Convincing 20 industry leaders to set aside 4-5 weekdays to come to a conference is not an easy thing, especially when said conference is also very hard to describe to the person (or people) who are approving the time off, travel, & expenses. With this in mind, Josh and I designed speakerconf to appeal to programmers who work very hard, and are often on the road.
Weekdays. I strongly hold the opinion that conferences should not be on weekends [more info]. Most of the people who attend speakerconf work very hard on an average week, and I don't want take a weekend away from them, their friends, or their family. I'm a very firm believer in work / life balance, and I don't want to be part of tipping the scales even farther in the 'work' direction. Additionally, it makes sense as a conference organizer. I want people showing up to speakerconf rested, refreshed, and ready for several days of intense collaboration. It's not enough to give a great presentation at speakerconf, you need to be on your game for 10-12 hours a day and you need to be able to do it for 3-5 straight days.
My opinion is not universally held - some people can't or don't want to be away from the office for that many days. While I see their point of view and note the benefits of switching to starting on Sunday, I simply don't believe that the trade-offs are a net win for speakerconf. Therefore, the best thing that Josh and I can do is ensure that speakerconf is such a "don't miss" event that people believe it is unquestionably worth being out of the office for a week.
Select an easily accessible location. Easily accessible has always been a requirement of mine for speakerconf. Like I mentioned, speakerconf presenters are often on the road - the last thing I want to do is require an additional connection or an extended drive. Aruba is a direct flight from many cities in the US, and the speakerconf hotel is a 15 minute drive from the airport. Aruba was great for the first few speakerconf events; however, when Josh and I created speakerconf we never anticipated that we would draw so much interest from people in Europe as well. Sticking with our ideals about easy accessibility, speakerconf now rotates between a location that is a direct flight from most US airport hubs and a location that is a direct flight from most EU airports.
Select an isolated location. Running a speakerconf in Rome really drove this point home - last February I asked if 2013 should be in Austin, SF, NYC, or Aruba. The majority preferred Aruba, and, more importantly, those that preferred Aruba were also the ones who were most excited about returning in 2013. Many presenters pointed out that if we were in an actual city they would be more likely to be distracted. The final dinner in Aruba proved their point. In Rome in 2011, 1/3 of the presenters went out to dinner* on the final night. Conversely, in Aruba 17/18 presenters went to dinner and all 17 continued their discussions at the hotel bar for many hours following dinner. The isolated location provided fewer distractions, and seemed to facilitate much deeper interactions.
Select a location with a concentration of restaurants. speakerconf takes a very different approach to dining. Josh and I aim to not only host an amazingly educational event, but to also provide the best dining experience of any conference. We don't provide conference center food for breakfast or lunch, instead we select hotels that are near great local restaurants that serve reasonably priced breakfast and lunch options. Dinners are done at some of the highest rated local restaurants - and we require the ability to select from several different options.
Dine well. Josh and I love food & wine, and our preferences definitely show in our dinner selections. The conference sponsored dinners at speakerconf are generally at restaurants that I prefer to take my wife to when we visit those cities on vacation. The dinner wine selections are usually done based on what Josh has loved drinking in the past. As an example, the conference dinners in Munich are at Boettners & Vue Maximilian, the number 1 & number 3 rated restaurants in Munich according to zagat.com. I could go on and on about the type meals that we aim to provide at speakerconf, but sometimes a picture truly is worth a thousand words - here are the 1,000 that describe a dinner at speakerconf.
Group dinners are better if you split to tables of 3-5. Many people loved being part of a large, group dinner table, but the conversations did suffer a bit. In 2011 we began making dinner reservations for "a party of 20, but we would like 5 tables of 4", and the conversations became longer, deeper, and more productive. As a side benefit, the restaurant staff seems to find this easier to manage as well - which means less issues with 19 people having their food, and awkwardly waiting for the 1 meal that didn't come out right.
On the surface it may look like speakerconf is a week off work, in a vacation location, dining like a king; however, if you look closely, each of those choices is based on a practical choice. The scheduling is a net win for everyone involved. The location facilitates distraction free, deep collaboration. The dining enhances the event by allowing the attendees to focus on collaboration while Josh and I worry about location selection, providing food that meets all dietary restrictions, and ensuring that the cost of dinner doesn't deter attendance. The result (or sum) is also greater than the parts - we provide an easily accessible, deeply educational, & enjoyable experience, which encourages some of the best of the industry leaders to attend, who's attendance encourages more of the industries leaders to attend.
* The final dinner is neither required, nor sponsored - thus it's completely fine for people to opt-out.