Asking Tough Questions

David Weekley: homebuilder, charity-grower, and hard-nosed inquisitor

There’s a table in David Weekley’s office, well known among Houston’s nonprofit leaders. “Large, green, marble-top,” Young Life vice president Eric Scofield describes it with a playful shudder.“If you ever go into his office to have a meeting and you sit at that table then you need to prepare yourself to be challenged, pushed, maybe even argued with. You’ll certainly walk away from that table licking your wounds.”

Those invited to sit down at the marble-top consider it a privilege, if an intimidating one. Former Houston YMCA president Clark Baker confesses, “I probably did more mental rehearsal and briefings with staff before I went into a Weekley request than with any other donor.”

As Weekley has developed a reputation as one of the toughest meeting partners, he’s also become a go-to person for strategic advice. “How can you grow faster?” he asks those who come to him. “Are you serving enough kids? Is your board strong? How do you know you’re making a difference?” For some nonprofit executives, the questions fall on deaf ears. They walk away without a check, and often into trouble.

“He’s looking for a leader who can actually perform,” says Scofield. “There have been people who come to the marble-top and David says, ‘I’d be more than willing to give you money. Come back to me with a plan and a board.’ And they never come back. From a charity standpoint that’s crazy, but it happens all the time.

For those willing to listen, however, this businessman from Houston offers them a chance to pick his mind as well as his pocket. Because when it comes to philanthropy, David Weekley means business.

David beats Goliath

Weekley never intended to be an entrepreneur. After graduating from Trinity University in San Antonio, he was accepted to Harvard Business School where he intended to follow in the footsteps of his older brother Bob. ButHarvard wanted all its students to have two years of work experience, so David delayed his acceptance and went jobhunting. He landed a spot in the warranty department of a homebuilder, and quickly rose to become a superintendent and then a manager. Observers saw that he had a knack for selling new houses.

When David heard that the company was going to change his compensation package midyear and raised the issue with his supervisor, he was fired. David had been married to his high-school sweetheart, Bonnie, for one month at that point.“I’ll never forget my wife coming home,” he remembers. “I was watching ‘As the WorldTurns’ or something like it, and she said ‘What are you doing home?’ I complained that I got fired, and she said ‘I know this was for better or worse, but this is a little quick.’”

What seemed like a disaster proved to be a blessing. Weekley’s entrepreneurial bent revved up. He got a loan from his brother Dick to begin building and selling his own homes, and some advertising from his father Weldon, founder of a successful marketing firm. The ad used a David vs. Goliath theme, portraying his son as the cheeky underdog against a behemoth industry.

Houston went for it. Sales soared over the next ten years, making David a millionaire before age 30. He became active in the Young Presidents Organization and regularly spoke in front of large groups. He built a fancy home and drove a BMW. “I thought I had it all figured out,” he says. “There wasn’t much I didn’t know.”

But David and Bonnie were in for a wilder ride. In the mid-’80s a downturn in oil and gas sent Houston into a slump. The housing market contracted from 30,000 new-construction sales per year to 6,000. “Most everybody was going broke,” says David, including himself.

Realizing that erecting houses in Houston wasn’t going to be profitable for a while, Weekley realized his only hope of saving the business was to expand to new regions. He hit the road to pitch his product.

Luckily, David Weekley Homes ended up being popular in Dallas and Austin, offsetting his other losses. Nonetheless,“we ended up selling our big house, and selling our expensive cars. It was a pretty sketchy time.”

Piled on top of the business stress was the sense of a missed opportunity. “I had literally millions of dollars flow through my hands, and no good had come out of it,” he remembers. “Money was there and then it was lost, and nothing had changed in terms of the world.” He saw a bumper sticker on the back of a car reading, “God, give me one more million and I won’t screw up the next one.” Weekley was starting to feel the same way.

Eventually, the market picked up again, and having made it through the downturn via regional expansion, Weekley’s business came out of the late 1980s stronger than ever. In fact, it became the largest privately held homebuilding company in America.

But something was changing in its founder. “I really thought that money motivated me,” he says.“But I learned it didn’t. Once I had enough, I lost some of my enthusiasm. Through my late 30s and 40s, I was a little dissatisfied. I’d made a lot of money, but there wasn’t necessarily any meaning or purpose in what I was doing.” He kept remembering the bumper-sticker promise.

