Before every big decision, I ask founders one question.
Not about the numbers. Not about the structure. Not about the regulatory position.
What does the worst version of this look like and can you live with it?
Most founders can describe the best case in vivid detail. The revenue projections. The market opportunity. The valuation at exit.
Very few have sat quietly with the worst case.
Not the mildly disappointing version. The real worst case.. the one where the deal falls apart, the partner turns adversarial, the market doesn’t show up, the lender calls the loan.
I’ve seen founders sign term sheets, joint ventures, and acquisition agreements without ever having that conversation with themselves.
The best case takes care of itself. It’s the worst case that needs a plan.
If you can’t live with the worst case.. reconsider the decision.
If you can.. proceed with clarity.
That’s not pessimism. That’s how good decisions get made.
What's a decision you made that you wish you'd stress-tested the downside first?
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