CareMonkey founder Troy Westley on speed dating for business partners and workshopping challenges with Richard Branson

CareMonkey chief executive Troy Westley. Source: Supplied.

The founder of medical information startup CareMonkey is no stranger to pitch events; over the years, his enthusiasm has seen him handed novelty-sized cheques and secure island getaways with Sir Richard Branson.

The platform, which lets schools and community groups collate and safely store children’s medical information and permission slips in a digital format, won StartupSmart’s Best Startup Idea Award in 2014. In the time since, Troy Westley set about connecting with the global startup community, and his talent for “the pitch” has even seen him win $1 million in investment when the business took out top prize in the Slush 2015 international startup pitch event—a prize that he turned down because he believed it wasn’t time to take on investment in that way.

“That wasn’t my reason for entering the competition. I still wanted to win and it was great publicity for us,” he said.

But it was the Talent Unleashed competition, which CareMonkey also won in 2015, which is responsible for two big endorsements on the company’s website, with Apple co-founder Steve Wozniak and Virgin founder Richard Branson both singing the praises of the startup.

“Certainly one to watch,” Branson says of the business.

The business was launched when Westley, who has seven children, started thinking about the use and security of health care plans for things like asthma, which have traditionally been hard to keep in a secure and useful format for schools, sporting clubs and community groups.

He left his job in the corporate world and spent more than a year by himself developing the platform. While the business doesn’t reveal exact turnover, Westley tells SmartCompany the business now has around 1.7 million paid profiles and is eyeing off reaching the two million mark. Profiles start at $3.00 each for club organisations and climb to $30 each for professional use.

Workshopping challenges with billionaires

Westley might not take every prize that is presented to the business, but the business has been able to take advantage of the networking on offer from pitch prizes. And Talent Unleashed presented a chance to workshop the company with some great business minds.

“One of the prizes was a receiving a trip to [Branson-owned] Necker Island where I spent four days with a group of other people around the world,” he says.

“We spent each day until lunchtime discussing various social issues and spent the rest of the afternoon and evening in Sir Richard Branson party style.”

Over that time, Westley got to pick Branson’s brain about how to balance the free side of the CareMonkey business, which was developed with a social enterprise mindset, with the need to generate revenue in the early stages of the company. The platform gives families access to personal profiles free of charge, while charging a subscription fee for schools and companies. Giving energy to both sides if the business was a challenge.

“[Branson] said to me, in particular because we were talking about the social side of things, it was quite alright to focus on profit first and then be in a position to give back,” Westley says.

“I was speaking to him about how I felt a bit bad that we hadn’t spent enough time focusing on the free side of our business.

“That’s when he said ‘it’s okay, you have to do that [building the other side] first’.”

The internet united the leadership team

Even as the CareMonkey business gains momentum, the struggles from the early days – and lessons learned during that time – are never far from Westley’s mind.

“I was running what you’d call a not-for-profit for many years,” he says.

Those challenges, however, were met with the help of a passionate business partner. While not every company founder would feel at home with speed-dating, online matchmaking proved crucial for CareMonkey’s leadership team.

“I’ve misjudged many things; when I quit my job and it was just me in the business, I said to my wife it will only take a year and we’ll be earning a nice income from it,” Westley says.

“I went solo for way too long, working from my garage at home. What I really needed from the get go was a co-founder who cared about the business as much as me.”

Westley jumped online and quickly spotted a co-founder speed dating event on He couldn’t actually attend the event, but the list of attendees was there, and he had already decided on some criteria for the perfect business partner.

“I specifically looked for someone who was about my age, in my position in life and I had already had 20 really good years in IT. I was in a position where I could take a risk – and wanted a partner who was in the same position,” he says.

“There had to be a cultural fit between us.”

Westley messaged Martin Howell, co-founder of REA Group, who was looking for new opportunities, and the duo’s combined experience has served the business well. Howell serves as chief technology officer, with Westley as chief executive officer, as the CareMonkey team continues to focus on expanding their user base.


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