1. Can you tell us about your first experience building software and how that led to founding JBK?

James Benham: I built my first software at age twelve, an invoicing program for my lawn-mowing business, because my neighbors weren’t paying me on time. I printed the invoices and left them on windshields or doorsteps, which definitely got their attention. That project sparked my passion for coding and problem-solving through technology. I kept building software through high school, including an encryption tool that placed at the state science fair. By college, I was managing IT systems for the Corps of Cadets at Texas A&M and freelancing for businesses that needed help with their operations.

The turning point came during my senior year in 2001 when I landed a paid software project with a lumber company. After that job, I sat down with my dad, who was also an entrepreneur, and pitched him on my idea for a tech company. He invested $5,000, my co-founder Sebastian came on board, and we launched JBK from my dorm room. It started with a Gateway 2000 computer and a whiteboard, and we bootstrapped everything from there. Over time, we built software solutions that help insurance companies streamline claims, improve risk management, and make smarter use of data. That early experience taught me that software wasn’t just cool; it could solve real-world problems, and if you reinvested wisely, you could build something big without outside funding.

2. You’ve bootstrapped your entire journey. Why was that the right choice for you, and what did it teach you?

James Benham: Bootstrapping gave me freedom. It let me build JBK on my own terms, without outside investors or the pressure to chase growth for growth’s sake. I wasn’t chasing headlines or funding rounds; I was chasing product-market fit, profitability, and staying in business long enough for good things to happen. That mindset shaped how we grew: carefully, sustainably, and always with purpose. It also gave us the resilience to weather downturns like the 2008 recession and the discipline to reinvest every dollar into building a stronger business.

It’s the foundation of my book, Be Your Own VC. Bootstrapping forces you to be scrappy, focused, and brutally honest about what’s working and what’s not. It teaches you to solve problems creatively, manage cash like your life depends on it, and say “no” to distractions disguised as opportunities. It’s not easy. There were days I wasn’t sure we’d make payroll. But it’s incredibly rewarding. We built a global company, retained ownership, and created a culture that values grit, accountability, and long-term thinking.

3. JBK has served top global insurance companies. How did your early focus shape your approach to enterprise software in insurance?

James Benham: Early on, I realized that insurance is one of the world’s most process-intensive, data-rich industries, and also one of the most underserved by modern software. With JBK, we build custom enterprise solutions that streamline everything from policy and claims management to underwriting and compliance. We’ve earned the trust of top global carriers, TPAs, and brokers by solving real problems, not just selling features. Our clients stay with us because we understand their business: how data flows, where the bottlenecks are and how to modernize without disrupting core operations.

That deep domain experience directly influenced the launch of Terra, my product company. Terra focuses on turning insurance data into actionable insights using AI and automation. It’s built on two decades of lessons learned in insurance technology: what works, what fails, and what actually moves the needle for insurers. Whether through JBK’s enterprise services or Terra’s cutting-edge platform, the mission is the same: to bring clarity, efficiency, and innovation to an industry that impacts almost every person and business on the planet.

4. What inspired the creation of Terra, and what problem is it solving in the insurance ecosystem?

James Benham: Terra was born from a realization: the Workers’ Compensation process needed a major evolution. Too many insurers and TPAs are still relying on legacy systems, manual workflows, and siloed data. Claims took too long to resolve, communication between stakeholders was fragmented, and there was little visibility into performance. After two decades of building enterprise software, we saw firsthand how broken and expensive these processes were and how ready they were for change.

We built Terra as a cloud-native Claims and Policy platform that reimagines the entire claims and policy lifecycle, from quoting to binding, from intake to resolution. With AI-powered triage, automated workflows, and real-time analytics, Terra helps carriers, TPAs, Self Insured Funds and employers reduce claim durations, cut costs, and improve outcomes. It connects all the players in the ecosystem with shared visibility and actionable insights. We also are revolutionizing the pricing and terms for how claims and policy software is sold and delivered. Terra is about more than just software. It is about bringing affordability, connectivity, and clarity to one of the most complex areas in insurance.

