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Sex, Booze and Downtown Streets Team’s Toxic Culture

Ex-staffers say San Jose leadership fueled ‘frat house’ nonprofit culture

A dozen former Downtown Streets Team employees say the nonprofit's leaders promoted heavy drinking at the office and at work functions.

As with many Downtown Streets Team staff functions, attendees say the liquor flowed freely during a 2014 holiday party at the nonprofit’s San Jose headquarters.

 A young female staffer hired a month prior recalls mingling with colleagues by the receptionist’s desk when Eileen Richardson, the homeless services provider’s CEO, walked up to join her. “Out of nowhere,” the employee recalls, Richardson asked, “So, you’re a lesbian?” 

“We were standing at the front desk chatting, tipsy on wine, and talking about how I liked the job so far,” the newcomer, who requested anonymity to protect future job prospects, later wrote about the encounter. The woman says she laughed at the prying question but answered affirmatively. Richardson then inquired about her relationship status and physical preferences before waxing poetic about feminine beauty, the ex-employee says.

“OK, so what’s your type?” she says she asked Richardson, who “suddenly got serious and sultry-eyed, leaned in and said, ‘Well, you are.’”

The night grew “increasingly strange” as guests helped themselves to boxed wine and spiked fruit punch, did keg stands—that is, a handstand on a keg to guzzle as much beer as possible—and took swigs of hard liquor, according to the woman, who says she drank so much that she threw up in the office toilet. All the while, the employee says, an “incredibly drunk” Richardson followed her around and “had her arm around me and kept telling my friends to go ahead and leave.” The staffer says her employer began “brushing my hair back from my face, snuggling her head into my neck” as onlookers shot worried looks at the pair. 

Those same concerned coworkers eventually laid her down on the floor in the office of Richardson’s son, Director of Program Operations Chris Richardson, where the employee remembers waking up at one point to see her boss lying beside her “staring lovingly at me.”

 One of the colleagues who witnessed the evening’s uncomfortably intimate conclusion checked in often during the next few weeks over Richardson’s “obvious coming on to me,” the employee says.

 Others found humor in the escapade.

 “Several other staff joked about Eileen having a crush on me, and there was a rumor that she’d kissed me,” the employee says. “If she did that night, I don’t recall.”

A couple months later, the employee says she attended a Super Bowl party at Chris Richardson’s home, at which Eileen invited her to have a beer and view a photo album at her adjacent residence, where she followed her and “kissed me in the doorway of the bathroom.”

‘A Frat House’ 

As Silicon Valley’s homeless population ballooned amid an unprecedented affordability crisis over the past decade, Downtown Streets Team (DST) emerged as one of the most prominent Bay Area organizations trying to lift people out of poverty. By 2012, it counted Palo Alto’s top cop as a board member and received nearly $400,000, about 40% of its budget, from direct government support. In 2013, the nonprofit expanded into the North Bay, landing contracts with the cities of San Rafael and Novato; four years later, it launched a team in Santa Cruz.

On the Central Coast, the group’s model of employing people experiencing homelessness to clean up Santa Cruz’s downtown had been floated over the years as one possible tool to address a large local chronically homeless population. Chip, the one-name, then-executive-director of the Downtown Association, threw a fundraiser for the nonprofit in the winter of 2017. A few months later, the nonprofit earned the blessing of a Santa Cruz City Council committee studying homelessness. Rock & Roll Hall of Fame Inductee Joan Baez spoke at the ribbon-cutting ceremony that October. Over the next two years, DST expanded, with crews now servicing Harvey West, downtown, the San Lorenzo Riverwalk, Cowell Beach, Main Beach, and even North County beaches. (A Santa Cruz program manager referred us to public relations in San Jose for comment.) 

Behind the do-good mission of employing the unhoused, however, a toxic workplace culture festered for years, according to a dozen former staffers.

