Mark Khavkin often finds his best ideas somewhere near the Golden Gate Bridge.

The Rula CFO tells us that he bikes from San Francisco across the bridge and into Marin County—not to compete, but to clear his mind, enjoy the view, and stop for a latte in Sausalito. “A lot of times great ideas come somewhere just before or after the bridge,” Khavkin says.

That preference for space and perspective also appears in how he leads. Compared with a decade ago, Khavkin says that he has become more comfortable trusting people to reach the right result, even when their path differs from the one he might have chosen. Rather than intervening with detailed instructions, he now tries to provide context. “I’m less prescriptive than I was ten years ago,” he tells us.

The shift does not mean avoiding hard decisions. At Rula, Khavkin says that new investments require clearly defined checkpoints and agreement—made in advance—about when the company will increase its commitment or stop an initiative. Once teams, careers, and expectations form around an experiment, he explains, ending it becomes difficult at a human level.

The same discipline shapes his view of AI. Khavkin cautions finance leaders against evaluating the technology primarily through cost savings. According to Khavkin, the greater opportunity is enabling people to perform higher-level work, make decisions faster, and access more organizational context.

For Khavkin, leadership is not about directing every turn. It is about creating the conditions for others to navigate—then knowing when to provide context, when to challenge assumptions, and when to let the road produce the answer.