When Darrick Ramsey first held the single dollar bill he’d been given, anxiety hit him hard. “I was very nervous, like I was anxious,” he recalls in an interview with Entrepreneur. 

Alexis Jordan had a similar reaction: “For me, I was very nervous,” she says. 

In February 2024, a documentary film team tasked these two students, along with about two dozen of their then-high school classmates, with an unusual challenge: Turn $1 into $100 in a week using all of the resources at their disposal. They started the challenge terrified of failing, then used their businesses, networks and hard work to turn $1 into far more than $100 in a week. A documentary film released last month called Learn to Earn: A Student’s Journey From $1 to $100 chronicled their experiences.

Both Ramsey and Jordan initially grappled not just with the math, but with the reality of trying to build something in “this economy,” as Jordan put it, where “what can you get for $1?” is a genuine question. The time frame added pressure: They had roughly a week, layered on top of school, sports and other commitments, to turn $1 into $100. “We had other stuff to do, so it was very time-consuming,” Jordan says. 

How Jordan flipped $1: services and Kool-Aid pickles

Once the shock of the $1 challenge wore off, Jordan went directly to the community she knew best. “My strategy was, where do people give the most money?” she says. “So for me, I was raised in a church; my church is like a big family. So I said, let me go to my number one supporters.” With that single dollar and her existing relationships, she offered labor and creativity instead of products she couldn’t afford to buy.

“Usually what I did was I cleaned their yards, I cleaned the church,” she says, describing how she exchanged services for donations and payments.

Then she layered on a homemade snack that became an unexpected hit: Kool-Aid pickles.

“It’s weird,” she says. “But a lot of people bought them. Everybody bought them, like everybody was going crazy over them.”

She explained the process simply: “You get the pickle jar, you pour out the pickle juice and then you just mix Kool-Aid packets and sugar with it, and then pour it back and let it ferment in the refrigerator for like a day or two, and then after that you put them in a Ziploc bag and you just sell them.”

With cleaning work for local small businesses and a snack that turned heads, she surpassed the $100 target.

Where she is now

More than two years later, Jordan, 19, runs a business called Blended Threads LLC, which centers on childhood diabetes, a condition she was diagnosed with in fourth grade.

She wrote a children’s book, Why Did Diabetes Pick Me, chronicling her struggles and how she overcame them. She is now working on a second book, this time a chapter book. She’s also a keynote speaker, turning her lived experience with juvenile diabetes into education and advocacy. 

“I wanted to broadcast and bring awareness to it, because you rarely hear anybody talk about childhood diabetes or juvenile diabetes,” she says, adding that people in her community were “shocked” to learn more and “glad” she published the book.

For Ramsey, the turning point came when he realized that the $1 was less important than the relationships he already had. He was part of the CEO program at his high school, and the program had taken students to tour businesses in the community. 

“We had a journal, and I wrote down each business owner, their name and their contact,” he says. When the $1-to-$100 challenge arrived, he asked himself: Why can’t I just reach back out to these guys to see if they can help me?

He recorded a simple one-minute video for those contacts: “I tried to keep it real short and simple, explaining, hey, my name is Darrick Ramsey. I talked to you in the CEO program before. I’m just wondering if you had any advice or if I can pressure wash your car or detail it for you,” he says. 

He had bought the power washer before the challenge with money from an hourly job.

The response was overwhelming. “I kind of overbooked myself with all the people that we had met and all the people they know,” he says. “I really got to see the community coming together. It was just great.”

He focused first on pressure washing and later added car detailing as demand grew. “It got to the point where I had to pressure wash in the cold, had to pressure wash in the rain; we had the car detail in the freezing cold, like cars were icing over as we were washing them,” he says, describing one of the busiest weeks of his life. By the end of the challenge, he’d far exceeded the target, earning $2,065. 

Where he is now

Ramsey, 20, was born in Decatur, Alabama, and moved between Chicago, Atlanta and Alabama before settling back in Decatur. He struggled “academically, financially” in school, which shaped his purpose now: “I feel like one of my life’s purposes has been trying to help the youth with what they do best, and keep excelling,” he says. He is a physical education teacher and mentor who “goes all over Decatur city schools” to connect with kids, pulling them aside to talk through “behavior issues and really just stuff I was struggling with.”

His business, PeerPressure, was born out of personal grief and bad influences in middle and early high school. After a close friend died the summer before ninth grade, he says, “I was peer-pressured into doing a lot of things that I really felt like I wouldn’t have done if I wasn’t around those bad friends.” 

In his sophomore year, with the help of teachers, he turned that story into a brand. PeerPressure now offers pressure washing, mobile car detailing, house washing and automotive light work, built over “about four years” and expanded through work with “many business owners within our community and outside of our community,” he says. 

His biggest challenge was internal

Ramsey says that he was his own “biggest enemy” solely because he didn’t really believe in community or family at the time. Academic and financial struggles left him feeling isolated and under pressure, which “created a lot of self-doubt” during that week.

Reaching out to people changed that perception. “They started showing me that I wasn’t alone,” he says. “Then I started to see a bigger vision.”

The lesson has stayed with him. He endured years of “long nights, a lot of crying, a lot of work.” Those years helped him define his purpose: “If I can change somebody’s life through teaching and mentoring, then I feel like I’ve fulfilled my purpose,” he says. 

This article is part of our ongoing Young Entrepreneur® series highlighting the stories, challenges and triumphs of being a young business owner.

When Darrick Ramsey first held the single dollar bill he’d been given, anxiety hit him hard. “I was very nervous, like I was anxious,” he recalls in an interview with Entrepreneur. 

Alexis Jordan had a similar reaction: “For me, I was very nervous,” she says. 

In February 2024, a documentary film team tasked these two students, along with about two dozen of their then-high school classmates, with an unusual challenge: Turn $1 into $100 in a week using all of the resources at their disposal. They started the challenge terrified of failing, then used their businesses, networks and hard work to turn $1 into far more than $100 in a week. A documentary film released last month called Learn to Earn: A Student’s Journey From $1 to $100 chronicled their experiences.