Channelling Genius: Coalition CEO Joshua Motta Talks Career Paths, Cyber and the CIA

Channelling Genius: Coalition CEO Joshua Motta Talks Career Paths, Cyber and the CIA
Joshua Motta is the founder and CEO of the cyber insurtech Coalition. At 15, he started working at Microsoft and, while still a teenager, cut his cybersecurity teeth at the CIA

In the late 80s and early 90s, a popular American sitcom that detailed the adventures of a fictional child-genius doctor called Doogie Howser M.D. was taking the nation by storm. The idea that a gifted child could step into the shoes of a highly educated adult and surpass all creative expectations, tapped into the imaginations of the nation.

But like all good imaginary characters, this one was based on reality. Gifted children – indeed, genuine whizz kids do exist – and the technology industry has scooped up its fair share of them. One only needs to skim through a few high-ranking CEO Linkedin profiles to see that age, especially at the lower end of the scale, is just a number.

Indeed, coincidentally, at the very same time that the fictional teenage M.D. was performing ‘pioneering surgeries’ for TV audiences, in a quiet suburb of Kansas City, another child prodigy was launching his first business venture. 

What stands out in our conversation, as we discuss Joshua Motta’s first forays into the technology and business world at the age of 13, is the genuine sense of surprise that his story would be interesting to others. It’s a refreshingly humble stance from a man whose sheer brilliance is behind the success of multi-billion dollar companies that continually innovate and disrupt.

He says, “I don’t know that I appreciated how technically minded I was as a child. It was boredom that pushed me in that direction. I grew up in a suburb of Kansas City, which perhaps isn’t the most exciting place in the United States. So, learning to program, the advent of the internet, my youth, etc., allowed me to explore and tap into the fascination I had.”

Entrepreneurial drive

That preoccupation with the IT industry struck such a chord that Motta, aged 13, decided to launch his first company. He taught himself HTML, and some other programming languages, and started building websites for local retailers and local businesses. 

Clearly, his interests were different from other kids his age – although he did embark on the venture with a school friend. He says, “At the time, I’m not sure I had the self-awareness to know that I was technical. But I was naturally entrepreneurial. My first job was to start a company, and I did that with a fellow 13-year-old classmate of mine. 

“I can’t say we were terribly successful. We’re still working to this very day, so early retirement eludes us. But, in any event, I think the combination of being naturally entrepreneurial, the internet and programming was an outlet for us. The anonymity of the internet, and obviously our parents vouching for us on credit card processing equipment allowed us to go into business. Many of our customers had no idea how old we were. Um, frankly, they didn’t care because we never interacted with them in person.” 

All of my coworkers were extraordinarily accommodating. I was billed as Microsoft’s ‘Wonderboy’, and they put up embarrassing posters of me all over the Microsoft campus.

On early days at Microsoft

The way he tells it, the venture was not much more than a childish foray into the business world. But just a year later, having had his activities noticed by Microsoft, Motta was offered his first job with the technology giant. He describes this opportunity precisely as, “a confluence of events that drove me into that space at a young age.” 

But of course, success begets success. And Motta’s first startup led him into an extraordinary situation.

“The success of the business that we created drew the interest of Microsoft, which ultimately led to a role there. They made an offer, and I was 15 when I officially walked through the doors and started working.”

He remembers that time as somewhat heady. “Everyone there was excited and found it [my age] to be extremely novel. All of my coworkers were extraordinarily accommodating. I was billed as Microsoft’s ‘Wonderboy,’ and they put embarrassing posters of me all over the Microsoft campus. It was exciting because it was 1999, the heart of the internet boom. The technology industry, Microsoft in particular, was growing dramatically.”

A journey into cyber with the CIA

But more opportunities beckoned, and after a stint at Sprint and another at Honeywell, Motta joined the cyber programme at the CIA – aged just 19. He was, in fact, the youngest employee at the agency to have a top secret sensitive compartmented information clearance. 

It was this step that saw his experience with cybersecurity evolve to a new level. He describes that period as a ‘fast, fun time.” But it was also a good move, practically speaking.

“It sort of happened fortuitously to some extent. In part, it was a way to pay for my college education. But both the intersection of national security with the direction that technology was going and all the experiences I had in those prior roles were building up the technical competencies and understanding combined with focus. I did a variety of things at the CIA, some of which certainly touched on the cyber side.”

It turned out to be a career move he loved. But because of his young age, he was also held back. There were levels in the Agency that he could not rise to and have clearance without additional years. 

“To progress at the CIA, particularly in the area that I was in, there were specific requirements. You had to be a certain age to apply for certain programs, which meant that by the time I graduated from college, and I’d worked for the CIA, I’d already been there for a while.”

Motta faced waiting several more years at his then level before he could progress within the Agency.

Banking and investment technology

That prospect simply didn’t appeal. And so, Motta took what he presumed was a sabbatical from the CIA. He followed his fellow graduating college buddies down the more conventional route of a career in the financial industry and landed a job in London.

“I was fortunate enough to receive an offer from Goldman Sachs, but, of course, to keep the parallelism throughout my entire career, it was in the technology investment banking team. I worked for Goldman and their ‘TMT’ – the technology, media and telecom team.” 

From there, he moved into other financial services jobs at private equity firms. And the original plan to go back to the CIA evolved into its own career and resulting “glide path”. 

