Why founders struggle to sell at the peak of success

Founders often resist selling when performance peaks, even though that moment is when buyers place the highest value on the business.

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Two business professionals shaking hands across a desk, symbolizing a high-stakes business decision and the moment of transition during a company sale.
Dr. Irfan Ali shares a people-first approach to leadership at CEO Connect

At TBBW’s December CEO Connect, Dr. Irfan Ali shared how trust, dignity and empathy shape effective leadership in Tampa Bay.

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Dr. Irfan Ali speaks during Tampa Bay Business & Wealth’s CEO Connect event, sharing his perspective on leadership, empathy and building a people-first health care organization in Tampa Bay.
Garrett Greco carries a Tampa legacy into the podcast age

Garrett Greco uses long-form podcast conversations to connect Tampa’s past with the decisions shaping its future.

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Garrett Greco records an episode of the Tampa Bay Developer podcast during a long-form conversation about Tampa’s growth and legacy.
St. Pete opens bid window for Gas Plant District

St. Petersburg opens a competitive proposal window for redevelopment of the Historic Gas Plant District.

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Map showing the Historic Gas Plant District and surrounding St. Petersburg neighborhoods before construction of Interstate 175.
Nelson Castellano leads Trenam with continuity and trust

How Nelson Castellano leads Trenam with steadiness, trust and long-term focus.

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Nelson Castellano, managing shareholder at Trenam, seated in his Tampa home.
Who pays for Tampa’s New Year’s Eve fireworks?

Tampa’s New Year’s Eve fireworks are privately funded by local businesses, not the city, a nearly 20-year tradition led by Jackson’s Bistro.

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Fireworks light up Tampa Bay as a Starship cruise vessel passes the downtown waterfront during New Year’s Eve celebrations.
Tampa Bay’s Top Companies No. 5: First Watch Restaurant Group

Part of TBBW’s ongoing Tampa Bay Top Companies series, spotlighting major employers across the region without ranking or order.

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Aerial view of downtown Tampa and the Hillsborough River highlighting First Watch Restaurant Group as part of TBBW’s Biggest Companies in Tampa Bay series.
How a Tampa company built a bar crawl business at scale

A Tampa company scaled a bar crawl model nationwide, with Gasparilla serving as its largest annual test of growth.

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Three founders of Tampa-based Downtown Crawlers pose inside a bar, reflecting the company’s growth from a Gasparilla event to operations in 28 cities.
Tiny Tap Tavern sold after more than 70 years

After more than 70 years, Tiny Tap Tavern has been sold, with plans to preserve its legacy while preparing for a careful next chapter.

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Exterior of Tiny Tap Tavern in Tampa with signage visible after the longtime neighborhood bar was sold.
The real estate developments shaping Tampa Bay in 2026

The projects defining where Tampa Bay’s growth, capital and urban density are headed in 2026.

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Downtown Tampa skyline with office towers and palm trees under a blue sky, illustrating major real estate projects shaping Tampa Bay.
Why Eskuad sees field operations as tech’s next frontier

Tampa-based Eskuad is building technology for the world where work actually happens, far from Wi-Fi, dashboards and boardrooms.

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Eskuad field operations platform displayed across desktop and mobile devices, showing offline reporting tools designed for remote industrial environments.
Why Tampa remains an early-stage luxury condo market

A look at why Tampa’s luxury condo market may be closer to the beginning than the peak, according to one of Florida’s most active urban developers.

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Interior rendering of a luxury condominium at ONE Tampa, showing an open living and dining space with floor-to-ceiling windows overlooking downtown Tampa.