Glenn Fleishman heads to Portland for the second XOXO festival, where a maker's heart can leave the body, be shared among kindred spirits, and know that it will be cared for.

The second outing of the snark-free, consensual hallucination known as XOXO took place two weekends ago in its permanent spiritual home, Portland, Oregon. Portlandia famously jokes that Portland is where young people go to retire. But that's only funny if one believes that work has to be a thing other than and separate from your own true self and in which you cannot be fulfilled. People reading this blog know intuitively or from practical experience that's not necessarily true.

I fell in love with the event last year, and renewed my vows this year. It was exhausting and exhilarating, and I don't regret falling in love all over again. I tried to explain last year why this event was meaningful to people who didn't attend; let me try again with an amazing year between under my belt that I owe in part to attending in 2012.

Born of Love from Two Minds

Andy Baio and Andy McMillan, the gentlemen behind the show, are makers of wonderful things. I like to say of Andy B. that whenever you find something on the Internet created with joy (Kickstarter and supercuts, to name two), he's likely to have had a hand in midwifing it. Andy M. built Build, a conference that combines technology with making things that's beloved by attendees, and which he will iterate for the fifth and final time this year. Collectively, they are the Andys: nearly brothers, dear friends, and mutual participants in dry-witted faux squabbles.

The reviews from XOXO 2012 were fairly ecstatic, including mine here. The Andys captured a form of practical inspiration in a bottle, and built a space in which attendees and presenters alike existed in a haze of oxytocin-infused trust. Love was present in the air and in our bodies' endocrine systems.

Part of that came out of the people who chose to attend a conference named for hugs and kisses. I didn't even perceive any issue with the valence of the name, but the Andys felt that anyone for whom that sort of warm fuzziness was anathema would be incapable of registering for the event. (It's literal, too. I'm a pretty huggy guy, and I don't think I have ever hugged or been hugged more in my life than at this year's outing. Ami Baio, Andy's wife, was the hugging center of the event, a tiny lighthouse with a 100,000-watt love bulb that shone this way and that.)

Presenters didn't tell us to quit our jobs (I don't even have a job) and run into the streets naked. What they told is that there are many keys and many kinds of locks we can open to take the stuff we love and make it anywhere from a small and meaningful to full-time and fully encompassing part of our lives. It was permission to make, create, build from people who had done it, and done it well, typically outside of the gatekeeper infrastructure for funding, manufacturing, marketing, and distributing.

The attendees at the event included some well-known folks, but mostly were people who work away modestly, and who are trying to find a path through life that makes them happy and feels contributory to the greater culture.

It's a trope at conferences that the audience is as great as the people on stage; at XOXO 2012, it was literally true. I had a thousand conversations, and learned a thousand things, and made a thousand personal connections. The speakers lit fires; the attendees smoldered.

I was worried that trying to capture this lightning in a bottle a second time might produce a damp fizzle. I needn't have. It was even better.

You May Find Yourself Living in a Shotgun Shack

I was high as a kite last year on the neurochemistry and hormones released by attending the event for at least two weeks afterwards. When I came down, I found myself in Tijuana, the proud owner of a hippopotamus and the deed to the Sierra Madre mine. Wrong story.

But my life did change in almost as disorienting and complete a way within weeks of attending XOXO last September, and then speaking at a more intimate and developer-oriented event called Çingleton Deux in Montréal the next month that had similar properties.

Leading up to this, a Kickstarter I'd launched during the summer of 2012 to fund a book about crowdfunding had failed — I'd killed it midstream, as it wasn't going to reach its target. But after hearing so many stories among both the speakers and fellow attendees at XOXO, and realizing that to do the book right, I needed to do more research and build an interested and engaged audience, I launched the weekly podcast series The New Disruptors. I just aired episode 42.

At Çingleton Deux, I met Marco Arment in person, a well-known Mac and iOS developer, Tumblr's first employee, and the creator of Instapaper. He had just launched The Magazine, a beautifully stripped-down publication-in-an-app that omitted all the cruft of most periodicals that begin life each issue in print.

