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Overcoming Adversity: 5 Founders on Surviving Their Greatest Defeats

Illustrated portrait of five business founders

Failure is just part of it. It goes hand in hand with success. It is the mechanism by which we learn, pivot, and become stronger. There is no better evidence of the power that failure holds than in the trajectory of small business owners, many of whom leap into a passion or a big idea without all of the answers—or the money. Some of the great entrepreneurs of our time pocketed a mountain of bad ideas and bad credit before building their legacies.

Reaching the other side of failure, overcoming adversity, is the harder part. In our series, Overdraft, we asked successful business owners about their most spectacular defeats—something we rarely talk about—and how they survived them. Some took on massive debt. Some sold all of their belongings. And others risked everything in the pursuit of something better.

These founders—floral designers, beauty influencers, breast cancer survivors, and Army vets alike—all share one thing in common: through failure, they’ve now achieved their own definition of success. And, they shared with us their vulnerable moments of financial hardship and lessons learned on their way back to black. 

Explore our top five stories about overcoming adversity.

1. Melony Armstrong on making something from nothing

Melony has been in business for 20 years—and she never once took money from a bank. There was a downside to bootstrapping, though. Melony built her business from her home’s tiny living room while her family lived paycheck to paycheck, getting by with a lot of faith and some timely kindness from strangers. She eventually saved enough to open her hair braiding salon, Naturally Speaking. But her biggest accomplishment was her advocacy work that helped change Mississippi law and pave the way for hundreds of other businesses.

Read Melony’s full story.

Those times, I’d say they were some of the best couple years of my life even though they were so difficult.

Benjamin Sehl

2. Benjamin Sehl on faking it (and making it)

Ben once walked 70 Brooklyn blocks at midnight when he didn’t have enough money to pay for transit to get home. It was a low point for a guy who admits he grew up pretty privileged. After losing his New York job, Ben moved back to his native Toronto—to live in his future in-laws’ basement. That space would eventually become the incubator for his sustainable cotton clothing line, KOTN.

Since then, Ben grew that dream out of the basement and into a multi-location global brand. But in the early days, he and his two business partners did what they could to find their footing—including signing a major wholesale deal for baby clothing before they even had the product designed.

Read Ben’s full story.

Ad for Overdraft series: stories of financial hardship and overcoming adversity

3. Jenn Harper on being a role model

Jenn understood the negative stereotypes plaguing her Indigenous community. When she fell into alcoholism and learned that she was a product of generational trauma, she decided that it was her role to help change the narrative—and to be a role model for Indigenous youth.

She achieved sobriety in 2014 and took steps to start her own business. With a mere $500 investment, her thriving sustainable cosmetics brand and social enterprise, Cheekbone Beauty was born. She recently quit her prosperous career to pursue the business full-time—and is facing the uncertainty of living on a fraction of her previous income.

Read Jenn’s full story.

4. Vivek Jain on rethinking your values

After achieving the dream—marriage, kids, a lucrative job in his field, a life in a tropical paradise—Vivek found himself back at square one, starting over. He was in an unfulfilling job and his marriage had fallen apart. The former venture capitalist’s money was then tied up with a divorce that dragged on, and he was forced to move back in with his parents.

Vivek’s definition of success changed with that experience. After a personal growth spurt, he decided to make career moves that made him happy and gave him more time with his kids. One of those moves was a financial flop, but introduced him to people who would eventually become his business partners.

Read Vivek’s full story.

I’m uncomfortable all the time. But it’s fulfilling in a way that no other job has ever been to me.

Natalie Gill

5. Natalie Gill on perspective

The worst day for Natalie now is better than her best day working at a desk job. When the gruelling San Diego commute and mind-numbing work became just too much for her, Natalie decided to make a change. She quit her job on a whim to pursue floral design. It was a major departure for the psych major who intended to apply for her PhD. But she spent her meagre savings, trained with a pro, and put up a Yelp page to launch Native Poppy from her apartment.

Years later, her blooming floral business occupies two storefronts and she now has a business partner. Her wins often came at a cost to her mental health and her debt load, but, “I’m just finding joy in the world,” she says, “and that’s success.”

Read Natalie’s full story. 

Illustration by German Gonzalez