A serious health complication in the early ’90s finally prompted him to re-examine his life. “I was working like crazy, 60 to 70 hours a week, not paying attention to my family.” He recalled a book he’d seen in his early 20s, God Owns My Business by Stanley Tam. “Tam gave half of his money up to do community work and nonprofit work.” Suddenly that concept didn’t seem at all crazy to Weekley. In 1992, he decided to do the same: From then on, he would devote half of his time and half of his income to philanthropic pursuits.


Marble-top conversations

“When I started doing half and half, I did what most people do: you get involved in local activities that you can see, touch, and feel,” Weekley explains. He joined a number of Houston charitable boards and gained experience as a leader. He helped grow the superb Houston-born charter-school organizations YES Prep and KIPP. Heled the Sam Houston Council of the Boy Scouts of America.

“I learned a lot, I made a lot of mistakes, I saw areas where I could contribute. Since I was giving time as well as money, I had to determine where my personal skills could best enhance nonprofits. As you would expect, in some I couldn’t help. I had to learn where my sweet spots were.” 

Those sweet spots turned out to be similar to what he had practiced during the crisis in his business: How to expand into new markets. How to track results and measure if new branches are performing up to speed. How to save the enterprise by thinking bigger, reaching more people, growing at the right pace.

When Positive Coaching Alliance founder Jim Thompson first met Weekley, he came armed with a lengthy PowerPoint presentation outlining how the organization trains coaches and players and parents to use sports as opportunities to build character. But he only got three minutes in when Weekley interrupted him. “Look, here’s what I’m willing to do,” laying out a three-year gift to establish a chapter in Houston, with a local board that would control the operation. At the time Thompson had no local boards—and no chapters outside his headquarters in northern California.

Ninety percent of the money that’s given away is given away locally, Weekley explained. Houston donors will be far more likely to engage with your program in their own city than as a California charity. There would have to be a local board that gives money, raises money, and has its own power. Weekley’s seed funding would taper off over three years, at which point the local board would be fully responsible for sustaining the chapter.

Thompson accepted both Weekley’s money and his advice. “That model he laid out for me in about 30 seconds is still basically the model that we use,” he says. PCA will soon open its fourteenth chapter in Portland, Oregon. The organization now reaches over 66,000 kids in Houston alone.

“Leadership is critical,” Weekley explains. “I hate to give to something today that might not be here or might not be effective 20 years from now…. It’s really up to good board governance to ensure that an organization continues.”

Tiger Dawson was in town in 1994 amid a drive to expand Young Life, a Christian outreach to teenagers, so he stopped by Weekley’s office. “I heard he was really good at strategic planning and wanted to help people be better at what they do.” In what Dawson calls “typical David fashion,” Weekley pushed him to improve. It’s“not really his style” to give a proposal a quick thumbs up or thumbs down—“his style is much more, let me beat you up a little bit,” Dawson laughs. “Most donor meetings are predictable. You know the beginning, the middle, and the end. I’m now great friends with David, and I still have no idea where meetings with him are going.”

Over the next two years Dawson met with Weekley and a few other philanthropists interested in extending YoungLife’s reach into urban areas. They arrived at a model where local donors would provide seed funding for new YoungLife clubs, decreasing over time until the club was self-sustaining.

With a successful model in hand, Weekley and his friends Rusty Walter and Terry Looper wanted to propel Young Life into new places. They initiated a million-dollar match: if local city boards are formed and local givers step up, they would give $1 million in seed funding to support their cause. Ultimately, five cities participated in the match.

Looper recalls giving with Weekley and Walter fondly. “Some of our most fun investments have been Christian camps for kids, especially the ones who are in trouble and need much more than just money. David usually takes the lead in the beginning and then we take over when he is ready to chase a new ministry in trouble or one on the cutting edge.” Giving as a team has proved to be “an effective model of accountability, new ideas, problem-solving, and a great way to fund ministries.”

Weekley cherishes close relationships with peer donors. “What happens once you’ve been fortunate enough to create some wealth is that you begin to think that you’re invincible, and that because you’re wealthy, you have some kind of overarching control,” he says. “It can be kind of heady. Giving people checks can create a sense of entitlement and power. When you have other people giving with you who are smart and competent, they can hold checks and balances, and remind you that your answer is not necessarily the right one.”

