[7] Pushing Without Forcing

There’s a narrow line between pushing and forcing.
You see it in sports. You also see it in private company investing.

Good deals don’t show up at your front door ready to close themselves. You have to push a process forward—dig in, do the work, don’t skip steps, and stay engaged long after the newness of the deal wears off. Progress requires effort, and sometimes a lot of it.

But pushing is not the same thing as forcing.

I’ve been thinking about fly fishing lately. A good cast isn’t about strength. It’s about timing, rhythm, and knowing when to let go. Grip the rod too tightly or muscle the motion, and the line collapses in a heap. You’re working hard—but you’re working against the physics instead of with them.

Deals are the same.

You have to care deeply and stay determined, but you can’t be so committed to the outcome that you turn off your filter. Red flags rarely show up as fire. It’s usually just a little smoke. You can always rationalize a higher price or explain away a negative finding in diligence. Always. And very smart people do it every day.

The paradox is that real conviction includes the willingness to walk away at any moment. Not emotionally—but decisively.

To be equally willing to give everything—or walk away—is hard.

Different sports, same lesson.
Have you ever seen the clips of Tiger Woods stopping his swing mid-motion because someone made a noise? That’s the idea. Full commitment—until the moment it’s no longer right.