For the past five years, I’ve been organizing a regular event here in Boston called the Web Innovators Group (aka “WebInno”). Every couple months, 700-1000 web & mobile entrepreneurs, techies, startup junkies, and investors gather for one big meetup of the community. It’s been personally fulfilling to start something which begun as a small informal gathering grow into a real component of the local startup scene (and now drawing people from New York and Washington DC). I had no intentions of becoming a large event organizer (nor do I now have aspirations to become one more than I have). However, as a venture capitalist I believe that it’s incumbent on me not just to be a member of the entrepreneurial community but also truly participate in and contribute to it. Having started WebInno with no previous “events” experience, I’ve fumbled my way through putting them together at times. But along the way I learned a few general lessons which can be applied more broadly to organizing events, so I thought that I’d share them:

1. 1. FREE is the right price. Not that people aren’t willing to pay. I am sure that a subset of attendees would. But a cash outlay, of any price, raises the bar to committing to an event in advance. It just adds an incremental amount of friction in the decision as to whether or not to attend. We have great sponsors* which affords us the opportunity to accommodate the crowd with a reasonable space, but when the event was smaller with a modest (read: no) budget we found venues which held us for free. People just showed up when they heard about it and of course they could leave just as easily. But it turns out they stayed… and came back for the next event. If you polled people if they would like (a) free drink(s) or food included with an event, of course they’d say yes. But I don’t think that’s a necessary ingredient. People want other people, and if they want a drink they can buy one. I’d attribute much of the success of WebInno to the fact that it was free when few other events around town were.

1. 1. Listen by loudly asking for feedback… It sounds cheesy but it’s true. Some people will tell you their opinion anyway, but it may not be a representative cross-section of the attendees and likely not the best sample from the people you’d ideally like to attend. But if you specifically and repeatedly ASK the entire crowd, they’ll share their voice, as everybody liked to be heard. I’ve tweaked the event in many many ways (from adding a separate room for demo tables to alphabetic check-in folders) based on direct input from attendees.

1. 1. … but stay true to your vision. With many opinions, you’re bound to hear conflicting inputs. When soliciting feedback, I think it’s imperative that you take each suggestion and run it by a gut-check of your own vision of what you want the event to become.

1. 1. Content isn’t your main draw – the people are – but it’s a helpful anchor. People attend events because they want to meet and see other people. Period. But I think adding content gives them something to talk about, something to hang a hat on for an initial conversation with a new acquaintance or an old friend. Programming content, in the case of WebInno the demos and sometimes speaker/panels, transform it from a mere gathering into an event.

1. 1. The web is your friend. Organizing and promoting an event without all the helpful web applications would have been so much more difficult ten years ago. I’ve used Eventbrite for the registration logistics and can’t sing enough of its praises. The www.webinnovatorsgroup.com website is built on WordPress with automatic updates maintained by Feedblitz. I use Constant Contact for the mass emailings. And of course social media has helped spread the word, from the nearly two thousand Twitter followers (@webinno) to all of the blog posts attendees write as follow up.

1. 1. The details matter. How bright the lights are. Where the podium is. How the chairs are arranged. Pauses during the program. Expectations about who’s attending. These are little things that affect how the event runs and how it’s perceived afterwards, and there are a lot of them. It’s imperative that you keep on top of them. All of them.

1. Be nimble. An event changes over time, both in the size and the composition of the crowd, but also in the context of the environment. When I started WebInno it was a dozen people gathering in a bar with nametags, now it’s certainly a production. Along the way I’ve tweaked the format quite a bit, sometimes for the better and sometimes with less positive results. I’ve found that people forgive authentic mistakes but not contrived errors. When I’ve been open and honest about experimenting with new features and they don’t go well, I surely hear about it, but for the most part attendees understand and return.
2. Ask for more feedback. I write it twice (and at it to a list of seven) because this one is the most important. Events spark magic when the right people go. I often hear stories about people meeting a cofounder of their company at WebInno, finding a customer, or connecting with a new employer. All of those stories make the work in organizing the event worth it. And so to that end, if you’ve attended the Web Innovators Group recently or in even the (way) past, and you have a suggestion, idea, or comment: I am open to hearing them. Feel free to comment on this blog post, message me @davidbeisel on twitter, or send me an email at [david at web innovators group dot com].

Wrapping up, I wanted to put a quick plug for the next WebInno event which is going to be held on March 1st: http://webinno25.eventbrite.com/. It’s open to everyone in the entrepreneurial web and mobile community here in Boston and outside it.

* Thanks to the 2010 platinum co-sponsors, Microsoft and Venrock, as well as newly added gold sponsor, Silicon Valley Bank.