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Kathy Oliver is uninterested in praise. Ask the long-serving executive director of Outside In about the organization’s extraordinary growth over 46 years, and the demure 65-year-old quickly diverts attention to her 140 employees, her veteran management team (the newest member has been there 12 years), and, most of all, her ceaselessly inspiring clients. Besides, she’s too busy pondering new ways to support Portland’s homeless youth to waste time preening. 

But Oliver’s powerful maternal role at the core of Outside In, a social services agency for homeless youth and other low-income communities, is hard to miss. 

Launched in a coffee shop in 1968, Outside In began as a free, volunteer-supported evening health clinic. Oliver joined in 1981, after earning a PhD in urban and public affairs and spending seven years at the Women’s Crisis Hotline. “I have always believed strongly in social justice,” says the Washington native. “And so I gravitate toward people who don’t have a voice, and who are not getting what they should get.” During her tenure, Outside In’s annual budget has increased to $9 million, and programs have expanded to include free medical care, housing, education, counseling, job training, and more. Over the course of that growth path, the quiet, quirky dog lover has bravely and assuredly steered the ship. “Kathy’s commitment to what can be heartbreaking work has never wavered,” says Kelly Anderson, development director of Outside In. “She is practical yet optimistic, diplomatic yet principled, aggressive yet strategic, innovative yet thoughtful.”

1981: Oliver arrives at Outside In, planning to stay on for two years to shore up its fundraising effort. But she doesn’t leave. “There was something about this agency that just caught me,” she says. 

1983: Oliver becomes Outside In’s first executive director and reinforces the organization’s focus on homeless youth. “I just kept thinking, ‘Why are there kids on the streets? Why is that even happening?’ They seemed like such an invisible group to most of the community.”

1989: Oliver pioneers one of the country’s first needle exchange programs, providing sterile syringes in exchange for used ones in an effort to prevent the spread of blood-borne infections, including HIV. “It was probably the hardest thing I’d ever done,” says Oliver of the insurance hurdles and community resistance. Outside In now exchanges about 750,000 syringes annually.

1989: Film director and longtime friend Gus Van Sant employs Outside In clients as extras on My Own Private Idaho. Van Sant has since donated the proceeds from all of his Portland premieres to Outside In. 

1992: Oliver and Outside In organize neighbors and businesses in a public stand against Measure 9, a notorious anti-gay-rights ballot initiative, wrapping their entire downtown block with a yellow ribbon and declaring it a hate-free zone. The statewide measure fails. Outside In goes on to develop support groups for LGBTQ homeless youth.

1999: Oliver receives an unmarked letter from the newly formed Bill and Melinda Gates Foundation containing a $1,000,000 check, which funds the construction of an expanded Outside In headquarters on SW 13th Avenue. The building opens in 2001.

2004: Oliver launches Virginia Woof Dog Daycare, a downtown business that also functions as vital job training for homeless youth.

2013: Outside In begins a training and dispensary program for naxolone, a drug used to counter the effects of a heroin overdose. Thus far, the organization has trained more than 800 people.

2014: Oliver starts her second business venture, Bespoke Smoothies, in which homeless youth sell “pedal-powered” smoothies mixed by blenders attached to custom-designed bicycles.

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