Exploring Dapper D's new concept in downtown Jacksonville
From This Week in Jacksonville: Business Edition by News4Jax and Graham Media Group
May 21, 2026 · 13 min
About this episode
Darien “Jack” Jackson discusses the challenges and excitement of launching his new venture, Dapper Cheesesteaks, in downtown Jacksonville.
Entrepreneur Darien “Jack” Jackson returns to This Week in Jacksonville: Business Edition to open his newest downtown venture in the Elbow: Dapper Cheesesteaks downstairs paired with a cigar lounge experience upstairs in the former 11 Ocean space.Jackson walks host Kent Justice through a year of delays—from a slow permitting process and repeated plan revisions to contractor turnover that even led to litigation—before finally landing with a new construction team and clearing inspections ahead of a Friday grand opening.He also explains why this project was bigger than his previous Dapper D’s locations: he’s effectively launching two businesses at once inside a 1909 building with major structural challenges. Learn more about your ad choices. Visit megaphone.fm/adchoices
People in this episode
Host: Kent Justice
Guest: Darien “Jack” Jackson
Topics covered
- entrepreneurship
- restaurant opening
- business challenges
- cigar lounge
- construction delays
- Jacksonville
Keywords
- Dapper Cheesesteaks
- cigar lounge
- construction delays
- Jacksonville
- entrepreneurship
- business opening
- restaurant
- 11 Ocean
- Elbow
Mentioned in this episode
Organizations: Dapper Cheesesteaks
Places: downtown Jacksonville, Elbow, 11 Ocean, 1909 building
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