TOP 100 MAGAZINE

Darryl Cunningham

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Darryl Cunningham’s story is rooted in resilience, shaped long before he ever stepped into a boardroom. Growing up in and around Boston as one of twelve children, he learned early what it meant to push forward, even when circumstances were less than ideal. That environment instilled a mindset he still carries today—mental toughness, discipline, and an unwavering belief that when things get difficult, you keep going. It is a philosophy built on experience, not theory, and one that has become the foundation of his leadership style.

 

His earliest professional influence came from the restaurant industry, where the emphasis on service left a lasting impression. Darryl quickly understood that success was not about the individual, but about genuinely understanding and serving others. That principle would follow him into every venture, shaping the way he builds teams, interacts with clients, and ultimately leads organizations.

 

Over the course of his career, Darryl has moved fluidly across industries, from hospitality to software, consistently finding ways to grow and succeed. He built and sold multiple businesses, each experience reinforcing his belief that hard work and adaptability can drive results in any field. His tenure as vice president of property services for one of the world’s largest property management companies further sharpened his perspective, giving him a front-row seat to both the strengths and shortcomings of large-scale operations. While he gained valuable insight, it also confirmed what he had always known; he was meant to build something of his own.

 

That vision came to life in 2023 with the founding of VIP Property Manager in Boston. Designed as a boutique firm, the company reflects Darryl’s deeply personal approach to business. Rather than relying on templates or reactive service models, his team is intentionally hands-on, assigning two professionals to every building to ensure accountability, consistency, and strong relationships. For Darryl, property management is not simply about maintaining buildings; it is about creating communities where people feel understood, supported, and at home.

 

At the heart of it all is his belief in leading by example. He sets the tone through his own interactions—listening closely, engaging thoughtfully, and always putting the customer first. That authenticity resonates across his organization, creating a culture that prioritizes service above all else.

 

Darryl also shares his philosophy through his upcoming book, Have a Mission, a focused and practical guide centered on mindset and perseverance. Drawing from his own journey, he offers readers real-world lessons on staying focused and achieving meaningful goals, even including a personal one on one coaching session to help them take action.

 

For Darryl Cunningham, success has never been about a single achievement. It is about growth, learning, and the willingness to step outside of comfort zones—again and again—knowing that each challenge brings him closer to something greater.

 

 

Darryl Cunningham
Owner and CEO
VIP Property Manager
Website: www.vippropertymanager.com

Website: www.haveamission.com  

LinkedIn: www.linkedin.com/in/darrylcunningham