Naturally, Weekley dishes at least as good as he gets. Says Dawson, “I think some people who know David from a distance can think he’s hard on them and pushing them, but he’s hard to help them succeed at their mission. That’s his contribution. His inputs are difficult questions. The outcomes are organizations that are more effective as a result of meeting with him.” 

“Every time I meet with David I gear myself up,” says Thompson. “Because it’s not just a frivolous meeting. Often he’ll focus on something that I haven’t thought of, and ask about it.  And then I realize I need to think more deeply about it.”

Daunting as it may be, Thompson appreciates the process. “When he thinks he has an important idea he pushes hard. But he respects you—he understands that I’m in charge of the organization, I’m the one who has to make it all work, not him. So he doesn’t hold a grudge if I don’t take all of his advice, which makes him an invaluable adviser.”

“If I’m funding organizations that are not the best in their class, then I’m taking away from the best organizations,” Weekley explains of his rigorous approach. “Since there aren’t market forces at work in philanthropy, the folks who usually get funded are those who do the best job of raising funds, not necessarily the folks who do the best job of executing their program and mission.”

Expanding to Africa

Recognizing his sweet spot as an inquisitor also led to another revelation for David: maybe his expertise could be useful outside of Houston. “After a while, I saw that there were terrific local leaders across the U.S. that could do a lot of what I could do. So I wanted to go where it was harder, where there were more challenges.”In the early 2000s he took a trip to Rwanda with evangelical pastor Rick Warren. His travels continued to China, India, and Latin America, doing “a survey of where I could be the most helpful.” He decided on Africa as his primary focus. “I could get seven times as much philanthropic mission done in Africa as I could in theU.S., just because of the difference in cost structure. But it was really challenging to find the right people to work with.”

One of his international partners came from his work in Houston. Tiger Dawson, moved on from Young Life, was starting a new organization called Edify to provide loans to private schools in the developing world. Weekley sent his international giving officer at the time, Josh Kwan, to travel with Dawson and help think through strategic questions. Dawson returned to Houston a few times a year to hear Weekley’s input, where he would“challenge us on how fast we’re growing and whether it’s wise to grow at that pace.” Edifyhas now aided 320,000 students by loaning money to nearly 1,500 schools.

HOPE International CEO Peter Greer was returning from living in Rwanda when he met Weekley. “The very first project we did together was simply coming up with a strategic plan,” he remembers. “He encouraged us to say ‘What would it look like to have a bigger-picture viewpoint? No one would ever accuse David of thinking small.” Weekley followed up by visiting HOPE’s programs himself. It’s important to“physically be on the ground with those organizations you give to,” he explains. “As a steward of what I’ve been given and earned I need to really see, touch, and feel.”

Stephen Maislin of the Greater Houston Community Foundation calls Weekley a “trailblazer in Houston with regard to international grantmaking.” The donor now devotes half of his philanthropic effort to international work and half to domestic causes. He’s an avid reader, devouring “everything from Hernando deSoto’s The Mystery of Capital, to William Easterly’s The White Man’s Burden, explaining we can’t assume that our culture can be implanted on foreign cultures, to Gary Haugen’sThe Locust Effect.” The new puzzles of giving internationally are welcomed by Weekley: “If you’re a person who loves continuous learning, philanthropy gives you an opportunity to practice that.”

A downturn comes again

This half-business, half-philanthropy career has finally settled David in a rhythm he enjoys. “I don’t see any reason I couldn’t do this to 70, or 80, or until I lose my faculties and ability to continue to contribute,” he says. “The concept of dying empty and done, using all your physical attributes and resources, appeals to me.”

This philosophy was put to the test in another downturn. As the 2008 housing bubble burst, Weekley knew that trouble was coming to his company. The blow necessitated “some very dramatic and drastic cuts,” reducing his employees by more than half.

But this time he could handle it differently. “We tripled the severance, we held onto people for a while. We helped them outsource. We did all kinds of things to attempt to be as generous as we could be within the reality we were facing. My definition of leadership is to define reality and give hope, and so all through the downturn we talked with our team about what was going on.”

