Tracy Liffey spent years helping launch retail brands including Old Navy and PINK by Victoria’s Secret, at one point overseeing creative teams of more than 100 people. She later left that corporate career and is now the founder of New General Cafe, a clean food and coffee cafe in Winter Park, Florida.
Liffey discussed the change on the B Student podcast with host Ashley Billings, covering the identity shift that comes with leaving a major job, the daily realities of entrepreneurship and working motherhood, and building a business that values community and connection over quick trends.
The chamber shared five takeaways from the interview. Among them: a job does not have to define a person; workplace learning can exceed classroom learning; aspiring founders should keep their day job while testing a venture in their free time; starting a business means wearing all the hats at first and finding your own resources; and startup life amounts to a 24/7 workweek. Liffey’s corporate marketing background included The Gap, Old Navy and Victoria’s Secret.
Press release issued by Winter Park Chamber of Commerce:
https://www.winterpark.org/2026/06/18/from-launching-old-navy-and-pink-to-building-a-local-coffee-shop/
🤖 AI-assisted content notice: This item was written with AI assistance from the source document linked above. The underlying facts come from that public source, not from our own reporting. No quotes, interviews or original reporting are implied. Spotted something wrong? Email corrections@theorlandoconnect.com.
