Be Anomalous

In this episode of Be Anomalous, Jessica Williams joins me for an insightful conversation about how culture, community, and psychology shape the brands we trust. Jessica is a senior brand and marketing leader who has spent her career inside some of the most influential companies shaping modern commerce. She currently leads Brand Marketing at Shopify, where her work sits at the intersection of creators, founders, and community-driven entrepreneurship—helping millions of entrepreneurs around the world build and grow sustainable businesses. Before Shopify, Jessica held leadership roles at Coinbase, where she helped build and lead the company’s first brand team following its public listing, and at Visa, where she worked across product, partnership, and brand marketing on global initiatives tied to the Olympics, FIFA, and the NFL. But Jessica’s perspective doesn’t come only from the rooms she’s been in . She grew up in a home where her mother ran a psychology practice out of their living room—surrounded by athletes, high performers, and people navigating mental health challenges. That early exposure shaped how she understands behavior, ambition, and decision-making—and why she believes marketing isn’t just a business function, but behavioral psychology in action. In this conversation, we talk about what it really means to build influence without being the loudest voice in the room. About why “playing it safe” is often the most dangerous strategy. About how creator-led brands succeed—or fail—based on authenticity and community. And about how ambition evolves as life, leadership, and responsibility grow. This episode is for founders building from scratch and for corporate leaders navigating power, culture, and change from inside the system. If you’re building a brand, a career, or a life that doesn’t fit neatly into a box, this episode is for you.