This year we’re changing things up a bit, the Startup Festival will be featuring an Office Hours tent where big names in the startup community will be available to have their brains picked—by you. One of these said big names is Edd Dumbill, the program chair for the O’Reilly Strata and Open Source Convention (OSCON) conferences. A notorious “dabbler,” he’s also known for creating the Expectnation conference management system, DOAP, and co-founding the Pharmaliscensing online intellectual property exchange. Sounds like a pretty knowledgeable guy, right? Stop by the office hours tent and you’ll have the opportunity to chat with Edd about whatever your heart desires!

StartupFest: What one thing did you realize was a completely wrong assumption during your career?

ED: The first and most stressful error I made was assuming that everybody thought like I think. As an entrepreneur you’re a self-starter, but your team won’t all work that way. Sharing vision and giving direction is important. What’s more, your customers don’t think like you either. And you need to rediscover this lesson time after time!

StartupFest: What advice do you have for entrepreneurs about selling early versus make big bets?

ED: Whatever you do, have no regrets. If you are well informed and have a reason for your choice then that’s good enough.

StartupFest: What one piece of technology could you not live without, which wasn’t here 10 years ago?

ED: Somewhat soberingly, I had everything I needed 10 years ago. However, I think Gmail is probably the biggest technological advance in my armory since then.

StartupFest: What do you think we’ll take for granted in 10 years that isn’t here today? What will look stupid and out of date?

ED: I’m really really hoping that somebody will have figured out scheduling by 10 years time. The way we schedule appointments right now looks stupid and out of date today, but there’s no alternative. The reality of life is that you spend a lot of time coordinating.

StartupFest: How do you think startups should handle the trade-off between doing good, making money, and building an open marketplace?

ED: Entrepreneurs should take time to become intentional people. By which I mean, regularly take a step back from what you’re doing and understand why. You want your choices to be intentional and deliberate. Then you can decide for yourself where to put that trade-off. The only real misstep is not to think about it, and be swept along by somebody else’s ideas or values.