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Jonathan Elcock, CEO and founder of CompariSure. Picture: Supplied
Jonathan Elcock, CEO and founder of CompariSure. Picture: Supplied

What’s your one top tip for doing a deal?

The dynamics of deal making in a startup are quite different to corporate — startups generally take on the majority of the risk and cannot afford the same legal rigour. You need to ensure a meeting of minds with respect to inputs, expected outcomes and the boundaries of the deal.

What was your first job?

My first job was an internship at an insurance startup where I offered to work for free and rose through the ranks. It was my first taste of entrepreneurship. I got involved in everything from building out the early admin and CRM systems, to designing products and running a 60-seat outbound call centre.

How much was your first pay cheque, and how did you spend it?

If I remember correctly it was around R15,000 a month. I was so used to student life that I probably saved more than half of it. Getting into the habit of saving early on helped build the capital base on which I launched CompariSure.

What is the one thing you wish somebody had told you when you were starting out?

Don’t procrastinate. Life is short and if you don’t move towards your ambitions early, you’ll run out of time.

If you could fix only one thing in SA, what would it be?

Skills development. SA needs to empower its youth to excel in the global economy.

What’s the most interesting thing about you that people don’t know?

I was diagnosed with dyspraxia, a brain-based motor disorder — receiving extra time in exams throughout school and varsity. The disorder helped build grit in overcoming everyday obstacles.

What is the one investment you wish you had made, or made earlier?

I wish I had bought my first property sooner after getting my first job. Property has produced by far the best return on investment in my portfolio.

What do you consider the most overrated virtue?

Idealism. There is no magical formula which solves all the world’s problems. Good leaders are able to judge where pragmatism produces a better outcome.

What is the hardest life lesson you’ve learnt so far?

Patience. I put my house on the line to launch CompariSure. This created an intense urgency to generate revenue and build a business case. I put pressure on business partnerships that didn’t share my sense of urgency, which often did more harm than good.

If you were President Cyril Ramaphosa, what would you change, or do, tomorrow?

I do not envy his position. I would focus on using technology to improve transparency and enforce accountability in the public sector.


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