There is nothing wrong with optimism. Deals require optimism. Buying a business without optimism would be almost impossible.

But one of the quiet truths is that the most dangerous person in many transactions is not the pessimist, not the critic, and not the appraiser. It is the optimist who has convinced himself he is being objective. That person is hard to reach. Because he does not think he is stretching. He thinks he is “balanced.” He does not think he is assuming too much. He thinks he is “being realistic.” He does not think he is emotionally attached. He thinks he has simply “done the work.”

Meanwhile, the assumptions keep leaning one way. The adjustments keep leaning one way. The forecasts keep leaning one way. The explanations keep leaning one way. And somehow all that leaning still gets described as discipline.

That is the trap.

Open optimism is easier to identify. Self-certified objectivity is much harder.

One of the quiet truths in valuation is that some of the weakest deals are not built by reckless people. They are built by intelligent people who became so committed to their own reasoning that they stopped noticing how often every judgment call seemed to benefit the same outcome.

That is not objectivity. That is attachment with better vocabulary.