The Nigerian Rapper Who's Building the Next Silicon-Valley Unicorn

The Nigerian Rapper Who's Building the Next Silicon-Valley Unicorn

By Taylor Mayol

Debo Olaosebikan
SourceMark Madeo for OZY


Because no less than the future of work is at stake.

By Taylor Mayol

Debo Olaosebikan decided to move to Silicon Valley on a Tuesday. By Friday he was crashing in a tiny apartment in East Palo Alto on a shoestring budget. Then came stints sleeping in his cousin’s dorm at Stanford and at his sister’s pad. Three years later, he’s running a company with backing from the Valley’s most elite — Andreessen Horowitz and Y Combinator — that has been named to Forbes and TrueBridge Capital Partners’ list of the next billion-dollar startups.

Olaosebikan, 31, is the cofounder and chief technology officer of two-year-old Gigster, an on-demand service for software development and design connecting a network of vetted freelancers with companies that need their talent. He is, in other words, incarnating the programming-gig economy and already boasts a client roster including companies like Square, MasterCard and Airbus. With revenue climbing from $1 million to $30 million in the last two years, the founders are optimistic. 

It’s a familiar notion, by now: Work is “increasingly getting disaggregated, being dispersed beyond the organization,” says Ravin Jesuthasan, coauthor of Lead the Work: Navigating a World Beyond Employment. Some call it the Fourth Industrial Revolution. Thumbtack, TaskRabbit and Lyft have all been able to cash in on the gig economy, offering platforms for contract labor for plumbers or drivers. Gigster’s focused on winning the hearts of the programming-freelance economy. In a creepily Silicon Valley–mindfulness turn of phrase, Lagos-born Olaosebikan explains that the 1,000 or so Gigsters (around 700 of whom are developers) on the platform earn or lose “karma” for hitting or missing deadlines, using positive language in the messaging platform Slack or reaching milestones early. Between 60 and 70 percent of Gigsters are U.S.-based, but Olaosebikan is proud that the same rate applies to coders regardless of location. He says some of his Nigerian buddies back home have relied on Gigster to fully fund their own projects, and he brags that a Nepali Gigster made enough money in a year to quit his regular job.

In 2011, Olaosebikan left his Ph.D. program in physics at Cornell; at Cornell, the fourth-year-grad student co-led a $6 million Department of Defense–funded project with MIT, Caltech and Stanford to build an electric silicon laser, part of an effort to create light-based computers. Oh, and before that he was a radio-featured rapper in Nigeria — though he likes to say he isn’t retired, just busy for now. He started writing raps, about social issues or for pure entertainment, as a preteen, preferring their relatability to obtuse poetry. 

Born to a doctor and a chemist — entrepreneurs themselves who run a hospital, health magazine and branding firm — Olaosebikan self-describes as a child fascinated with tinkering. He dreamed of one day having a law named after him, à la Moore … or Newton. In his mind, he needed the U.S. to make his dreams a reality, to “contribute to humanity,” he says. (He has a fondness for grandiloquent speech.)

Though he found himself in the lab, building on his undergrad physics research, the laser wasn’t the “big idea” he always dreamed of, he says. The doctoral program gave him space and some income to consider what that might be, but as each year ticked by without the “aha,” he felt like he was failing. (On paper, he did not fail: He made discoveries related to stimulated emission, the first stage of getting to a silicon laser.) Soon enough, he says, he realized that the “awesome magical stuff” he wanted to make would come not in the form of scientific journal publications but in a company. 

Debo olaosebikan 5641

Debo Olaosebikan

Source Mark Madeo for OZY

An employment startup may seem less rigorous, on face, than advanced physics, but Olaosebikan says he hews to scientific rigor even while juggling the qualitative elements of the business world. For Olaosebikan, that means personally interviewing candidates, coming up with algorithms for rating Gigsters and leading what will be known as Gigster’s R&D lab, incorporating machine learning and artificial intelligence into its portfolio. Cofounder Roger Dickey refers to Olaosebikan’s “independent contrarian” way of thinking.


Of course, Gigster is far from the first or only player in this game, notes Rick Devine, founder of TalentSky and a longtime Silicon Valley recruiter. And because many Gigster projects cost between $45,000 and $90,000, with average teams of three to five people, “they’ll never compete with the big guys” like Accenture and Upwork, he says. And then there remains the complicated legal and ethical landscape of the post-traditional-employment economy, says Jesuthasan. Uber and its ilk have been facing questions like whether contractors will become 1099 employees entitled to full benefits — something that may not apply to Gigster’s community of white-collar workers. But Gigster freelancers may bring their own legal burdens — some work nine-to-five jobs at companies like Facebook or Google and moonlight on the side, raising issues of intellectual-property lawsuits or conflicts of interest. (Olaosebikan says, for his part, that they ensure Gigsters are either not working on any directly competing projects and/or they are helping in other capacities, like with interviewing, code reviews and project management.) To help stave off some of those worries, Gigster recently launched a fund to give its freelancers access to equity in the companies the fund invests in.

But the biggest challenge Olaosebikan sees is the gulf between talented coders and people who want to hire them. The talent is there, he notes, but the reason people like him and Dickey don’t freelance is the headache of raising one’s hand and waving over the work. That money might have served him well back when he was living on $600 a month in the money-leeching Bay Area. Since then, much has changed. But some old habits die hard. His current residence? Crashing with his cofounder between leases. This time, though? In a moneyed San Francisco pad.