What Navy SEALs Can Learn From Entrepreneurs

A month ago, I ran a program for a group of Navy pilots and SEALs. My role was to teach them how to think and act like entrepreneurs so they could bring the entrepreneurial mindset back to their organization to solve problems, navigate bureaucracy, and communicate better.

When I kicked off the session it was as if I had fired a starting gun at a track meet. No hesitation. No looking around or waiting for permission. Everyone sprang into action, launching into whiteboarding and prototyping the challenge at hand.

How would they deal when I threw a wrench into their plans?

A classic technique for getting teams to move faster is to disrupt time constraints. After establishing a task around a specific problem, I set a big timer for ten minutes and let them get to work. Moments later, with as much fanfare as possible, I mustered up my best Dr. Evil grin and reduced the timer to two minutes. 

They barely reacted. Someone in the back yawned. Nods of affirmation and right back to work.

Next, we moved on to the concept that how you pitch an idea is almost as important as the idea itself. Most of the time when I’m teaching people the value of pitching and winning over a room, shyness holds them back. None of this group needed encouragement to pitch to their ideas. For 90% of people, public speaking is their greatest fear. I guess if your work involves the possibility of getting shot at, fear of public speaking is low on the list.

So it turns out Navy pilots and SEALs are already entrepreneurial in many ways. But not in every way. Here’s what they learned.

Costs of Failure in Large vs. Small Orgs

One advantage that entrepreneurially-minded workers in startups have over large organizations is that failure is “cheaper.” 

This is because failures are part of the DNA of startups; every seasoned entrepreneur knows you have to try a lot of things that don’t work to find something that does. On top of that, smaller orgs have less people, which means there are less eyes critiquing your work. 

Starting a project that goes nowhere inside of a big company carries a career cost—your name and reputation become tainted when you’re attached to a dud. Maybe you’ll be passed over for a promotion or get dinged in a performance review. 

Their eyes lit up when I shared strategies for lowering the cost of failures in big orgs, such as:

  • Permissionless innovation: for low-risk projects, simply get started without telling anyone. If the projects fail, keep quiet. If the project brings promising results, then you’re safe to communicate upwards.
  • Everything is a pilot: “pilot program” is a magical phrase in that it makes it clear that what you’re doing is experimental and exploratory, which lowers expectations. Lowering expectations makes it easier to underpromise and overdeliver.
  • Portfolio-ize innovation projects: de-risk failure by managing several small experiments as opposed to major investment in a single experiment. Whichever of the small experiments show promise, re-invest.

The First Idea Isn’t the Final Idea

Most Navy personnel have never worked in Silicon Valley or software development. When I showed them the first iteration of some of the world’s biggest tech companies, their eyes went wide.

I get it. It’s hard to imagine world-changing companies such as Youtube, Twitter, and Shopify looking like a nights-and-weekends side project.

But these images don’t lie:

Youtube was a video dating site before it became the world’s biggest video platform
The original version of Twitter—a multi-billion dollar company with 240 million users—looks like a high school project
Before Shopify became the biggest ecommerce company in the world, they sold snowboards

These people from the Navy were used to messiness; life in the field and large-organization bureaucracy is rife with disorder and chicken-wire-and-duct-tape solutions. They expected the private sector to be tidy and orderly.

By the end of the day, they knew that entrepreneurship and innovation—in the form of building new products, speeding up communication inside an organization, and seeing the world through the eyes of a founder—involves the same sort of chaos.