Personalized Finance and Fintech with Jessica Chen Riolfi

2 min readFeb 22, 2021

Last week, on Tuesday, February 16th, we hosted our first virtual event of the semester: “CFMA x Ontrail”. We welcomed speaker Jessica Chen Riolfi, co-founder and CEO of OnTrail, a personalized finance service that offers undergraduate and graduate students optimized financial advice with regards to student loans, retirement savings, credit, and much more.

A graduate of Harvard Business School and Dartmouth College, Riolfi touched briefly on her extensive background in fintech, which included product development with companies such as Earnin, TransferWise, and Robinhood. She then went on to address her concerns within the fintech industry. First, she noted the incredible speed at which the financial industry is changing, a challenging factor in understanding the realm of personal finance. Additionally, Riolfi pointed to hurdles like hidden fees, social media, and the United States government, all of which further complicate the process of individualized finance.

On the consumer side, the stark reality of Americans’ finances shows a need for basic and stringent financial services. Many American families have little to no retirement savings, as the wealth gap continues to grow and Social Security benefits decrease.

Riolfi, although acknowledging these wary statistics, offered a way to bridge the gap. What if we used the power of compound interest, along with deliberate saving, to help Americans achieve their financial goals? She held, “It’s not just about saving money. It’s about finding every cent and letting ALL of it compound.” She means making use and taking advantage of tax savings, company benefits, better terms, lower fees, etc… This is the vision Riolfi has for OnTrail, a comprehensive, personalized financial service.

She went on to explain her vision. She built a service that offers general financial assessments, personalized recommendations, on topics like bank accounts, debt, goals, and benefits, and chats with a real financial advisor or “coach”. The website states, “Tell us what you want out of life and we’ll tell you the simplest way to do that. Spend your time on something better.”

During the question and answer portion of the event, Jessica carefully attended to students’ concerns about student loans, long-term investing, building credit, and emergency savings funds. She also answered entrepreneurial questions about how she began OnTrail, dealing with funding, and marketing herself and her company.

We thank Ms. Riolfi for her time and thoughtful presentation! If you are interested in reaching out with questions, you can find her on Linkedin.




The Collegiate Financial Management Association’s mission aims to promote financial literacy and personal finance skills in order to ensure financial stability.