Paul Graham recently wrote an excellent essay on independent thinking. A topic I’ve thought a lot about is the key differences between early stage entrepreneurs vs. successful big company managers. They require distinctively different skill sets, the most stark of which is the importance of independent thinking. Having spent 5 years at a corporate behemoth, 2 years consulting for a variety of corporate behemoths, and now 6 years in venture capital, the correlation of independent thinking with success in different kinds of organizations is a fascinating topic.

For large organizations, the importance of large-scale execution and leadership often takes precedence over independent thinking in succeeding within the organization and moving up the ranks. The organization as a whole must move in the same direction. In Paul Graham’s words:

[The need for independent thinking] isn’t universal. In fact, it doesn’t hold for most kinds of work. In most kinds of work…All you need is to be right. It’s not essential that everyone else be wrong.

On the other hand, startup founders create companies from scratch and there is no organizational momentum to anchor on. Strong independent thinking is critical as all aspects of the business must be defined and progress must be made on rapid iteration and execution.

You don’t want to start a startup to do something that everyone agrees is a good idea, or there will already be other companies doing it. You have to do something that sounds to most other people like a bad idea, but that you know isn’t

Paul Graham lays out three key components to being independent-minded: fastidiousness about truth, resistance to being told what to think, and curiosity.

“Fastidiousness about truth means more than just not believing things that are false. It means being careful about degree of belief. For most people, degree of belief rushes unexamined toward the extremes: the unlikely becomes impossible, and the probable becomes certain.”

In large organizations, questioning the truth and attempting to go against the inertia of the organization is risky and can indeed make the unlikely seem impossible. The overall goals of a large organization are compartmentalized and then compartmentalized some more. Each manager is in charge of the success of a particular component and improving that individual component may not necessarily improve the success of the overall jigsaw puzzle. As I wrote in the past, for those of us in startup-land, a mindset shift is required to understand what moves the needle for a large organization.

The second component of independent-mindedness, resistance to being told what to think, is the most visible of the three…It’s not mere skepticism, but an active delight in ideas that subvert the conventional wisdom, the more counterintuitive the better.

In addition to the challenge of resisting inertia, skepticism of previously made decisions also carries a degree of risk in large organizations. All decisions were made at some point by a decision maker and being skeptical about a decision may offend someone, or even worse offend an entire team. The nature of seemingly minor decisions contrasts greatly with a startup where decision making in general is much more agile.

The third component of independent-mindedness, curiosity, may be the most interesting…In my experience, independent-mindedness and curiosity predict one another perfectly…Everyone I know who’s independent-minded is deeply curious, and everyone I know who’s conventional-minded isn’t.

I believe there are plenty of highly curious people in both large and small organizations. Those who choose the entrepreneurial route have a higher risk appetite and likely a higher degree of independent-mindedness that nags at them towards acting on their ideas.

There are plenty of stories of independent thinkers at large corporates who identified massive opportunities based on evolving technologies applied to existing services. The Snowflake founders realized while at Oracle that Oracle’s dominant architecture for databases was not optimal for the needs of the rapidly growing cloud ecosystem. So they left Oracle to start Snowflake and 8 years later Snowflake is a $85B public company.

Similarly, Matt Daly and Philip Lorenzo were working on LiDAR based 3D scanning and Building Information Modeling (BIM) at FARO Technologies and McCarthy Building Group, respectively. When they saw that LiDAR isn’t yet practical for daily production tracking purposes and BIM doesn’t yet have the level of development (LOD) and ecosystem-wide penetration, they went against the grain to take a different approach. Matt and Philip started StructionSite based on the conviction that computer vision technology had advanced to the point where images from off-the-shelf cameras could provide the information needed for construction site managers to easily track production daily.

Successful entrepreneurs must be independent thinkers to start and grow a company from scratch against all odds. As the company scales, entrepreneurs must learn to create equilibrium between independent thinkers and managers who are more proficient at large scale execution.

VC Investor at D20 Capital. Formerly at Amasia, Formation 8, McKinsey, Samsung, Columbia Business School, Seoul National University, University of Illinois