David Drewry
By Lynne Strang, Late Blooming Entrepreneurs
How did a guy who was supposed to become a shop teacher end up as his own boss?
As David Drewry will tell you, it happened for several reasons, with one of them being fate. “I was very lucky to be in the right place, at the right time,” he says.
Drewry, 68, is the president of Drewry Home Inspections (DHI), a family owned and operated business in Haymarket, Virginia (about an hour from Washington, DC). According to its website, DHI’s mission is “to assist prospective home buyers in the decision-making process regarding the purchase of new and resale homes in Northern Virginia.” Drewry and his son, Mark, handle the home inspections. His wife, Anna, is the office manager.
A Long Road Traveled
Born in Tennessee and raised in Mississippi, Drewry has come a long way from his self-described days as “an LD student who was more interested in working.” After three years of mediocre grades at a community college, he transferred to Mississippi State University, where he changed his degree from engineering to industrial arts education and became an A/B student.
Upon graduation, Drewry had 26 offers to teach shop. Instead, he went to graduate school, earning a Master of Education in Industrial, Vocational and Technical Education from Mississippi State in 1966. He then joined the U.S. Air Force, where was commissioned a second lieutenant one year later and began a 21-year military career that took him to Japan, Korea, Turkey and Thailand, among other places.
By 1988, he was a lieutenant colonel stationed in Indian Head, Maryland. When a promotion to colonel didn’t materialize, he decided it was time to retire from the military. He considered going back to teaching, but didn’t want to start from the ground floor again. “I had a choice,” says Drewry. “I could utilize post military training, or do something different.”
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“It’s important to do detailed research to ensure you and your family will be compatible with the proposed business.”
— David Drewry, Drewry Home Inspections
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He chose the latter largely because of two contacts, both former Air Force officers who had gone into real estate. They recognized Drewry’s aptitude for the home inspection business and encouraged him to go that route. Drewry thought it was a good fit as well.
“As a shop teacher, I had an understanding of mechanics and had always had an interest in buildings,” he says. “From the military, I had accumulated experience in management and personnel oversight.”
Building a Professional Network
In August 1988, he founded Drewry Home Inspections at the age of 45. While researching his new industry, he came across a website for the American Society of Home Inspectors (ASHI) and signed up for one of its training conferences.
“I asked myself how I could get the most out of this conference,” says Drewry. “The answer was to buy as many drinks as I could to pick the brains of the other participants.”
The networking yielded several new contacts, including some who became instrumental in his business. One was a Milwaukee home inspector who helped him develop forms he needed to serve his customers.
After that initial training event, Drewry became an active member of ASHI, eventually serving on its board and founding its Northern Virginia chapter. He credits the organization with providing him with valuable connections and a thorough understanding of the home inspection business.
For several years, Drewry taught an adult education class, “How to Spot Defects in Houses, Townhouses and Condominiums,” because he kept encountering people who weren’t educated about the home inspection process. “I figured the class also would help generate new business – which it did,” he says.
Drewry estimates that his company has done 15,000 home inspections since its start. During the real estate peak that ran from the mid 1990s to the early 2000s, he was doing four inspections per day, six days per week.
Like others in his industry, he’s experiencing slower times because of the weak economy and unsettled housing market – something he can put into context because he’s been around longer.
“Younger people get more concerned about dips in business because they haven’t survived the peaks and valleys,” he says.
Principles That Work
As a business owner, Drewry enjoys cultivating long-term relationships and “the feeling that I’m providing a service that people appreciate.” His success comes from the discipline he learned from the military, along with the application of its principles. Among them: be above board, professional, reliable and timely.
For future entrepreneurs, he offers this practical advice: do a careful evaluation of the financial risks.
“My own comfort level would not be as high without military retirement,” he says. “Make sure you have a financial cushion, or a working spouse to keep income coming.”
Next year, Mark Drewry will take over the company when his parents retire. “It’s important to do detailed research to ensure you and your family will be compatible with the proposed business,” David Drewry says.
“You have to be meticulous and detail oriented,” he adds. “And be open to change.”
A little luck doesn’t hurt, either.
Late Blooming Entrepreneurs 
“I figured the class also would help generate new business – which it did,” he says. and his last line “And be open to change.” I really like this. In addition to his open point of view, his career journey follows such a logical path. He certainly doesn’t believe in magic. He made it happen systematically.
Good point. As part of that systematic approach, he assessed his strengths thoroughly and found a suitable business to apply them. That’s an important part of the process.
Great story. I like the way your storytelling relates how each part of his career was useful in the next. His path highlights the importance of reaching out to a network as he sets off in a new direction — definitely more than luck at play.
I agree. He’s a good example of Thomas Jefferson’s quote. The harder he worked, the more luck he seemed to have!
It is so important to have your family on board–“compatible with the proposed business.” I have known situations where both spouses were not in agreement about it. When it got tough, the one who was afraid and did not really want to do it got their way. The business died, and they almost lost everything.
That’s unfortunate. Given the magnitude business ownership has in their lives, it’s important for entrepreneurs to share it with those who matter most and turn to them for emotional support.