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.”
By his own admission, it remains his biggest regret.
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.
Long before the passport, there was a market in Lagos
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.
A tweet, fifty replies, and an agency he never planned to start
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.”
Trading a content agency for the US
Even as JDI expanded, Otomiewor continued balancing the agency with full-time employment and freelance work rather than choosing between them.
He said that after his daughter was born in 2019, fatherhood became his primary focus while JDI supported the family financially. Outside employment, he said, became something he pursued “for the passion, not the money.”
According to him, it was during that period he bought his first property in Lagos.
In 2022, he returned to paid employment, joining Bluecap AI, a Canadian company, as a product marketer after being recruited through his Upwork profile.
He said the salary was not the main attraction. Instead, he wanted to understand the rapid advances in artificial intelligence before they reshaped marketing and content creation.
“Having access to AI at Bluecap was very important for me career-wise,” he said. “Because it showed me what was coming, [and] how to prepare for it.”
Looking back, Otomiewor said that experience became one of the reasons he later decided to pursue business school.
Around the same period, he also worked as Senior Manager for Market Intelligence and Product Strategy at BitForex, a China-based cryptocurrency exchange. According to him, he led a 15-person team across three countries and helped secure a $50 million strategic partnership that generated an additional $10 million in revenue.
In 2022, he also co-founded Edaki, a startup that has since shut down, with an India-based entrepreneur he met through an online founders’ community.
According to him, he spotted a problem where African tech coverage skewed overwhelmingly toward payments companies—a Paystack, a Flutterwave—when there was a bigger, unaddressed opportunity in democratising access to startup investment itself, for founders and first-time investors alike.
He said that Edaki matched 30 early-stage startups with first-time investors, managed a $2 million portfolio, and built project management and marketing pipelines for 15 SMEs that increased conversion rates by 30%, with cross-functional growth work generating $10 million in annual revenue across the startups it supported.
It was also during this period that Otomiewor was diagnosed with cancer.
He went on to beat cancer, but he said that the drastic health change motivated him to achieve his many life goals sooner; one of them was going back to school.
“If I wanted to die, I wanted to read my name with an MBA [Master of Business Administration] at the end of it,” Otomiewor said.
While recovering from his health challenge, his first introduction to business came from a book. Soon, he wanted the real thing: he enrolled and was admitted to Rochester’s Simon Business School in New York and NYU Stern in New York, but chose the University of Georgia’s Terry College of Business in Georgia, all in the United States.
He said he was drawn by the school’s fully funded scholarship offer, its track record with Nigerian graduates, and its location in the American South.
“In Nigeria, at the time, I felt like I’d been living the Lagos dream,” Otomiewor said. “You have your own house, your own nice car. Technically, you could just coast through life. I just didn’t want to coast through life.”
He now holds a full-tuition scholarship, alongside the Terry Excellence Fellowship and the National Black Fellow Scholarship, and is completing a dual MBA in strategy, marketing, and management, alongside a Master of Science in analytics.
Otomiewor boarded a flight to the United States on July 20, 2025. By then, relocating was no longer the defining move of his career; it was closer to the next chapter of one he had spent nearly a decade writing.
The move forced one decision he had managed to avoid while juggling multiple ventures from Lagos: visa restrictions on international students meant he could no longer legally run a business on the side. After nearly eight years, he handed JDI over to someone else to run full-time, he said.
In its place, he has built a new set of commitments. Alongside his coursework, he is three months into a project management internship at Peterbilt Motors, a company he noted whose trucks are a familiar sight on Nigerian roads, even though its scale in the US dwarfs what he had imagined.
According to him, he’s also building Aarin, a travel-focused venture that was born from his travelling experience through Lagos, Cape Town, and now the American South, and beyond.
“There are only things you can dream of based on your environment and your experience,” he said. “I could only dream of creating a company that would change how people see the world because of how I’ve seen the world myself.”
For Otomiewor, migration gave him access to a different calibre of network than he was used to in Lagos; he secured mobility credibility that has allowed him to travel further and have conversations around investment that were harder to have in his home city.
“It doesn’t matter if you want to stay back in Nigeria. If you want to travel, that’s okay too,” he said. “But it’s always good to see the world, because it changes how you think, what you think is possible, and how you approach solving problems.”
The Internet helped Otomiewor build a global career without ever leaving Lagos. But migration to one of his preferred countries is taking it farther.
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I am the CEO of 9JAGISTLAND.My name is Adedeji Timothy and my co-owner is Oyekola Damilare.This blog is born out of our passion to educating to people in all aspect of internet life.We are enthusiastic about writing posts and articles online.
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