In letters prepared by attorneys and echoed in reviews on job-rating platform Glassdoor.com, ex-employees accuse both Eileen, 58, and her son Chris, 33, of sexual harassment, making lewd comments, paying women less than men for similar work, and promoting a culture of heavy drinking. Employees have described the workplace as “toxic,” “a frat house,” “full of nepotism and favoritism,” and “a joke.” Multiple people compared working at DST to being in an abusive relationship. 

Yet reporting misconduct proved difficult because of close friendships between the Richardsons, their strategically appointed board of directors and other managers, including Chief Operating Officer Elfedra Strydom, who until earlier this year fielded all personnel concerns. 

In all, more than a dozen former employees allege harassment, sexual assault and discrimination at DST. Two of those ex-staffers are coming forward publicly with their claims for the first time.

“Things got really, really bad,” says 34-year-old Zia MacWilliams, a former DST program manager who left the nonprofit in 2017 after four progressively stressful years on the job. “I honestly believe in the mission and loved working with my clients, but internally it was just out of control.”

Both MacWilliams and Michelle Fox Wiles, 29, accuse DST of perpetuating a pay gap that privileged their male counterparts.

After she left DST, MacWilliams teamed up with Wiles and nine of their ex-colleagues to pursue legal recourse. The nonprofit Community Legal Services in East Palo Alto (CLSEPA) took the case and offered the DST board a chance to resolve the allegations out of court. (At this point, the Santa Cruz branch was only a few months old.)

It took a year and a month before the DST board agreed to hire a law firm to investigate the allegations.

The probe, which commenced in late 2018 and concluded this past July, “substantiated a culture of drinking and inappropriate joking in the workplace,” according to an Aug. 28 letter from CLSEPA lawyer Jennifer Smith to the 11 claimants. “The board seems to be genuinely concerned about the work environment that was described,” she wrote, though, “they believe that things are better now than they were three to five years ago.”

While the board insists that the investigation found no evidence of a gender-based pay disparity, Smith said in her letter that trustees expressed a desire to “see changes made.” One of the most significant changes, Smith wrote, is that DST ramped up its reporting system by allowing employees to complain to the board directly and created a human resources position for the first time in the organization’s 14-year history. The board also conceded that alcohol “has been an issue,” Smith said, and instituted a “total prohibition.”

Richardson says she never read any of the Glassdoor reviews and is only vaguely aware of the CLSEPA negotiation. But she denies there were ever any problems with DST’s work environment. “Those claims,” she says, “were unfounded.”

 A Bold Vision

A successful venture capitalist who gained global notoriety on the cusp of the 21st century as the CEO of the groundbreaking but controversial music-file-sharing platform Napster, Richardson brought her change-the-world ethos to the charitable sector. 

Under the DST model, local governments and business associations hire a team of homeless people to clean up streets in exchange for gift cards and case management. 

DST’s “win-win-win” system of hiring the homeless, cleaning up trash and benefiting the broader community garnered renewed acclaim for the elder Richardson. Since its inception, DST has blossomed from a cash-strapped experiment in Palo Alto to a burgeoning enterprise spanning a dozen cities in two states with an $8 million annual budget. 

Richardson—who makes upward of $200,000 in base pay as president and CEO of DST and an affiliated nonprofit clinic called Peninsula Healthcare Connection—has since racked up accolades. The San Francisco Chronicle named her a recipient of the Visionary Award earlier this year thanks to nominations from, among other dignitaries, San Jose Mayor Sam Liccardo and his counterpart in Oakland, Mayor Libby Schaaf. “The honor salutes leaders who strive to make the world a better place,” the Chron wrote about the distinction. 

The New York Times gave her a similar honor a year prior. Also in 2018, the League of California Cities and the California State Association of Counties’ Joint Homeless Task Force recognized DST’s model as a “best practice” for supporting homeless people. 

In a blog post a few years back, Richardson credited her success for running her charitable enterprise the only way she knows how: “like a high-tech startup rather than a social service—action-oriented versus service-oriented.” To that end, she said, “We improvised, tried new ideas and constantly corrected our course.”

