When Robert Smithson studied philosophy at Cambridge University, he didn’t imagine he would be questioning assumptions and stripping down arguments to help reshape the auto insurance industry. Yet, those foundations of critical thinking, analyzing challenges, and pushing back have often defined his career spanning finance, sports analytics, and now as founder and CEO of technology-driven insurance innovation Just Insure.
At Just Insure, Smithson is using artificial intelligence and telematics to make car insurance smarter, fairer, and more affordable, particularly for low-income drivers long disadvantaged by traditional pricing models.
Philosophy to Fintech
Smithson’s background in philosophy honed his ability to think abstractly and pragmatically.
“Philosophy teaches you to question assumptions and to reason from first principles,” he explains. “That’s invaluable when building businesses that challenge entrenched industries.”
His early career in finance at Goldman Sachs, Arete Research, and THS Partners deepened this analytical instinct. Smithson sought what he calls an “informational edge” – finding data signals that others overlooked. This fascination with information’s predictive powers led to his first major entrepreneurial venture, Genius Sports, originally Betgenius.
At Genius Sports, Smithson’s team collected and analyzed data from sportsbooks to predict sports performance. Data is similarly used by Just Insure to understand and price driving behavior. “I’m a big believer that there are so many signals and information in the data, we just need to harness and analyze it in the right way,” he says. What to do with the data became a recurring question as he sought to replace subjective judgment with objective evidence.
Data-Driven Leap into Insurance
After selling Genius Sports in 2018 for $280m, Smithson turned his attention to insurance, an industry he saw ripe for transformation. Similar to finance and sports betting, insurance revolves around risk assessment, but has remained stuck in an outdated model. He says: “Players fall into two categories: those who have an incredible intuitive judgement for the right price for a risk, and those, like me, who are creatures of numbers and systems and building the right model.”
“Insurance is the most data-driven profession of all, but was slow to recognize change. It relied on slow-changing demographic factors such as age, zip code, and marital status. This missed the extraordinary amount of data being collected in real time about drivers, and how we could measure actual driving and behavior.” This insight sparked the creation of Just Insure: a technology company first, and an insurer second. The mission was simple yet radical: use telematics and AI to price insurance based on how people really drive, not on who they are or where they live.
“Sports analytics taught me that data without context is dangerous. And it’s the same with driving data,” he acknowledges. “A sharp brake might look risky, but if it’s to avoid an accident, it’s evidence of good driving. We built our telematics models with that in mind, not just measuring acceleration and braking, but interpreting why they happen.”
He adds, “When I realized how broken the incentives were, how much of an opportunity there is to move the needle, and how big the potential market is, I couldn’t resist. It’s an industry that directly affects people’s financial lives. If you can use technology to make it cheaper and fairer, you’re not just building a business, you’re giving people the right incentives to make smarter, safer driving decisions.”
Harnessing Telematics and AI
Telematics is the technology that allows Just Insure to measure driving behavior in real time. Using data from smartphones and vehicles, the company’s AI models analyze when, where, and how people drive. This data-driven approach with dynamic, personalized risk assessments replaces traditional pricing, which looks backward using broad demographic averages. “Safer drivers pay less,” says Smithson. “We’re able to identify and price risk as it changes, not just at renewal time.”
By building its own policy management system and pricing model from scratch, Just Insure has achieved loss ratios more than 20 points better than the industry average. The system continuously refines its understanding of risk by analyzing billions of data points from time of day and road conditions to driving maneuvers and traffic density. AI is central to this process. It interprets telematics data in context, distinguishing risky driving from safe, defensive maneuvers. It can also predict the likelihood of a claim with precision beyond traditional actuarial methods. The feedback loop is constant: behavior influences pricing, and pricing influences behavior. “This makes insurance not only fairer but also a tool for promoting safer roads. If you want people to trust you with their data, you have to earn that trust every day,” he says.
