Illustration by John Thomas

ON THE FIRST DAY, Portland Startup Weekend had all the glamour of a mandatory office meeting. Attendees mingled uncomfortably, eating free pizza and playing silly icebreaker games while straining to stay awake through a few pseudo-motivational speeches.

It was a rather unceremonious start to what would become an intense and fascinating event. Nearly 100 web developers, designers, and coders had gathered to invent the next great app or game-changing piece of hardware. Portland Startup Weekend (PSW) is both a social experiment and business accelerator, posing one central question: Can eight people who have possibly never met before, using the guidance of onsite mentors and fueled by free meals and soft drinks, give the world something they never knew they always wanted? Oh, and can this team of eight pull it off in 54 hours?

"There are so many things in our culture fighting against our nature to create things," Luz Bratcher, senior designer at UP Global and a facilitator of PSW, told me a few days after November's event. "We want to make coming to the table with a business idea as simple as possible, and create a context to explore that idea."

The event is a multi-tiered competition. A slew of ideas for apps, websites, and hardware concepts are pitched to the attendees, who then vote on which ones they like best. The top pitches then put together a team that will attempt to create a working prototype and business model to support their idea in a little over two days. On the last day, the teams present their efforts to a panel of judges, with the top three earning prizes in the way of legal and technical support, as well as a chance to compete in a larger startup contest that could earn them an even bigger audience at the much-ballyhooed Consumer Electronics Show in January.

On paper, it may sound as exciting as a Future Business Leaders of America hoedown—but what's at stake is the ability to positively impact the world with a successful idea. Not to mention millions of dollars in potential venture capitalist funding and staking a claim in Portland's booming tech industry. With that in mind, I decided to sit with one team for the entire weekend—either watching a new Instagram be born, or die on the e-vine.


The first step in this process was the pitch. About 50 people lined up around the conference room shaking off public speaking jitters, or looking like they'd already won the weekend. Most were white dudes who didn't seem like they venture outdoors much—but there were a fair number of women and people of color. There was even an 11-year-old who wanted to create an intriguing but definitely civil rights-violating app using facial recognition software to pick out criminals or terrorists from a crowd. One by one, they were all given exactly one minute to wow the audience with their idea. If they had more to say and time ran out, everyone in the room would drown them out with applause.

The pitches varied as wildly as you would imagine. One gent looked to get ahead of Oregon's pending marijuana legislation by creating an app to connect sellers and buyers. His friend wanted to build a better grip for PS4 controllers. There were several new social networks proposed, including a site for women working in the creative and tech world to connect, and another couched as "Craigslist meets Meetup." There were two separate pitches for apps to aid with toilet training. And one baffling idea looked to help businesses create "a second website for customers just looking for information about that business."

From there, things got a little chaotic. Each attendee was given three small stickers to use as votes. The budding entrepreneurs worked the room, either standing and shouting like carnival barkers, or glad-handing attendees to get a vote. (Naturally, one of the men who pitched the potty training app did so with a disposable diaper on his head.) As they did, everyone else squeezed past or clambered over lines of chairs to affix a sticker on the placard for their favorite idea.

At around 9 pm, everyone filed downstairs to a cavernous boardroom filled with conference tables. On each table was the name of one of the top 12 vote-getters. These semifinalists were then courted by potential teammates—designers, developers, and marketing experts. Then began the heated discussions about where to begin.

I gravitated toward a quieter, unassuming batch of people who were all listening to Matt Fountain—a soft-spoken gent in a cloth cap who'd pitched earlier in the evening. Like me, they saw the potential in his idea, Homing In—a mobile-friendly website designed to help the homeless find available beds in local shelters.

Fountain was one of many folks who paid to attend PSW hoping to get some traction on his startup idea, but also to climb aboard the fast-moving train that's the local tech industry. Several people I spoke to were currently unemployed or had just moved here, and saw this as a perfect networking opportunity.

In Fountain's case, he quit his day job two months ago and has since been learning database languages at PDX Code Guild, while volunteering at p:ear, the mentorship program for homeless youth. It was there he hit upon his startup idea.

"I was really surprised to learn that so many of the kids who came through had smartphones," he told me. "Almost 70 percent of them, according to my research."

Fountain was also inspired by Link-SF, a website providing locations of shelters, medical care, and food options for San Francisco's homeless.

"It's an open-source app that uses a Google Maps API," he tells the seven teammates huddled around the table. "It shows you how close you are to the nearest shelter, and icons for what services they have—but it doesn't check availability."

As if on cue, nearly everyone at the table cracks open their laptops to pore over the site. Various side conversations cropped up about the best way to build their version: funding possibilities, and the potential difficulties of getting shelters on board. Fountain was getting frazzled, watching the discussion spiral out of control, but he was quickly saved by an announcement: At 11 pm, the alarms in the building would automatically kick on, giving us only about 10 minutes to scram.


The first thing each startup team needs to prove is the viability of their idea. Is this actually going to be something people will want and use? For some of the Homing In team, that meant spending a good portion of the day on the phone with local shelters, asking whether this site and service made sense for them and the people they serve.

But for Ryan Perkins and Anton Bilbaeno, the two most affable members of the crew, it meant braving the cold to talk with some homeless people. Their secret weapon: a bucket of Voodoo Doughnuts pinched from the event's breakfast service.

"We found the perfect candidate," Bilbaeno said excitedly. "He was sitting there with the Rose City Resource guide [the directory of services for homeless people published by Street Roots] and a smartphone just trying to figure out where to go next."

The consensus was positive. The kids they spoke to might not have 3G plans, but they do know where to find free wifi so they can access the site. And users without smartphones can still head to a library and access it via the web.

The harder sell was with the shelters. Portland Rescue Mission seemed excited, but others thought it would involve more work for their already overtaxed staff. In addition, Homing In's other idea of keeping a database of homeless people in the area was viewed as a little suspicious.

Back at the Portland Startup Weekend headquarters, the rest of the team was sitting down with onsite mentors—advisors who could help move their idea forward, or pivot them toward ideas with better legs.

There was little concern about the app's tech or the team's good intentions. But as attorney Leigh Gill—one of the mentors volunteering his time for the weekend—told them, they were eventually going to have to look way beyond the seven people around the table if this project was to have any kind of future.

"You need to identify each constituency," Gill said. "The city, the shelters, the police. You need to make sure they're all on board, and ask the question of whether or not this would be valuable to them. Get them involved."

It was all good advice—but you could see it started to overload the brains of the team. Their once simple goal was suddenly far more complicated.


Much had happened for the Homing In team during the 12 hours since I last saw them. The whole crew had packed into a small, fishbowl-like conference room to wrap up their work for the weekend, and they'd made huge strides by completing a working prototype of the site.

"I was up until about 4:30 am finishing this," said lead developer Guy Halperin, sounding relaxed, but looking extremely exhausted.

The site he and co-developer Amy Boyle built is just about perfect, a clean design that's easy to dive into with no directions. A large Google map dominated the left side of the page, with the familiar teardrop-shaped markers indicating certain spots in the city. Click on one, and a box pops up, giving you the address of the shelter as well as little icons indicating what amenities they offer. Also in each marker was a number, indicating the number of beds currently available.

The biggest change the group went through was deciding to rebrand themselves as PDX Shelter. Though it sent the event organizers into a tizzy trying to update their websites and PowerPoint slides to reflect this change, the new name better fit the group's goals. Potential donors and supporters would have a much easier time connecting that moniker to the larger idea.

While these advances may have somewhat reduced their stress, there were other issues to contend with. In a few hours, the team would have to present their finished product to a panel of judges, including a strategic business development manager at Intel and a senior project manager for Google. The prospect had Fountain looking a little freaked out. This feeling was only amplified after he ran through his five-minute presentation for another mentor, Michael Gray, the CTO of mobile ticketing service GlobeSherpa. The pitch was bumpy, with Fountain unsuccessfully trying to pull the listener's heartstrings, while sounding apologetic about only getting one shelter to agree to be a test case.

"Your story convinced me this won't work," Gray told the team. "You need to focus less on the question of whether the shelters would have time for this, and more on the problem you're trying to solve."

Fountain nodded his head, trying to translate this feedback into a rewrite, and eventually excused himself to find isolation from the swirl of people and activity going on throughout the building.

As I sat there watching the team put last-minute touches on their slideshow and website, I marveled at how easily it all came together. During Bratcher's opening address to the troops, she advised them not to worry if arguments happened. It was all part of the process. PDX Shelter was able to avoid disputes by keeping their goal simple: help homeless people find a bed for the night. There were occasional shots of tension now and again, but even those quickly dissipated.

"I'd be surprised if we won this thing," Perkins told me as we waited for the winner to be announced. "Still, spending the afternoon creating something—trying to solve a problem where most people would throw up their hands in frustration—is awesome. Now, if you'll excuse me, I have to let my team know they should be panicking."

The closing hours of the weekend were as awkward as the beginning: a drawn-out Q&A with the judges, more motivational speeches, and then, at last, the final presentations.

Some groups had pivoted away from their original concept in a big way. For example, Minnow was initially pitched as a networking site for people looking to sign up with a business mentor, but turned into a site where users put a price tag on a secret. A dirty detail is revealed about a person or a business and for a fee, you can find out exactly who or what it is. Though cute, the idea was dead on arrival, and not helped when the team leader decided to take a couple of vape hits before his presentation.

Most, though, stuck to their original business models with slight modifications that came out of testing and mentor sessions. And almost all came up with something that felt very much tied in with the values and interests of Portland: an app to connect restaurants with organic farmers, a piece of hardware to test for E. coli in water supplies, and, yes, a way to avoid expensive and environmentally costly disposable diapers.

PDX Shelter seemed to slot somewhere in the middle of the startup pack. Their slideshow and web design weren't as sleek as others, and the speeches by Fountain and Halperin were still rough-hewn. Yet their concept was far more fleshed out and well researched. I had to admit, as much as I was rooting for them, I didn't anticipate they'd take home the big prize. In fact, when PDX Shelter was announced as the winner of the Best Customer Validation Award, I figured this was their consolation prize.

Then judge and speaker Paige Hendrix Buckner grabbed the microphone.

"Um... so the overall winner is... drumroll, please..."

Everyone in the room started slapping their knees or the table in front of them.

"PDX Shelter."


"It felt like a Capra film, where a little person voices a well-intentioned idea into a loud and competitive situation, and then an amazing thing happens," Fountain wrote via email a week after the big win.

"You realize that almost everyone shares those good intentions and wants to do something positive—they were just waiting for someone to say it's okay to have them. The takeaway, for me, is if you have an idea that might actually benefit your community, you're already part of a loving team of supporters."

He and his team are now moving forward—to the next stage of the competition, and reaching out to the Portland Development Commission, Housing and Urban Development, and other stakeholders who could benefit from what PDX Shelter is looking to offer.

As for everyone else involved in the weekend, there's always next year: other startup ideas to try out, more battles to organize, and more opportunities to preach the entrepreneurial gospel.

"So much of this world we live in relies on people creating businesses," Bratcher said. "Everyone's looking for spaces and likeminded people who want to work shoulder to shoulder on a project. And when they find them, incredible things can happen."