At 3 AM, the problems are waiting. Every successful entrepreneur knows this hour, when sleep breaks and fear floods in, when you lie awake questioning the decision you made yesterday, the contract you signed last month, the investor you brought in last year. This is the reality nobody talks about in business school or on magazine covers.
Four African entrepreneurs gathered to break that silence. Between them, they’ve built companies worth hundreds of millions of dollars, expanded across multiple countries, employed thousands, and lost almost everything at least once. What they shared wasn’t a success manual, it was survival truth.
This is the conversation African entrepreneurs rarely have in public. In a candid discussion for the Founders Battlefield show, four seasoned business leaders shared the unfiltered truth about building companies across Africa, the 3 AM fears, the political pressures, the family sacrifices, and the occasional triumphs that never make it to magazine covers.
Michael Anthony Macharia built a technology company from nothing to a $58 million valuation, expanding across multiple African countries and working with giants like Safaricom. Then it collapsed.
“We went from a billion shillings revenue from one customer to less than 50 million within 14 months. Sixty percent of our workforce was under one customer. How do you retool that?” he questions,
Lenny Nganga, founder and CEO Omnicom Media Group, lost 60% of his business when his biggest client left, just one month before COVID-19 hit.
Pauline Warui, founder and CEO of East Africa Customer Care Centre LTD, after managing 1,600 employees at Safaricom, was fired on a Friday afternoon and found herself trending on social media by Saturday, with bloggers inventing stories about stolen millions.
“Monday was empty. I’d never seen the parking lot during the day. That’s what corporate life had been,” she recalls.
The founders identified patterns that plague African businesses; building on single customers creates catastrophic risk when management changes or politics shift.
Raising capital means discovering that investors aren’t friends, they’re new bosses with IRR targets and board seats. Government contracts offer massive revenues but deliver 90-day payment delays and political interference.
When your personal brand becomes synonymous with your company, every failure becomes your failure publicly.
“You don’t own your business. Your business owns you. Your customers own you. Your bank owns you. You have to be comfortable with that,” Peter states.
The group traced how Kenya’s business environment has transformed across three political regimes. From 2003-2012, merit mattered, you got business if you were good at what you did. The middle years shifted toward relationships and connections.
Today’s ecosystem has become transactional, focused on extraction rather than building for the long term. Being Kenyan once meant automatic respect in markets like Zambia and Rwanda. That advantage is fading.
Despite the war stories, the founders aren’t discouraging entrepreneurship, they’re demystifying it.
Scale through acquisition or franchising, not just opening branches. Never let one customer control more than 30% of revenue. Separate your personal brand from the company.
Use advisory boards to bring in experienced founders for specific challenges. Own your story publicly before others define it for you. And understand that the fear at 3 AM is real, learn to make decisions despite it.
Pauline brought a crucial perspective often missing from these conversations: “You’re juggling children, husband, relatives. You travel constantly. By the time you come back, you’re the second wife.”
Her sister once told her: “I’ve never admired you. Your child is even my child because you’re never present.”
The success metrics for women become more complex, balancing business growth against family stability.
In Kenya’s advertising industry, Lenny notes, only one company has successfully transitioned to the second generation. The rest collapsed when founders fell out or aged out.
Peter’s children show little interest in taking over. The path from founder to legacy business remains largely unmapped in Africa.
“Your problems are opportunities for others to learn from. Come and say your story. Otherwise, the story will be owned by other people,” Michael urged listeners to stop hiding.
The Founders Battlefield series aims to create exactly that, a repository of unfiltered truth from entrepreneurs who’ve built, lost, and rebuilt. Not sanitized success stories, but real experiences that can guide the next generation.
“We romanticize entrepreneurship. The process is tough. The results are often taken by other people, your investors, your family, sometimes just fate. But you dust yourself up and go to the next gig. You’re not going to die,” Peter explained.
Because building something meaningful in Africa requires more than capital or connections.
It requires the courage to scale despite the fear, the wisdom to know when to hold and when to fold, and the humility to learn from those who’ve walked the path before.
