Elliott Caldwell lands Tampa Bay Business Journal 40 Under 40 honor

Elliott Caldwell, CEO and co-founder of The Rise Collective, was named to the Tampa Bay Business Journal’s 2026 40 Under 40 list in St. Petersburg. The recognition comes days after The Rise Collective became a finalist for GrowFL’s Florida Companies to Watch Awards, underscoring the company’s rapid growth in real estate and hospitality.

Why it matters: - Caldwell’s recognition puts a spotlight on The Rise Collective’s growth story and the broader rise of Tampa Bay entrepreneurs building in real estate, hospitality and related services. - The honor also comes as The Rise Collective gains outside validation for its business model, which is centered on vertical integration and recurring revenue.

What happened: - Elliott Caldwell, CEO and co-founder of The Rise Collective, was named to the Tampa Bay Business Journal’s 2026 40 Under 40 in St. Petersburg. - The Business Journal selected 40 executives from a competitive nominee pool for growth, innovation and community engagement across Tampa Bay. - The announcement followed The Rise Collective’s selection four days earlier as a finalist for the 16th Annual GrowFL Florida Companies to Watch Awards. - More than 500 Florida companies were nominated for the GrowFL program, and 95 advanced as finalists after review of growth, innovation, resilience, community involvement and economic impact.

The details: - Caldwell’s path to entrepreneurship began while he was a high school teacher earning about $37,000 a year. - An introduction to real estate investing and passive income led Caldwell into short-term rentals and a partnership with Michael Elefante. - Caldwell and Elefante co-founded Home Team Luxury Rentals, which grew from managing a handful of properties into a vacation rental management company operating across more than 20 states. - As the business expanded, Caldwell and his partners built specialized companies to handle real estate, financing, construction, design, property management, marketing, tax strategy and other services. - Those businesses became The Rise Collective. - The Rise Collective now includes 13 companies built around real estate, hospitality and wealth creation. - The group was built without outside funding. - The company operates through a vertically integrated model that lets individual businesses stand alone while supporting other businesses in the collective. - The portfolio spans short-term rental and hotel management, real estate, construction and design, financing, tax and accounting, investment education, marketing and business services. - Home Team Luxury Rentals remains one of the group’s flagship businesses and provides recurring property-management revenue plus a nationwide operating platform. - Caldwell said the mix of vertical integration and recurring property-management revenue is the “secret sauce” behind the model. - Caldwell recently said The Rise Collective recorded its first $2 million month in EBITDA. - Caldwell also said year-over-year profitability increased 212%. - Caldwell said the company is still early in its trajectory and that the path ahead is clearer than ever.

Between the lines: - The two honors suggest The Rise Collective is gaining both local recognition and statewide business credibility at the same time. - Caldwell’s background as a teacher turned operator reinforces the article’s theme of entrepreneurship as a path to financial and personal reinvention. - Caldwell’s emphasis on family, faith and entrepreneurship signals a brand built around mission as well as growth. - The company’s vertically integrated structure appears designed to keep revenue, expertise and referrals inside the ecosystem instead of depending on outside vendors.

What's next: - The Rise Collective is positioning itself for further expansion as its operating model scales across real estate and hospitality. - Caldwell is continuing to use his website and podcast to share founder conversations, leadership lessons and ideas about financial freedom and purpose. - The company and its leader are likely to keep leaning on recent recognition as proof points while they pursue additional growth.

The bottom line: - Caldwell’s 40 Under 40 nod is less a standalone award than a snapshot of a broader business engine that is still accelerating.