I was fascinated by it and the business model. Marco was handling 100% of the work himself. While I'm not shy, I was made even bolder by the recent conferences, and I pitched myself to him as "executive editor," offering to handle most of the editorial functions. He quickly agreed, and I came on board around issue 2.

Within a couple of months, about 85% of my working life had changed. I was pursuing my interests, which include constant collaboration with other people and telling people's stories, and had an enormously larger amount of control over everything I did. That expanded further in June 2013, when Marco decided he was ready for new challenges, and sold me the app and the publication. (Marco announced at this year's XOXO that he has been working on a new podcast app.) The Magazine celebrates its first year of publication on October 10th with issue 27.

With all of that behind me, I approached XOXO 2013 with excitement and trepidation. I had my own stories to tell, and would meet many of the people in person who I had interviewed or published. I was, as Andy Baio put it, the "poster child" for XOXO. And I wanted more. XOXO is a drug.

People, Let Me Tell You 'Bout My New Best Friends

I'm not really an extreme outlier among the people I talked to at this year's outing. (Although just wait for what's yet to happen in my upcoming year; even I don't know the extent.) Let me tell you about my two new friends from XOXO 2013, Alli Dryer and Jenni Leder. (I share their stories and our friendship with their permission.)

We had become friendly in the last year on, a development infrastructure platform led by Dalton Caldwell (who I had the pleasure to meet at this year's XOXO as well), that presents itself primarily so far as a microblogging alternative to Twitter. (It has storage, authentication, messaging, and all kinds of other neat stuff that allows developers to not have to build such plumbing themselves and to avoid depending on Facebook and Twitter. It's a dumb pipe and smart about it.) has some of the properties of XOXO. It started as a paid service which required invitations to join (and pay). Over the last few months, it's expanded to include limited free accounts and toted up 170,000 registered users. But even with more people, the spammers and douchebags have mostly stayed away. It's a comfortable and surprisingly safe space, in which conversation (which has 256 characters per message to luxuriate in) seems to be civil and can involve many rounds of back and forth. Its conversation threading actually works.

As Jenni put it, comparing Twitter to

The space is too big. This is stadium seating. is like the black box of a small theatre production.

I saw they were coming to XOXO and was looking forward to meeting them at the Thursday night opening party. I found myself without a dinner plan on Thursday night, though, and this was XOXO: I should introduce myself to people I haven't yet met, like at camp or an encounter-group session.

Alli and Jenni seemed like friendly cusses and good company, so I asked them if they minded if I crashed dinner. They welcomed me; we found a sushi place, ate fantastic food, had an enormous amount of conversation, then walked a mile to the party. (Bamboo Sushi, guys: B Corporation, sustainable fish, totally delish.)

Social networks often provide the loose ties and vetting that let you trust people before you know them in real life, but you need the IRL part to create strong ties that last and enrich the friendship. Affinity matures to philia.

Alli and Jenni have been close friends for a couple of years, and lived in Texas until recently. They both work on aspects of user experience: designing interfaces with which users interact in software. Alli created Meat Soap with friends; Jenni curates Maple Mark. They are supremely interesting and creative people.

The two of them and their husbands — that's one husband each — attended XOXO in 2012. It sparked a lot of change. Both couples fulfilled a long-standing dream to move to San Francisco: Jenni and her husband moved in May, and Alli and hers in August. All four changed jobs.

I'm working in the same basement I was a year ago. So perhaps the two couples are better poster children for XOXO than me — except that I heard similar stories over and over again. The guys behind BrewBot were app developers and home brewers a year ago when they attended XOXO. This year, they launched a Kickstarter for their automated brewing hardware at the event, and had prototypes to show off. They're halfway to their total goal already.

Other people quit jobs or took new ones, started companies, launched new products, managed crowdfunding campaigns, accepted risks they hoped would pay off (it sounded like many did), and generally opened their lives to more experience and more ways in which they could fulfill themselves through artistic or professional expression. XOXO 2012 sparked a lot of positive change.

