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Hey folks,
I’ve been reading The Art of the Deal by Donald Trump.
He’s a polarizing figure. And the book is clearly part autobiography, part marketing machine.
But if you strip away the personality, there’s something worth studying:
How he thinks about deals.
There’s one principle that stood out to me more than anything else:
Patience is a weapon.
Returns Are Just Math
At its core, investing isn’t complicated.
Your return is driven by three variables:
What you pay
What it’s worth
How long it takes to realize that value
That’s it.
So if you want better returns, you only have three levers:
Pay less
Increase value
Shorten the time to exit
Most people focus on #2.
Great investors obsess over #1.
Where Patience Comes In
Here’s the part most people miss:
You can’t consistently “pay less” without patience.
Trump’s approach (at least as he describes it) is aggressive:
He pushes hard in negotiations
He asks for more than seems reasonable
He’s willing to walk away—even late in the deal
That style isn’t universally applicable.
But the underlying principle is.
He never needs any single deal to work.
And that changes everything.
The Real Advantage: Indifference
The biggest mistake investors make?
They fall in love with the deal.
They like the story
They picture the upside
They start mentally “owning” it before they actually do
Once that happens, your leverage is gone.
Now you’re negotiating against yourself.
Trump avoids this by doing one thing extremely well:
He always has other options.
He’s constantly looking.
Constantly evaluating.
So when a deal doesn’t meet his criteria, he can walk.
Not because he’s emotional.
Because he’s indifferent.
Who This Strategy Actually Works On
Here’s where it gets interesting.
That aggressive negotiation style?
It only really works in one situation:
When the other side needs the deal more than you do.
In other words:
They’re under time pressure
They have financial stress
They want certainty more than maximization
That’s where outsized returns come from.
Not from brilliance.
From asymmetry in urgency.
The Takeaway
You don’t need to copy Trump’s personality.
But there are a few lessons worth stealing:
Don’t fall in love with deals
Always have multiple opportunities
Be willing to walk away
Wait for situations where the other side is under pressure
Because in investing:
The best deals don’t come from being smart.
They come from being patient when others can’t afford to be.
One Question to Think About
Where in your life are you rushing into decisions…
…when waiting would give you leverage?
If you enjoyed this, I may do a few more breakdowns on negotiation, leverage, and deal psychology.
—Dakota
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