That constant course-correction may guide the nonprofit’s growth-focused public mission, but sources tell Metro that it elided internal mismanagement, which exposed employees to workplace abuses and, at times, put vulnerable clients at risk.

Wine and Dine

When one of DST’s original clients reconnected with his estranged daughter, two case managers wanted to celebrate his success by taking the pair out to dinner at a white-tablecloth restaurant in Mountain View. Since the client had struggled for years with alcohol abuse, the case managers told Richardson they planned to keep it a dry affair.

“By the time I showed up with the client, Richardson already had a bottle of wine at the table and was obviously a few drinks in,” one of the case managers wrote in a play-by-play of the occasion to the DST board a few years later. “We all kind of side-eyed one another. It was super awkward and completely inappropriate.”

The case manager, who asked to withhold her name, added that Richardson got more and more intoxicated during the uncomfortable dinner and repeatedly offered the client alcohol.

The client abstained, according to the two case managers. But Richardson drank enough that she began slurring her speech, they say, and one of the staffers felt the need to drive her home. “On the way out of the restaurant, Eileen asked [the client] if he needed her to buy him a couple of beers at 7/11 to tide him over, and he declined,” the case manager-turned-chauffeur wrote in the same summary. “I had to help Eileen walk to my car. On the way to my car, she accosted two strangers in the middle of their conversation. It was like she was leaving a concert venue or a New Year’s party; she was far too intoxicated to be the CEO of a company that just left a business-related dinner.”

After the case manager got home, she called her co-worker to ask whether she should continue working for a boss who offered booze to a client trying to get sober. 

At holiday parties, former employees recall, it was common for managers and staffers alike to bring sleeping bags so they could crash at the office after drinking enough to pass out.

Erstwhile employees say one high-ranking director who was known for heavily imbibing while dressed up as Santa Claus at annual functions made it something of a tradition for attendees to sit in his lap before they could claim a gift from under the Christmas tree. A photo of holiday office party in 2015 shows him in his red-and-white St. Nick finery rubbing an oversized dildo on his face while Eileen Richardson apparently tries not to laugh. Another from that same event depicts the Santa cosplayer pouring a bag of white wine straight into the mouth of Chris Richardson, who kneels on the floor with his right fist thrust victoriously in the air.

Like mother, like son.

“Eileen had a history of getting extremely inappropriate at office functions,” one former staffer wrote in a review of her multi-year tenure at DST. “Some of these moments were kind of funny, even to me, such as the time she twerked upside down at the office Christmas party. However, similarly to Chris, Eileen did not know when to rein it in.”

Then there were the weekly Costco runs for booze, staff meetings where managers would partake and frequent klatches at Wine Affairs and other restaurants and bars near the office. Richardson didn’t respond to Metro’s query about whether the nonprofit footed the bill for any of the alcohol purchases.

One manager complained that not only were these outings inappropriate, but also that staffers often felt uncomfortable sitting them out because they were a place where conversations about promotions often happened.

MacWilliams says she felt the same way about the lushy overnights, which included annual trips to wine country where, “everyone gets belligerently intoxicated.” On one Napa excursion in late August 2016, she recounts how a manager asked Chris about having sex with a former co-worker. “Did you fuck her in the ass?” the manager allegedly asked. “Chris laughed and went on to describe their sexual relationship,” MacWilliams says.

One could technically opt out of the management trips, she adds, “but it is pretty well known that you won’t have a chance at a promotion if you don’t participate.”

 MacWilliams says she’s concerned that public agencies continue to grant DST millions of dollars a year in taxpayer money without demanding more from the nonprofit’s leadership. 

She hoped the investigation would lead to some sort of leadership change, compensation for the women she felt were underpaid, and an apology.

“Years later, none of this has happened,” she says. “Although I have come to peace with this, I truly believe that DST should not have access to public funds until those responsible for irrevocably hurting so many people have been held responsible.”

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