Wesley W. Gilliland is the Managing Principal of Rudolph Legal, Ltd., and holds leadership roles across affiliated entities, including Rudolph Investment Company and Rudolph Management, Ltd.
With a career focused on law and real estate investment, Wesley’s areas of expertise include legal counsel, financial strategy and operational leadership. He is known for guiding clients through complex commercial real estate transactions and ownership transitions. His experience managing and scaling his own investment and management platforms is put to good use when working with each client.
Wesley’s expertise includes:
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Commercial Transactions: Structuring acquisitions, dispositions, leasing, financing and 1031 exchanges.
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Real Estate Development: Advising on zoning, entitlements, construction and execution—with firsthand experience as a developer and investor.
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Investment Strategy: Helping clients and private entities navigate structuring, capital deployment and long-term stewardship.
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Property & Asset Management: Through Rudolph Management, overseeing daily operations, property performance, and capital planning for a diverse portfolio.
Beyond his legal and real estate practice, Wesley plays a long-term leadership role in a set of closely held investment and operating entities. He regularly serves as trustee, manager and counsel in guiding those enterprises through governance, restructuring and strategic transitions.
Wesley graduated cum laude from The Ohio State University’s Fisher College of Business in 2007 and earned his law degree from Capital University Law School in 2010, where he graduated second in his class and received the Presidential Merit Scholarship.
Wesley began his career at Casto, a leading regional real estate firm, and joined Havens Limited (now Rudolph Legal) in 2010. In 2025, he assumed control of the firm and related entities as part of a structured succession and ownership transition.
A lifelong Columbus resident and Bishop Watterson graduate, Wesley lives in Lewis Center with his wife, Amelia, and their two children, Austin and Madison.