There is a standard, expected lifecycle for a serial technology entrepreneur. A founder builds a startup, scales it, and eventually experiences a liquidity event, either an acquisition, a public offering, or, more often, a quiet shutdown. Following this, the founder takes some time off, brainstorms a new idea, and starts the cycle again.
But occasionally, the timeline folds in on itself. A founder starts a company, leaves to start a second company, and then uses the second company to acquire the first company. To an outside observer, this looks like a glitch in the corporate matrix. Buying a company from oneself sounds like the sort of infinite loop that ought to violate the laws of financial physics.
This exact manoeuvre occurred in the African technology ecosystem this week. Cloud9, a Kenyan digital banking platform targeting businesses and young consumers, acquired Chpter, an AI-powered conversational commerce startup. The detail that captured the market’s attention is that Tesh Mbaabu founded both of them.
The founder launched Chpter in 2024 after their previous venture-backed e-commerce platform, MarketForce, shut down its core operations during the global funding winter. By September 2025, Mbaabu and another co-founder, Mesongo Sibuti, stepped away from the daily operations of Chpter, leaving co-founder Mark Kiarie to run it. Weeks later, they launched Cloud9. Less than a year after that, Cloud9 returned to acquire Chpter in an all-stock transaction.
