Behind The Desk: Jason Toledo
“I wouldn’t trade this for anything.”
That’s how Jason Toledo sums it up – his life as a business owner, a husband, and a father of two.
Jason has been with Gar Wood since 2018, but his journey into independence started long before that. After building a successful team for someone else, he made the leap to launch Toledo Trade – a DBA of Gar Wood Securities serving self-directed traders worldwide. What started as a business decision quickly became something much more personal.
“In the last seven years, I’ve been through just about everything,” he says. “Three surgeries. Two hurricanes. A failed adoption. And then – finally – a successful one. Now I’m a dad to two amazing boys.”
Jason is based in St. Petersburg, Florida, where he endured the wrath of Hurricane Milton. “There were moments when everything felt like it was falling apart around me,” he says. “But I never felt alone. That sense of support – not just as a business owner, but as a human being – made all the difference.”
He’s worked in both boutique firms and large institutions with hundreds of offices, but says nothing compares to the freedom – and responsibility – of building something on your own terms. “You learn quickly what really matters,” Jason says. “For me, it’s trust, independence, and being present – for my family and my clients.” It’s exactly that balance that he’s found at Gar Wood: the space to lead his business with autonomy, and the support when it matters most.
With Toledo Trade expanding into U.S. markets and launching a new website, Jason’s focused on growth – but not just in numbers. “I want my boys to see what it looks like to build with purpose. That you can be proud of your work, and also prioritize the people you love.”
Fatherhood reshaped Jason’s outlook on everything. “It makes you sharper, softer, more patient. It makes you want to leave something better behind. That’s how I think about the business now – it’s not just a job. It’s part of the legacy I want to build.”
This Father’s Day, we’re proud to spotlight Jason – not just for what he’s built, but for the values that guide him.
Jason Toledo,
Managing Director, Toledo Trade – a DBA of Gar Wood Securities