The Balance of Science and Art in the Entrepreneurial Journey: A Member Spotlight with Matt Rosendin
The Balance of Science and Art in the Entrepreneurial Journey:
A Member Spotlight with Matt Rosendin
For our latest Member Spotlight, I had an illuminating conversation with Matt Rosendin, a tech-visionary who anchors his work at a dedicated desk in the main space here at The Pearl Works. We discussed his journey from the testing grounds of Silicon Valley to the evolving landscape of AI and finance.
With a background that spans the rise of cryptocurrency to integrating blockchain for global payment giants, Matt brings a deep well of hard-earned wisdom to our community. I hope you enjoy reading this conversation as much as I enjoyed having it.
Dana: To start, can you describe your background and how you arrived at the work you’re doing today?
Matt: I grew up in the South Bay, so pretty close to Silicon Valley, during the 2000s, right between the .com boom and bust. I went to Santa Clara University, just a mile from my high school, which was a formative experience. I taught myself to code and served as co-president of the Entrepreneurs Organization there.
From there, I spent time at Stanford and eventually landed at Zendesk in San Francisco just as they went public. It was an exciting time to be in the city. Later, while in graduate school at UC Berkeley, I started a company with friends in the cryptocurrency space. That eventually led to a 2.5-year stint at Ripple. After that, I founded Trustline for 1.5 years, worked at the acquirer Linqto for 1.5 years, and led CapSign for 2.5 years. Altogether, I’ve spent eight years in the crypto and fintech world. Today, I’m still at that intersection, but with a heavy focus on AI.
Dana: You mentioned being the co-president of the entrepreneurs' club in college. What were the core themes of being part of that group?
Matt: It was a campus organization tied to the Center for Innovation and Entrepreneurship. We focused on exposure and involvement. One of the most exciting things I did was organize a Startup Weekend; a three-day hackathon in partnership with Google and Techstars. We brought in judges, like VCs from Plug and Play. One of the groups from that weekend actually went on to create a highly successful business. It was all about getting people in a room to meet and work on ideas.
Dana: It seems like you’ve had a through-line of building and collaborating. Do you have a personal definition of what it means to be an entrepreneur?
Matt: Today, the term has taken on a massive meaning because our tools allow us to do so much, but at its core, it’s about risk. If you are going to take a risk and build something that people may value—that motion of creating—that is entrepreneurship.
Dana: There’s an element of risk, but also, as you’ve mentioned, a level of vulnerability. You’ve had to pivot or "fail forward" several times.
Matt: Exactly. That’s part of the reality—figuring out what works and what sticks. It is both an art and a science.
Dana: When you’re in a season of building, what mindsets or tools do you rely on?
Matt: You have to start from within—the "wellspring" that sparks the idea. But the most important tool is talking to people to get feedback. Your target customer is what makes or breaks an idea.
In terms of frameworks, I rely on the Lean Startup methodology and the teachings from Y Combinator’s "Startup School." These frameworks have helped build companies with proven success, like Airbnb and Coinbase. But even with those, it always goes back to customer development, market sizing, and understanding finance and accounting.
Dana: How has being a member at The Pearl Works influenced your projects?
Matt: It’s been a very positive influence. The community is supportive, and having people around to give feedback is invaluable. Just today, a catch-up with a fellow member provided some great enthusiasm for the direction I’m taking.
Events like the Demo Shares are a cool way to get feedback in a different format. Plus, the energy of being in downtown Monterey is just better than working from home. It puts me in the right place to walk into local businesses—like hospitality or property management—and talk to people about their real-world problems.
Dana: Word association game! What's the first thing that comes to mind when I say…
Collaboration?
Matt: Work and feedback.
Plan?
Matt: Roadmap.
Burnout?
Matt: Vacation.
Creativity?
Matt: Art.
Alignment?
Matt: North Star.
Dana: If you had one piece of advice for someone ten years behind you, what would it be?
Matt: Focus. Within a couple of years, the opportunities in SaaS (Software as a Service) won't be what they once were. I’d say focus on atoms instead of bits—physical hardware or supply chain-based enterprises. You can use AI to build whatever you want now, but don't count on that being a "sure bet" forever.
Dana: Is there anything else you wanted to mention that we didn't cover?
Matt: It was great to reflect on some of the lessons from the last 15 years. I think we covered a lot of ground on what it actually takes to start a business. I don't have anything to add—it was a great conversation!
Matt is deep in both the art and science of building his latest project, focusing on the intersection of AI and financial clarity. You can check out his latest venture here: Axiomatic: The first AI-native ERP for your entire business.
Matt’s perspective highlights the beauty of entrepreneurial motion as a constant cycle of building, validating, testing, and pivoting. By focusing on solving real problems and remaining open to the ground truth, he leverages his technical expertise to create new possibilities for his clients. As he continues working at The Pearl Works, Matt is navigating the rapidly changing landscape of AI and finance with the perfect balance of a strategic roadmap and a clear North Star.
The Pearl Works provides the supportive container for your ideas and a community to help them grow. Ready to find your seat? Book a Tour