The Window Opens Before It Is Obvious
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The Window Opens Before It Is Obvious
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In Episode 6 of The Mike Ye Briefing, I look at timing asymmetry — the difference between waiting because time is working for you and waiting while your options quietly disappear.
I share examples from Express, where we exited as growth plateaued and fast fashion was beginning to reshape retail; Intel Capital, where we monetized more than $5 billion across over 200 investments before the dot-com bubble fully burst; and South by South West, where the Covid shutdown created an unexpected window and Penske Media was first to build the relationship before a formal sale process existed.
The lesson is not that great timing means predicting the future perfectly.
Sometimes timing is judgment.
Sometimes it is luck.
Usually it is some combination of both.
The important thing is being ready when the window opens.
Because the better question is not only, “Is now a good time?”
It is:
What happens to my options if I wait?