organizing a speakerconf

About 5 years ago I expressed an idea to Josh Graham.

Let's take the parts of traditional conferences that the presenters like the most, and make that an entire conference. Specifically, we should have plenty of discussion time with drinks available & we should have group dinners every night.

I'd expressed this idea to a few different people, and never done anything with it. Luckily, by the time I'd woken up the following morning, Josh had already set up the speakerconf website. Organizing speakerconf has been an interesting and enlightening journey. The past few blog posts have been about what speakerconf is, what presenters are responsible for, & logistics - this post is about how we got started and the organization and participation lessons I learned.

The Beginning
Once Josh created the website I knew it was time to see if we could actually make the event happen. I started by emailing my network to see who liked the idea and would attend. I always knew that 15 was the minimum number of presenters that I would want for a speakerconf, so I sent the emails and waited to see if we had enough interest or not - luckily we did. I also knew I wanted to have a group dinner every night, and the only way to convince 15 people to attend the same restaurant was to pay the bill - so I set out to find sponsors. The management at DRW is incredibly supportive and they quickly offered to sponsor. I also had a great relationship with Forward and they immediately offered to sponsor as well. With both of those sponsors committed, we had the minimum amount of money required to pay for the conference room and cover the cost of the group dinners. At that point there was no looking back, and we began building the hype via Twitter.

Quality, not Quantity
I believed that getting a commitment from a few high-profile speakers would cause plenty of other speakers to jump on board, but the speakerconf idea didn't really generate much buzz the first year (from my point of view). Once the idea became a reality, things changed drastically. The first event was a huge success. We had over 30 people sign up for speakerconf 2010 (in those days, if anyone you knew was going you could go as well). The second event was also a success, but we all agreed that 30+ was too many people. Following 2010, speakerconf became an invite only event and was limited to 25 people.

We were happy with 25 people at each speakerconf, but we ended up learning that less is an even better situation. speakerconf Aruba 2012 had 12 people cancel, which left us in a terrible place. Replacing a speakerconf presenter is extremely hard. The net result was that only 18 people attended, and it worked out perfectly. The collaboration, quality, and enjoyment all seemed to go up significantly. I believe it became a case of addition by subtraction, due to the interactions becoming much richer. After the success of Aruba 2012 Josh and I decided that future speakerconfs will have between 18-20 presenters.

Another Point of View
At speakerconf, your participation in discussion is just as important as your presentation. At the first few speakerconfs I had unreal expectations about people spending every waking minute participating. It was the center of attention for Josh and I, but for the presenters it was just a great event that they needed to responsibly balance with their other commitments. After the first 2 speakerconfs I learned that we needed to set aside time for everyone to take care of work and personal business. At this point, Josh and I allocate 2 hours before dinner each night where presenters can take care of non-speakerconf related issues.

You do not talk about speakerconf
As programmers, we like to optimize. Sadly, I've wasted countless hours and other people's time at speakerconf by discussing how to tweak speakerconf. My intentions were good, I wanted to improve the event. Unfortunately, there's two issues with this: We could be talking about technology instead, and it brings attention to any issues I'm noticing. I believe the old advice that the party takes on the mood of the host - and I don't want to bring speakerconf presenters into my perfectionist world that constantly focuses on otherwise unseen flaws. Plus, if I'm hanging out with some of the best from our industry, it's much more beneficial to hear about what they're working on these days.

I'm not going to lie, it's not easy to stop myself for asking for feedback while the event is running, but I do believe it's the right choice. I'm more than happy to discuss tweaks if someone else brings it up, and I definitely solicit feedback once the event is over; however, speakerconf time is for discussing technology, and the conference benefits when I remember that simple suggestion.

The Best, Last
The last 2 lessons are unquestionably the most important: be flexible and get a co-founder. Brian Goetz mentioned to me many times - get smart people together and let them figure out how to have a good time. Whenever people suggest we tweak something, Josh and I do our best to accomodate and see where it takes us. Above all else, we remove distractions and get out of the way, so presentations or ideas can reach their full potential. Occasionally that means letting a presentation run long, switching the presentation order, taking a quick break, or moving to open discussion ahead of schedule. The schedule always suffers, but the experience always benefits. At this point, Josh and I have learned to roll with whatever comes our way, as long as it enhances speakerconf.

speakerconf requires Josh. I hear it's true that start-ups need a co-founder, and I couldn't have done speakerconf without Josh. I tell him I'm quitting at least once a year. Josh seemed like he might quit last year. However, we carry each other when we need to, and I'm very proud of what we put out each year.