Speak, Friend, and Enter

The coverage of the 2012 event was so positive, the two Andys worried about how they would handle selling tickets in 2013. Nobody planning an event wants the same people to attend year after year as it becomes stale and cliquey. But neither do you want to alienate a core audience who wants to attend, because then you clearly don't appreciate them, and it can sour the mood before and during an event. The demand would clearly be high for the 500 seats in the conference and additional ones for the festival that they would make available.

Instead of opening tickets on a purely first-come, first-purchased basis, the Andys created a sort of modified queue. They didn't explain precisely what they were doing, which led to supposition, and they apologized for it both after registration and at the event.

The key reason for the application they created was to try to weed out (or at least de-prioritize) people who didn't make things, but who were attending the conference to market at other attendees. The Andys wanted to create a massive internetworked conversation, which involves parties who want to talk with each other, not sell things to one another. But it seemed that the application process was a test for how cool one was; it was not, as Andy Baio explained on his blog months ago.

The Andys reserved 20% of the conference passes for people they thought were involved in projects interesting enough that they were sure to contribute to the milieu, whether they had attended in 2012 or not. The other 80% went to folks in the order received for registration on the site, excepting people whose answers to questions about what they make and do made it clear whether they would contribute to or subtract from the event.

(The Andys said it turned out to be very clear which people were senior brand management strategy consultant marketing thought leaders, and which delighted in making, whether for personal or commercial purposes, and whether it was art, software, advertisements, or stuff.)

There were and seem to remain some hard feelings by those who missed Andy B's explanation or who don't believe it was an accurate depiction of reality. But I think it's obviously and objectively true. The conference wasn't made up of net.famous cool kids. There were cool people there, and some famous ones, but they were a tiny minority of the whole.

Most attendees were like Alli, Jenni, and me: people who work hard trying to sort out what we do with ourselves, not those to whom people cater to try to earn our attention. (A telling fact? Most of the non-self-employed people I asked had to take time off and pay for travel and the conference out of their own pockets.) I may have a media profile in some circles because of my writing and podcasting (and Jeopardy!), but nobody caters to me, nor would I want that or accept it. I want to be treated like everyone and I want everyone to be treated well.

To my mind, the Andys achieved this in spades.

For Chrissakes, What Is It Like?

It might seem like I've been digressing on the way to an actual description of the event, but the context of XOXO is just as important as what goes on there. You can't see the trees without the forest.

The event is divided into festival and conference portions, most parts of which take place at the contemporary art center YU — the former Yale Union Laundry — and at the Holocene across the street. (This year, XOXO had full passes for the weekend conference and all other events for $500 and festival passes for everything but the daytime Saturday and Sunday talks for $100.)

The festival events included an opening night party, an opening day keynote and a day of open houses at Portland companies (like Panic and Wieden-Kennedy), musical performances (by Jonathan Coulton and Jack Conte, among several others), filmmakers showing new work, videogame playing (some not available generally), and tabletop gaming (including some not-yet-released games). The closing party, a few blocks away, ended with people gathered around a fire. There were open bars. Many, many open bars. Many.

At the tabletop night, I breached my Cards Against Humanity (CAH) virginity, and had a wonderful time. I knew Alli and Jenni were CAH veterans, so I found them and their new friend Bryan. Max Temkin, one of the games' creators, its public face, and a speaker at the event (and a swell fellow) sat in on a round with the group and used a "mental" card that had been written but not yet incorporated into the game. (I won. Max's mental card was, "Man, this is bullshit! Fuck ______!" I played a card that read, "Cards Against Humanity.") CAH is a perfect match for XOXO: there's no way to win, per se; it's a shared experience as you say and hear horrible, funny things; and people were dealt in and out over hours.

