Today we’d like to introduce you to John Simmons.
Hi John, please kick things off for us with an introduction to yourself and your story.
I was pursuing my MBA at George Washington University’s School of Business, and my team was consulting for a freelance videographer who wanted to break into federal contracting. He had the talent and the ambition, but he had no roadmap for navigating the public sector. He didn’t know how to position his company, how to get on the GSA Schedule, or how to tell his story in a way that made federal decision-makers pay attention.
We built him a tailored strategy: organizational structure, hiring framework, positioning, the full playbook. He was energized by the plan, but I didn’t know if he’d actually carry out the plan that we created. Six months later, I walked into a federal technology symposium and there he was, running all media production for the entire summit. He had taken the plan and turned it into a thriving business. That was the moment I understood what I wanted to do next.
I spent thirty-five years in the federal government, and the most important thing that career taught me wasn’t how to plan. It was how to act. In the military, you rarely have perfect information, but you move anyway. You execute with what you have, you adjust in real time, and you trust that momentum will reveal what deliberation never could. That mindset is the single greatest asset I brought into entrepreneurship, because the number one thing that keeps aspiring business owners stuck isn’t a lack of ideas. It’s waiting to feel ready.
Today, I run a digital marketing agency within WSI’s global network of over 300 agencies across 80-plus countries. But what sets our work apart is who we serve and how we serve them. I specialize supporting defense, and emerging technology companies, the firms building the tools and platforms that are advancing national security. These are brilliant organizations, but many of them struggle with the same fundamental challenge: market visibility and competitive differentiation. They attend the expos and apply for the incubators and fight to get on GSA Schedules, but their messaging is vague and marketing strategies are often misaligned to make them distinct from many other companies in their space. We help them craft that narrative, a clear and compelling brand story that makes public sector decision-makers understand not just what they do, but why they matter.
I also work with veteran and military-connected entrepreneurs, because I know firsthand that the transition out of service doesn’t have to mean the end of your mission. It can be the beginning of a new one. The same drive that carried you through a military career, the discipline, the adaptability, the instinct to serve, translates directly into building something meaningful in the private sector. Too many veterans don’t realize that, or they don’t have anyone in their corner telling them it’s possible.
On a personal note, I’m a proud Disney adult. Going to the parks and sailing on the cruises is a multigenerational family tradition. There’s something about those experiences that connects to why I do what I do: you meet people from all over the world and from completely different backgrounds, and everyone is there to share something together. It has something for everyone, especially the young at heart. That spirit of bringing people together and creating experiences that resonate across differences is at the core of how I think about storytelling and brand building.
That’s ultimately where I see this heading. Beyond the agency work, we are building toward a scholarship, training incubator, or foundation dedicated to supporting aspiring veteran entrepreneurs. Service doesn’t end when you take off the uniform. It evolves. And I want to make sure every veteran who has the ambition to build a business also has the tools and the community to make it succeed.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
The road has certainly been a winding one. Transitioning from the military to federal employment and then to entrepreneurship was no small leap; it’s a completely different mindset. One of the earliest challenges I had to confront was what’s known as founder’s risk: the reality that in the beginning, everything depends on you being directly involved in every aspect of the business. There’s no safety net, no institutional structure to fall back on. Just you, your vision, and your decisions.
That said, I learned quickly that you don’t have to navigate it alone. One of the most valuable things I’ve done is lean into community. Connecting with other agency owners, joining the local Chamber of Commerce, and engaging with business development centers here in Maryland has been both grounding and energizing. What surprised me most was how willing fellow local business owners are to volunteer advice and open doors, and many of them carry that same service-oriented mindset that drew me to this work in the first place.
At the end of the day, I’ve come to believe that business success is less about going it alone and more about the relationships you build along the way.
Thanks – so what else should our readers know about WSI Digital Marketing – Simmons Group?
We are a local marketing strategy and AI consulting agency specializing in emerging and growth-stage defense contractors and technology firms. Our clients are companies developing real capabilities but who haven’t yet cracked the code on how public sector agencies evaluate, understand, and adopt new solutions. That’s exactly where we come in.
What sets us apart is perspective. Most marketing firms approach government-facing clients from the outside looking in. We bring years of experience from the buyers’ side: evaluating emerging technologies, managing requirements, and allocating budget within federal agencies. We don’t just understand how to tell your story; we understand how the people on the other side of the table think, and we help our clients speak that language fluently.
We are also proud to be part of a larger global organization of over 300 agency owners operating across 80 countries and serving more than 150,000 businesses worldwide. That network, backed by over 30 years in the digital marketing industry, also positions us as a leading voice in AI adoption for businesses. Locally rooted but globally connected, we bring enterprise-level resources with the personalized attention of a boutique agency.
So, before we go, how can our readers or others connect or collaborate with you? How can they support you?
John Simmons
Marketing Strategist and AI Consultant
Phone: 410-929-3978,
Email [email protected]
Website: https://simmons-group.wsiworld.com
LinkedIn: https://www.linkedin.com/in/simmons-john
Pricing:
- Our pricing is tailored to each client’s specific needs.
- We start with a free marketing audit and create tailored marketing strategies.
Contact Info:
- Website: https://simmons-group.wsiworld.com
- Facebook: https://www.facebook.com/jsimmons.wsi
- LinkedIn: https://www.linkedin.com/in/simmons-john
- Other: https://share.google/VSAK2LMmZhceqLFpq
