

Building a Portfolio of Nostalgia Restaurants
Sep 9, 2024
In a fascinating discussion, Jackson, a former real estate investor turned restaurant owner, shares his entrepreneurial journey. He reveals how he transitioned to owning nostalgic eateries like Cowgirl Kitchen and Pizza by the Sea. Jackson discusses the unique challenges of managing restaurants in a tourist town, the strategic importance of cash flow, and the thrill of acquiring multiple locations. He emphasizes the emotional connections customers have with dining experiences and highlights innovative ways to boost revenue through technology and strong branding.
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Early Influences
- Jackson Speaks' father, a land broker, showed properties to wealthy blue-collar clients.
- This early exposure inspired Jackson's entrepreneurial spirit and interest in equity.
Shift to Restaurants
- Jackson transitioned from real estate to restaurants after realizing the scale needed for desired cash flow.
- A friend, Carter, connected him with a nostalgic restaurant owner in Rosemary Beach, Florida.
Cowgirl Kitchen's Potential
- Cowgirl Kitchen, located near the beach, offered casual dining in a high-end area.
- Jackson and Carter saw potential in its laid-back atmosphere and inefficiencies.