Leadership

This simple tactic helped a CEO sell his business for $1 million at age 21—here’s how to do it

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John Henry, co-founder and co-CEO at LOOP.
Greg Doherty | Getty Images Entertainment | Getty Images

Hardships and setbacks can make it difficult to give 100% at work — unless you find a way to use them to your advantage.

John Henry, co-CEO and co-founder of startup Loop Car Insurance, says he's proof: Growing up, he was more concerned about helping his struggling family than positioning himself to launch a startup someday. Using his background to influence his strategic decisions benefitted him more than an MBA ever could, Henry recently told LinkedIn's "The Path" podcast.

Specifically, his teenage solution to his family's financial woes — a dry-cleaning company — sold for $1 million in just three years, setting him on the path to serial entrepreneurship, Henry said.

"I grew up born and raised in New York City, and I come from an immigrant family from the Dominican Republic," said Henry, 30. "Seeing my mom and pops constantly struggle to make rent and also meet the financial demands of having four young children ... Being exposed to those pressures made me feel like I really wanted to help out."

At age 18, while in college, Henry took a job as a doorman to ease the burden on his custodian mother and his dad, a presser at a local dry cleaner. As a doorman, he connected with a resident who ran a different dry-cleaning company, and offered to teach him the economics behind the business, he said.

After getting fired from his doorman gig, Henry realized he was learning more at the dry-cleaning company than at school, so he dropped out, he said. "Entrepreneurs don't make for good employees," he told CNBC Make It via Instagram, adding a laughter emoji.

But when another resident reached out to him with a laundry opportunity, he knew his dad was the man for the job. "Turns out, he knew the wardrobe supervisor of the 'Wolf of Wall Street' movie, and they were looking for a new dry cleaner," Henry said on the podcast.

Pleased with the work, the wardrobe supervisor recommended Henry's dad to NBC's "Law and Order." So Henry created a new dry-cleaning business, hired his dad and took on the television job — leading to more entertainment work, including "The Amazing Spider-Man" and HBO's "Boardwalk Empire."

After three years, Henry sold the company to one of its vendors for $1 million, Forbes reported in 2016. Dry cleaning was never Henry's passion, and it embarrassed him growing up, he said. With the money, he created a tech nonprofit in New York's Harlem neighborhood, later turning to venture capital investing and co-founding Loop in 2020.

How to use your 'onlyness' to get ahead

Using your life's experiences as a source of creativity and financial inspiration is a smart tactic, leadership advisor Nilofer Merchant said on the podcast. She referred to it as embracing your "onlyness," a term she coined.

Your experiences and background shape "what you care about" in your career and why, Merchant said. She recommended asking yourself:

  • What five events in your life have formed and informed you?
  • What have you decided because of it?
  • If you could solve anything, what would it be?

"What I'm actually doing [by asking these questions] is drawing a through-line by saying, 'What brings you to today? And where do you want to grow and become?'" Merchant said.

Turning setbacks into success is easier said than done: Stress can contribute to focus problems, burnout and limited productivity. Lean on your support system, and find at least five people you can always vent to and feel accepted by, Merchant advised.

"The key is, do we have five people on text? Do we have five people that we can turn to over a Sunday brunch and go, 'OK, I'm struggling with this thing. Help me figure it out,'" she said.

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