Lessons from Marcus Ryu

Marcus Ryu is the co-founder of Guidewire and a partner at Battery Ventures. His words offer a deep dive into his philosophies on entrepreneurship, leadership, and building a lasting company.

On Authenticity and Self-Awareness

"You must speak to your own strengths and your own nature. Sometimes you feel as a founder of a company that you have to represent yourself as something else. It always fails. People see through it. People hate inauthenticity." [1]
"I have a fairly simple career. After graduate school, I ended up at McKinsey briefly...then worked for a software company here in Silicon Valley called Ariba...and then in 2001, completely to my astonishment, decided that I was put on this earth to be a software entrepreneur." [2]
"I approached sales with a kind of disdain, a kind of completely elitist snobbery. And now I regard sales as a noble profession and I'm proud to be a salesman. I think I'm probably better at that than most other things. And I learned that by necessity in the Guidewire journey." [2]
"I love to think, I love to read, but I didn't know I wanted to be a monk." [3]
On reflecting on his career path: "I've been running a race and doing it pretty well but I've been running the wrong race." [3]

On Building a Company and Strategy

"We're going to build software as a craft. You'll be treated with respect, know exactly where things stand, and be regarded as an end, not a means." [4]
"One thing we got right...[was] identifying the boundaries of our product and saying we're going to build a core system for insurance." [1]
"It was a theory of what needs to be built, and the sequence thereof, what was the MVP, what were...the company's product strategy for the next decade." [1]
"The market is always right. You must ask, you must get as close as you can to the end market and you must ask as many questions relentlessly...you must try to understand what does that end market really think." [3]
"It's a very great danger to just try to invest in an ivory tower and think how do I feel about it right and sometimes I have to resist my own tendency to abstract that away instead of just getting you know to the coldface." [3]
"How lucidly, precisely, consistently can the leadership, especially the CEO, articulate the diagnosis of the market and a plan of attack. And it's remarkable. Sometimes you have very talented, very charismatic CEOs who are not good at that." [3]
"When you don't have glamorous things to sell, then you have to find a way not to apologize for your weaknesses. You have to make them your assets." [3]
On the difficulty of the work at Guidewire: "That's a feature, not a bug. You are joining this company to do something difficult, something substantial, something arduous." [3]
"The startup as insurgent." [5][6]
On specialization: "The Vertical Advantage: How Specialisation Drove Success in Insurance." [2][7]

On Leadership and Team Building

"As a CEO, your power isn't just about making decisions; it's about shaping the agenda. Your ability to set priorities, decide who participates, and determine when discussions are complete makes all the difference." [4]
On recruiting talent for a non-glamorous problem: The value proposition was straightforward: "We're going to build software as a craft. You'll be treated with respect, know exactly where things stand, and be regarded as an end, not a means." [4]
On the founding team of Guidewire: "We identified in each other kind of a very, very strong intellectual affinity." [2]
"I'll tell you, I left at year 19 and we were still founder-led sales. Because the nature of what we sold was so mission critical. It was so high stakes." [2]
"Good decisions are the result of experience and experience is the result of bad decisions." (a Mark Twain quote Ryu often uses) [1]

On Entrepreneurship and Resilience

"It's one thing for things to be game over after year two, quite another thing when it's game over at year nine...We overcame it and that's its own story." [1]
On facing a lawsuit that nearly killed the company: "The adversity forged a deep sense of moral purpose and 'white-hot rage' that increased the team's loyalty to Guidewire." [4]
"Why you need recklessness to start a company." [8]
"I have never heard someone say, 'I would have started a company, but tax rates were too high' or 'I wouldn't have started this company, but then George W. Bush cut tax rates, so I did.'" [9]
"It's so difficult when you're starting a company, when you have no assets and you just have a dream and everything seems impossible." [2]
"The motivator is terror of failure that was infinitely more powerful." [3]
"Founders who have had too comfortable a life generally aren't ready for the kind of suffering and the setbacks and the frustration." [3]
"Startups are insurgents." [8]
On the early days of Guidewire: "When we ever get a customer to pay for us, pay for this software, that felt like an impossible dream." [2]
The first sales cycle is like "wandering in the desert." [8]
On embracing challenges: "More Mountain." [3][10]

On Venture Capital and Investing

On his approach to investing: "You could call me promiscuous in that sense. I fall in love with pretty much every founder I meet at some level." [1]
"I find that in almost every entrepreneur I meet, even if there's some degree of insanity...there's some degree of...spiky insight." [1]
"Uninformed confidence is a fine line between uninformed confidence and just recklessness, right? You have to be confident. You have to be secure in yourself and takes a fair amount of ego to do that." [1]
On what he looks for in entrepreneurs: "A kind of restlessness, a kind of insecurity, if you will an eagerness or requirement to just to prove something." [3]
"I pay a lot of attention to the strategic coherence." [3]
As an investor, he underwrites the leadership team because "so much of the journey is unpredictable." [3]
On becoming a venture capitalist: "I decided to make a major career transition and become a venture capitalist...it's certainly much more competitive than I would have ever imagined, but that has its own rewards too." [2]
Having been an entrepreneur informs how he acts as an investor now. [2]
"AI is an instrument...it's a layer of enablement and instrumentation that will make a huge difference to companies of all sorts. But still you have to deliver a core value proposition." [3]

On Life Philosophy and Career

"As we, all of us reflect on our lives, we realize just how random and improbable, you know, the little decision, the little butterfly's wing that caused us to marry this person or choose this career or whatever." [1]
On the dot-com bubble: "I was, let's just say repulsed, you know, by a kind of excess, a kind of, kind of unhinged exuberance that applied during that time." [1]
"Whenever you have huge amounts of wealth, being created in too short a period of time, everything goes off the rails. People can't think straight. Relationships fall apart. No one can build anything. No one can concentrate. Nothing happens. Nothing good happens. Right?" [1]
"What are the real agents of history what what really makes a difference in this world what what moves the world...it's mostly entrepreneurs that are on the vanguard of advancing and taking the risks that you know that make the world what it is today." [3]
On the satisfaction of difficult work: "Something that will deliver a kind of satisfaction on its achievement that you cannot get if you're doing a trivial project." [3]
"When you see a mountain you think I've got to go around this somehow it's an obstacle. and said what if you just embrace it as your destiny and you're going to just tunnel through it." [3]
On his opposition to certain tax cuts: "Four out of every five dollars in proposed tax cuts will flow to the top 1 percent, an egregious wealth transfer to those who least need it." [9]
"It certainly never felt easier. In some ways, it felt harder for different reasons, but it never felt easier." [2]
On Guidewire's revenue growth: "This number would have seemed to me like science fiction in the early days." [2]
On his career change to venture capital: "The kind of learning that I've been able to have in the last few years, just from one company, learning from entrepreneurs, learning from experts that are advising about that, has been fantastic." [2]

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