Building Community, One Small Business at a Time: Chris McGurk’s Journey as a Wingman Planning Franchise Owner
Starting a business is never easy. It takes courage, persistence, and a willingness to embrace uncertainty every single day. That’s exactly what Chris McGurk has experienced since becoming the newest Wingman Planning franchise owner serving the Toms River community.
On a recent episode of the Grit Won’t Quit Podcast, Chris sat down with Wingman Planning founder Tom to discuss what life has been like during his first few months as a franchise owner, the lessons he’s learned, and why helping local businesses succeed is more than just a job—it’s a mission.
From Networking Connection to Business Owner
Chris’s journey with Wingman Planning didn’t begin when he signed his franchise agreement. It started years earlier through a networking event, where he first met Tom.
What stood out wasn’t just the business—it was the culture.
“I loved the vibe,” Chris shared. “I loved what Wingman stood for. The culture was all about helping people.”
That philosophy stayed with him for years before he made the leap into business ownership himself.
Today, he’s bringing that same people-first mindset to business owners throughout Toms River and the surrounding communities.
Why Small Businesses Need a Wingman
One of the biggest themes throughout the conversation was the unique challenge of owning a small business.
Unlike large corporations with departments dedicated to every task imaginable, entrepreneurs often wear every hat themselves. Marketing, customer service, operations, sales, technology, finances—the responsibility falls on one person.
Tom emphasized something many entrepreneurs know all too well: unless you’ve owned a small business, it’s difficult to appreciate just how demanding it can be.
That’s where Wingman Planning fits in.
Rather than treating clients like account numbers, the team focuses on becoming trusted partners who genuinely understand each business and its goals.
For Chris, that relationship-first approach has already made an impact.
“I’ve heard so many horror stories in the last several weeks,” he said. “People feel like it’s a breath of fresh air when they meet me because they know we’re here to help.”
Building Trust Through Relationships
Launching a business isn’t just about finding customers—it’s about earning trust.
Chris has spent much of his first few months doing exactly what successful entrepreneurs have always done:
- Meeting people face-to-face
- Attending networking events
- Visiting local businesses
- Having genuine conversations
- Learning about each business before trying to sell anything
As Tom explained, people still want to do business with people they know, like, and trust.
Even in today’s digital world filled with AI, automation, and online communication, personal relationships continue to be one of the strongest competitive advantages a local business can have.
Learning That Entrepreneurship Is a Marathon
Like every new business owner, Chris has discovered that entrepreneurship comes with challenges.
One surprise?
Just how many small businesses exist throughout Ocean County.
Every day presents another opportunity to meet someone new, learn about another local company, and find another way to make a difference.
That excitement is balanced by the reality that success doesn’t happen overnight.
It takes consistency.
It takes showing up.
And most importantly—it takes grit.
As Chris put it, “You have to hit the ground running, keep a smile every day, and just get out there and meet people.”
Supporting Clients Beyond Business Hours
One of the stories that perfectly captured Wingman Planning’s approach involved helping a client with a Google Business Profile issue late one evening.
Instead of waiting until the next business day, Chris and Tom worked together immediately to resolve the problem before handing it off to the rest of the team.
It’s a simple example, but it reflects a larger philosophy.
Business problems don’t always happen between 9 and 5.
Whether it’s a website issue, a technology problem, or an urgent digital marketing concern, being available when clients need help builds trust that lasts.
Helping Business Owners Tell Their Story
Another exciting initiative discussed during the episode was Made in Jersey.
The concept is simple:
Many business owners aren’t comfortable sitting through a 20-minute podcast interview, but they would gladly spend one or two minutes introducing themselves and sharing their story.
Those short videos have become an approachable way for entrepreneurs to showcase who they are, what they do, and why they love serving their communities.
Ironically, Chris admitted that he wasn’t initially comfortable on camera either.
Now?
He’s looking to film multiple business spotlights every day.
What started as stepping outside his comfort zone has become one of his favorite parts of the job.
Community Comes First
One of the most meaningful parts of the conversation centered around giving back.
Wingman Planning has always believed that supporting local businesses goes beyond marketing services.
It means:
- Supporting community events
- Partnering with nonprofits
- Helping families during the holidays
- Shopping locally
- Investing back into the neighborhoods they serve
Tom reflected on how the company’s annual Thanksgiving turkey drive has grown from distributing around 70 meals in its early years to providing complete Thanksgiving dinners for more than 500 families.
Chris hopes to help expand those community initiatives throughout the Toms River area as his franchise continues to grow.
For both of them, success isn’t measured only by business growth—it’s measured by community impact.
Looking Ahead
When asked where he sees himself in the next few years, Chris didn’t focus on numbers.
Instead, he focused on relationships.
He wants to become the trusted resource local business owners rely on. He wants to drive through town and see businesses thriving because he had a small part in helping them grow.
That’s the vision behind becoming a Wingman.
Not simply providing services—but becoming someone businesses can count on.
Advice for Future Entrepreneurs
Chris closed the episode with simple advice for anyone thinking about starting a business:
Just go for it.
There will be difficult days.
There will be challenges.
There will be moments outside your comfort zone.
But those are often the moments that lead to the greatest growth.
As Tom reminded listeners, growth isn’t about expanding at any cost—it’s about growing with integrity, staying humble, remembering where you started, and never losing sight of the people who believed in you from day one.
For Chris, that journey is only beginning—but it’s already clear that his focus on relationships, service, and community is exactly what local businesses are looking for.
Sometimes every entrepreneur needs a little support.
Sometimes they just need a Wingman.
This podcast episode was filmed at Wingman Planning in Belmar.
