Start to Scale: The Wumdrop Journey with Simon Hartley

The Mashstartup Podcast

Simon Hartley — the entrepreneur behind Wumdrop, a last-mile delivery startup that grew from humble beginnings into a game-changing logistics platform, eventually acquired by Makro. Wumdrop started with a simple idea: deliver nappies on subscription. But when Simon and co-founder Roy Borole handed scheduling power to customers, they uncovered a much bigger opportunity — on-demand, tech-enabled logistics that put convenience and control first.

Simon shares how early mistakes, like outsourcing deliveries, nearly cost them customers — and how rebuilding around owned operations and customer experience became their edge. That shift led to partnerships with major brands like Builders Warehouse, Standard Bank, and Zando.

The breakthrough moment? Winning the Business App of the Year in 2015. The recognition gave Wumdrop credibility, opened doors with enterprise clients, and proved the platform’s potential at scale.

In 2017, Makro acquired a majority stake, using Wumdrop's tech to power three-hour delivery — a defining milestone for both Simon and South Africa’s tech startup ecosystem.

We unpack the lessons behind building something scalable and acquirable: product-market fit, defensibility, and staying customer-obsessed.

If you’re building with the long game in mind — or aiming to scale toward acquisition — this one’s for you.