Writer. Director. Actor. Producer. Podcast Host.
Jeff Macolino is an award-winning independent filmmaker, actor, writer, producer, and podcast host based in St. Petersburg, Florida. Through Macolino Entertainment Network, he develops and produces original entertainment, with a particular interest in character-driven stories, dark comedy, and projects that don’t necessarily follow the traditional Hollywood playbook.
His path into entertainment wasn’t exactly conventional.
Born and raised in St. Petersburg, Jeff attended the University of South Florida while working five seasons in the Tampa Bay Rays’ front office, earning a 2008 American League Championship ring that was subsequently stolen. He then spent more than a decade building a career in the insurance industry, getting married, raising two children, navigating a divorce, and eventually realizing that professional advancement wasn’t necessarily the same thing as personal fulfillment.
After a difficult period in his personal life, Jeff began pursuing the creative ambitions he’d spent years putting aside.
In February 2021, he launched The Jeff Macolino Podcast and began performing stand-up comedy. What started as a podcast recorded on his phone eventually grew into a show featuring more than 300 episodes, with conversations spanning entertainment, comedy, filmmaking, and an assortment of people with interesting stories to tell.
His growing interest in performance led to sketch comedy and independent film acting, ultimately developing into a career both in front of and behind the camera.
Filmmaking
Jeff wrote, directed, executive produced, and starred in the feature comedy Thanksgiving, Again?! (2025), a holiday time-loop story that has received festival recognition, including the Audience Choice Award and Best Feature Screenplay at the Tampa Bay Underground Film Festival. The film is available to stream free on Tubi.
He also stars as Anthony in the independent drama The Last Ryde (2026), directed by Christopher P. Smith, for which he also served as executive producer. His performance has received multiple Best Actor awards on the independent festival circuit. The film is also streaming on Tubi.
Beyond his completed films, Jeff continues developing original feature screenplays across comedy, crime, drama, and thriller genres. His projects include Spaghetti Face, a dark crime comedy in development, alongside several additional feature-length scripts.
Jeff’s approach to filmmaking is straightforward: create compelling stories, assemble talented collaborators, and find practical ways to get projects made.
Beyond the Camera
Alongside filmmaking, Jeff continues hosting The Jeff Macolino Podcast, interviewing entertainers, filmmakers, comedians, entrepreneurs, and guests from a wide variety of backgrounds.
His entertainment career has also included stand-up comedy, sketch performance, sports broadcasting, and numerous podcast guest appearances.
A lifelong resident of St. Petersburg, Jeff remains closely connected to the Tampa Bay area, where much of his filmmaking work takes place. He’s also the proud father of two children, both of whom have appeared in his films, Thanksgiving, Again?! and The Last Ryde. Getting to share his passion for filmmaking with his kids has made the experience even more meaningful.
And yes, he’s still waiting for someone to return that stolen American League Championship ring.