What does it really take to build profitable technology companies without outside funding, and why does that mindset matter even more as AI reshapes every industry?
In this episode of Business Tech Perspectives, I sat down with James Benham, a lifelong technologist, serial founder, and unapologetic bootstrapper who has spent more than two decades building enterprise software businesses on his own terms. Broadcasting from Texas, with stories that stretch from Louisiana to Argentina to the UK, James brings a rare mix of candor, humor, and hard-earned perspective on what it means to survive and grow in technology when there is no safety net.
James shares his journey from writing code as a teenager to running an early dial-up internet service provider, before going on to co-found JBKnowledge and later launching Terra, a modern core system transforming workers’ compensation and insurance operations. We talk openly about why he chose bootstrapping over venture capital, how that decision shaped his leadership style, and why cash discipline still separates companies that endure from those that quietly disappear.
The conversation also explores why insurance, often dismissed as dull from the outside, becomes endlessly fascinating once you understand how deeply it touches everyday life. James explains how risk, data, and claims connect everything from football matches to flight safety, and how working inside the industry fundamentally changes how you see the world around you. It is a reminder that some of the most meaningful innovation happens in places that do not shout for attention.
We spend time unpacking lessons from his book, Be Your Own VC, including why survival matters more than growth headlines and how many founders underestimate the emotional toll of building companies over decades. James does not shy away from discussing the hard days, the moments of doubt, or the reality that technology leaders are always one misstep away from trouble.
As expected, AI enters the discussion, not as a buzzword but as a genuine shift in how fast software can be built and how quickly businesses can fall behind. James offers a clear-eyed view on why speed to market, trust, and execution now matter more than ever, especially in regulated industries like insurance where legacy processes still dominate.
We close on a deeply human note, talking about creativity, music, flying, and the role of art in staying grounded while leading global teams. It is a reminder that the best business leaders rarely draw their energy from work alone.
So as automation accelerates and building software becomes easier than ever, how do you design a career and a company that can still last for decades, and what would you do differently if you truly had to bet on yourself?
Useful links
- James Benham’s personal site
- JBKnowledge:
- Terra Workers’ Compensation Platform:
- Be Your Own VC book:
- InsureTech Geek Podcast:
- James Benham on LinkedIn:
Thanks to our sponsors, Alcor, for supporting the show.