The conference comprised two days of 20-minute talks, capped at the end of each day by a 45-minute session. On Saturday, yours truly interviewed the illustrious editors of this site, never before seen on a stage together at one time, to celebrate the fucking 25th anniversary of Boing Boing! (It started as a zine made by Mark and Carla in 1988, and rolled up editors and Web site features in Katamari Damacy style over the intervening decades.) Tim Schafer of Double Fine Productions finished off the Sunday slate.

There was a dynamic, generally positive tension across the entire four days of the event that came, I believe, from the effect of trust and receptivity people had during it. I have never, anywhere, felt so comfortable walking up to a stranger or a group of strangers and being included in a conversation, introducing myself, and enjoying it. Likewise, a hundred times people came up to talk to me or someone I was talking with. This was true with nominally or actually famous speakers or attendees too. Most people weren't shy; most people weren't diffident, either.

You get a buzz off this. This is not how life normally works. The social niceties and prickly people and pecking orders prevent this sort of things. Andy Baio suggested it actively during his opening remarks on Friday, and alumni/ae tried to both spread the notion and accept it. Snark and cynicism took a holiday, as did irony and sarcasm. (Yeah, right.)

It was probably rough on introverts. I'm gregarious when I travel; more introverted and quiet at home. I realized last year that I was freaking some introverts out by not understanding their space. I was a bit more docile this year, and had some great conversations with folks for whom a multi-day social event is something they yearn for, but also have to cope with.

One of my only disappointments was how many people I had hoped to meet or have time with who were there, but with whom I never had a chance to find or exchange more than a few words. One has to get over that: with any sufficiently large number of like-minded people, at a party or a multi-day event, you can't talk to everyone you want. There are simply too many great people and never enough time.

The individual talks varied in content and inspiration, but none were insipid. A few in particular made me stamp my feet and cheer, but I learned from almost all of them.

Jack Conte of Pomplamoose explained the three-year gap between his and Nataly Dawn's YouTube success and his subsequent creation of a crazy-ass awesome robot video, which led to the founding of a subscription crowdfunding site, Patron. Jack explained that millions of YouTube views can lead to dollars in revenue — like literally $25 for a video with 400,000 views. He told his own story of pain and breaking through. He now has pledges for almost $6,400 per video that he produces.

Jack Cheng gave a beautiful talk about funding a novel and documenting his progress in it as a peaceful refutation of all the gatekeeping advice he had been given. Cabel Sasser blew the doors out by revealing his fear of the future during the work on a flagship software product's development, and his collaborative, consultative path to resolution.

Nobody gave us a cookie-cutter approach to success. Some speakers told their own journey; others explained what they thought the journey should be. All of them have striven for and achieved a high degree of independence and a strong connection to their audience — who are often patrons or even collaborators — whether working by themselves or in companies. They chart their own course, even if there's a crew or passengers aboard.

The time before, between, and after the sessions, including the beautiful expedient of inviting some of Portland's best food trucks to set up on the blocked-off street in front of the YU, led to an enormous amount of mixing and conversation. Those who wanted a little quiet could walk from a few feet to a few blocks to get to a dozen or so restaurants and cafes.

Talking wasn't mandatory; listening was.

I felt something bloom inside me over the course of a few days, even larger and more meaningfully than the year before. Part of that came from friendship: my two best new friends, Alli and Jenni; other folks I made a real connection with over a few minutes or days; some online friends now woven into experiential life; and deepening bonds with so many old ones.


It was not all wine and City of Roses, although there was plenty, plenty, plenty of wine. I don't want to cheapen XOXO by portraying it as Elysium.

I started my oxytocin/serotonin party early, and that led to a quicker depletion. Through the help of friends and colleagues, I arranged a variety show on the day before XOXO at a bar in Portland with music (by a group that formed around the show, Unicornucopia), comedy (Scott Simpson), and interviews a la The New Disruptors. A hundred people came out and it was a hoot.

By Sunday morning, I had an incipient cold, and was starting to need to not see people. But I also didn't want to miss enjoying the last day. Through dint of hard effort, I continued to make conversation, listen intently, and interact as much as I could.

