“Forward-thinking and focused on making a difference.”

Robert S. Understein, CPA, is a seasoned financial leader, real estate advisor, and nonprofit advocate whose 60+ year career stands as a testament to unwavering dedication, innovation, and impact across multiple sectors. From the bustling political corridors of Washington, D.C. to strategic boardrooms shaping nonprofit outcomes, Bob’s influence is as far-reaching as it is profound. A natural connector and trailblazer, Bob has seamlessly blended financial acumen with strategic foresight to guide real estate ventures, charitable organizations, and high-profile corporate relationships with poise and integrity.

Bob’s professional journey began in 1963 at Understein and Associates, a prestigious financial planning firm co-founded with his father in the Greater Washington, D.C. area. The firm quickly grew into a powerhouse of high-end financial and tax planning, serving elite clients including U.S. senators, presidential candidates, cabinet secretaries, and Fortune 500 executives. One of his key mentors and lifelong clients was David Lloyd Kreeger, the visionary CEO and Chairman of GEICO, who entrusted Bob with significant financial responsibilities that helped shape his multifaceted expertise.

Between 1972 and 1985, Bob helped raise approximately $300 million in equity for close to $1 billion in commercial real estate and communication property investments through private placements. These ventures expanded his reach into equity placement, tax strategy, and complex transaction structuring. The firm’s success during this period positioned Bob as a thought leader in the intersection of finance, real estate, and innovation.

After divesting the family business in the late 1980s, Bob transitioned into working with mid-sized to large enterprises, frequently as an interim CFO. His ability to step into leadership roles and quickly drive transformation has been a hallmark of his post-firm career. Notably, he served as CFO of a mid-sized public company in Las Vegas for two years, leading the business through expansion and financial recalibration. This company had one major shareholder, a seasoned (over 100 years) trust, as well as a strategic real estate partner that was one of the largest privately held companies in New York.

After 18 months of service, he observed substantial irregularities in the financial statements (audited by BDO). He brought these to the attention of the outside legal counsel, the CEO of the trust/major investor, and the President of the strategic real estate partner. These findings led to the company entering Chapter 7 bankruptcy. The trust was able to recoup its investment through asset sales, and through the relationship established with the trust, Bob later identified another investment for them in Las Vegas that delivered a 5x return on investment. The New York real estate company minimized its financial exposure and engaged Bob in a consulting relationship for several years thereafter.

Bob has also held influential roles with prominent CPA firms, including RSM-McGladrey and Cohn Reznick, where he provided advisory support across strategic financial planning, real estate development, and nonprofit financial health. His guidance continues to shape organizations such as Avison Young, Ardent Companies, and USI Insurance.

A passionate supporter of social good and transformation, Bob played a pivotal role with the Government Transformation Initiative (GTI) from 2013 to 2017. Collaborating with national figures such as Dave Walker (former U.S. Comptroller General), Barry Melancon (CEO of the AICPA), and Steve Goodrich, Bob worked to advance legislation focused on government accountability and operational efficiency. His dedication to public service extends to numerous board positions at institutions including the National Osteoporosis Foundation, George Washington University Heart & Vascular Institute Foundation, and Communities in Schools.

Education has always held a special place in Bob’s career. A proud graduate of the University of Virginia (BS in Accounting) and the Washington College of Law at American University (JD), he has maintained strong alumni ties. He served on UVA’s McIntire School of Commerce Advisory Board for over three decades, led the Jefferson Scholars Foundation as National Chair, and was a Trustee Emeritus for The Fund for American Studies. He was instrumental in the founding and development of The Fund for American Studies (TFAS). He was one of the co-founders, Board member and CFO for 33 years. The Fund for American Studies (TFAS) was founded in 1967. TFAS is an educational nonprofit that is developing leaders inspired and equipped to protect and advance the ideas of individual liberty, personal responsibility, and economic freedom in their communities and throughout the world. By offering a portfolio of more than 30 academic programs, fellowships and seminars, the TFAS Journey helps cultivate future leaders from high school, all the way through to their university studies and professional careers. TFAS builds the intellectual rigor and sustained relationships over time that result in deep impact and long-term change. After more than 50 years of programs, the evidence of TFAS’s success is clear. TFAS alumni are the leaders our nation needs right now and in the decades to come. Today, there are nearly 50,000 TFAS alumni making a difference in their communities and throughout the world by upholding the values essential to the preservation and success of a free society.

His global exposure further enriches his perspective. Having represented the U.S. through the American Council of Young Political Leaders in Japan, Australia, Germany, and the UK, Bob remains an active international thinker. His global experience helps him navigate cross-cultural business nuances and advise firms with a global footprint. In addition to his three international exchanges and active Board Leadership, he was President of ACYPL from 1987–89.

Bob’s distinguished network spans the highest levels of real estate, finance, media, education, and government, including former executives from Hilton, Avison Young, Crow Holdings, and Major League Baseball. These relationships speak to his trustworthiness and stature within elite business circles.

Now, as Bob seeks to dedicate his deep well of experience to board service, he is especially passionate about engaging with organizations in real estate and the nonprofit space. His blend of practical financial strategy, high-level relationship management, and a deep moral compass uniquely qualifies him to offer sage counsel, bridge generational insights, and help organizations thrive in today’s competitive environment.

Character:

Bob exemplifies steadfast integrity, lifelong commitment to helping others, and a clear moral compass that has guided his every professional and personal endeavor. His leadership is built on trust, discretion, and a service-oriented mindset.

Knowledge:

With more than six decades of experience across finance, real estate, nonprofit leadership, and public sector innovation, Bob is a wellspring of practical, historical, and strategic knowledge. His ability to advise leaders from startup founders to federal policymakers underscores his depth and breadth.

Strategic:

Bob’s strategic thinking is rooted in action—from raising hundreds of millions in real estate equity to advising government reform. He consistently identifies opportunity, mobilizes people, and delivers long-term impact for organizations of all sizes.

Communication:

Bob’s communication style is clear, persuasive, and adaptable—equally at home speaking before 1,000 attendees or guiding an executive team in private session. His ability to build relationships and earn trust has made him a powerful communicator and mentor.