Two industry trailblazers leave their mark on Flint Hill.

GREAT EXPECTATIONS

“Expectations should be high, but without creating an environment that sparks motivation and sustains engagement, you may not meet them.” 

– Mike Corkery

As CEO of Deltek, the leading provider of software and solutions for project-based businesses, Mike Corkery has perfected the art of setting and meeting high expectations. Business has grown three-fold since he took the helm of the Herndon-based company in 2012. Today, Deltek employs over 3,000 people and services more than 30,000 customers worldwide.

With Mike, it’s never “me” — it’s always “we.” He gives credit to his team when discussing Deltek’s successes, like being named one of the best places to work in the D.C. area by the Washington Post — seven times. “We’re very proud of that recognition,” Mike says. “We try to make sure our employees are set up with the tools and inspiration they need to excel at what they do.”

He believes in giving employees the time and space to balance their priorities at home and in their community with their responsibilities in the workplace. “We want team members to bring their whole self to the office,” Mike says, contending there’s a definite correlation between feeling seen and appreciated and high productivity levels. “Our customers defend the country, keep our information secure, and build roads and arenas. We’re passionate about helping them deliver on those missions.” 

Twice now Mike has been named to the Virginia 500 Power List, a listing that recognizes the state’s most influential leaders by sector. Embracing Deltek’s core values of innovation and evolution has been central to his accomplishments. Mike emphasizes the need to “evolve at the pace of your market and your customers, not at the pace that’s comfortable for you.” He applauds Flint Hill for that same willingness to step into change. “The outside world dictates the speed at which you innovate. Flint Hill has embraced that fact,” he says, celebrating the School’s nonstop growth and progress.

Back in 2010, when he and his wife, Alison, were searching for a school home for their daughters, they were impressed by Flint Hill’s unique combination of community and academic rigor. “There was this level of support balanced with a level of accountability that’s really rare,” Mike recalls. He commends the impact Flint Hill has had on his daughters, Hailey ’16 and Chloe ’18. “They are so much more self-directed and aware of opportunities than I ever was at that age,” he notes. “They have the ability to self advocate because that was an expectation at Flint Hill.”

Mike joined the Board to ensure the School stayed in the position to deliver that experience to other families. He admits he’s “never been shy with [his] point of view.” His fellow trustees welcome that straightforward style as a complement to the Board’s growing diversity of thought. Characterized as an insightful sounding board and shrewd strategic partner, Mike helped see Flint Hill through major milestones like the completion of the Peterson Middle School and this year’s leadership transition. As Head of School Patrick McHonett puts it, “Mike brought a clear, no-frills New York approach to our conversations that always cut to the heart of a matter, and allowed Flint Hill to bring laser-like focus to the needs and opportunities available to enhance our Husky experience.”  

Evolve at the pace of your market and your customers, not at the pace that’s comfortable for you.

— Mike Corkery

Mike and Alison will soon make their gradual relocation to Florida official and thus Mike will exit Flint Hill’s Board after six impactful years. “We’ve been part of this community for 13 years, we’ll never fully leave it,” Mike promises. He departs with confidence in the School’s ability to continue delivering on its important mission and with great expectations he knows Flint Hill is more than equipped to meet.

FAMILY FIRST

Gary Rappaport credits this guiding philosophy for the indelible mark he’s made as a devoted family man, commercial real estate developer, and contributing member of the greater DC community. 

While his passion for business and commitment to philanthropy has shaped Gary’s career, his dedication to family is clearly what drives him. Of the two dozen or so photographs displayed in his office, almost every one is a sweet salute to his large family, which includes his wife, five daughters, and eight grandchildren. Gary’s learned that being consistently present for them takes prioritization. “We can always find the time if we wish to,” he affirms. 

“In life, first spend a third of your time with your family, and then a third of your time dedicated to your business, and a third of your time giving back to others.” 

– Gary Rappaport

Gary started his real estate company, Rappaport, in 1984 when he raised $35,000 to buy a shopping center in Baltimore — a property he still owns today, along with several dozen other commercial properties. While he’s been amassing square footage for five decades — over 14 million — he’s also been earning admiration and respect. “My reputation is what is most important to me,” Gary says of the importance of being regarded well by his tenants, employees, and peers.

He was raised to value hard work. At 12, he began shadowing his father who worked as a tie manufacturer in New York City. Along with learning about darts and loop labels, he also learned the intrinsic value of taking pride in the work you do, whatever that may be. “There was a man whose only job was to press the ties,” Gary recalls. “I’ll never forget how seriously he took that job.”

While he has echoed his father’s work ethic, Gary adopted a different approach as to risk. “My father grew up with the fear that comes from living through the Depression,” Gary explains.
“I was privileged. I never had to worry about a roof over my head or food on the table. I was willing to take great risk for great return.”

His risk-tolerant real estate strategy is detailed in his book, Investing in Retail Properties, which he wrote with young entrepreneurs in mind. The third edition of the book is presently available for purchase with all proceeds going to the ICSC Foundation – the retail trade association educational foundation. “You don’t make money on business books,” he says. “I wrote the book to help others reach their dreams.” He also brings those lessons into the classroom as a frequent guest lecturer at universities like Johns Hopkins, Georgetown, American, and George Mason. “If I can help one to reach their dreams sooner than they otherwise could have done,” he says, “the hope is that one day they will do the same for someone else.”

The responsibility to pass it on is what led Gary to Flint Hill’s Board of Trustees in 2013. At one point, Gary had two daughters and three grandchildren at the school at the same time. He wanted to give back in recognition of how they benefited from a Flint Hill education – particularly for his daughter Jessica ’17, who burgeoned into a talented artist during her time as a Husky and is now an accomplished glass blower and ceramicist. 

“I was asked to join the Board because of my financial expertise, but there is a time to leave,” Gary says about his decision to roll off the Board. “Young, dynamic, intelligent people need to see a place on the Board and I want to make sure there’s a seat for them.”

He’s most proud to have overseen a growth in financial stability during his time as Chair of the Finance Committee. “Without Gary’s steady hand and visionary partnership, we would not be in the strong position we are today,” notes Head of School Patrick McHonett. “Knowing when to be aggressive as we were in building the Peterson Middle School and when to be prudent — in growing our endowment — is equal parts art and science. Gary helped steer us in the right direction at every turn.” 

If I can help one to reach their dreams sooner than they otherwise could have done, the hope is that one day they will do the same for someone else.

— Gary Rappaport

Gary will conclude his 10-year Board service with the unwavering respect of his fellow trustees, immense gratitude from the Flint Hill community, and hopefully, a little more time to spend with his family.