Entrepreneurship Requires Contrarian Thinking (5 Examples)

5 paradoxical problems all entrepreneurs need to overcome.

Scott D. Clary
Scott D. Clary
2 min readNov 26, 2022

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Building a business is hard.

The requirement to apply contrarian thinking to (seemingly) obvious business rules makes it even harder.

Here are 5 paradoxical problems all entrepreneurs need to overcome (as often as possible).

The Guess

Entrepreneurs are self-believing people who take action.

But when funded by VC’s, entrepreneurs are stressed, revenue milestones are forced and everything is optimized for speed.

Before you even realize, it’s too late to rectify.

Contemplate > Guesswork

Creativity ≠ Manageability

It is deep-rooted in our psyche that we can either be creative or methodical, mechanical, and manageable.

Creativity-driven founders often make wrong decisions due to this stereotyping.

Going outside the box often = Unpredictability = Unsustainable.

Good Planning, Good Research = Good Execution, Good Results

The Webvan team (failed grocery delivery) went the B-school way.

Meticulous research and planning over every aspect of the grocery business (that didn’t translate into results).

The real world doesn’t allow paper trading logic to entrepreneurship.

Consistent approval from customers for the W!

All Ideas Are Good Ideas (They’re Not)

Retrofitting an already flourishing idea with some sort of innovation is tempting.

However, it must be learned that existing players make such adaptations’ naturally.

If it is doable, thinkable, but undone, don’t do it.

Entrepreneurship Is A Trait

Entrepreneurship is often thought of as a trait, talent, or innate skill.

Most founders don’t consider “learning” it.

Like creativity, entrepreneurship can be & should be polished.

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Scott D. Clary
Scott D. Clary

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