Michał Trochimczuk: Current challenges: The world is currently facing numerous geopolitical, economic and environmental challenges. Which do you consider to be the most important from your perspective? How are you tackling them?  

Marcus Ryu: We are facing a new kind of fragility. 

For a long time, we believed that the barbaric past – marked by wars, conflicts, communism, and fascism – was behind us. It felt obvious and unquestionable that those times were over. But now, that certainty is gone. The basic principles we relied on have started to erode. 

This shift is deeply connected to what I see as an exhausting and perhaps unresolvable cultural war. And that worries me the most – not just as an entrepreneur, but also as a parent and a husband. 

In response, I urge the organizations I am involved with to be truth-seeking, regardless of the turbulence happening around us. 

Michał Trochimczuk: What are the factors that have made Guidewire successful?

Marcus Ryu: Guidewire’s success came down to three core principles: deep focus, fundamental respect, and clear differentiation. 

We had a deep focus on property and casualty (P&C) insurance, which is fundamentally different from life or health insurance. In the early 2000s, few believed that investing in a core system tailored to a single industry could be venture investable. But we understood the complexity of enterprise software in insurance – systems evolve over decades, unlike the rapid build-and-replace cycles common in Silicon Valley. 

It was critical to define a strategic frame early on: what we aspired to do, and just as importantly, what we chose not to do. That clarity was essential. Unlike the Silicon Valley approach of constantly pivoting, we held firm to our direction. From day one, we committed to building a standard, upgradable software product for P&C insurers. It sounded obvious, but wasn’t – especially when considering large, complex insurers. 

We made only one major strategic shift: evolving from on-premise to cloud, which of course wasn’t a viable option in the early 2000s. 

We deliberately excluded life and annuity, as well as self-insurers like workers’ compensation. At one point, we thought self-insurers were similar enough to include. Guidewire won several of them and was excited – but it turned out to be a mistake. The differences were too great. We ended up returning every dollar and stepping back to refocus. That was a hard moment emotionally, especially since selling was so difficult and every dollar mattered. But I’m proud of how we handled it, especially around 2005. 

We always maintained a plain proposition – not tailored to investors, but grounded in a clear market diagnosis. We made many mistakes, but not this one. Strategic clarity and a simple, focused proposition were key. 

At the time, Silicon Valley was in the midst of the internet boom. There was a widespread excitement in a magical future unlocked by technology – somewhat similar to what we’re seeing now with AI. But overreaching and overpromoting those dreams led to a massive crash.  That why today I emphasize to insurance companies that their operations can benefit enormously from AI, but their ambitions should not exceed the actual capabilities of the technology. 

Back to Guidewire, our culture was defined very differently from companies of the boom era. We were highly ambitious but not primarily driven by personal wealth or ego. Our goal was to build quality software, work shoulder-to-shoulder with great colleagues, and solve real problems in the sector. 

We told people: you won’t get rich, your mom won’t understand what you’re doing, and it’s going to be hard work. And somehow, that worked. The founders led by example – they worked harder than anyone and offered others the same path. 

It was also a moment in time when the industry needed a product like ours. Venture capital was expensive and often unfair to founders and employees. Back then, we didn’t think much about it – but now, I see it differently.