Poking sleeping giants – Click2Sure’s insights for the CLC Lean Innovation Safari

Daniel Guasco took a leaf from Elon Musk’s playbook about poking industry behemoths when he started Click2Sure. But instead of going for the motor business or NASA, Daniel is challenging one South Africa’s oldest, slowest and most staid industries: insurance…

Members of the Creative Leadership Collective (CLC) and delegates on the CLC Innovation Safari got an exclusive presentation and Q&A session with Daniel and his business partner Wayne Gosling at their offices in Cape Town during the Safari, where the two unpacked the story and business process behind Click2Sure.

A remarkable new insurtech business, Click2Sure is a bolt-on product offered during the checkout process, where the customer can opt for an insurance policy on the item they’ve just purchased.

The product has been designed with simplicity and transparency in mind and – since it does away with the brokers, quotes, and forms – is also able to keep costs significantly down.

The success of their scale-up is influenced by the wealth of experience and start-up attitude Daniel and Wayne bring to the table.

Founders of former Groupon South Africa, entrepreneurs and investors, the two had many insights to offer delegates when it came to building companies that talented people want to work for.

Main takeaways were a focus on maximising start-up culture in a scale-up business and cultivating next-level management involvement, especially with regard to customer feedback and building teams on The Law of Crappy People.

A principle put forward by Marc Andreessen, The Law of Crappy People states that ‘for any title level in a large organisation, the talent on that level will eventually converge to the crappiest person with the title’.

Talking to some of the CLC Innovation Safari delegates over coffee on Greenmarket Square after the presentation, there was a real interest in how businesses like Click2Sure attract and retain talent with an open and responsive culture, shares, and other small tweaks to outmanoeuvre corporates.

For Daniel, opening the floor to the CLC was about mutual learning, making connections and opening doors: ‘Through the questions we’re asked our thinking is challenged and we get exposure to people who are obviously interfacing with corporates and who might see opportunities here.’

Insider tip from this talk: Have an entrepreneur in residence who will go look into the future for you and who will solve the next problem for your business.


We’d like to extend our thanks to Daniel and Wayne for taking the time to host one of the events on the CLC’s Lean Innovation Safari. The Safari was held 22–24 April 2018 and provided delegates the opportunity to explore the innovation ecosystem in Cape Town.

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