5. In your book Be Your Own VC, you outline 10 bootstrapping principles. Which of those principles do you believe every Insurtech founder must embrace today?

James Benham: A principle from Be Your Own VC that I believe every TPA and broker should embrace is “Make Innovation a Process and a Habit.” Innovation is not a one-time initiative or a flashy rollout. It is something you build into the culture and rhythm of your business. For TPAs and brokers, that means regularly asking where time is being wasted, where errors are creeping in, and how workflows can be streamlined—not just once a year, but continuously.

Some of the most successful organizations we work with at JBK & Terra are the ones that treat innovation like operations. They create repeatable processes to identify bottlenecks, test solutions, and measure outcomes. When innovation becomes a habit, not a reaction, you gain a real competitive edge. You stay agile, deliver better results, and build a business that evolves with the needs of your clients.

6. You’ve been on 400+ stages around the world. What’s the boldest idea you’ve shared about the future of insurance?

James Benham: The boldest idea I share on stage is this: the future of insurance is not about disruption. It is about reinvention through data. Insurance companies are sitting on a goldmine of untapped insight. If we use that data not just to price risk, but to predict it, prevent it, and personalize experiences around it, we can completely reimagine how the industry works. The future is not about patching legacy systems. It is about rebuilding smarter, faster, more connected ones from the ground up.

At conferences like The Future of Insurance USA, ITC Vegas, and TEDx, I challenge leaders to think beyond efficiency and cost savings. The real opportunity is in eliminating friction entirely. That means turning ten-step processes into two-click workflows, breaking down silos, and creating systems that serve everyone better: carriers, TPAs, brokers, and policyholders alike. That is not just bold. It is necessary.

7. How has your time as a University Regent, elected official, and professor at Texas universities influenced your leadership?

James Benham: Public service grounds you. As a city councilman, I had to make decisions with real consequences, not just for business owners, but for families and communities. At Texas Southern University, I serve as a Governor’s Appointee on the Board of Regents to ensure students have access to transformative opportunities. And as an adjunct professor at Texas A&M, I had the privilege to teach and learn from some of the brightest young minds. These roles remind me that leadership is about stewardship. Whether you’re running a company or a classroom, your job is to build something that outlasts you.

8. You’re a licensed pilot with multiple certifications. Has aviation taught you anything about building and scaling companies?

James Benham: Absolutely. Flying teaches discipline, risk management, and how to trust your training. You don’t guess at 10,000 feet, you rely on systems and checklists. The same applies to business. You build systems, test them, and then scale. Being a pilot also taught me how to stay calm under pressure and how to balance confidence with humility. And just like flying, entrepreneurship is both exhilarating and unforgiving. Aviation tests you in ways that you could never imagine, that’s why preparation and mindset matter so much.

9. What makes a great InsurTech product, in your view? Is it code, timing, culture, or something else?

James Benham: It’s empathy. You can have the best code in the world, but if you don’t understand your user, it won’t matter. Timing helps, culture matters, but empathy is the secret sauce. At Terra and JBK, we build with the end-user in mind. That means talking to adjusters, agents, TPAs, and making sure what we’re building truly fits their workflow. Great tech disappears into the background and makes your life easier. That’s what we aim for every day.

10. Looking ahead, what excites you most about where Terra and the broader InsurTech space are headed?

James Benham: What excites me most is the shift from reactive to proactive insurance, especially in Workers’ Compensation. For too long, the industry has focused on what happens after someone gets hurt. But with the right technology, we can predict risk, prevent injuries, and accelerate care when incidents do happen. That is not just innovation—it is empathy in action. It is about using data not to replace people, but to protect them and make their lives better.

At JBK, we’ve spent over two decades building custom software for some of the largest insurance companies in the world. That journey gave us a front-row seat to the gaps and opportunities in the system. Terra was born with a mission to streamline the entire claims lifecycle and deliver better outcomes for everyone involved. What inspires me now is seeing the Insurtech space mature. We are moving past buzzwords and into real transformation. The future of insurance is connected, intelligent, and deeply human. And both JBK and Terra are proud to be part of shaping that future.