"Simon has a unique ability to inspire and motivate. His business acumen, strategic thinking, and exceptional leadership skills make him invaluable."

Paris Philippou - Vice President in eCommerce, Walmart Africa

Authentic & compelling stories from the front lines of a startup’s journey from foundation to maturity that will inspire, challenge, and motivate

I didn’t always have a good handle on this business thing. I founded WumDrop in 2014 after spotting a gap in the African market for an anxiety-reducing, surgically efficient final-mile delivery service - a gap I’d spotted while running a diaper ecommerce business that I’d started on a hunch with my college buddy, because as naive 25 year-olds we both (incorrectly) believed our bosses at the time to be clueless. So we quit our jobs to sell diapers online. After all, what could go wrong?

“A lot, apparently. But a lot also went right. By experiencing the operational pain that is ecommerce delivery and believing that we weren’t the only ones feeling it, we pivoted into a final mile logistics business called WumDrop. A majority stake in WumDrop was acquired by Walmart subsidiary Massmart in 2017, with Walmart completing 100% acquisition of both WumDrop and Massmart in 2021, after my team and I scaled the business to generate annual revenues in the hundreds of millions of Rands. In 2024, I exited WumDrop, Massmart and Walmart after achieving all earn-out targets, and was honoured with a Walmart Leading The Way Award in the process. Was it easy? No. Out of ignorance, did I often make it harder than it needed to be? Almost certainly. Did I learn invaluable lessons from it all? Of that, there’s no doubt.

Your team can benefit from those lessons and insights by booking me for a speaking engagement, today. Prior consultation and guidance is included in every keynote engagement to find the perfect topic for your team. To get your thinking jump started, see examples of keynotes that I’ve delivered before, below.

  • What the life of a delivery driver can teach us about resilience and purpose

    Ideal audience: Company all-hands, conference, lecture or workshop attendees

    Subject: Mission as an antidote to burnout and an engine for creativity, innovation and advantage – and how to cultivate it and keep it within your team

    Outcome: An appreciation for and understanding of the relationship between purpose and resilience in the workplace, resulting in lower rates of burn out and churn, and higher levels of innovation and creativity.

  • The worst boss you ever had didn't know the difference between leadership and management

    Ideal audience: Senior leadership and high potential individuals

    Subject: The critical difference between leadership and management, the indispensable value of both, and how to be an executive team that excels at both

    Outcome: A new understanding of and appreciation for the critical roles that both leadership and management play in your organisation, resulting in significantly improved ways of working, lower costs, higher output, and happier reports.

  • Everything in business is a story, and that's a good thing

    Ideal audience: Senior leadership, middle management, and high potential individuals

    Subject: How storytelling can save, stabilise, and grow your business – and how to master it

    Outcome: A team of executives with a radically improved ability to inspire and influence their peers, reports, and leadership for the purposes of hitting their goals.