After the financial crisis, Tom made the bold decision to leave the security of corporate America — a stable job and guaranteed paycheck — to venture out on his own and become the Wingman for small businesses. What started with helping contractors establish their digital presence soon grew into something much bigger, and that’s how it all began.

Wingman then relocated to the Jersey Shore, where Tom set up shop working from his dining room table. Despite the move, Tom continued commuting to New York three days a week to meet with clients who had no idea he had relocated. They still believed he was coming from Hicksville, Long Island — unaware that he was actually navigating the Garden State Parkway, Staten Island, and the Belt Parkway just to get back to Long Island for those meetings.

After bringing on two employees to work from his dining room table, Tom realized it was time to find a dedicated office. After some searching, Wingman found a location in a business complex, where they initially shared space with other companies. It was in this new environment that Wingman’s growth truly began to take off. As the team expanded and services broadened, the company quickly outgrew the space — a sign of just how much Wingman was evolving.

This was also the time when Wingman started giving back to the community. What began as small efforts, like organizing food and toy drives, became something the team was incredibly proud of. These initiatives may have started small, but they marked an important milestone in Wingman’s journey — a reminder that growth isn’t just about business, but also about making a positive impact.

Wingman took the leap and moved into a 4,800-square-foot building, transforming a dated 1970s real estate office (similar to the Glen Gary office) into a state-of-the-art tech hub. The vision for this space was something you’d expect to find in the heart of Manhattan, a trendy area of Brooklyn, or even in California. It was here that Wingman began to expand on all fronts — from growing the team to refining the brand. The new headquarters became more than just an office; it became a place that employees and clients alike would recognize and remember. It was where Wingman began to truly build a culture and establish itself as a forward-thinking, innovative company.

Wingman then expanded with a second location in Belmar, creating a collaborative space designed to foster new connections and expand the brand’s presence. Belmar quickly became a hub for creativity and collaboration, where teams could brainstorm, pitch marketing ideas, and engage with clients. The space also became a venue for lunch-and-learns, networking events, and other initiatives that helped build relationships and strengthen Wingman’s growing footprint in the community.

Then, the Grit Won’t Quit podcast was born. Tom had long considered starting a podcast to give business owners a platform to share their stories of resilience and perseverance. The idea was to create a space where entrepreneurs could showcase the grit that drives them. From humble beginnings to extraordinary achievements, each episode highlights the tenacity, determination, and unwavering spirit that empower entrepreneurs to overcome adversity and keep pushing forward.

After years of dedication and a deep passion for giving back, the Wingman Foundation was established. Since 2015, Wingman has held a strong vision to support the community they call home. With the help of local nonprofits, Wingman has been able to make meaningful contributions each year, steadily growing in size and impact. Today, the foundation helps countless families and organizations, and its commitment to expanding its reach and support continues to grow.

We officially filed for two trademarks on our Wingman logo! This exciting step helps protect our brand and ensures our signature look stays uniquely ours.