Cars for a Cause: San Diego’s Freedom Street Garage

Written by Ken Lewis


Jon Ossie American flag

Jon Ossie of Freedom Street Garage is a local entrepreneur in the Bird Rock neighborhood of La Jolla. Ossie captains the online brand which is a blend of “donation and inspiration” as he describes it.

The brand is a sweepstakes based model but with an undertone of service to others and supporting Non-profit organizations like Operation Surf.

“When I was working on my doctoral dissertation at the university of San Diego in 2021, we kicked off a research study partnered with Operation Surf and “Whoop” (boston, MA) where we examined ocean therapy for military veterans”, Ossie says. “As part of our research we are utilizing wearable technology to encourage analytical data driven decisions for mental and physical health. Our hope is the veterans channel the healing power of the ocean to restore hope, renew purpose, and revitalize community as there have been significant findings in neuroscience that involve being in, on, or around water.”

Freedom Street Garage, as a model, presents a new dream vehicle every quarter that followers can win via a sweepstakes . “We have given away all kinds of amazing dream vehicles,” says Ossie. “From All-American muscle cars to big trucks, even Harleys and Indian Motorcycles. with the best yet to come.

Part of the attraction to this business model is that it allows Ossie to tie in his love of cars with his background in business and his philanthropy. “We have so much fun building fun prize packages and getting to see winner reactions. It’s truly amazing to change someones life while also giving hope that the next winner could be you.”


As far as the vibe of his business, he wanted to blend in all aspects of his persona to encapsulate a vibe that he enjoys sharing with the public.

“Being of service to others, especially to our military veterans, is one way we give thanks for the freedoms we get to enjoy. We strongly believe in supporting our local community, and as San Diego is a big military town. we feel its important to strengthening our local community through action.”

To learn more about Freedom Street Garage, visit their website at

About the author


Ken Lewis

Surf / Snow / Skate industry veteran. Knows his shit.