About John Charles Gilmore
Fractional COO and startup builder with a bias toward clarity, acceleration, and radical operational honesty.
Fractional COO and startup builder with a bias toward clarity, acceleration, and radical operational honesty.
After fifteen years leading operations in high-growth startups, I specialize in building systems that scale with the founder—not around them. My work spans finance, people, legal, product, and revenue ops—and I'm most useful when a company feels stuck and no one can say exactly why.
My principles: Protect your ability to see, not your ego, embody error correction as an identity, prioritize systems over sentiment, depend on others to sharpen your thinking, accept that slow is fast, and choose to swim, not surf. I rely on the system that is formed by these principles to guide my decision making and would recommend you discover your own core principles — that's a good step in building a machine that will help you cover your blind spots etc.
If you're building something fast—and it's already outgrowing your team, systems, or clarity—I'll help you catch up to your own vision.
In fast-moving organizations, clarity is your most valuable asset. I help you build systems that maintain visibility into what's really happening, even as you scale. This means creating feedback loops, establishing clear metrics, and ensuring you have the right data to make informed decisions.
Protecting your ability to see often costs your ego dearly. We must fight hard to get the truth, even when it hurts. This principle is about maintaining operational clarity at every level of your organization, even when the truth challenges our self-image or comfort.
As David Deutsch argues in "The Beginning of Infinity," all problems are soluble. However, systems that emphasize error correction are critical for continued knowledge growth. We must BE that system ourselves rather than thinking of ourselves as completed people.
When errors become data points rather than failures, your organization can iterate and improve at unprecedented speed. This isn't about avoiding mistakes—it's about making them productive and using them as stepping stones to greater understanding.
While culture and team dynamics matter, they need to be supported by robust systems. I help you build operational frameworks that align incentives, clarify responsibilities, and create predictable outcomes.
As Ray Dalio emphasizes in "Principles," we must make decisions based on principles, not how people feel. This means knowing how you will act when you get somewhere tough so you don't get swayed by your emotions. Good systems make good behavior easy and bad behavior hard. They're the foundation of sustainable growth.
This is about rejecting positive regard and social mores in favor of using social interaction and your team as a sharpener. When you tap into your team's collective wisdom without seeking praise, you make better decisions and build stronger buy-in.
Rushing to solutions often creates more problems than it solves. I help you build systems that prioritize thorough understanding and careful implementation over quick fixes. This means taking time to diagnose root causes and design sustainable solutions.
When you invest in doing things right the first time, you avoid the costly rework that often comes from rushing.
This has been one of the slowest principles for me to learn because I was a very fast learner and thinker. It took getting kicked in the face by life several times for me to discover this principle.
Deliberate, straightforward effort is better than riding a wave. I help you build systems that prioritize devotion to the plan over momentum. This means creating sustainable growth through consistent, intentional action rather than relying on temporary advantages.
When you choose to swim, you build the strength and endurance needed for long-term success, regardless of market conditions.
This is one of my most important principles, because it's one on which I believe I wrongly held the opposite view for so many years of my life as a natural surfer. Only with many years of experience have I begun to understand that no surfer ever made it as far in any chosen direction as a strong swimmer.