When You Dine at This Tampa Restaurant Group’s Joints, You’re Family

Why It Matters

In a climate of rising inflation and shifting consumer expectations, Pineapple Hospitality’s experience‑first, family‑driven approach shows how restaurants can sustain growth and profitability by turning hospitality into a competitive advantage.

Key Takeaways

• Family-like hospitality drives repeat visits and strong loyalty
• First 90 seconds shape guest emotions and lasting impressions
• Multiconcept taco portfolio fuels creativity and market differentiation
• Hiring staff with innate hospitality ensures consistent, family‑like service
• Value defined by experience quality, not just menu price

Summary

In this episode of Takeaway with Sam Okus, founder Jim Ree and vice‑president of culinary Jessica Tomlinson discuss how Pineapple Hospitality Group builds a family‑like atmosphere across its growing Tampa‑area portfolio. The conversation centers on the belief that treating guests as relatives creates repeat business, and that a multiconcept, taco‑centric strategy lets the team unleash culinary creativity while appealing to both locals and tourists.

Ree emphasizes that the first 90 seconds of a diner’s visit are critical for emotional connection, citing Maya Angelou’s reminder that people remember how they feel more than what they hear. He describes hiring practices that prioritize innate hospitality, rigorous training, and a leadership team that lives the culture—what they call the “pineapple juice” of caring more than anyone else. Jessica adds that tacos serve as a versatile canvas for innovative, chef‑driven dishes that keep the menu fresh yet approachable.

Memorable moments include the story of repurposing a hurricane‑damaged site into Chico’s Grill, the family’s move from New York to Florida for cost‑of‑living reasons, and the vivid metaphor of “pineapple juice” symbolizing genuine, personal service. The duo also highlights the importance of consistent, high‑quality ingredients and the belief that value is measured by the overall experience, not merely price.

For restaurateurs, Pineapple’s model illustrates how a strong, family‑centric culture can differentiate full‑service venues in a price‑sensitive market. By focusing on guest emotions, hiring for hospitality, and expanding through distinct yet related concepts, operators can generate loyalty, command premium pricing, and weather economic headwinds.

Original Description

In this episode of Take-Away with Sam Oches, Sam talks with Jim Rehm, the founder of Pineapple Hospitality Group, alongside vice president of culinary Jessica Tomlinson. Pineapple owns five going on six restaurants in the Tampa area, and the restaurants flourish on homey atmosphere that Jim has been developing over the course of his nearly 50-year career in restaurants. In fact, Jim believes so much in restaurants treating guests like family that most of his actual family is involved in the business. Jessica, meanwhile, is a veteran of restaurant chains that was brought in last year to further fuel the culinary creativity across Pineapple’s five concepts. Sam recently sat down with Jim and Jessica inside their restaurant Craft Street Kitchen & Drinks to talk more about their commitment to hospitality and creativity and how it’s helped them through this challenging economy.

In this conversation, you’ll find out why:

People remember how you made them feel more than what you said

The first 90 seconds that a guest is in your restaurant are among the most important

Great hospitality starts at the job interview

When launching a new concept, you’re writing a new story to share with guests

A multi-concept portfolio will allow your team’s creativity to flourish

Have feedback or ideas for Take-Away? Email Sam at [e-mail].

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