Q1: What’s it like running a conference?

Running a conference is a lot of work but it’s totally worth it. It takes months to plan and organize an event that’s just 2 days long. Luckily, I have a great team that is able to pull this all together.

Q2: Is there anything about running a conference that surprised you?

No matter how many hours of planning or backup plans you put in place, something will always happen at the event that you can’t control. You just have to roll with the punches and move on. Luckily, I was able to learn this lesson while planning WordCamps Minneapolis 2013 and 2014.

Q3: How does your Prestige conference differentiate itself from others in the WordPress space?

One way we’re different is Prestige is 100% focused on running your business. The advice I give to speakers when we are working on session topics is, “Give a 5 year younger version of yourself some business advice.” We are all strong in some areas and weak in others. Prestige is here to give you a few more tools to use in the growth of your business. We also produce the best-designed swag around!

Q4: What do you look for in a city when planning a conference?

When choosing a city, we look at many different elements. We like cities that have an amazing tech community and also have plenty to do within walking distance of the venue/hotels. It costs a lot to travel to conferences – we want to make sure that our attendees can also have fun during their down time. A few of us on the planning team are baseball junkies. If we can catch a game leading into the event, we love that city even more!

Q5: How should conferences work, in contrast to how they do now?

There’s a trend with conferences just collecting speakers. There’s no rhyme or reason to the selection and you might even have two of the same or similar talks back to back, at the same event. Events should be planned by taking time to get to know what your speakers are passionate about and then helping to create a schedule that is “in sync.” This all promotes content that is well rounded and bound to connect, in some facet, with everyone in attendance.

Q6: If your best friend was going to start a conference, what basic advice would you give them?

Don’t do it! Haha! With all joking aside make sure you have the proper support to make it a success the first time. Remember that you have three different perspectives to consider to make your event a success. Create a great experience for the speakers, sponsors, and attendees; then you’ll have a successful event.

I did a podcast with, my favorite publisher of business content in the WordPress ecosystem, Matt Medeiros on this very topic. It was right after our first event but the information is still true today.

Q7: In your opinion, what will conferences look like in 2030?

Sadly, we’re moving towards more virtual conferences. While it’s great to be able to share info with people across the globe, you miss out on the in person networking that happens at live events. I’ve had countless people thank me for the knowledge they’ve gained from the first three Prestige Conferences. Almost every one of them has mentioned the open sharing of information between “should be competitors.” Take advantage of being able to talk to these brilliant business minds in a casual environment!

Q8: What did you think about the first WordCamp US in Philadelphia?

WordCamp US was incredible! I’m not surprised the planning team did such an amazing job – Philadelphia has always been one of my favorite camps. I honestly think they should just leave it in Philadelphia every year. The convention center has a lot of room for us to grow into it. Let’s move it to a warmer time of year and leave it in Philly!

Q9: How long have you been working with WordPress and what peaked your curiosity about it?

I started using WordPress in 2008 because a band I was in needed a website and I wanted to find a way to manage content better than I had been doing with static sites, up until that point. The rest is history… Now I barely play music but I use WordPress every day.

Q10: If you were in charge of the self-hosted WordPress software, what changes would you make?

We’ve gone off the rails. I thought we were talking about conferences… I’ll keep it to conferences then for my answer. I’d change that WordCamps are run through a non-profit foundation. I would like to see it run as a “for-profit” business. I think that change would have a domino effect helping us overcome many hurdles currently in place. Just one example… Sponsor benefits are virtually non existent when donating to support WordCamps under the current structure. We should be able to promote the companies that help us to put on the amazing conferences around WordPress. I could go on and on but this probably would deserve its own set of 10 questions.

Also, I’d tell everyone to go to PrestigeConf.com tomorrow Wednesday Feb 17th at 9am Pacific time for our super early bird tickets. There are only 25 available and they’ll go fast!

Brian Jackson

Brian has a huge passion for WordPress, has been using it for over a decade, and even develops a couple of premium plugins. Brian enjoys blogging, movies, and hiking. Connect with Brian on Twitter.