In some cases David and Bonnie decided to step in themselves. To replace the Christmas bonuses the company could not give out, they wrote personal checks to 400 employees. He credits such empathetic touches to Bonnie. “My wife’s great at the heart-giving, and I’m better at the head-giving. It might be better if I were more like her in a lot of ways. She can help me see and understand people at a different level, she sometimes asks questions that cause me to pause and rethink. Sometimes I can drive, drive, drive, and miss the human aspect.”

When it came to their personal philanthropy, they did not cut back, despite the hit to their assets.“Sometimes I wondered if I was going to deplete the foundation and no longer be able to help as a philanthropist,” he recalls. “But I decided to keep going, use the resources in difficult financial times because they’re probably more needed now than they would be in the future. To me, that was a faith statement.”

“He dug even deeper,” says HOPE’s Peter Greer. “He increased his generosity at a time when the market, when the business, when everyone else was saying ‘We should take a step back from such active philanthropy.’ David was going in the opposite direction.”

“He’s big-hearted,” says Tom Lewis, a private homebuilder and philanthropist in Phoenix who sold his company to David Weekley Homes in 2011. (Lewis also followed Weekley’s lead in bringing Positive CoachingAlliance to Phoenix.) “By nature, he’s incredibly generous, not just with his money, but with his time and talent.”

Fellow donor and friend Jeff Sandefer concurs: “David tells the truth in a joyful way. It’s that simple. He’s humble, warm, and tough—not an easy combination to pull off.” Asked what hard questions Weekley has put to him, Sandefer recalls being asked, “Are you giving enough each year?” Sandeferanswered “No,” which sparked a follow-up: “Then he asks: ‘So you think a foundation or the government will do a better job when you are gone?’ His words haunt me every day.”

Weekley’s advice “has saved me from some serious mistakes, when I have been wise enough to listen, and his encouragement has provided a dose of courage when I needed it most,” says Sandefer. Dozens of leadingTexas entrepreneurs and philanthropists, he adds, could say the same. “On a personal level, even the value of David’s advice pales by comparison to his influence as a role model. So many of us have been lifted up by his example as a Christ follower, husband, father, and entrepreneur. The ripples of his generosity extend from one end of Texas to another—and far beyond.”

David’s brother Dick, one of his earliest champions, continues to admire his example: “It’s not easy to be a successful investor in philanthropy. There aren’t the same measures that you have in business. It’s more difficult to be effective in philanthropy than it is in business,” Dick says. “Like most things in life, to be successful takes a lot of hard work and dedication. You’re not born with it, you’re not gifted with it. David certainly has incredible gifts, but basically it’s just hard work and dedication. Decide to do it, then go do it.”

Growing up Weekley

Generosity runs in the Weekley family. David’s father, Weldon, taught third-grade Sunday school at MemorialDrive Presbyterian Church and raised three sons—Dick, Bob, and David—with his wife, Rosalie. Most of their giving was done in secret, but the sons noticed their good deeds and followed the example.

“We had some friends and relatives who were not well off, and mom and dad would take them on trips and pay for their expenses,” Dick recalls. Bob once had a woman describe how his father, when he was just starting his business years earlier, needed to sell his car for $2,300. She wanted the vehicle, but could only pay $2,000.Learning that she was in desperate straits, he accepted her offer, then placed her check right back in her hand, saying she needed the money more than he did and she could just take the car.

All of the Weekley family have been loyal supporters of the Houston YMCA (which they see as a great equalizer in a rapidly growing and very diverse city), which is named for the whole family with an inscription by the sons above the entrance: “May this building built in honor of a loving Mom and Dad be a constant inspiration to develop and nurture a healthy Spirit, Mind, and Body and promote faithful service to family, community, and our nation, forever.”

A third generation of Weekleys has volunteered as interns at the Houston Y. “The family has worked hard at a sense of responsibility,” says former director Clark Baker. “My greatest fear,” says David, “is that my success will harm my kids, either in terms of their motivation, or in terms of their outlook on the world, or their sense of who they are. It’s been a real journey to figure out how to attempt to enjoy life and what we’ve earned and been blessed with while at the same time raising great kids with an understanding and belief that they owe things to a broader world.”

Ashley May is managing editor of  Philanthropy. 

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