Fairness and Inclusion
Smithson is particularly motivated by the inequities in traditional auto insurance pricing. “Lower-income Americans often live in zip codes with higher premiums and have lower credit scores. That means they pay sometimes two or three times more, even when they drive just as safely.” Indeed, in the U.S., auto insurance can consume a far larger share of income for poorer households. Around 14% of Americans drive uninsured, compared to less than 1% in Europe or Canada: a gap driven largely by affordability. Smithson acknowledged: “Just Insure tackles this head-on. By basing premiums on real driving behavior rather than a person’s credit score or zip code. It offers tangible savings to safe, low-mileage drivers, sometimes up to 80% less than traditional insurers.” Once a customer has logged 3,000 miles of verified driving data, Just Insure even ‘fades’ the impact of credit score to zero, effectively eliminating one of the biggest sources of pricing bias.
Smithson comments: “Credit score and zip code are not bad measures of risk in general, but they create systematic unfairness. “A good driver in a low-income area shouldn’t pay double what a worse driver pays in a wealthier one. That’s not fair, and technology now allows us to do better. We price people on how they actually drive, not on where they live, their education, or how much they earn.” This shift also empowers drivers. “You can’t change your credit score or where you live overnight,” he adds, “but you can change your driving habits. Telematics makes insurance more equitable by turning it into something people can control. You can actively improve through your own actions.”
Building Smarter Systems
Behind Just Insure’s success is a philosophy of disciplined innovation, with Smithson drawing heavily on his financial background. “Finance taught me to evaluate risk and make decisions under uncertainty. That experience has been invaluable as an entrepreneur. It’s one thing to dream big; it’s another to make sure the numbers work. Entrepreneurship is really about understanding probability.” He also emphasizes hiring great people and giving them autonomy. “Micromanagement kills creativity. The key is adaptability: knowing when to step back, when to push, and when to listen.”
Smithson has combined the aggressiveness of U.S. Startup culture with the U.K.’s more thoughtful approach in its execution. “I like combining the two: the boldness of American entrepreneurship with the analytical rigor of the British approach.” The company’s structure reflects that ethos. Its modular technology allows small, agile teams make rapid decisions measured in hours, not weeks. “As we scale, we’ll need more systems.” Smithson concedes. “But we must never lose the speed that makes us effective. We’re not chasing vanity metrics but focus on the fundamentals such as low loss ratios, efficient capital use, and customer satisfaction.”
Partnering for Growth
The arrival of Gary Tolman as Chairman marks a new chapter for Just Insure. A veteran of Esurance and Noblr, Tolman brings deep operational and regulatory experience.
“Gary and I quickly realized we shared the same philosophy that data-driven insurance can genuinely improve people’s lives,” says Smithson. Their partnership blends “old-school discipline with new-school innovation,” balancing Smithson’s startup speed with Tolman’s industry rigor.
Under this leadership, Just Insure aims to become America’s most profitable auto insurer by being the smartest. By pricing risk more accurately than competitors, the company can offer lower premiums to good drivers while maintaining strong profitability. “In a $300 billion market, accuracy beats size,” he adds. Smithson’s roadmap includes expanding into new U.S. States, scaling the Just Unlimited product, and achieving sustained profitability by early 2026.
Risk and Leadership
The defining insight across Smithson’s ventures is that risk and opportunity are inseparable. “The key isn’t to avoid risk but to understand it better than anyone else,” he says. “If you can measure it properly, risk becomes a competitive advantage. Ultimately, it’s about replacing guesswork with evidence and bias with understanding. If we can make insurance both smarter and fairer, that’s not just good business. That’s progress.” It’s a lesson that extends beyond business. He advises younger entrepreneurs to “be patient but persistent” and to think long-term: “Most people overestimate what they can do in a year and underestimate what they can do in ten.” Smithson’s hobbies of flying and reading detective novels echo his professional mindset. He explains: “Flying forces you to think ahead; you can’t improvise at 5,000 feet. And detective stories remind you that the truth usually hides in plain sight.” Both help him stay calm under pressure and think several moves ahead, while keeping a firm, if not a philosophical eye, on the bigger picture.
