Casey Williams is a Partner & COO at Fenway Summer, a VC firm investing in early-stage fintech companies. She focuses on companies building infrastructure for the financial system, with a particular conviction for founders raising their first institutional round in complex, policy-adjacent markets.

Casey has walked a non-linear path to venture capital. She began her career as a fourth-grade math teacher through Teach for America, an experience that shaped how she thinks about problem-solving, resilience, and working in under-resourced environments. She then moved into financial inclusion work at Kiva Microfinance and, later, product and R&D at Wells Fargo. Her venture capital career began on the operating side of the business, when she first joined the Fenway Summer team in 2020 as an Operations Associate. She was quickly promoted to COO and has spent years managing every aspect of the business side of the firm, from fund administration to tax and audit processes.

Casey has a demonstrated pattern of conviction on non-consensus founders, looking for ideas that sit outside the comfortable consensus of what fintech “should” look like, and a track record of being early. She holds a Master's in Public Administration from the University of Oklahoma and a B.A. in English Literature from Elon University. She lives in Washington, D.C. with her husband, two kids, and a growing collection of rescue animals.

During this episode, we discuss:

• Casey's nonlinear career path that led her into investing
• Her advice for aspiring VCs
• What she does at Fenway Summer
• The three things she looks for when evaluating early-stage fintech founders
• Why distribution has become the ultimate moat in financial services
• How her operator background makes her a genuinely hands-on partner
• A common misconception the VC world got wrong
• What Fenway Summer is announcing later in 2026

And more. Tune into this episode as we dive into all things fintech investing!