The thing that made Escobar killed Escobar

Pablo Escobar was a horrible dude. (Hot take, I know.)

But I just finished a video about him, on my new leadership channel, and there’s a valuable lesson in his downfall:

Even winning strategies stop winning eventually.

Pablo Escobar’s winning strategy was being more aggressive than anyone else in the room. It’s how he clawed his way up from nothing and got to the top of the drug world.

It worked for a long, long time.

But eventually, the government turned on him. For the first time, he had an opponent he could never beat.

And he had a choice: recognize his leverage was gone and pull back, or fight harder.

So he kept fighting, even as his empire crumbled, his family fled the country, and his whole world was crashing down around him.

Escobar assumed the way forward was to push through.

He couldn't tell that what had always worked had stopped working. Most leaders can't.

Because usually you can’t tell when it stops working.

Robert Greene's The 48 Laws of Power at least once.

Half of it reads like an instruction manual for becoming a jerk.

But the parts about knowing your actual position, when you hold leverage and when you're just bluffing, are worth the whole book.

So next time you're in a standoff or a hard negotiation, stop and write down what leverage you actually hold.

If the honest answer is "none," that's your signal to stop swinging. That's the read Escobar got wrong and Lara got right.

Grab the book here.

Thanks for reading.

Michael

P.S. What are you doing in February? Want to go skiing and talk business with me? Check out Compound Conference.

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