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XOXO is an arts and technology festival organized by Andy Baio and Andy McMillan, held in Portland, Oregon.

This two-minute wrap-up video is a pretty good summary of what it was about:


I’ve been to a lot of conferences, and while I complain loudly about them (#firstworldproblems), I tend to secretly enjoy even the most soul-grinding trade shows because of the opportunity to see industry friends and colleagues. There are also exceptional cases like Books in Browsers where I genuinely look forward to the proceedings as much as the conversations.

XOXO is different; the background of the attendees makes it impossible for anyone to know everyone. It’s still majority Internet-Famous people, and some reflections by Internet-Famous people have wrestled with that, but the people that I met were as likely to be academics, comic artists, boardgame creators, and indie developers as much as wealthy startup founders.

Talk videos have been posted; the complete set from both 2012 and 2013 are available on XOXO’s YouTube channel. Here were my favorites:

Max Temkin, Cards Against Humanity

Max’s talk resonated with me in two ways. First, he articulates a progression of values > strategy > tactics. Values guide product or corporate strategies, which in turn inform day-to-day tactics. When I was a startup founder, I would’ve said our company had strong values — promising only what we could deliver, honest accounting and billing, giving back where we could — and I think we were true to them. But I wasn’t mature enough as an entrepreneur to reflect on whether our long-term initiatives were the best representation of our values, or whether the day’s list of tasks were really the most effective way to realize our strategies.

The second half of Max’s talk is about having no idea what you’re doing. I’m still working on that one.


Maciej Cegłowski, Pinboard

Maciej talks about what he’s learned from reading Thoreau. It’s lovely.

“Perseverance: there’s a pernicious idea in startups that you should fail quickly. I’ve always been a proponent of failing really, really slowly. Success doesn’t come labeled any way unless you’re in it for the money, in which case you can just count your way to success.

“You only get a couple of chances in your life to work on something for a really long time. Don’t abandon those projects lightly. There’s no substitute for working on something for a long time, even if it doesn’t bring you success in a way that you recognize.”


Jack Conte, Pomplamoose/Patreon

“I have this urgent need to express my undying gratitude to you for watching what I’m making. You’re the reason that I’m making stuff. But to an advertiser, you’re one-one-thousandth of a CPM and your attention is worth half a penny.”

Jack’s presentation tells the origin story of his band and its surprising commercial success… and then keeps going. Many of the talks at XOXO followed this pattern — not exactly “Behind the Music” exposés, but honest accounts of the challenges that come after the first “hit songs.”


The independent artists at XOXO are painfully honest about the role of money in their lives. In the technology world, netting a lump of money is usually the goal (typically euphemized as an “exit”). This provides simple narrative arc: you have the origin story in the usually mythical garage, followed by the rising action of growth or VC interest, the climax of the acquisition/shrimp fountain/champagne luge launch party, and the epilogue where the founders ride off into the sunset in their Teslas.

For artists or companies with different goals, the narrative arc is less clear. The goal is not to reach a specific point or metric, but to be successful, more or less forever, or at least until it stops being fun.

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Cabel Sasser, Panic

“The one thing that has been bumming me out lately is seeing these original, creative people make amazing things, go to market, and then immediately get swallowed up by big companies… They were this inspiring, cool voice, and now they are instantly gone, never to be heard from again.”

Cabel’s talk, about his crisis of faith as the president of an independent software company, closed XOXO. Since the event I’ve been considering his message as a personal challenge to me — who did “sell out” — to not disappear. It’s hard to do.

Being acquired by an established company can be the Innovator’s Dilemma at a human scale: I’m responsible for my part of the corporate org chart as much as I was brought on to enable new products and generate new ideas. How should I balance my fiscal and managerial responsibilities with my implicit goals to be innovative? How do I foster the technology culture I believe in while retaining the pride of individual teams? How can I stay motivated to do creative work outside of my job, creative work inside of my job, and have time left over for a rewarding personal life? I’m lucky to have such challenges, but they are real challenges, and I’m grateful to XOXO for the reminder to retain that balance.

But do watch Cabel’s talk for yourself, and see if it speaks to you as well.


Tags: beards, conferences, founders, portlandia, startups, talks, xoxo,


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