Meet the Self-Starting Millennial Who’s Mentoring the Next Generation of American Leaders

Daquan Oliver has entrepreneurialism in his blood. When he was a cute third-grader living in New Rochelle, N.Y., his mother Alison found out that he’d been wandering in a nearby housing project selling copies of “The Money Saver,” a free newspaper stuffed with coupons, door to door. “He’s trying to make his own money,” said one woman who had handed Oliver a five-dollar bill, “and I applaud him for that.”
In middle school, Oliver used his enterprising spirit to talk his way out of assignments. “With him, everything’s negotiable,” one teacher vented to Alison. But as a single mother who’d gotten pregnant at age 17 and was now working low-wage jobs around the clock, Alison wasn’t going to let her son get away with skipping homework. “You have two strikes against you. One, you’re African American. Two, you’re an African-American male,” Alison warned him. On top of his schoolwork, she assigned monthly book reports and made him copy words from the dictionary and write his own definitions in a composition notebook.
By senior year in high school, Oliver ran his own business. He bought Pop-Tarts, Capri Suns, candy and chips in bulk at Target, and three “employees” sold them to classmates, netting $1,000 in profit each month. Four years later, in 2014, as he was set to graduate from Babson College, a Massachusetts business school well known for incubating startups, Oliver founded the nonprofit WeThrive, to bring together middle and high schoolers and college students for near-peer mentoring, a model where both parties can connect emotionally over present challenges, not just distant objectives. Now 24, Oliver works in Los Angeles’s Silicon Beach and hopes WeThrive participants internalize the same lessons in entrepreneurship that helped him break the expectations of his upbringing.
For kids 13 years old and up, WeThrive’s mentoring program consists of at least eight weekly, 90-minute sessions on entrepreneurship. So far this semester, more than 100 have signed up to work with college students from Columbia, Cornell, Syracuse and the University of California, Los Angeles. Oliver thinks children learn best when doing, so the course is focused on launching an actual business. By the second class, groups “choose a problem that has a product or service-based solution,” and they have until the end of the semester to turn it into a working business model, Oliver says. In the past, one cohort founded UNI, an anti-bullying nonprofit, and sold water bottles that changed colors based on temperature and were emblazoned with the slogan “Be the Change.” Another started an apparel company called Difference that prints T-shirts with multicolored bar codes as an expression of individuality.
A typical WeThrive class might focus on finding a target market. Avoiding business jargon, the mentors ask: What what kind of customer would like to buy their product? A silent leader (who is discretely chosen by the mentor at the beginning of each class) manages the discussion and keeps everyone focused without calling attention to herself. Ninety minutes later, the kids fill out learning logs, writing one piece of knowledge they gained that day, how it applies to their life and how they will implement it through the next week.
Oliver wants students to learn goal setting, public speaking and personal finance, and lessons on these topics are reinforced week after week — like his mother’s vocabulary teachings — until they become habit. It doesn’t matter whether a business model finds financial success. What’s important is that those involved learn how to lead a team, assemble a team and can speak publicly about their business so that others believe in the concept and the vision.“This isn’t about creating a business; it’s about honing skills required to enter a lifestyle, so to speak.”
Oliver also wants to see them develop an emphasis on doing social good. So he seeks out participants who would have founded WeThrive if he hadn’t done it already, the students who are passionate about giving back but need a platform to get engaged.

Although Oliver starter WeThrive just two years ago, the idea for the nonprofit started percolating when he was a 14-year-old, a time that can be described as the worst of his life. His mother lost her hourly job, and while she looked for new work, she sent Oliver to live with his grandparents. The family soon didn’t have cash for deodorant, so he started dodging sports practice at a summer enrichment program. Several times, he and his mother skipped meals.
“He started getting that hopeless feeling. He was worried about the next move, how things were going to change, if they were going to change at all,” Alison recalls. “The situation, it kind of placed him in a position where he had to be a grown-up for a little bit. And when I say grown up, I mean as far as his thoughts, as far as processing things.”
Late one night, Oliver couldn’t fall asleep. He felt sick, sweating in his sheets. Normally a happy-go-lucky kid, his mind kept replaying how many hours his mother worked and how little her hard labor paid off. But in a sudden epiphany, he realized it wasn’t his mother’s fault. A structural barrier had “always been holding us here.” He promised himself that he would overcome it and return home to assist those like him.
That moment was where Oliver first came up with his definition of entrepreneurship, a broader approach — a lifestyle, really — beyond simple business advice. “Turning obstacles into opportunities,” he phrases it, adapting Niccolò Machiavelli’s definition from “The Prince.” “Every time I see a challenge, I think entrepreneurially about it and think my way through it.”

As WeThrive expands across the country, Oliver is looking for a way to beef up the curriculum’s incorporation of the latest technology, such as offering intros to coding or hosting off-site discussion via Slack. And he’s introducing more behavioral metrics to see if the lessons are changing behavior. Are kids reading more for pleasure, for instance, and do they feel they have a positive influence on their peers? Oliver admits it will be nearly impossible to gauge whether WeThrive has an impact on grades or graduation rates, since there’s a myriad of factors that affect academic success, but he hopes to determine whether entrepreneurship is becoming part of his students’ daily lives.
One can wonder if, in creating WeThrive, Oliver simply put together the education he wished he had on those tough days at his grandparent’s house in New Rochelle. But Oliver disputes that. “Maybe if I had this program, I wouldn’t be able to do the things that enabled me to live out my dreams.”
Oliver has seen more ups and downs than most who are twice his age. He knows what failure looks like; it surrounded him in his neighborhood and his high school classes. But at WeThrive, he’s getting — and sharing — a glimpse of success.
MORE: This 23-Year-Old Has Figured Out a Way to Make Kids Want to Attend Summer School