Negotiate Like a Millionaire: The Art of Caring Just Enough

When it comes to negotiating like a millionaire, here’s the golden rule:

“Care… but not thaaat much".” Herb Cohen

That’s right. Success in negotiation doesn’t stem from domination or desperation, it stems from emotional discipline and perspective.

Here’s what that looks like in action:

You show up. You care. But you’re also willing to walk away.

That mindset alone, not needing the deal, gives you an edge. When you’re not emotionally reactive, when you’re not desperate to “win,” you begin to see the playing field more clearly.

It’s about having options. And one of those options should always be: no deal.

The Empathy Advantage

But don’t confuse detachment with disconnection.

Empathy…true, practiced empathy… is a secret weapon. As Chris Voss, former FBI negotiator, put it:

"Empathy is not the truth or reality. It is merely the other side’s point of view."

In other words, great negotiators aren’t just focused on their own needs. They’re obsessed with understanding what the other person thinks they want—even if they’re not saying it outright.

That’s where Munger’s Rule comes in:

"I never allow myself to have an opinion on a matter unless I know the other person’s argument better than they do." Charlie Munger

Know their side. Know their reasons. Know their fears.
Because when you do, you can craft a solution that speaks to their real motivation; not just their words.

See the Deal Through Their Eyes

Ask yourself:

• What does this person truly want?

• What might they be hiding behind their words?

• Can I see the deal from their perspective—even if I don’t agree with it?

This isn’t manipulation. This is mastery.

To negotiate like a millionaire, blend detachment with empathy, logic with curiosity, and firmness with flexibility.

Because the person who understands both sides of the table…wins. And sometimes, the real win… is walking away.