05/17/2026
A very successful founder called me with what sounded like a big opportunity.
This is someone I respect.
The Michael Jordan of his industry.
Ferraris.
Multiple wins.
Sharp mind.
Someone approached him about joining forces. Bigger company. Bigger presence. Bigger competitor in the market.
Itās the kind of deal a lot of people are exploring right now.
Before we even got into the numbers, I asked him something that caught him off guard.
āDid you and your wife go through pre-Cana before you got married?ā
He laughed and said yes.
I told him thatās exactly what you should do before going into business with someone.
Because when you merge businesses, youāre not just making a financial decision.
Youāre getting married.
Youāre tying together:
⢠money
⢠decisions
⢠pressure
⢠reputations
⢠and long-term consequences
So before we talk about the marriageā¦
we started with the numbers.
I asked him about ten questions.
Smart guy that he is, he already had most of the answers.
And when the math finally came together, I told him something blunt.
āIt smells bad.ā
Deliberately blunt.
Because sometimes leaders need clarity more than politeness.
The valuations on both sides didnāt make sense.
Either the people across the table didnāt understand the businessā¦
or they were trying to get one over on him.
And both of those scenarios lead to the same question.
Do you really want to be in business with people like that?
The right partnership should make the business stronger.
Not harder to trust.
So hereās the real leadership questionā¦
When you look at the deals in front of you, are you evaluating the opportunity, or the people youād be tied to for the next decade?
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