03/31/2026
When three-quarters of your wealth sits inside one company, the math changes.
Not the actual math.
The math you're able to do.
You start weighing scenarios you can't possibly score. Hold for growth you can't predict. Sell before a crash you can't time.
It doesn't feel like paralysis.
It feels like diligence.
The tension isn't between holding and selling.
It's between the decision you can defend later and the one that's right now.
Most founders resolve this three years later than the moment required.
Not because they lacked information.
Because concentration doesn't just create risk.
It creates invisibility to the decision itself.