also helps guide a growing number of uninsured "cash pay" patients to find the right price for their care — helping you find every tool at your disposal that the system doesn't want you to know about.
I'm building it with a few principles that matter to me:
Your data stays on your phone. You own your healthcare. You own your data. Full stop. Medical bills contain some of the most sensitive information about your life. Kupu processes everything on-device by default. No data warehouse. No "anonymized research datasets." No third-party sharing. Ever.
Free during beta. I'm not building a tool that only people who can already afford a $200/hour medical billing advocate can use. The healthcare system hits hardest on the people who can least afford to fight back. If this only works for people with resources, I've built the wrong thing.
Stubborn on the vision, flexible on the details. If bill auditing isn't what drives adoption, I'll find what does. Healthcare financial dysfunction is the mission. The product form is negotiable. The mission isn't.
People ask why I didn't go back to supply chain. The money's better. The network's deeper. The expertise is proven.
Honest answer? I spent nearly thirty years making businesses more efficient and executives wealthier, and the world doesn't need me to do more of that. When Pandion closed, I had the financial security and the space to ask myself what actually matters. And what matters is building something that helps real people with a real problem — not shaving 1.3% off someone else's cost-per-unit.
I have three kids — one about to graduate college, one a freshman in college, and one a junior in high school figuring out where she wants to play college soccer. My wife is a teacher who's serving society's future until she retires in a few years. I want to spend the next phase of my life building things that matter, being present for my family, and leaving something more meaningful than a faster more efficient supply chain.
There's a phrase my first battalion commander in the Marines used to say: "Bloom where you're planted." You can't control where you end up. You can only control how you grow once you're there.
I ended up in healthcare because my family's medical bills were a disaster and I had the skills to do something about it. That's not a grand plan. It's just what happened. And now I'm building the tool I wish existed when I was on the phone for the third hour, trying to figure out why my kid's surgery claim was denied.
Kupu is in beta. If you've ever tried to navigate health insurance or looked at a medical bill and thought this can't be right — trust your gut. It probably isn't. And now there's something you can do about it.