For people who work on the web, we are blessed with a flexibility that has rarely been available to men and women throughout the ages. We can work from anywhere. Live anywhere. And work with and talk to people from anywhere. This flexibility also allows us to meet in person those people that inspire us in our work.

For me, my situation is slightly less flexible than many. I have a good sized family and live far from the larger cities where most events take place. And so my first web focused conference has been a long time coming. I was very excited to get down to Portland for XOXO last week, along with my amazing wife.

Here are some of the things that caught my attention.

Washington and Oregon are amazing

We flew from in to Vancouver, but decided to drive to Portland. It was reminiscent of our honeymoon, our first and last holiday without children until last weekend. A long drive with no one asking for crackers or cheese from the back seat was fantastic!

And if you're from the US and have never taken the time to check out the northwest, you're missing out. Thursday was clear and sunny, around 80° F. The foliage was just starting to turn and the views were as good as it gets. I especially enjoyed the Olympia area.

Portland is great, Portland is weird

If you like food, coffee, or beer, you'll like what Portland has to offer. I did not have a bad meal there … not even close. We went to high end restaurants, little dives with 3 tables, and food carts and every meal was top notch.

Portland is also the city of dietary restrictions. My wife doesn't eat eggs or gluten, which means she doesn't eat out much. On this trip, no one blinks an eye. It's also a beautiful city in many ways, albeit nowhere near as nice as Vancouver.

Portland is also different. We watched a guy polish off three bloody Mary's over breakfast at 8 AM on Saturday morning. Looking around we noticed we were the only ones not consuming alcohol. This is not normal where we com from, but you can be sure the people of Portlandia are relaxed!

Last, be careful which doors you use around there. I experienced this when I discovered the restaurant we were eating at shared a washroom with a very small strip club. Thankfully, the nice lady on the stage directed me to the correct door once I recovered from my surprise.

Conference talks

There was a pretty good lineup for the Saturday and Sunday sessions. There were a small handful of speakers I wanted to hear, plus a bunch of others I was not familiar with. In the end, I ended up missing most of the ones I had planned to see. But for good reason; the talks I did catch were so very good that I took time out to contemplate what I had heard.

I found that I could only sit through 3 or 4 talks in a day. There was so much to take in, I felt that if I didn't walk away, none of it would stick. I don't know how some of you can listen to 6 or 8 people in a day and retain anything at all. I'll be waiting for the conference videos to be available to pick up the gold I've already forgotten.

A few highlights:
  • Val Hart: wow, what a lively gal. A funny presenter who can roll with the punches. Her presentation froze at one point and she just asked for Andy Baio to bring her his guitar. My roommate ended up being a human capo for the lack of the real thing
  • Jack Cheng: one of the speakers I was most excited about, he’s as thoughtful a presenter as he is a writer
  • Molly Crabapple: a great writer (see her recent piece on Guantanamo Bay), Molly read her speech on stage, almost a performance in itself
  • Ev Williams: a few interesting things to say, but not the most dynamic speaker
  • Jay Smooth: the highlight of the conference started on Sunday afternoon with Jay Smooth, one of three most polished, sincere, and authentic people on the stage. Through telling some of the history of hip hop, Jay encouraged the audience to make the most of the connections we make. One of his main themes struck a chord with me (paraphrased), “Challenge people while being respectful of the connection you share.”
  • Christina Xu: another dynamic stage presence, she was focused on encouraging us to build platforms or systems that reduce friction for creatives. Amen
  • Mike Rugnetta: … I'm not sure what to say. Mike was very intelligent, but he seemed to fit 45 minutes of content into his 20 minutes on stage. Another watch of this talk will be required for more reflection, but his focus on community is worth it

Seeing people speak in a venue was a great reminder that even though many of us have good thoughts, and can communicate those in writing, it doesn't mean we're all great speakers. This is an obvious thought, but I found it refreshing. And humbling. Everyone here was real.

The speakers who I found the most dynamic were those who have active video blogs. Practice makes perfect in live action!

And although I missed hearing Marco and Cabel speak, I'm glad for it in a sense. As I've followed them for years online, I've heard their thoughts plenty of times. It was great to hear some new voices and be challenged by what I heard.


XOXO is more than just a conference. There were a lot of other interesting activities, including live music, a film night, and table top sessions for playing games (some times with the game creators).

I'm not much of a gamer, but I enjoyed seeing creators and fans playing, watching, and listening in the same place. Jonathan Coulton and Anamanaguchi put on a good show on Friday night. Holocene is a small venue, which made for an intimate show!

The people

Without ever being to a web focused conference of the past, I've read enough about them to know I'm more interested in the newer types of events. Like Brooklyn Beta and Greenville Grok, I believe XOXO is more about the times in between events than the events themselves.

That was the case for me. It was a pleasure to finally meet in person some folks I have followed online for a while. People like Josh Bryant, Kai Brach, Aaron Draplin, Sean Sperte, Matthew Buchanan, and Mike Myers. As a bonus, I was able to meet new people I had no familiarity with: Chelsea Otakan, our housemate and aforementioned human capo being a great example.

There were also many other talented folks I would have liked to have met up with, but I never recognized their faces. Avatars are limiting!

Ros & Nathan

The highlight of this trip for me was getting to know these two people a little better. A lot better. Ros is a co-worker and we chat each week. And we've even hung out together in Fiji. But for this quiet introvert, nothing beats good conversation over good food with a small number of people.

Erica and I had the chance to spend a lot of time with Ros and Nathan over the weekend. Sharing meals, [Powell's books], and the Portland fair were made all the better while talking with these two. A weekend with two thoughtful, intelligent, and talented Australians makes for a very good time. Thanks for the memories, you two!

Next up for me is Userconf in San Francisco next month, where I'll finally get to meet Garret St John and Noah Stokes in person. I'd love to see other folks as well: if you're available, let me know.