How to Fund Raise Like Leo DiCaprio in Inception

Persuading venture capitalists and investors in general is just like Nolan’s blockbuster psychological thriller Inception. Art imitates life.

You, the entrepreneur needs to subtly place your big idea in the VC’s subconscious mind, and quietly leave so they wake up thinking the idea was theirs all along.

Let’s see what lessons we can learn from Leo aka “Cobb” in Inception:

Lesson one:  Do you know why you are trying?

It’s getting fairly cliche these days to talk about the entrepreneurs whose hearts are not in taking pride in their projects, but are only attracted to the superficial aspects of entrepreneurship, aka Money.

The point is Leo couldn’t have pulled off the most complicated job in his career as an Extractor if the only meaningful things left to him in his world, his children, weren’t at stake.

He could not have gathered together a ragtag band of eccentric geniuses, overcame the dark demons from his past, and found the courage to take a ton of experimental drugs – just to do it for Money.

Leo had to succeed, or he would never see his family again.

When there are no excuses left to be given, the battle is already won.

Lesson two: What is the key to persuasion?

Persuasion fails because the persuader doesn’t have a good story to tell. A terrible story will fail even the most talented story teller. The heart has its own reasons even when the mind is asleep and dreaming.

How do you find a good story to tell about why you want what you want?

Reach into your past and pierce together everything that nature and nurture has given you and you alone, then tell it like a human being, to another human being.

People are getting better and better at detecting persuaders who simply spit out a scripts in a soothing voice.

Lesson three: Be sublime

Leo had faced the impossible. He had to convince the Heir of the Fischer Conglomerate to break up the empire his father spent his whole life building. How did he manage to do it?

He did his homework and he got the best people possible for the job.

By meticulous researching everything about his Target and everyone around him, he could gather enough data to generate psychological profiles to use to his advantage.

By getting the most talented people at each of the task required to pull off Heist of the Century, he could maximize his chance of success in an improbable project.

Bonus lesson: Do you have an Ariadne?

Maybe it’s the intractable uncertainty.

Maybe it’s the constant barrage of affirmations and rejections.

Maybe it is the constant anxiety of disappointing everyone around you.

Whatever it is, entrepreneurship is a bit like gazing into the Abyss – sometimes you find it gazing back at you.

Leo saw the demon(ess) writhing below the surface of his psyche when he took the elevator all the way down to his abandoned, neglected personal hell. Luckily he had the young Ariadne to pull him back from the abyss.

Do you have an Ariadne in your life that can help you find your way back from the heart of the labyrinth?

It is not a coincidence that the burden of running a hugely successful enterprise is almost always shouldered by not one, but two (or more) founders.


To convince a human being to enter into a relationship with you, one that is as intimate as the relationship between enterpreneur + investor, takes a sense of inevitability, a worthwhile mission, relentless hardwork, and companions who will help you along the journey. What great ideas will you try place in the mind of the people who can help you make a difference in the world?