Veterans are no strangers to crushing entrepreneurship. Stepping out of combat boots and into bootstrapping businesses, vets owned nearly 2 million businesses and employed more than 5 million workers in 2018, according to the US Small Business Administration.

Margo Jordan exemplifies this by prioritizing a mission to boost self-esteem among children.

She founded Enrichly, a gamified self-esteem learning platform.

The 35-year-old joined the military after high school to get an education outside the classroom. “I saw a major opportunity for my own personal development,” she said.

She honed leadership skills and self-discipline in the US Army from 2007 through 2015, while also getting an education inside the classroom, too.

Balancing military and higher education pursuits between 5 a.m. and 8 p.m., she trained, hit the classroom and toggled back to training at night. “It was a hefty schedule, but I managed it all,” Jordan said.

After graduating with a bachelor’s degree in finance in 2013, she landed an investment-banking job in Houston. However, “I realized quickly that was not the right career for me,” she said. “I’m a numbers girl, but I had this fire in me. I want to do something better for the world.”

Jordan had lost a few friends to violence and suicide back in Milwaukee where she grew up, and recognized low self-esteem as a common root cause.

To help young girls avoid negative outcomes, she launched a learning center in Houston. She later expanded it to include boys, ultimately reaching 10,000 kids before 2020.

The pandemic meant switching to a digital-learning platform, which 200,000 kids currently log onto.

Paid subscriptions are funded through school districts, youth-focused organizations, health-care foster homes, the Abu Dhabi Early Childhood Authority and more.

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Big businesses are taking notice, too — over the past few years, the platform’s received funding from super angels such as Google, IBM and Microsoft, to name a few.

Over 50 games are available, as well as courses, prerecorded webinars and content with guest speakers, such as actors from the Disney series “Raven’s Home,” who in 2021 talked about how social media impacts self-esteem.

Working alongside a team of 17 people including an educational psychologist who’s also the company’s co-founder and COO, Jordan eyes the big picture.

“It’s not only for improving self-esteem in an individual, but really solving major problems that our society faces — youth violence, low academic achievement and poor mental health,” she said.

For instance, in the game “Defeat the Dragon of Negativity,” children recognize negative versus positive statements regarding goals they’re trying to achieve.

After a game or lesson is completed, they earn digital badges that are housed on the platform as the site simultaneously measures outcomes.

Creating a game for parents to develop self-esteem and launching an app are currently on tap for the expanding platform.

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Through it all, Jordan credits the military for developing and honing her vital skills of self-discipline and adaptability.

“Everything is constantly changing in the world of startup land,” she said. “I’m so grateful — there are so many founders that I meet who don’t have the same training that I received in the military. The military gave me a certain skill set that I just don’t think one would get anywhere else.”

Jocko Willink no doubt would agree. He served in the military for 20 years and retired in 2010 as a lieutenant commander in the Navy SEALS, where he was responsible for training and preparing troops for deployments to Iraq and Afghanistan and leading them into combat.

During his military service, the 52-year-old co-founder and CEO of leadership development company Echelon Front learned how to have “an open mind” and “adapt to the changing battlefield, environment and enemy.”

Upon his military retirement, Willink didn’t have a clear vision for his future other than spending time “surfing, hanging out with my family and doing jiujitsu.”

Then, after speaking with leaders in the civilian sector, he had a lightbulb moment.

“I realized that all the leadership principles I had applied myself, and taught to others while in the military, were directly applicable to all leadership scenarios, in any industry, at any level of leadership,” said Willink.
As he dove into entrepreneurship, the former Navy SEAL officer found having an open mind was critical to learning and adapting.

“The minute you think you know something, you don’t. So instead, I was always suspicious of myself,” said Willink. “I was constantly thinking and asking myself, ‘What am I missing? What don’t I know? What don’t I see?’ ”

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Now, he’s the host of the “Jocko Podcast” and co-author of the best-selling book, “Extreme Ownership: How U.S. Navy SEALS Lead and Win” (St. Martin’s Press).

He’s also a MasterClass instructor of critical leadership thinking, for which he relies on strong military acumen by taking complex challenges and simplifying them into something that all levels of a team can understand.

In his new MasterClass, the San Diego, Calif., resident outlines four laws of combat leadership: cover and move, keep it simple, prioritize and execute, and decentralize the command so everyone leads.

“The stereotypical leader — both in the military and civilian sector — is someone who barks orders and tells everyone what to do,” Willink said. “But that type of tyrannical leadership is not good. Good leaders listen, take advice and put their team and mission above all else.”