Digital Nomads: Eseandre Otomiewor built a $100,000 business. Then started over in the US.
Somewhere in Eseandre Otomiewor’s memory is an alternate version of his life in which he is, by his own joking estimate, a billionaire.
Somewhere in Eseandre Otomiewor’s memory is an alternate version of his life in which he is, by his own joking estimate, a billionaire.
It began years ago when a client on Fiverr offered to pay him in Bitcoin instead of cash. Otomiewor declined. He wanted dollars, not a volatile cryptocurrency that, at the time, most of his family, friends, and clients barely understood. It was not an isolated offer. He said other clients proposed the same arrangement, and he turned each of them down.
“I think [my] story should be [about] the man who should have been a billionaire [and] accepted Bitcoin; I said no,” he told TechCabal, laughing at his own expense. “In hindsight, maybe I would have a lot of money by now. But you know, we’re still good. When you’re where you are right now, it’s easy to look back—but it’s never easy.”
It is also, in an unexpected way, the quickest route to understanding him: someone who has spent the past decade making uncomfortable bets on himself—underpricing his work as a freelance writer to build a reputation, walking away from a company he built from a single tweet, and leaving a comfortable life in Lagos, Nigeria, for the United States (US)—and, more often that not, seeing those bets pay off.
Today, Otomiewor is far removed from his early days as a freelancer. After securing a fully funded scholarship, he moved to the US in 2025, where he is pursuing a dual master’s degree.
His career had crossed borders long before he did. From Nigeria, he built a client base spanning China and the US without ever setting foot in either country. Now, he is building the next chapter of his career from the latter.
Otomiewor graduated from Delta State University in Abraka, southern Nigeria, in 2014 with a degree in international studies after his original ambition to study law “did not pan out.”
Although international studies was not his first choice, he said the discipline gave him “a much broader perspective to life, creating, and writing,” a foundation that helped him build a freelance writing career that afforded him a comfortable life in Lagos, Nigeria, before eventually taking him abroad.
His first job after university was at WuraTV, a US-based streaming platform owned by a Nigerian entrepreneur that distributed Nigerian and African content to audiences in the diaspora.
Otomiewor recalls that the company saw itself as the leading competitor to New York-based BET at the time. From there, he moved into a business strategy role at Maliyo Games, a Nigerian independent game studio. The job occasionally took him beyond the office.
To promote Maliyo’s mobile game “Aboki Run,” Otomiewor said he visited Computer Village and Alaba International Market in Lagos—two of the city’s largest electronics and phone-repair hubs—and persuaded phone vendors to pre-install the game on customers’ devices before they left with newly purchased or repaired phones.
According to Otomiewor, his manager at Maliyo Games doubted the idea and declined to allocate a budget for it. But the strategy proved successful enough that, he says, the company’s founder eventually drove him to Alaba to watch the pitches himself before later attempting to recruit him to another company.
“I’m not someone to just sit down and watch things happen,” Otomiewor said. “Sometimes you’ve got to try things that are not conventional to make a change.”
By December 2017, he had moved again, this time to Digital Raves, a company that helped businesses expand into diaspora and Middle Eastern markets. That same month, almost as an afterthought, he created an account on Fiverr, the global freelancing platform.
Otomiewor had been writing since university, mostly producing academic papers for other students, and Fiverr felt like a natural way to turn that skill into income. What he did not anticipate was how quickly demand would outgrow his capacity.
Client requests began arriving faster than he could handle. One day, he posted what he describes as an “innocent” message on X, asking whether anyone wanted to take some of the overflow. He expected two or three replies. According to him, more than 50 people responded.
“It wasn’t pre-planned,” he said. “It was something that just happened and became very big.”
He named the business “JDI,” short for “Just Do It,” a phrase loosely inspired by Nike. What started as a way to outsource a handful of articles became a content agency that, over eight years, trained and paid more than 8,000 African writers, according to Otomiewor.
He said many alumni went on to work at Nigerian and international media organisations, while others secured roles at global companies, including Amazon.
Having helped Nigerian writers access overseas clients also exposed what he believes was the industry’s biggest obstacle.
“It was not a skill thing,” he said. “Nigerians here in the US, globally, have the same skill set. [But] we have to work ten times as hard as another person just to get the same opportunity.”
According to Otomiewor, Nigerian freelancers on platforms such as Fiverr were sometimes overlooked in favour of equally qualified Western writers for reasons unrelated to the quality of their work.
Even competing internationally required significant upfront investment: a virtual private network (VPN) to bypass geographical restrictions, an international payment solution and a reliable laptop—costs that many aspiring freelancers could not afford.
Rather than compete on prevailing Western rates from the outset, Otomiewor deliberately charged less to establish credibility.
“If [it’s a gig] an American would charge $20 for, I’d charge $5,” he said. “Do not look at what someone in America or the UK earns. Ask yourself how you can build a reputation to scale.”
He said the strategy worked. Repeat business became common, new clients continued to arrive through referrals, and the lower prices helped him establish a reputation before gradually increasing his rates.
According to Otomiewor, his Upwork account generated about $250,000 in lifetime earnings. He said his first Fiverr account earned nearly $400,000 before it was permanently suspended following a mistake made by one of the writers working under him. After opening a second account, he said it generated an additional $27,000.
JDI also expanded rapidly. Before the COVID-19 pandemic, Otomiewor said the agency generated about $100,000 in annual profit. As lockdowns pushed more businesses online and demand for content surged, he said weekly profit reached at least $3,000 during its strongest periods, lifting annual profit by about 30% to between $130,000 and $140,000.
“Pandemic was a good time for me to reset,” Otomiewor said. “I know it was a bad time for a lot of people, and I don’t want to be insensitive, but we didn’t have issues at JDI. We scaled at that time.”