A meeting of minds in CloudFlare

That path saw Motta move to CloudFlare – which was, at that time, a small operation with just 20 employees. CloudFlare was founded out of Harvard Business School by Matthew Prince; at its peak, it saw a US$65 million market cap. Now, it has a workforce of 3,500+ employees and, according to reports, is used by more than 20% of the entire Internet for its web security services.

At 20 employees, I think someone described us as ‘muffler repair for the internet’. So, the vision of the future perhaps wasn’t as rosy as it ultimately became.

On working at CloudFlare

Motta recalls, “Matthew, in many respects, had sort of a renaissance approach to his career. I think he would describe himself as a ski instructor and a recovering lawyer. He’d founded another company before CloudFlare so was a bit of a polymath. We were simpatico; I suppose that is the best way to put it. 

“He asked if I was comfortable coming on and helping CloudFlare do various things, and the answer was, of course, no, I’d never done them before. So I wasn’t comfortable with it. But he seemed to overlook that and hired me anyway.” 

At that time, CloudFlare did not appear to be a high-flying opportunity. “At 20 employees, I think someone described us as ‘muffler repair for the internet’. So, the vision of the future perhaps wasn’t as rosy as it ultimately became.” he laughs.

Joshua Motta (left) and Mathew Prince (right) in Hong Kong, 2015 on the company’s partnership with Baidu

The birth of Coalition Insurance

After CloudFlare, the natural progression for Motta was to set up his own venture once again. With such a robust understanding of the technology industry, the cyber environment and the financial technology industry, he found the perfect outlet for his experiences. 

He launched Coalition in 2017 as a managing general agent that specifically targets SMEs – a market traditionally underserved by cyber insurers. Today, the company has a valuation of US$5 billion and is one of the leading unicorn insurtechs in the US. 

The company has also recently launched a new cyber risk modelling solution that makes cyber insurance a far more viable prospect through its measuring capabilities. 

Motta says, “Coalition, essentially, is what happens when you combine a financial service, in this case insurance, with a technology company, and an intelligence community mindset when it comes to data collection and analysis.

“My background in financial services, technology companies, building CloudFlare, and then, of course, the experience I had within the US intelligence community, has uniquely led me to found this company and pioneer a different approach.” 

Innovation and disruption in cyber insurance

Talking about the beginning of that journey, Motta says he was far from certain that Coalition would succeed – especially since he had no prior experience in the insurance industry. It was, to an extent, a leap of faith. 

“I hoped it would be as successful, but I suppose I’m too analytical or quantitative to have total certitude. Statistically, I knew that the likelihood is that it would fail and perhaps that it would no longer exist in five years.”

The ability to take a calculated risk – and be prepared to fail, is the unique domain of the entrepreneur – and it’s a space Motta is exceedingly good at. He is self-deprecating about his achievements though. 

“In many respects, what right did we have, did I have, in building an insurance company? I’d never stepped foot in the insurance industry prior to starting Coalition. But that’s the fun thing about being an entrepreneur. I suppose you come into it with a different perspective – right?”

Ignorance, he says, was in some respects “the best weapon” they had. “We didn’t know that things in the industry were considered impossible.”

Future-proofing success for commerce

For many years, cyber has been one area of the insurance industry that has been deemed untouchable – an impossible space to adequately quantify risks. Yet, by combining comprehensive insurance coverage and cybersecurity tools, Coalition offers its Active Insurance products in the US, UK, and Canada through relationships with leading global insurers, as well as cyber capacity through its own carrier, Coalition Insurance Company.

You know, we have an internal saying at Coalition, that after every accomplishment (this active cyber risk model being the latest one) we finally made it 1% of the way there.

On pioneering cyber risk modelling

“As the industry continues to dwell on catastrophic cyber events and how best to offer coverage, if at all, one thing remains abundantly clear: cyber risk is insurable,” he says. “The insurance industry is uniquely positioned and capable of mitigating and protecting organisations from emerging cyber risks, and we are committed to protecting the hundreds of thousands of customers we serve.”

Motta is understandably passionate about Coalition’s offerings and the fact that the insurtech has the capabilities to help customers recover their business operations, restore them, and mitigate the damage that’s happened. “Many, many [insurers] don’t understand [cybersecurity]. And as a result, its ability to potentially aggregate. The easiest solution is to say, “it’s uninsurable”. And that can be true if you don’t have the understanding and you don’t have the data or the tools to be able to understand it.”

But like any genius worth his salt, Motta believes the brilliance he and his team have achieved, is only a small fraction of the journey. “You know, we have an internal saying at Coalition, that after every accomplishment, (this active cyber risk model being the latest one) we finally made it to 1% of the way there. 

“We celebrate that milestone with every new accomplishment we have. And it’s a reflection of the fact that our vision is expanding at the same rate as our ability to execute against it. And so there’s still 99% of what we hope to accomplish ahead of us.”

He adds: “I certainly hope there’s a lot that happens over the next 12 to 18 months in terms of advancing the capabilities we bring to our customers, to the brokers, our partners and the reinsurers that we work with. But, you know, sadly I think we may still only be 1% of the way; there is always more work to be done, and that’s okay.”

Interview by Insurtech Insights Editor, Joanna England

Share this article: