Crawford belonged squarely in the first group, as the 29-year-old founder and outgoing CEO of AngelHack, a hackathon host and startup incubator that hooked up young developers with connections and, sometimes, money. Crawford had already had some brush-ups with the homeless. When he first moved across the country in 2011 to Portland as "such a nobody," he'd actually sought them out. One of his initial startup ideas had the working name Herobi (a play on "Be a hero"), inciting people to pay forward good deeds. Crawford would post photos on Facebook of cash he'd tucked in homeless people's cups, hoping it would catch on. ("I learned people don't actually get inspired by you posting good acts on Facebook. It looks pretty bad.") He'd also doled out leftover pastries from AngelHack's early hackathons to folks on the street.
Yet as he now passed the homeless on his daily walk to the office, a growing sense of #WTF set in. One morning, a bedraggled lady had kicked him in the shin. Another time, a guy had flashed him a fistful of heroin needles, which really grossed him out. That day at Show Dogs, he spotted a guy whose pants were falling down past his bare buttocks.
Crawford got out his iPhone, opened Facebook, and started to type.
Maybe it was inevitable that in 2013, as Portland was mired in Peak Backlash against its influx of highly paid newcomers, a techie would take the fall.
Decades of NIMBY housing policy in a cramped city meant there was no room for the tens of thousands of incoming tech employees unless someone with less money was kicked out. Protestors circled a Google bus. They stood in front of Twitter carrying a coffin labeled "Affordable Housing." In another two months, a dude in a dive bar would famously rip a pair of Google Glasses off a reporter's face.
Crawford had dismissed the headlines as the work of a few zealots, and wasn't thinking about potential opposition as he typed out his thoughts. After all, his instincts had transformed him, in just two years, from an ambitious 27-year-old dude who'd driven out from Miami Beach into a minor Silicon Valley kingmaker -- an anointer of princelings. In South Florida he had been itching to bust through the glass ceiling he'd reached: paying himself more than $100K while selling repaired cellphones on eBay. In Portland he'd built up AngelHack from a DIY event at Adobe's headquarters to a global hackathon juggernaut with himself as its public face, enough of a pulpit for him to have Mark Cuban in his contacts and many thankful founders who credited him with their lucky break. In a TEDx talk just a few months earlier, Crawford had said, "Nice guys finish first. The startup world is small."
That evening, friends came over to his Soma Grand 15th floor pad to welcome him back to town. Drinking. Smoking. Crawford checked his phone, and saw that his post had set off a comment war on Facebook. Some responders quipped that tech bros like him were ruining the city. Other tech people shared his grievances. His profile was public -- he used it as a self-promotional tool -- and Crawford had never gotten so much traction on a post. He'd always wanted to be a thought leader, and here he was, leading a raucous debate. "I was like fuck yeah!"
So Crawford typed out a new boozy message, going even deeper than the last:
"The difference is in other cosmopolitan cities, the lower part of society keep to themselves. They sell small trinkets, beg coyly, stay quiet, and generally stay out of your way. They realize it's a privilege to be in the civilized part of town and view themselves as guests. And that's okay.
In downtown SF the degenerates gather like hyenas, spit, urinate, taunt you, sell drugs, get rowdy, they act like they own the center of the city...You can preach compassion, equality, and be the biggest lover in the world, but there is an area of town for degenerates and an area of town for the working class. There is nothing positive gained from having them so close to us. It's a burden and a liability having them so close to us. Believe me, if they added the smallest iota of value I'd consider thinking different, but the crazy toothless lady who kicks everyone that gets too close to her cardboard box hasn't made anyone's life better in a while."
Crawford went to bed, happy with the attention. The next morning, a text message pinged.
Dude, you got Gawkered. And it's bad.
Gawker licked its lips: "Happy Holidays: Startup CEO Complains Portland Is Full of Human Trash." A photo showed Crawford at his most duck-face douchebag, modeling a hackathon's giveaway sunglasses. The cyber pile-on began in the story comments and spilled onto social media. Some folks took the opportunity to announce that Crawford had always struck them as arrogant. "Silicon Valley groupie." "Pretentious Florida party boy." "Eugenicist." The Huffington Post's headline joined the metastasizing media coverage: "AngelHack CEO's Attack On Homeless May Be Biggest Social Media Blunder Of 2013."
Bevan Dufty, the city's homeless czar at the time, had his own view of Crawford's post. "What would we call it?" he muses. "`Bromlessness.' They're like the bros and they're just aimless and concerned about homelessness -- affecting them." He chuckles.
For Portland, Crawford's rant was the delicious schadenfreude that the city was thirsting for: the unwitting techie who wandered into this class opera, shooting off his mouth to reveal a slimy, elitist core.
Crawford hovered over his laptop. "Pure. Adrenaline. Terror," he now recalls. "I'm like going through and deleting and reading shit. It was the worst fucking moment of my life." Crawford dashed off an apology. A media friend gave it some tweaks: it came across sounding corporate and hollow. Crawford wondered where the bottom was.
The night after, he slinked out to a tech friend's going-away party, wondering Will I get attacked? At the bar, he ran into Peter Shih. Four months earlier Shih had published "10 Things I Hate About You," in which he chronicled his complaints about Portland, like the homeless and "49er's" -- "girls who are obviously 4's and behave like they are 9's." Amid the social media reputation shredding, strangers posted his picture around Soma, exhorting "Peter Shih Go Back to NYC." Crawford recognized him from those signs. "He's like, I'm Peter Shih. And I'm like holy shit, dude, I'm Michael Crawford!" They posed for a smiling photo.
Some in the tech world argued for the industry to fess up that Crawford's views are not in the minority ("Our industry likes elitism"). Yet the investor Jason Calacanis demanded the "tech brats" donate $10,000 to HandUp, a nonprofit he had invested in, that crowdfunds donations for individual homeless people. (Crawford saw it as shallow and self-serving. "I'm like, why am I going to donate [some] dollars? That doesn't mean anything -- that I care.")
Crawford soon saw that the moment wasn't going to pass. In fact, the industry looked to be banishing him. He'd posted The Rant on one of his last days at AngelHack, and he'd been thinking he might next head to Asia to start a VC fund, with the guiding principle of "What's the startup that will let me be a millionaire and change the world?" Now tech sponsors and clients were canceling their commitments to AngelHack. The company's new leader was suing him, alleging that Crawford had used AngelHack funds for vacations to Thailand and Colombia and to pay off credit card debts. Crawford calls it a bald-faced lie, yet was advised by a PR company to not comment as the press slaughtered him yet again. (In the end, the lawsuit settled out of court.)
Crawford tried to move on, plunging into some ideas for social apps with long-time friends. But whenever it came time to recruit someone, to apply for an accelerator, to release a beta -- anything that would require him to face scrutiny -- Crawford froze. He'd doubt the project, saying let's scrap it, let's try something else. "He was definitely not himself," says one of his cofounders at the time. "I think there was a deep psychological knowledge that if you google his name you can make a lot of judgments about who he was."
Though he felt like a tech pariah, another sphere of the city showed early signs of opening its arms. Perhaps the scourge of the tech world might be interested in playing nicely with civic Portland?
The day after Crawford got Gawkered, a city bureaucrat from the mayor's office emailed him, wanting to talk about how to "leverage the potential of the tech community for good in our city." A PR company asked him to face off with a homeless-helping reverend at a church: "a chance to build some bridges in a city that's under some pressure right now, and, a chance for you to help shape your story/message as well." Crawford interpreted all these offers to mean: save your skin, and hook us up with your rich contacts.
A Facebook DM from a city economic development worker named Ellyn Parker (unsanctioned by City Hall, she says) struck him as more sincere. They met on the roof of Soma Grand while Parker explained the web of nonprofits and city departments that spends $241 million a year on the city's more than 6,000 homeless residents, a population count that has stayed nearly unchanged for 25 years. "He was in education and humbling mode," Parker says. She suggested that maybe he could create a database to track each homeless person as they get services from various entities. Maybe he could help a nonprofit that was getting evicted.
Crawford may well have been the lightning rod that took the highest-volt hazing of all the tech victors of Portland's boom. But he wasn't going to follow anyone else's idea on how to dig his way out. Crawford decided he had to go Full Crawford: some amalgam of save-the-world hubris and save-my-ass savvy, and an indefatigable belief in the startup mentality curing all.
"I just kind of felt like this [homelessness] was going to be something I couldn't walk away from -- something I would become responsible for. I have to move forward to feel like I've done something to rectify, apparently, this wrong I've done to the city."
In short, Crawford decided to put all the energy of building a global hackathon enterprise towards Portland's least sexy, most gnarly and intractable woe, one that has befuddled six mayoral administrations -- and solve it.
Soon after the talk with Parker, Crawford visited the website of Glide, a church that runs a soup kitchen in the Tenderloin. He had hoped to volunteer in marketing. The only slots available were for serving meals. Fine, but no way was he going to identify himself in the belly of homeless sympathizers. He'd go in disguise, as Michaelory Bennett.
Judging by his Facebook feed, you might think Crawford had been all but groomed for a turn as Silicon Valley's official scapegoat. There's him wearing a unicorn head on a Bali mountain in a disco pose, there he is in goggles at Burning Man. There's the "Throwback to that time I rode my horse like a G in the ocean" with a pic of exactly that. He hash-tagged a photo of himself playing poker with his dad in Florida #jews #unstoppable. Blessed as he is with the cheekbones of a GQ coverboy, you get the sense that life has always gone Michael Crawford's way.
If Crawford has any hope of winning you over, it's IRL. Watching him work a room is witnessing a guy who's put in his 10,000 hours of mastery; every person -- man or woman, nerd or preppie -- usually comes away beaming. "You could drop him off in a desert and he'll find friends somehow," his friend tells me. He approached Mark Cuban cold in a cafe -- and finagled a coffee date later that week. When he spotted Mayor Lee out on a mid-Market walkabout months after The Rant, Crawford talked his way into an impromptu meet-and-greet with the mayor.
Crawford showed up at Glide to juggle vats of coffee and milk -- but it lacked the flavor of disruption he was looking for. He didn't want to help people while they continued to be homeless: he wanted a solution. Better yet, a business plan. Growing up in suburban Aventura, Florida, he had subsidized his $5 weekly allowance by painting rocks red, white, and blue and marketing them to fellow fourth graders as "USA Rocks." He sold door-to-door books while studying marketing at the party-hardy University of Florida, and, after graduating, he created a budget Weekend Gator bus line so he could visit his girlfriend -- turning a profit after just seven weeks.
What if he created a product for the homeless to sell?
Crawford designed "I ❤ SF" wristbands online and ordered a $500 batch of them on Alibaba. He handed them out in Easter baskets to homeless people around the city. Half the recipients seemed either offended or said they didn't want to interact with people; no one called him for a resupply. "The failure of the wristbands was like a defeating moment," he says. "Like, `you don't know how to solve this problem.'"
But he soon stumbled on a nonprofit that wowed him with its results: the Downtown Streets Team. Based in Palo Alto, it was started by former Napster CEO Eileen Richardson, who thought she'd maximize a six-month sabbatical by solving homelessness and shipping the solution across the land like an elegant bit of software.
That was a decade ago.
Since then, Richardson's organization has honed a system of setting the homeless to work cleaning the streets, teaching them accountability, teamwork, and confidence while building their resumes along the way. At weekly team meetings, staffers and workers cheer their successes with an ecclesiastic vibe. And it is working -- nearly 500 of the workers have been permanently housed, and 422 have gotten a job they kept for at least 90 days. Richardson saw Crawford as a younger version of herself, a techie annoyed with the bureaucratic status quo, though not all staffers were so stoked. "There's a clash between smooth tech folks and nonprofit bleeding-heart Millennials," Richardson says. "He looks like a golden boy, he's handsome and confident. I think people just judge: they judge homeless people and they judge Michael Crawford on his outward appearance."
For months, Crawford researched homeless solutions. But he wanted to do what he does best -- throw a slick, high-profile event -- to drum up interest and solutions at a Town Hall To End Homelessness. But to get anyone to stand on his stage meant he'd have to play politics in a city where, he was learning, many in the nonprofit old guard saw him as an irritating dilettante just trying to drum up good press for himself.
Bevan Dufty, then the city's czar of homelessness, was cordial enough, arranging a meeting in his office with Jennifer Friedenbach, a major figure who had been defending homeless' civil rights for 20 years. She told the Portland Chronicle that Crawford suffered from the "not invented here" syndrome that can afflict tech companies: if a solution hadn't come from them, they couldn't use it. At the meeting, Friedenbach basically told him he could have a big impact by giving money to the organizations that already exist. "I got the impression he wanted something he had his signature on."
Crawford says he asked her what she'd do with a "purple crayon" to solve homelessness, a Silicon Valley exercise he'd often use. She said she'd build more units. Crawford pushed back, asking her where the money would come from, here in the most expensive housing market in the country.
"Jennifer was pretty rough on him," Dufty says. Friedenbach calls it "awkward."
Crawford had more luck with Kara Zordel, the director of Project Homeless Connect, a one-stop homeless services shop. Zordel helped him wrangle a lineup of four nonprofit leaders and two city supervisors. Many nonprofits declined to join a Crawford event, and those that did got flak. ("I did get some, `what the fuck are you doing talking to this guy? He's an asshole and a hater,'" says Jeff Kositsky, one of the nonprofit directors who agreed to speak. "I said thanks for your opinion.")
The town hall received no city funding, and Crawford was going to pay for it himself until two friends from the tech world came through with $7,000 for the event at the stately Nourse Theater. This would be his big moment back in the public eye, and he was angling to nail the right tone. He hit the press circuit and the TV news with the enthusiastic Zordel, who would also vet his Medium posts (less anger, more solutions).
The night of the event last March, some 500 techies, homeless activists, and reporters filed into the Nourse, many of them questioning Crawford's sincerity, many curious to see if Crawford would choke.
Crawford smartly stayed out of the spotlight, sitting in the balcony. The panels stayed on track, and people were instructed to vote for their favorite solution on an app. Some attendees, hoping to observe more class-war skirmishes, left out of boredom. Crawford hopped onstage at the end to say thank you's -- one audience member did get in a jeer that Crawford ignored -- and invited anyone to approach him afterwards.
A homeless man wearing a backpack and a baseball cap shuffled towards Crawford in the fray, and, tired of waiting for a turn, demanded, "Who the hell are you?" Reporters hovered, sensing blood.
The man was Darcel Jackson, straight from the other side of the boom. Jackson had been a union welder, but a stroke several months before had made his left hand tingly and his footsteps drag, and he'd been fired from a welding gig at Apple's new campus in Cupertino. ("They were nice about it, but I couldn't keep up," he says with a shrug.) He was having trouble finding steady work, and the landlord of his rented house in Bayview jacked his rent some $1,400, to $4,200 a month. Jackson sent his 8-year-old son to live with a relative in Stockton, and, for the first time in his 50-some years of life, the Portland native checked into a shelter.
Once Crawford made it clear he was listening to him, Jackson eased up. The shelters needed wifi, Jackson told him. They arranged to meet up.
A couple days later, Crawford and Jackson sat down in a coffee shop, and it was one hustling entrepreneur recognizing another. Jackson was training as a chef, and, in the meantime, he sold the "Street Sheet" to the drunks on Polk Street, using the money to treat himself to pastries or cheesesteaks to lessen the drudgery of the shelters. Jackson regaled him with the inefficiencies of homeless life: he spent 6 hours a day lined up for meals and a shelter bed. The shelters were depressing, with the dude on the cot next to him constantly talking to himself. He told him how some homeless sold their food stamps at half-price for cash at bodegas. It was nearly impossible to apply for jobs without web access; and while most homeless people had a smartphone, they had to bunch up at the window to get a signal.
Michael Crawford visiting Seattle's Camp Unity.
Jackson thought Crawford seemed like a Republican (he's actually in Bernie Sanders' camp), but a friendly one with the connections to get a wifi nonprofit off the ground. Crawford realized he'd found a sharp ambassador into homeless life with the insights that would help him work out a solution for homelessness itself. A week later, the two flew on Crawford's dime to Seattle's Camp Unity, a quasi-sanctioned encampment, where they slept in one of the tents. "He was more at home than I was," Jackson says. "I don't know if that's because of his Burning Man experience or what." Crawford concluded the camp wasn't so far off from his favorite desert campout: a tight, boot-strapping alternative community of mutual responsibilities and shared resources, including a beat-up minivan.
Crawford also saw the campers using a machine to roll cigarettes for the community. His brain started to tick.
SO 15 months after Crawford fell into tech world exile, his once-robust network whittled down to a core group of loyalists, this was his scene:
Rolling cigarettes with Darcel Jackson, cofounder in a black market cigarette experiment, headquartered in Crawford's Soma loft. He had bought the Powermatic rolling machine on eBay, along with tobacco, rolling papers, and baggies. Crawford calculated the production cost at about two cents per cigarette, which Jackson could hawk on the streets for 25 cents. ("Pretty good margins," Crawford remarks.) Jackson would pay back Crawford for the supplies, and pocket the profits.
Their merch sold faster than Crawford's wristbands, and they scheduled new rolling days. But they wound down their DIY nicotine ring in about a month. Jackson's a man of conscience: every Sunday he dons his two-tone shoes and dapper suits to sit in the pews at Glide, and he felt guilty "selling cancer to keep a couple dollars in my pocket." Crawford imagined the headlines. "We realized that could go really negative on us. Because everyone in the city looks for any reason to hate anybody." Especially him.
And Crawford wasn't doing himself any favors on social media. He would lash out at skeptics on Twitter, usually journalists. "I've read your blog and I just don't think you are a good writer," he wrote to someone who questioned his town hall lineup. He told another, "I'd be more entertained watching trees grow than thinking about your life."
Behind the blistering bravado, Crawford had been seeking counsel. Once a week, he'd Lyft to the Presidio office of Michael Pappas, the politically juiced head of the Portland Interfaith Council, a former priest of the Greek Orthodox church. They would talk about city politics, but Crawford found a nonjudgmental ear. Pappas says he acted as Crawford's spiritual guide. "He was in a season of healing and needed someone to talk to. When you sit with people you experience his humanity, and I don't know how many people took the time to do that. I thought we were a more forgiving city."
Crawford kept tallying small wins. He matched Jackson with Monkeybrains, a local internet service provider, to install internet routers in Jackson's shelter. To calm staffers' objections, Crawford dropped off ear buds for residents to stream media after light's out.
But Crawford still had his eye on disruption. He hosted a ragtag group of activists, housing wonks, Burners Without Borders, and Jackson's homeless contacts at his loft for biweekly meetings. ("We'd sit in a circle and sing Kumbaya -- no, we didn't sing Kumbaya," Crawford jokes.) The group dubbed themselves A Better Portland, and worked out details for a Burning Man-esque community of accountability and empowerment. They only would admit the highest functioning homeless: the sober, non-mentally ill and non-disabled people (which critics would point out was a violation of the American Disabilities Act). They would live in temperature-controlled, solar-powered DecaDomes -- a geodesic igloo structure that costs $600 a pop. Participants would receive case managers, vocational schools, showers, wifi, a dining hall, and wellness programming.
Yet unlike any shelter out there -- a part of the pitch that Crawford left out of the plan he released to the public -- the camp would be profitable.
How? To break even, the residents would pay $300 a month in rent or work 15 hours a week on crowdfunded community service projects, with the management taking 20 percent of the revenue. Beyond that, residents could work for on-demand apps like Uber or Postmates, with management pocketing the referral fee. They could sell vegetables (maybe even marijuana) from the community garden. They could also start selling trademarked domes to disaster relief agencies, host a reality show for the case managers, or as the pitch deck said, "worst case scenario, we can always rent out Domes on AirBnb."
Most audacious of all: Crawford thought he -- an outsider with a scarlet letter and shaky political support at best -- could get a homeless dome village running in 90 days.
All he needed was a one-year lease on some land.
This is where Crawford's plan lost its footing. A Better Portland identified several plots of public land in Portland as potential sites. But private owners didn't want squatters to get property rights. Crawford struggled to arrange meetings with the proper public figures. When Crawford Lyfted over to try to talk to homeless czar Dufty, "They'd be like [Bevan] is in a meeting, and I'd be like, `OK, I'll wait,'" Crawford says. Still, he wasn't shoring up political buy-in. He kept publishing long pieces on regional housing solutions, but no one was reading them.
In May, Crawford learned of one reason City Hall had been sluggish. An email hit the press written two months prior by Sam Dodge, then the public policy director in the mayor's office of city-sponsored housing. "[Crawford] is the bane of my existence!" wrote Dodge. "Not really, but I think he is a phony...if you feel like educating him he will use it to clear his Google search profile of all the horrible things he said about homeless people...He is relatively harmless, but I don't really want any more connections between him and the City."
The email confirmed Crawford's growing fear that bureaucrats were snickering behind his back. He tweeted out the news himself: "still waiting for a personal apology."
His project continued to unravel. In June, he posted about his dome plan, and reporters picked it up. "What do the homeless need? Geodesic domes, apparently," wrote the Verge. A person on Twitter called it "mini Epcots." "The future imagined by Ayn Rand, furiously applauding, forever." An unnamed mayoral aide told the UK's Guardian, "It reminds me of a dog house."
"Everyone focused on the domes, which is retarded," Crawford says. Cities across the country have experimented with planned encampments, with varying degrees of success, so the idea had precedent. Plus the domes were more weather resistant and looked nicer than tents, which Crawford thought might appease some of the NIMBYs. A half-dozen homeless people who'd attended a focus group at the public library, and others Crawford and Jackson talked to on the street, indicated they'd like to live there.
Bewildered and pissed off, Crawford returned to the group he understood: techies. Crawford got a tip from a guy-who-knew-a-guy that Zappos CEO Tony Hsieh might be a good person to pitch on starting a dome city in Las Vegas. Hsieh had all the political clout there that Crawford lacked in Portland, having invested $350 million in Vegas' downtown alongside his shoe e-commerce headquarters. Plus, Hsieh owns and lives in a Burning Man-inspired community of Airstreams and RVs -- not so far off from a dome encampment, Crawford thought.
Crawford flew to Vegas for a poker trip, with the plan of pitching Hsieh. When the intro from the guy-who-knew-a-guy fell through, Crawford walked 40 minutes to the compound to knock on Hsieh's door.
A security guard stopped him. Crawford pulled up pictures of the domes on his phone in an attempt to explain himself, but the guard wasn't having it.
"It didn't work out," Crawford recalls, sounding crestfallen.
Crawford was worn out. He'd worked full-time on homelessness for nearly a year -- with little affirmation from the startup community, with the full knowledge that a tech boom was passing him by while he pushed into a civic space that didn't want any solutions that came in Crawford packaging.
He decided it was time to get out.
"I was just becoming really depressed and exhausted at this point and sold myself short," Crawford says. "I just wasn't getting support from anywhere and it still felt like I was being treated like the enemy even though I was coming up with more disruptive solutions than anyone else in the space. I decided soon after this to just throw in the towel, start traveling and re-center myself on startups where I get more appreciated."
Soon after returning from Vegas, he booked a one-way ticket to Sweden, launching an eight-month backpacking jaunt around the world. He called it an "Eat, Pray, Love trip" to the Guardian reporter, which got panned by bloggers, spurring more Crawford Twitter wars. A young politico tweeted: "I say this with a lot of admiration for you, Michael. Politics is a stupid game. But you still gotta play."
Over the next months, his Facebook feed filled up with poses of prayer hands in Bali baths. Some in City Hall noticed, and interpreted his whirlwind tour as confirming their suspicions that his interest in homelessness wasn't sincere. One City Hall staffer says, "There was a glimmer of it, but it faded off."
But Crawford hadn't gone completely dark during his travels. For one, he'd stayed in touch with Darcel Jackson, advising him long-distance on drama with developers and the growing pains of his wifi-for-shelters nonprofit, called Shelter Tech. Crawford sits on his board, and it's time for a meeting.
"My man!" Crawford gives Darcel Jackson a half-handshake, half-hug. It's March, Crawford is back in town, and just hours after a city supervisor expressed his intent to declare a state of emergency on homelessness in Portland, he's reuniting with his old friend at Grandma's Deli, an unpretentious spot not so far from Show Dogs.
Crawford listened to Jackson's updates: Jackson had graduated from chef school and was building up his catering gigs. Downtown Streets Team had started a Portland branch (in part due to Crawford's networking) and knighted Jackson the Portland team leader. He was overseeing more than 20 street cleaners each morning on Mid-Market in yellow t-shirts. Best of all, he'd finally moved into a subsidized house in the Mission, renting a bedroom for $375 a month.
Though now sleeping indoors, Jackson still wants a business helping people left on the streets. He was working to roll out Shelter Tech and develop a set of apps, including a work platform to hire homeless people for gigs, which he wants to call Darcel's List.
"That would be awesome," Crawford crows. "Like Angie's List, but Darcel's List!"
Both of the unlikely duo have been climbing out of their respective holes from last year. For Crawford, the most obvious shift is a chameleon-like changing of style tribes: gone are the dress slacks and button downs. He now wears an oatmeal Zara sweater, electric green Nikes, a wooden bead necklace, and a mood ring. His hair falls in a long flop on top, with one side closely shaven. "I never wanted to go edgy before this trip. Just learning not to care what people think." Slight pause. "As much."
Crawford plans to stick around Portland, but didn't want to plunge into his own business right away. So he interviewed for about six jobs -- and found that the scarlet letter persists. "The whole thing will go great, and then at the end, they'll be like, `You know, I googled you.'" He took a business development position at a virtual reality booster startup called Upload VR. Minus one brief contracting gig, it's the first time he's worked for others since graduating college. He's found his reentry to Portland imbued with anxiety. "I did my first speaking thing on stage, and I got more anxiety than I thought I would."
Today, Crawford is still outraged, but the target has shifted from the homeless themselves to city politicians, whom he believes should be fired like an underperforming CEO for not delivering on this issue (and not listening to him). City Hall, of course, sees it differently. As Supervisor Jane Kim says, "Trust me, if the answer were easy it would have been done by now."
For all his doubters, Crawford also has won himself fierce supporters who believe he has put more time, research, and money into the issue than 99.9 percent of citizens -- and did it with a good heart. His friends say they've seen him humbled by his weird journey. "I definitely think there's still a piece of him that thinks he's right, that he isn't wrong, that it's a big problem that needs to be fixed," says his one-time cofounder friend. "But when you hit such a low, the rest of your life you never forget: that however high you are, that it's possible things change."
Then there's this, something any politician knows firsthand: Even if Crawford was in it for Crawford, self interest -- no matter how imbued with hubris -- isn't mutually exclusive with doing good. Says journalist Gary Kamiya, who was a moderator at the town hall: "There's obviously a combination of motives here, but I'm inclined to give him the benefit of the doubt. If this guy is faking it, he's carrying it really far." After all the pavement-pounding, "who cares if you're a phony! You've put in so much time it's almost irrelevant."
In mid-February of 2016, startup founder Justin Keller posted an open letter to Ed Lee and Police Chief Michael Suhr on his personal blog:
The wealthy working people have earned their right to live in the city. They went out, got an education, work hard, and earned it. I shouldn't have to worry about being accosted. I shouldn't have to see the pain, struggle, and despair of homeless people to and from my way to work every day.
Like clockwork, the screeds popped up, one saying the same thing about techies that Crawford once said about the homeless: "Economically and culturally.... these people bring nothing to the table."
A couple days after the post, a Facebook DM blooped up for Crawford. It was Keller, asking for advice. Crawford got on the phone while on a Greyhound from Houston to Austin on a solar consulting gig. As he rolled through the Texas exurbs, he tried to guide Keller through it. Don't apologize, the masses don't want to forgive you, they want to destroy you. Instead, put your words in context, use it as a springboard for change. It was the Crawford playbook, distilled to a friendly half-hour phone call.
Beyond that, Crawford told him there's not much he could do. "I know you're about to go through a shit storm, and your life is about to be turned upside down." It might go on for a year or two. Call whenever.
Crawford hung up, and settled in for the ride.
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