The grit of a tycoon: Obama's journey from village truant to car yard king

Obama was not the most disciplined boy in Girigiri village in Kuria, Migori county.

He was known by nearly every inhabitant of that small village, and he had developed a habit of sneaking in and out of class through windows while teachers were writing on the blackboard.

Villagers often saw him roaming when other children were in school, but there was usually a reason.

Sometimes, he had been sent home for lack of fees; other times, he was fetching firewood or working on his family farm. The farm work was the only reason everyone knew was genuine.

“In the mornings, we were woken at 5am to go to the farm until around 9am. I’d take a quick bath and rush to school, sneaking into class at the right moment,” Obama recalls.

Born Nyaiboye Charles Robi in 1984, he grew up in a polygamous family with over 30 siblings. His education became more challenging after his father married a fourth wife.

In 1999, Obama joined Matare Boys High School, a day school, trekking 12km daily. But when Form 3 and 4 required boarding, he had to move to Siria High School in Trans Mara, Narok county.

His mother struggled to pay his fees and rent for a shared house with two other boys.

To support himself, he worked during weekends at Maasai Mara, loading gravel onto lorries from which he earned Sh200 to cover food for the week.

These early hardships taught him resilience and instilled a promise: his children would never endure what he did.

After high school, he returned to Girigiri and opened a small retail shop, which did well until thieves stole nearly everything. With only Sh600 and two sets of clothes, he left home for Kericho, determined to start life afresh.

He arrived tired and hungry, spending the night in a disused Telekom call box. The next day, he began hawking pineapples.

Through hawking, Obama met a former classmate who introduced him to selling small merchandise like pens, socks, and handkerchiefs.

The job involved traveling to towns including Kisii, Sotik, and Kisumu, often staying in guest houses provided by the company.

Observing wholesale operations in Kisii, he began buying pens himself and selling them at a profit, which led to his dismissal but also marked the start of his own business.

Obama’s entrepreneurial journey expanded across Kenya—Kakamega, Kitale, Kisumu, Nairobi, and eventually Mombasa—where he became one of the largest wholesale merchandise sellers.

 Later, he transitioned into insurance sales, but when the company failed to provide promised accommodations in Garissa, he reverted to merchandise sales.

With Sh20,000 saved and a friend’s support, he rented a shop in Mombasa and borrowed Sh150,000 to stock merchandise.

His business grew steadily, eventually becoming one of the city’s major wholesalers.

Faith played a significant role in his journey.

Through church, he met car dealers and became interested in the trade.

He borrowed Sh300,000 from his wife to buy his first car, a Toyota Vitz, which he sold at a profit. His second car, a Toyota Spacio, further solidified his reputation.

Challenges continued. Once, while withdrawing Sh415,000 to buy stock, he was abducted by thugs outside the bank. They took away the cash.

Strangers in Eastleigh, recognising him from business, generously provided merchandise on credit, allowing him to recover.

Back in Mombasa, he suffered a financial setback when a client defaulted on a Mitsubishi Lancer sale, but these hardships only strengthened his resolve.

With resilience and mentorship from friends like Anthony Kimani, Obama became the third African to start a car yard in Mombasa, a trade once dominated by Indians, Pakistanis, and Arabs.

Today, he owns seven car yards across Mombasa with about 300 vehicles, both new and used.

Beyond business, Obama mentors his employees to become entrepreneurs, just as he had been guided in his early days.

“I don’t want my employees to be simply be employees. I want them to be entrepreneurs, so I hold their hands, just like some people held my hand in their small ways,” he says.

Faith continues to guide him. Grateful for the role of church in his life, he started the MarketplaceFellowship, a weekly gathering for car dealers to praise, worship, and share experiences.

Different preachers volunteer during the sessions, held rotationally at various car yards, blending entrepreneurship with spiritual growth.

Obama’s story is one of grit, resilience, and self-belief.

From sneaking into school through windows to hawking pineapples, building a merchandise empire, surviving abductions, and eventually becoming a car dealership tycoon, his journey underscores a simple truth: determination and faith can turn even the toughest beginnings into extraordinary success.