Aaron chats with Simon Hartley, founder of WumDrop, who takes us through his rare journey of selling the same company twice, first to Massmart, then to Walmart.
From humble beginnings delivering diapers in a Ford Fiesta to building one of South Africa’s most innovative logistics companies, Simon shares the real behind-the-scenes story of how WumDrop pivoted, scaled, and ultimately became a strategic asset inside two of the country’s biggest retailers.
In this episode, Simon breaks down the emotional and strategic lessons from both exits, what founders get wrong about dealmaking, and why post-acquisition integration is where most companies are either made or broken.
He also dives into the importance of staying teachable, how the wrong early investor structure nearly killed the business, and what it was like to be mentored by a senior Walmart executive during his earn-out.
KEY TAKEAWAYS:
Pivoting from E-commerce to Infrastructure: How one customer insight shifted WumDrop’s entire business model.
Early Funding Pitfalls: Why raising too little from too many angels cost more than expected.
The Massmart Exit: Why the first sale brought relief—but not results.
The Walmart Integration: How real mentorship and strategic alignment turned WumDrop into a top-performing asset.
Post-Acquisition Wisdom: Why integration planning and executive growth are critical to post-deal success.
BEST MOMENTS:
“I wasn’t selling diapers—I was selling delivery experience. That changed everything.” “Massmart bought us cheap. Walmart built us properly.” “If you’re not learning frameworks, you’re operating on raw talent alone—and that has limits.” “The second exit only worked because Walmart had a plan, and a person, to make us succeed.”
FIND US ON:
Spotify: Link to show
