1. IF YOU HAD DONE SOMETHING ELSE WHAT WOULD IT HAVE BEEN?
It would have been in training or people development, because my father was a school teacher and educational psychologist so I grew up in that context. I’ve always enjoyed teaching people things and understanding the process of learning myself.
2. WHAT ELSE WOULD YOU NAME YOUR BUSINESS?
I suggested we call it Mail Friday. Our software does help you out with email issues, so there’s a parallel with Robinson Crusoe and his Man Friday. I don’t think my co-founder would’ve started the company with me if I’d insisted we had called it that.
3. IF YOU COULD BE BASED IN ANOTHER CITY WHERE WOULD IT BE?
I really love Cape Town. I grew up there - it’s a very beautiful city and there’s a lot of creative energy.
4. WHEN YOU STARTED, HOW DID YOU RAISE MONEY?
Both my co-founder and I had our respective tech companies bought from us in the late 90s, so we had a bit of a cash to get things started. We also have very understanding wives, who were happy to go from well above the cake line to almost the breadline for several years.
5. WHAT HAS BEEN YOUR MOST IMPORTANT DECISION SO FAR?
Starting. That is the destiny-defining decision, and maybe the only decision that can ever be bigger than that is deciding to stop.
6. WHAT HAS BEEN YOUR BIGGEST MISTAKE?
Overestimating people’s capabilities and then leaving them to learn and fail on their own.
7. WHAT IDEA DO YOU WISH YOU HAD COME UP WITH?
Twitter, Facebook and LinkedIn, because they’re so obvious in retrospect.
8. HOW DO YOU HANDLE STRESS?
Keeping fit and maintaining a positive inner voice - talking nicely to myself.
9. WHAT WAS YOUR FIRST JOB?
I worked as a runner and a waiter in a chain restaurant a bit like TGI Fridays called Mike’s Kitchen in Cape Town when I was 16. At the end of the night you’d roll up your apron and walk out the door and you wouldn’t have to think about it until your next shift.
10. WHAT WAS YOUR WORST JOB?
I was backpacking in the UK in about 1995 and I got a job as a telemarketer selling restaurants and gym memberships for a hotel. You really have to believe in your product otherwise it’s pretty depressing. I left after about a week and I never came back. I didn’t even tell them.
11. WHAT WAS YOUR BEST JOB?
The very first business I created was very enjoyable, because we distributed physical items - school supplies in Cape Town. We had warehouses with things on shelves, piles of pencils and reams of paper, and it felt really tangible. A tech business is all swimming around on wires. It’s great, but I do also miss the physical products.
12. IF YOU WERE ON THE APPRENTICE WOULD YOUR TEAM BE NAMED?
13. WHAT COMPANY WOULD YOU INVEST IN RIGHT NOW?
Tesla, because, again, in retrospect it’s obvious. You can see the inevitability of why electric cars have to be done by somebody who doesn’t have a vested interest in the oil industry.
14. APART FROM PROPERTY, WHAT IS THE MOST EXPENSIVE THING YOU’VE BOUGHT?
Apart from property, I don’t buy a lot of expensive things. My car - it’s just an Audi Q5.
15. SUIT OR JEANS?
I used to wear suits, and then I lost a bunch of weight and my wife told me I looked really good in jeans.
16. FLEXIBLE WORKING OR OFFICE HOURS?
I don’t believe office hours are enough. The question isn’t flexible working; it’s more a case of flexible living.
17. WHAT IS YOUR FAVOURITE THING ABOUT THE OFFICE?
I like the buzz, the vibe. It feels like being in a beehive, like being part of something.
18. WHAT APP CAN’T YOU LIVE WITHOUT?
The British Airways app as I fly a lot between US and the UK and it helps me with all the organisation
19. WHO IS YOUR BUSINESS IDOL?
Jim Collins. He’s written some great books, such as his most recent one ‘Great by Choice’. It’s really well researched analysis on what has made companies great on an enduring basis.
20. IF YOU WERE PRIME MINSTER FOR THE DAY, WHAT WOULD YOU CHANGE?
Ban the army. Costa Rica did this quite a few years ago. They don’t seem to live in fear and they get to spend considerably more on public services as a result. We can play rugby against each other instead of having wars.