The Superb Simon Hartley

Just call him The Transporter

Try this entrepreneurial business path on for size: online subscription box diaper delivery service, to grilled cheese delivery service, to just plain (and subsequently award-winning) delivery service. Wumdrop's Simon Hartley has had an interesting ride.

What’s the next thing you’d like to tick off your bucket list?

I'd like to write a book that gets published.

Are you a morning person or a night owl?

What do you call a person that prefers to sleep at both of those times? I'm that one.

What are the top 10 things on your Wishlist?

  1. Profitability.
  2. The Pig 'n Whistle Inn in Bathurst - It was founded and built by my grandparents many times over, and I want it back in the family.
  3. Singing in Carnegie Hall.
  4. A Thomas Baines original, capturing his buddy and my ancestor, Henry Hartley on expedition.
  5. Louis Vuitton Keepall 55 in black.
  6. Lowry Blade Works Marabou.
  7. BMW R Nine T.
  8. iPad Pro + Apple Pencil.
  9. Seven days with no phone signal.
  10. A manly nod of respect from my father-in-law.

What’s the weirdest thing in your bag right now?

A Cocoon Grid-It organiser, which looks like a serial killer's kit.

What’s one question you would ask the president?

What's more important as you get older? Flexibility, or cardio? Because I'm already jealous of what your knees can do.

What’s the last thing you bought?

A bottle of Warwick First Lady and three cheeseburgers from Junior, to eat amongst the boxes of a friend's new flat.

How did you start doing what you do?

When my co-founder and I decided to start a business, we had absolutely zero experience, but we knew that we wanted to do our own thing. So, we figured we'd sell something. What, you ask? Great question. We didn't know either. So, with the expectation that our lack of experience would definitely lead to our ruin, we chose to sell a product that absolutely couldn't fail, so that when our business did, we would have one less variable to worry about when picking over the bones of the thing for the sake of learning.

Long story short, we launched WumWum.com, which was a subscription-based e-commerce store for diapers. Our USP for our customers was regular delivery of baby products, at the time and day that they wanted them. As our quantity of customers grew, so too did our need to outsource our delivery. But there was a problem: delivery companies sucked. So much in fact that we were forced to bring delivery back under our control. With no choice but to take a crash course in last mile logistics, we spun up a test company, the Grilled Cheese Club, with the goal of delivering 1000 hot, cheesy sandwiches to people in Cape Town ourselves, without risking the WumWum brand. And this is where we got lucky. We just happened to have a real knack for last mile deliveries. We knew what pissed business and end users off, because we had been those people. Businesses around the Woodstock Exchange, which is where we were at the time started to notice that we were good at deliveries, and in short order we were making more money from moving other people's stuff than our own. WumWum became WumDrop.

What advice do you have for young entrepreneurs wanting to start a business?

How much of your current life are you willing to go without? If there's any part that's off limits, don't start the business. It will get taken away from you before you get it back (if you get it back), especially if it's your first venture. You simply don't know enough not to make mistakes that will cost you many things that you like, and some things that you loveThere is zero shame in not starting a business, but if you do, promise yourself that you'll make it out the other side, and then hold yourself to that promise when it would be easier to be doing literally anything else.

What’s the best advice you’ve ever received?

Respect is the foundation and starting point for love.

What would you do with a R100 000 investment?

I'd aggressively spend on recruitment to win the best drivers away from my competitors. And one bottle of Pol Roger.

Which words or phrases do you overuse?

"Two-sided marketplace", "Uber", and "my cats"

Name the talent you’d most like to have.

Mathematics, My father and wife are genius-level gifted - their comfort with mathematics is so natural. I have a slightly more forced relationship with numbers.

If you could change one thing about yourself, what would it be?

I would care much less about what people think of me.

What do you consider your greatest achievement?

Managing not to ruin the beautiful thing that is the WumDrop team and culture.

What is your most treasured possession?

My grandfather's WW2 military kit trunk. It's just a rectangle made of metal and wood, but it is a great reminder of how wonderful or terrible moments in human history are still a composite of the most mundane stuff.

What are some of the biggest challenges you’ve had to face in doing what you do?

The biggest challenge to date was getting out of bed every day in December 2015. When you've run out of money, have annoyed your investors by mismanaging communication with them because you're spending every minute scrambling for solutions, are coming to terms with your co-founder quitting on you, and have been stripped of every last feel-good chemical in your brain, just deciding that you aren't going to break is a hell of a thing. I refused to die - and almost no one besides my wife knows how close I came. It is one of my proudest personal moments, because I didn't give in, and because I know that it made me a significantly stronger version of myself.

What is your most marked characteristic?

My devastating puns, and my faulty beard.

Which historical figure do you identify with the most?

Charlie Chaplin. He had some complex and not always happy thoughts about the condition of humankind, but he had the good graces to always lead with a joke.

What is your biggest regret?

Not having the courage to face up to the fact that I was saying goodbye to my grandfather for the last time, when we both knew that I was.

When and where were you happiest?

I have travelled to some incredible places in my life, but my happiest moments have been with my wife, and on stage singing. A particularly moving performance of Ukuthula in Cape Town and Ubi Caritas in Bratislava come to mind. The act of making objectively beautiful music with a group of people is a seriously transcendent event - my hunch is that the same goes for most corporately creative things. Otherwise - and I swear this is true - being with my wife, Lize, makes me so happy, every day. She's an incredibly fierce person (and therefore terrifies a lot of people because the world is still getting to grips with powerful women), but she is equally silly, hilarious, kind, and gentle - it's a side of her that a privileged few get to see, and I'm chief among them. So whether it was Paris, Prague or Parow, being there with Lize has made me happiest.

What causes you to lie?

The desire to please someone.

What is your idea of complete happiness?

When success divided by expectation approaches a quotient of one.