I made it to the closing night party, exhausted and asocial, met and talked with a few last people (including Maciej Cegłowski of Idle Words and Pinboard, who I had been dying to meet!), and went back to my in-laws, where I was staying, and mildly collapsed.

Thoughtful and powerful essays have come out in the few days since XOXO ended on September 22nd. My (new) friend Leah Reich wrote a kind exegesis on the value of criticism, "The Uncanny Valley of Earnestness," which she found missing from XOXO, to the extent that some attendees policed negativity. A trusting place is good, she writes, but appropriate critique is how we improve.

Frank Chimero tore the top of my head off with "The Inferno of Independence," about living inside and outside of severe change, and coping with the pain of taking one's own path. He cites Italo Calvino on the metaphor of the inferno of life. I think also of the crucible: the test or tests that try our will to the breaking point — or even the path not taken when roads diverge.

XOXO isn't a tech event as such — hardware, software, and the Internet are pervasive and necessary as tools and conduits, but there's almost no discussion of tech itself. But it has one of the problems of tech events: a lack of gender balance, odd in creative fields in which women and men are in a more even ratio, and a lack of diversity of background, whether socioeconomic, ethnic, or racial. Among other considerations, the full event cost $500 plus travel expenses and housing for those outside of Portland. (The conference made ample use of volunteers, however, who had full access when not handling their tasks.)

Ariel Meadow Stallings of Offbeat Empire found the predominance of white men indicative of the technology industry's continued implicit bias. She works in the wedding industry and spends most of her time interacting with women, putting an even higher contrast on it for her. But she also acknowledges that the emotional quotient of XOXO distinguished it from purely tech events she'd attended in the past, and she was happy to attend.

One the worst and best things about XOXO is encapsulated in the raw and beautiful account by Kelly Kendziorski, a Portland filmmaker and XOXO volunteer, "Harassment and Inclusivity at XOXO." Kelly writes of being in the position of many women who consider attending tech-ish conferences. The potential of harassment coupled with the potential of having their concerns ignored overwhelm their interest in attending. She overcame that.

But within a few hours of starting her volunteer work, she was verbally harassed by an attendee in explicit sexual terms. With a little encouragement from a friend, she went to the Andys about it. And they responded, as one could only hope they would. The attendee was booted from the event, and Andy Baio discussed it briefly the next morning. Kelly writes, "I never thought I would be the asshole who walks away from being sexually harassed thinking it was a net positive, but experiencing that resolution was an amazing gift for my creativity." Read her whole essay.

Keep XOXO Alive in Your Heart

The Andys spoke to the special place that Portland is, and that the way the YU, an old building in the middle of a real neighborhood, fits the vibe they intend. It can't grow. It can't happen in other cities. XOXO will remain constrained.

But it is not intended to be an exclusionary event. The idea of XOXO, creating a space largely free of empty speech, talking at, and cynicism, to explore new ways of developing creativity into fulfilling self-expression and, yes, successful business ventures doesn't have to happen only during a few days in a Northwest city.

I went through treatment for cancer in 1998, and I call that year the best one of my life. I have had many moments, days, and longer since that are wonderful: my wedding, my children's births, riding with sled dogs briefly on a glacier, and so on. But that year, despite the discomfort and exhaustion of chemotherapy and radiation, left me open to experience unmediated love. It was not mystical; it was palpable.

I have striven ever since to recover that feeling in my life, and XOXO comes closest to offering it. It is the notion that, in the midst of things, we can be together and produce something meaningful, whether the end result is a play, a book, a movie, a dance, a gizmo, a game, or something that can't be characterized, and whether we do it for pure satisfaction or to make a small mint.

XOXO is a way to take our heart out of our body for a few days, share it, and know it will be cared for before we return it to its cage.

Photo: Glenn Fleishman

More of Glenn's photos of XOXO 2013 can be found in this set at Flickr. The photo used as the thumbnail for this feature is by Duncan Rawlinson, released under the Creative Commons. There are also many more to enjoy from other photographers.