Make Money Mondays, Evergreen Content

Going broke scares me, because I've been there - Darren 'Whackhead' Simpson

Very humble beginnings… My dad was an auditor. Then he got bored and decided to open a trading store. But it didn’t go so well… he was unemployed, forever… My mom was a nursery school teacher… I used to pack shelves at Pick n Pay… We were short of a lot of stuff… I ended up working in a butchery…

Darren 'Whackhead' Simpson

I bought two apartments – one for each of my kids… This is going to secure their school fees… they’ll have an asset at the end of it… I’d like to think I’ve secured their school fees forever…

Darren 'Whackhead' Simpson

Going broke [scares him], because I’ve been there. I’ve lived in a garage twice in my life. I’ve lived in a caravan twice in my life… That’s what motivates me. To never ever go back there…

Darren 'Whackhead' Simpson

Each week The Money Show’s Bruce Whitfield interviews a famous person about her or his attitude to money (hopes and fears, successes and failures, etc.) as part of his weekly “Make Money Mondays, Personal Edition” feature.

This week he spoke to radio personality Darren ‘Whackhead’ Simpson, a man loved and hated in equal measure for his prank calls on 94.7 (Johannesburg) and KFM (Cape Town).

In 2016 two of Simpson’s prank calls featured on Comedy Central’s list of “10 Famous Prank Calls That Will Never Not Be Funny".

Click or tap here to listen to Simpson’s best pranks.

  • What does Simpson believe about money?

  • Does it keep him up at night?

  • Does he spend like crazy or save compulsively?

  • How did his childhood experiences shape his views about money?

Listen to the interview in the audio below (and scroll down for more quotes from it).

Cape Town just offers so much!

Darren 'Whackhead' Simpson

I was the youngest commercial broadcaster in South Africa… I was terrible…

Darren 'Whackhead' Simpson

Radio was good to me… stand-up comedy can be very profitable…

Darren 'Whackhead' Simpson

Around 2005… I got a financial planner… I had all my money in a savings account…. I didn’t trust investing… He said, if your money isn’t growing faster than inflation, then you’re losing money… So, I bought my first place [property]…

Darren 'Whackhead' Simpson

We [wife] opened a school… I’ve put all my money in it… It was a great success, and still is…

Darren 'Whackhead' Simpson

Buying cars [when asked about his worst money decisions]… I’m not talking Ferraris…

Darren 'Whackhead' Simpson

As a dad; it’s hard to say ‘no’ sometimes…

Darren 'Whackhead' Simpson

Money for me… it’s the security that it provides that excites me…

Darren 'Whackhead' Simpson

I married a young wife. It’s one of the luxuries of the business!

Darren 'Whackhead' Simpson

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