The plane was somewhere over Nebraska. Dick Kramlich sat across from me. We were on the same board then, and the rides together had become their own kind of conversation. He talked 1:1 the way certain men do when the clock has stopped mattering: without hurry, without the need to impress.
I asked him the question that had been riding with me for a while. After decades of sitting with founders, after watching tens of companies rise or disappear, what was the difference? What separated the ones that made it from the ones that simply ran out of road?
He didn’t answer right away. He looked out the window for a moment, then back.
They had done a study once, he said — a hard look at outcomes, not opinions. What it found stuck with him ever after: the companies that survived were almost never the ones that had stuck to the plan. Success required the pivot. Not once, but again and again, until the company that arrived was almost unrecognizable from the one that had set out.
Then he gave the image that has stayed with me longer than any spreadsheet or term sheet.
He looked for great open-field runners.
Not the ones who could only run between the tackles, powering straight ahead into the line. The ones who could see daylight where it did not yet exist, who could plant a foot and cut, who understood that the shortest path is rarely the one that gets you home. Zig and zag. Feel the defense shift and refuse to be trapped by the original play call. Keep the ball moving toward the only thing that matters: the space that opens when you stop insisting the field must look the way you imagined it on the whiteboard.
I have carried that sentence for years. Great open-field runners.
It never felt elegant inside the room.
Kramlich had seen enough to know that the founders who could do this were rare. The ones who lasted treated the plan the way a great running back treats the designed play: as a starting point, not a contract with the universe. They trusted the daylight more than the diagram.
I think about him sometimes when the ground shifts under something I thought was settled — when a strategy that once felt inevitable begins to feel like a trap, when the clean line on the page starts to look like a cage.
Dick is gone now. The rides are over. But the image remains, clean and sharp as the day he offered it at thirty thousand feet: a runner in open space, eyes up, cutting toward the light that only appears after you abandon the path you thought you were supposed to take.