From Launching Old Navy and PINK, to Building a Local Coffee Shop
June 18, 2026
Local Entrepreneur Traded Fortune 500 Career to Build New General Cafe from Scratch
Tracy Liffey spent years helping launch some of the most iconic retail brands in the world, including Old Navy and PINK by Victoria's Secret, eventually overseeing creative teams of more than 100 people. But despite a highly successful corporate career, she chose to make a major pivot. Today, she is the founder of New General Cafe, a beloved clean food and coffee cafe in Winter Park, Florida.
In this episode of the B Student podcast, host Ashley Billings sits down with Tracy to talk about what it takes to leave corporate America and build a business from scratch. Tracy shares an honest look at the identity shift that happens when you leave a major job, the daily realities of entrepreneurship and working motherhood, and how to build a business that values community and connection over quick trends.
Watch the episode below and read our top 5 takeaways from this interview.
1. Your Job Doesn't Have to Define You
When Tracy Liffey worked at PINK by Victoria’s Secret, a comment in a closed-door meeting changed her entire perspective on how her accomplishments should define her, not the company or industry that she works within.
2. Corporate Learning Beats Classroom Learning
New General Cafe owner Tracy Liffey tells her children all the time that she’s learned more in the workplace than she did in a college classroom setting. Practical knowledge and skills come with on-the-job training, which can’t always be taught in the theoretical discussions of an academic setting.
3. Don't Quit Your Day Job, But Try Your Hustle in Your Free Time
Looking to start a creative venture? New General Cafe owner Tracy Liffey has some advice: don’t quit your day job. That said, find opportunities to see if there is a want or need in your community for the service you want to create and find opportunities to explore that venture until it’s ready to launch.
4. Starting a Business Means Finding Your Own Resources
When Tracy Liffey started New General Cafe in Winter Park, FL, she’d come from a corporate marketing background that included The Gap, Old Navy, and Victoria’s Secret. She learned quickly that starting your own business means you wear all the hats in the beginning.
5. Startup Life is a 24/7 Workweek
Starting your own business means that you’re the one in charge, for both good and bad moments. New General Cafe owner Tracy Liffey shares what that adjustment is like.