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JR appears in the Top 100 

People in Real Estate Magazine

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J.R. Hess


In the bustling world of multifamily real estate, few stories stand out as vividly as that of J.R. Hess, vice president of DBC Real Estate and managing member and partner of Pennwood Capital. From his humble beginnings in the family construction business to spearheading multimillion-dollar real estate transactions and managing nearly half a billion-dollar portfolio, J.R.'s journey epitomizes the fusion of hard work, determination, and a steadfast commitment to legacy.

J.R.'s immersion in the family trade commenced at an early age, following in the footsteps of his father, John M. Hess. Under the influence of his father, JR was able to help further progress of what would become one of the state's most prominent non-union general contracting firms. Yet, it wasn't a path paved with privilege; it was one etched with sweat and grit. At the tender age of 12, J.R. found himself donning the cloak of manual labor, learning the trades from carpentry work to roofing, with each summer offering a new apprenticeship.

The pivotal moment from construction to real estate arrived during the throes of the 2008 recession, when J.R. recognized the need to augment his practical knowledge with academic prowess. Despite being entrenched in the family construction business, he humbly acknowledged his deficiencies and embarked on a journey of education. Armed with an MBA and MPSRE from Georgetown, J.R. returned to the fray, equipped not just with experience, but with the acumen to navigate the complex terrain of commercial real estate.

The inception of Pennwood Capital marked a significant milestone in the Hess family story. With a vision to expand their horizons and fortify their foothold in the industry, JR, alongside his brother, Micheal, and their father, John, ventured into the realm of private equity asset management. It wasn't merely about financial growth; it was about stewardship and trust, as evidenced by the enduring relationships forged with repeat investors. Nor was it just about accumulating assets—for J.R. and the Hess family, Pennwood Capital and DBC Real Estate would emerge as the epitome of their ethos—an entity that not only acquires properties, but nurtures and manages them with meticulous care.

DBC Real Estate and Pennwood Capital’s main emphasis lies in investing in and overseeing existing Class B and workforce multifamily apartment properties. Additionally, they actively pursue the development and management of new income-generating real estate ventures through adaptive re-use strategies. Moreover, they excel in managing income-producing properties not only for themselves but also on behalf of qualified owners and investors.

The pinnacle of these two companies’ collaboration manifested in a momentous recapitalization endeavor. With approximately 30 properties and nearly 5,000 units under their belt, this strategic move allowed them to return partners’ capital to such an extent that only 5 deals within the portfolio retained equity. In essence, out of the $65 million in equity deployed, they successfully returned nearly all deployed capital to their valued investors.

Reflecting on his journey, J.R. articulates, "To work alongside my brother and father and perpetuate a legacy is profound. Some may aspire to carve out their own path, but for me, preserving generational legacy holds paramount significance."

In the ever-evolving landscape of commercial real estate, J.R. Hess stands as a beacon of integrity, resilience, and the enduring power of legacy—a testament to the adage that some structures aren't built with bricks and mortar, but with dreams, determination, and an unwavering commitment to family.


J.R. Hess
Principal and Managing Partner of Pennwood Capital
Vice President of DBC Real Estate

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