As a young woman, Brandi Tillman never thought of herself as a financial role model.

Growing up in Chicago, she was raised to believe that navigating the financial world was a task that was best left to men.

“I know firsthand, boys in my family are taught to save money," says Tillman. “Work a job, save money, 'this is how you get a house, this is how you get a car.' The girls [weren't] taught that [as much]."

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Orlando Madison believes in second chances.

But for him, a 50 year-old Arkansas native, his second chance has been a long time coming.

In 2003, after serving a six-and-a-half year sentence for a drug felony charge, Orlando returned to his hometown of Benton, Arkansas, determined to make some big changes.

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Natasha Rossi believed she had the perfect life.

She had two awesome kids — two and a half-year-old identical twins — and the love and support of her boyfriend, Desi. Life, she thought, could only get better.

All photos via Upworthy/Walgreens.

Then, in January 2019, she was hit with some of the hardest news that anyone can hear.

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