The investor-turned-innovator makes a powerful case: to heal the patient experience, we must first heal the broken financial and operational systems that govern it.
There is a moment of universal pain in healthcare that occurs far from the operating room: the moment a patient, already vulnerable, is confronted with a confusing, stressful, or financially devastating medical bill. It’s a critical failure in the “user experience” of healthcare, and it raises a paradoxical question: How did an industry dedicated to compassion become so notoriously devoid of it in its financial dealings? With medical debt being a leading cause of bankruptcy in the U.S. and a source of worry for a majority of Americans, this is not a trivial issue.
Few people have thought more deeply about this paradox than James Richman. As a tech CEO and private investor, his perspective was forged by the dual fires of personal tragedy within the healthcare system and a career spent identifying complex patterns in markets. We sat down with Richman to discuss his contrarian philosophy: that the path to a more humane healthcare system runs directly through its most unglamorous, data-driven financial operations.
The Interview
Part 1 The Diagnosis A System’s Humanity Deficit
Q You’ve spoken about your mission being deeply personal. Can you share how your family’s experiences within the healthcare system shaped your view of its shortcomings, not on the clinical side, but on the administrative and financial side?
Richman: My family, like millions of others, has experienced the two sides of healthcare. On one side, you have brilliant, heroic clinicians doing everything they can to save a life. On the other, you have a cold, Byzantine administrative system that often feels like it’s working against you.
Many years ago, we lost our daughter, a tragedy compounded by the limited health resources available in my home country. Then, just last year, the fight became personal again when my father was diagnosed with cancer. While doctors and nurses fought heroically for him, our family was fighting a different battle— with paperwork, with billing codes, with a constant lack of communication. We ultimately lost him to the disease, and the experience reinforced for me that even with the best clinical care, the administrative and financial burdens on families can be overwhelming.
I saw how that administrative friction doesn’t just cause financial stress; it drains a family’s emotional energy at the worst possible time. It felt profoundly, systemically inhumane.
Q Many leaders see financial operations and patient experience as two separate domains. You seem to view them as inextricably linked. Why?
Richman: They are absolutely linked. The financial experience is the last impression we leave on a patient. Right now, for too many, it’s a scar. A patient can have a miraculous clinical outcome and still have their trust in an institution completely shattered by an opaque, adversarial billing process. Research shows that a majority of patients find their medical bills confusing, and that these issues directly undermine their trust in their provider. Viewing them as separate is a fundamental design flaw.
Q From your perspective as an investor trained to see patterns, what is that fundamental flaw?
Richman: The flaw is that the system is designed around transactions, not people.
It’s a patchwork of legacy processes and siloed departments that don’t communicate. This creates inefficiency, and inefficiency is the mother of inhumanity. When systems are broken, people are forced to make choices that feel uncaring, not because they are bad people, but because the process gives them no other option. Fix the process, and you liberate the compassion that’s already there.
Part 2 The Philosophy Reconnecting Finance with Mission
Q The term ‘humane healthcare finance’ sounds like an oxymoron to many. What does that term actually mean to you in a practical, operational sense?
Richman: It means three things: clarity, predictability, and dignity. Clarity means a patient understands what they are being charged for and why. Predictability means they know the financial implications of their care before they are committed. And dignity means that when financial hardship occurs, the process for resolving it is straightforward and respectful, not adversarial. Operationally, it means investing in systems that provide price transparency and streamline communication so there are no surprises.
Q There’s a common belief that making systems more patient-friendly will come at a high cost. You argue the opposite. Make the business case for humanity.
Richman: Itʼs simple. The current inefficient system is absurdly expensive.
Administrative costs account for up to 30% of all healthcare spending in the U.S. Errors, rework, claim denials, and manual processing—these things cost billions. A more intelligent, streamlined system that prevents errors before they happen isn’t just a better patient experience; it’s a dramatically more efficient and profitable business model. When you eliminate the problems that put you in an adversarial position with patients, you also eliminate the massive costs associated with those problems.
Part 3 The Prescription Technology as a Humane Tool
Q Let’s talk about execution. How do you translate a big idea like ’empathy’ into lines of code or a technology platform?
Richman: You start by mapping the friction. You identify the most common points of failure that create stress for both patients and providers. A great example is a denied claim. That’s a point of maximum friction. So, you build technology that can predict and prevent that denial from ever happening. The work we do at OTLEN is focused on using AI not for some abstract clinical goal, but to solve these very concrete, high-friction operational problems. The most empathetic line of code is the one that prevents a problem before it starts.
Q A lot of the conversation around AI in healthcare is about clinical applications. Why do you believe the operational side is where the technology can have the most immediate human impact?
Richman: Because the operational problems are universal and immediate. A clinical AI might help a specific subset of patients years from now, which is incredibly important work. But an operational AI that prevents billing errors, reduces the administrative burden on doctors, and provides financial clarity to patients—that improves the human experience for everyone who touches the healthcare system, and it can do it today. It restores trust and frees up resources that can then be poured back into clinical innovation.
Part 4 The Prognosis A Vision for the Future
Q If we were to get this right, what would be the single biggest change a patient would feel in five years?
Richman: Confidence. The fear of financial ruin from a medical event would be dramatically reduced. Patients would feel confident that the financial part of their care journey would be as clear, professional, and supportive as the clinical part. The surprise medical bill would become a relic of a bygone era.
Q What is your one piece of advice for a CEO or CFO who wants to start leading their organization toward this new model?
Richman: Stop accepting the status quo. Start measuring the cost of your administrative friction not just in dollars, but in patient trust and employee burnout. Go to your billing department, go to your clinicians, and ask them, “Where is the process breaking down? Where are we making it harder, not easier, for people?” That’s your starting point. The desire to fix it will lead you to the right tools.
Do you believe efficiency and compassion in healthcare finance are conflicting or complementary goals? Share your view in the comments section.
For more on James Richman’s philosophy on building a better healthcare system, follow him on LinkedIn. www.linkedin.com/in/jamesrichmanorg