Charting Success: CS Alum Jonathan Chen on Entrepreneurship

The path to entrepreneurship is rarely straightforward. For many, hands-on experience in building projects, learning from failures and adapting to challenges can be just as valuable as formal education. University of Maryland Department of Computer Science alum Jonathan Chen (B.S. ’14, computer science) knows this firsthand. From co-founding FiscalNote to leading Nitra, Inc., a fintech company focused on financial solutions for healthcare providers, Chen has experienced the realities of launching and scaling startups. 

On March 13, Chen participated in the Mokhtarzada Hatchery Speaker Series at the Brendan Iribe Center for Computer Science and Engineering. The series, hosted by the Mokhtarzada Hatchery Program, connects students with entrepreneurs to share insights on building startups. Now in its fourth year, the program funds student teams with up to $10,000 annually to develop their business ideas.

In a Q&A session, Chen discussed his journey into entrepreneurship, the challenges he faced in securing investment and the lessons he has learned in leadership and startup culture.

Q: Can you start by sharing your background and what led you to entrepreneurship?

A: I grew up in Rockville, Maryland, and attended high school in Montgomery County. I had always been interested in computer science, mainly because my mother, who was an accountant, encouraged me to pursue it. She saw the potential in tech as early as the early 2000s. I took computer science courses throughout high school, and when I got to UMD, majoring in computer science felt like a natural choice.

Initially, I aimed to study hard, get good grades and land a job at a major tech company. I had my sights set on working at Google. But that changed when I met a classmate running an email marketing business during my sophomore year. He was making about $10,000 a month while still in school. That was my introduction to the idea that entrepreneurship could be a real path, not just something for people with years of experience. We started building mobile and web applications together, leading me into the startup world.

Q: During your time at UMD’s Department of Computer Science, were there any experiences, classes or mentors that helped shape your journey as a founder?

A: There were several. One that stands out is CMSC 435, the software engineering course. It emphasized teamwork and collaboration on software projects, which was a shift from working on assignments individually. That experience was helpful later when I started working with co-founders and teams.

Another course that had a lasting impact was CMSC 421, the artificial intelligence class. It introduced me to AI concepts and machine learning, which were not as widely discussed then as they are today. It gave me a foundation for understanding and navigating the current AI landscape.

Lastly, the CMSC 216 course, which focused on C and low-level programming, was invaluable. Understanding the fundamentals of lower-level programming languages has been helpful in technical decision-making across different ventures.

Q: What was the inspiration behind FiscalNote, and how did the idea take shape in its early days?

A: FiscalNote started with my co-founder, Tim, who was working in government at the time. He had the idea of using AI and natural language processing to analyze government data and make it more accessible. The timing worked well because I had already built multiple applications and had learned from those early failures.

We launched FiscalNote during college, and the early days involved rapidly iterating on the product while figuring out how to secure funding. We combined technical problem-solving with business strategy, learning as we went.

Q: You’ve navigated the journey of securing investors—what were some of the biggest lessons you learned in that process?

A: One of the key things I learned is that securing investment is a numbers game. Many first-time founders put investors on a pedestal, thinking their rejections are a definitive judgment of their business. In reality, most investors say no for various reasons that don’t necessarily mean the business isn’t viable.

It’s essential to reach out to many investors—100 is the bare minimum, and in many cases, you need to pitch to 200 or more. If you only pitch to 10 investors and get rejected, you haven’t talked to enough people. The process requires persistence and learning from each interaction.

Another key lesson is that investors often have specific areas of interest or theses about the market's direction. If your startup aligns with their thesis, you have a higher chance of securing funding. Understanding what an investor is looking for can help you tailor your pitch effectively.

Q: You unexpectedly met Mark Cuban early in your journey. Can you tell us about that experience and its impact on your startup?

A: Meeting Mark Cuban was part of the same numbers game approach—reaching out to as many investors as possible. Cuban happened to be one of the investors we pitched, and he saw potential in what we were building. His investment gave us credibility early on, but looking back, I believe that if we had kept pitching, we would have secured funding elsewhere.

A key takeaway from that experience was that persistence, and high-volume outreach matter more than any single lucky break. If you talk to enough investors, eventually, someone will see the value in what you’re building.

Q: Startups often face significant challenges. Can you share a time when you hit a major obstacle and how you overcame it?

A: Challenges happen regularly. There's always something, whether it’s a major client leaving, an employee deciding to move on, or financial difficulties. What matters is how you react.

I’ve learned to take an analytical approach—assessing the situation, listing possible solutions, and moving forward quickly. In the early days, I used to panic over significant setbacks, but I’ve become more focused on problem-solving over time. Every startup will face major challenges; the key is adapting and moving forward.

Q: Now, as the CEO of Nitra, Inc., how has your approach to leadership evolved?

A: In the early days at FiscalNote, I approached leadership more flexibly, focusing on ensuring employees were comfortable. Over time, I realized that decision-making needs to be efficient and aligned with clear company goals in a fast-paced startup environment.

At Nitra, I focus on ensuring that decisions are made quickly and we have clear accountability. Speed is a startup’s biggest advantage, so it's critical to have a culture that prioritizes execution over drawn-out discussions.

Q: The Hatchery Speaker Series is about sharing insights with aspiring entrepreneurs. What advice do you have for students looking to launch their startups?

A: If you’re serious about starting a company, you must be prepared to go all in. The early stage of a startup requires significant time and effort—often seven days a week, long hours and a high level of commitment.

Surrounding yourself with the right people is also crucial. A strong, aligned team significantly impacts execution and overcoming obstacles. Lastly, persistence is key. Most startups don’t fail because the idea is bad; they fail because the founders stop trying. If you keep pushing forward and learning from each setback, you increase your chances of success.

—Story by Samuel Malede Zewdu, CS Communications