Riley is a seasoned real estate professional and a key leader within Wilkinson, bringing a wealth of expertise to the company’s acquisitions and development teams.

Early Journey and Inspiration

At 17, Riley initially planned to join the military but instead found himself teaching English in Afghanistan and Pakistan, an experience that really shaped his path. Those early adventures, combined with business trips alongside his father, sparked a passion for real estate and business. While attending college, Riley joined Wilkinson to gain hands-on experience and quickly fell in love with the complexities of market dynamics, lending, and acquisitions.

After stepping out in 2016 to successfully grow a videography company and pursue small real estate projects independently, Riley rejoined Wilkinson in 2019, bringing a renewed perspective. His journey from entrepreneur to leader has given him a unique understanding of ownership, accountability, and execution.

At Wilkinson

Since first joining Wilkinson in 2009 as a senior housing development analyst, Riley has played a critical role in expanding and optimizing the company’s real estate portfolio. His experience spans market research, site selection, acquisitions, due diligence, entitlements, financing, and dispositions. He has underwritten hundreds of deals each year, contributing to millions of dollars worth of acquisitions.

Riley thrives on crafting and executing strategic business plans, collaborating with teams, and ensuring the company delivers on its promises. “Performance is key,” he says. “We earn the right to do business every day by executing what we say we’re going to do.” His commitment to thoughtful development and strong partnerships has driven numerous successful projects in both senior housing and multifamily real estate.

Leadership Philosophy

Riley firmly believes that relationships are the foundation of business success. “People are essential to how we do business,” he explains. “It’s a ‘who, not how’ type of business.” His focus on building strong, collaborative relationships underscores his approach to leadership and client service.

Riley credits his father and mentor Lonnie as major influences, along with thought leaders like Charlie Munger, Jocko Willink, and Jim Collins. A believer in continuous growth, Riley starts his day with coffee, a workout, an ice bath, and reading—though family time is his most cherished way to begin any day.

He draws inspiration from the philosophy outlined in Ryan Holiday’s The Obstacle Is the Way and holds firm to the belief, “Acknowledge Him, and He’ll make your path straight.”

What Sets Wilkinson Apart

Riley attributes Wilkinson’s strength to its history, experience, and ability to stay on the cutting edge. “Competitive advantages shift,” he notes, “but what really matters is how we execute business plans that are both lucrative and impactful. We have a strong foundation, but what we do today is what really counts.”

Riley’s advice for those starting their investment journey is simple: focus. “Be masterful at one thing,” he says, emphasizing the importance of discipline and commitment.

Beyond the Office

When he’s not working, Riley enjoys spending time with his three young children and engaging in outdoor pursuits like surfing, skiing, and music production. “Take what comes and ride it,” he says, drawing a parallel between his love of surfing and life’s challenges.