Six failed businesses on, Dropmyemail’s John Fearon says, “I’m amazing”

“I’m a good boss, I really am,” John Fearon, founder and CEO of DropMySite, tells me, in full earshot of his employee at their office in Block 71, Ayer Rajar Crescent, considered the nexus of Singapore’s technology startup scene.

He was making a point about how he’d be a bad subordinate but a good leader who is comfortable with starting things.

“I’m one of those that can go into the room and self-combust.”

With all his self-confidence (whenever he speaks at conferences, he start with,”Hi, I’m amazing”), it’s easy to assume that John, who comes from South Africa, has a string of successful businesses to stand on. Not at all.

I prod him about the number of failed businesses he had.

(Photo: John being featured in an Amazon Web Services video)

John struggles to find his words, which is a rarity. He’d lost count, but finally arrived at an initial figure: Five.

His first business collapsed after six months, burning through the $3,000 that his parents gave him as initial capital.

His second business was launched while he was holding a full-time job, and that failed too.

John worked on an online nursing startup next. But after building the technology, he discovered that government regulation restricted the percentage of commission he could take. He abandoned the idea.

While working in Oman, he started an insurance business, but that floundered too because he couldn’t secure the insurance contracts.

Later, he came up with Rentedworld, a Craigslist for home rentals. He built the website but never launched it, since he realized it couldn’t become a big business.

After chatting for a while more, John finally realizes that he has a sixth failed business — when he was still in university.

“I’m not afraid. I’ve been poor, and I know what it’s like, and I’ve been pretty wealthy, I had a Jaguar, the parties, and it didn’t make me happy.”