Ryan McKindles drives the strategy and execution of investment decisions at Caduceus Capital, bringing nearly two decades of experience across healthcare technology consulting, entrepreneurship, and law. We sat down with him to get his unfiltered take on the future of digital health, what it takes to build a standout company, and the advice that has shaped his career.
What area of digital health has you most excited right now and why?
For years, I’ve been going to healthcare conferences and sitting in rooms full of thoughtful, experienced leaders who would all say some version of the same thing: technology isn’t really moving the needle. AI is going to transform healthcare, just not yet. That refrain was so consistent and went on for so long that it started to feel like a permanent condition of the industry. And then something shifted. The tools got good enough, the appetite grew, and the excuses started to run out.
One of the areas where I’m seeing real possibilities for genuine change is payer reform and alternative payer models that realign incentives in a way the industry has needed for a long time. The structures that govern how care gets paid for have been stubbornly resistant to change, but I’m starting to see real creativity emerge around models that actually put the right incentives in the right places. What’s accelerating that is the speed at which new tools, AI chief among them, allow founders to build and iterate. The gap between a good idea and a product someone can use has collapsed. That matters enormously in a space like payer reform where the ideas have often existed but the ability to execute on them quickly enough to sustain momentum has not. When you can keep the creativity flowing and get something in front of users fast, you have a real shot at changing things that have been broken for decades.
What separates a founder who catches your attention from one who doesn’t?
The ones who catch my attention have usually lived the problem. Not read about it, not consulted on it. Lived it. Healthcare is a domain where insider knowledge matters enormously, and the best founders I’ve backed have either come out of the system or spent years embedded in it. Beyond that, I look for people who have a clear-eyed view of the regulatory and reimbursement landscape. A brilliant product that can’t get paid for is just a science project. The founders who get both the clinical and commercial sides of the equation early are the ones I want to back.
For aspiring entrepreneurs, what are the most important things to get right before you ever launch?
Know exactly who your first customer is. Not your target market, your first customer. A specific person at a specific organization who will sign a check. Everything else flows from that. Second, understand your reimbursement pathway before you build anything. It shapes every decision that follows. And third, build your advisory network early. The right clinical advisors and operator advisors don’t just open doors; they stress-test your assumptions in ways that save you enormous amounts of time and money.
What should someone consider before committing capital to a venture fund?
Beyond the obvious, track record, team, thesis fit, I’d encourage LPs to think hard about whether the GP has genuine, differentiated access to the deals that matter. In a sector like digital health, the best opportunities aren’t broadly shopped. Does this team have the relationships and the reputation to see deals early? I’d also think carefully about portfolio construction and how the manager thinks about reserves. And frankly, I’d want to understand what the GP actually does for their portfolio companies post-investment. Writing checks is the easy part.
What’s the best piece of advice you’ve ever received and who gave it to you?
Early in my legal career, my first boss, Tom Nemes, who later became my partner at the law firm, watched me tie myself in knots trying to figure out the perfect next move on a matter. He stopped me and said something I’ve never forgotten: just do something. A good decision made quickly and adjusted as you go will almost always beat a perfect decision made too late. It’s probably the single biggest reason I have the bias toward action that I do, and in venture, that instinct serves you well.