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A meeting of the Lakeside Programming Group, with Paul Allen, Ric Weiland and Bill Gates. (Lakeside School Photo)

Ric Weiland — Microsoft’s employee No. 2 — was a tech geek to the core.

In the summer  of 1969, when he was 16 years old, he was offered a contract working on computer software for $5,000 — an exorbitant sum at the time. Along with Bill Gates, Paul Allen and another classmate, he founded the Lakeside Programming Group at their elite high school in north Seattle. He postponed his last undergraduate year at Stanford University to join Gates and Allen in Albuquerque, N.M., helping create Microsoft. He eventually became a lead programmer for the company.

So it’s little wonder that when Weiland shifted his attention from programming to philanthropy almost 30 years ago, he applied the same rigorous, analytical, fearless, bold and passionate energy to charitable giving.

“He was a contrarian in the way he looked at the world as a programmer and an investor,” said Mike Schaefer, Weiland’s widower.

Mike Schaefer, left, with Weiland and their puppy, Kofi, around 2002. (Schaefer Photo)

And Weiland’s intrinsically tech-oriented, breaking-the-mold approach paid off. His philanthropy has helped fuel innovative university research, medical advancements in HIV/AIDS and important legal, social and educational change in the LGBTQ community.

Weiland retired from Microsoft in 1988 at age 35 and began his second “career” as an influential donor in the Northwest and beyond. Weiland, who died in 2006, gave away $21.5 million before his death, and bequeathed an additional $170 million.

His donations supported 11 different LGBTQ nonprofits, Stanford, United Way of King County, Seattle Children’s Hospital, Fred Hutchinson Cancer Research Center, and other environmental organizations and educational institutions.

Last month, the Seattle Pride Foundation distributed the final payments from the Weiland estate to the LGBTQ organizations. Lamba Legal was the largest recipient after the Pride Foundation, receiving $12.7 million over eight years.

Attorney Judi O’Kelley, Lambda Legal’s director of leadership, said Weiland’s tech traits served him well in philanthropy.

“There is that quality of going big and being bold,” O’Kelley said. “And also with people who come from the STEM background, there is a deliberateness and attention to detail within that boundary of risk taking. I see that very much in how Ric went about this philanthropy.

“He made bold, significant gifts that were truly transformational in scope,” she said. “But he was deliberate in structuring his giving so he could ensure the long-term health of each organization he supported.”

Willing to test and fail

Schaefer, current photo.

When Schaefer and Weiland met in the 1990s, the Microsoft retiree was still figuring out how to actually be a philanthropist. The two would attend fundraising events and find themselves surrounded by seniors. People always thought they must be there with parents or someone older.

There typically weren’t 30-something-year-olds writing checks, Schaefer said. “We’d show up and say, ‘We’re learning how to do this.’ ”

Weiland’s philanthropy was largely financed by his Microsoft stock, initially worth $4 million. That value grew to $22 million by 1992, and $100 million by 1999.

Weiland, who was HIV positive, quickly zeroed in on core issues that he wanted to target with his resources, including many related to the LGBTQ community.

“What do geeks do? They have a passion, and his passion was LGBT,” Schaefer said. “The challenge of being a philanthropist in those areas was there were not established organizations.”

At the time, there was no federal funding for AIDS research and President Reagan urged abstinence to curb the spread of HIV, he said. “That was a weird time to figure out how to spur innovation.”

So Weiland gave to the Hutch and New York’s amfAR, now called The Foundation for AIDS Research. He also started making smaller donations to local LGBTQ organizations, some of which were newly off the ground.

The investments weren’t so much going to mom-and-pop nonprofits, but “mom-and-mom and pop-and-pop” organizations, Schaefer said. Many of the first donations paid for the groups to build websites to increase their outreach and transparency. He picked the groups carefully.

“His R&D was exhaustive, and he did a lot of the due diligence,” said Kris Hermanns, CEO of the Pride Foundation.

Weiland crafted a meticulously detailed will that took effect following his death from suicide in 2006. Weiland was being treated for chronic depression and coping with the deaths of his father and sister, his only sibling, as well as concerns about his HIV status and treatment options.

His bequest earmarked $19.8 million for the Pride Foundation, which had the responsibility of distributing an additional $46 million to 10 LGBTQ organizations over nearly a decade. Weiland had carefully vetted the groups, and settled on an approach meant to help the organizations become firmly established and able to ride out economic downturns.

“He realized that if he wanted to fuel the change that he saw was possible and felt was needed, that he needed to invest across organizations that were working on different issues but covered the full experience of the LGBT community,” Hermanns said.

Weiland on the coast of Northern California. (Schaefer Photo)

That included marriage, health, education and tolerance. And since his death, there has been tremendous progress in many of these areas, including the nationwide legalization of gay marriage, treatments that prevent HIV from developing into AIDS and the end of the “don’t ask, don’t tell” policy that banned openly gay people from serving in the military.

When Weiland was crafting his will, he likely could not have imagined this progress coming so relatively quickly. But he was willing to take a chance on organizations, many of whom played key roles in these advancements.

Weiland’s stance was, “I’m willing to test and fail, and be a reliable supporter through that process,” Schaefer said. “If you don’t have a framework for that kind of risk, then you’re not going to be the kind of philanthropist who has a big impact.”

‘A perfect philanthropist’

Stanford received more than $54 million from Weiland, who directed the money to pay for scholarships, fellowships and endowed chairs. And he didn’t only target engineering and tech-related academics. His gifts fund medical, humanities, social innovation, physics and LGBTQ programs.

“He was this marvelous person who listened so carefully and thought about things strategically,” said Laura Breyfogle, senior associate dean with Stanford Engineering’s external relations. “He gave with trust and love. His personal spirit came through.

“He was a perfect philanthropist.”

Weiland and Gates in New York City in 1976. (Schaefer Photo)

A portion of Weiland’s donations to Stanford support people doing multidisciplinary work, combining sometimes unlikely fields of expertise to bring new perspectives to challenging problems.

Breyfogle and others said that another of Weiland’s strengths was his ability to do careful research into his recipients’ programs, but give them the freedom to use the money as needed. Part of his tech-bent was an aversion to micromanaging.

“If you trust the people, you give them a lot of latitude to run with their ideas,” Breyfogle said. ”And he seemed to get that in a research university like Stanford, not everything works out, but it’s a place where you take risks and make big leaps in understanding — and not just incremental changes.”

Schaefer hopes that others will be inspired by what Weiland accomplished. He emphasizes how rewarding it is to engage in philanthropy as an active participant, rather than simply bequeathing donations. He urges people to get involved with their families and coworkers, and give whatever they can.

“People don’t get how much richness being engaged in the community with your kids and your work brings to your life,” Schaefer said. “That builds a happier employee, a better community and it exposes you to the real users of the tools you’re designing.”

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