What Makes a Community?

I normally write articles that carry a bit of authority. I usually write what I know about and have a high degree of confidence writing. I don’t write often because I want what I do write to carry authority and be hard-hitting.

This is not really one of those articles.

I haven’t done what people like Alex Hillman has done in creating collaborative working environments for independent entrepreneurs at Independent’s Hall in Philadelphia.

I haven’t been an organizer and champion of city-wide entrepreneurship like Josh Baer has in Austin.

I haven’t fostered a product community like they have over at StudioPress with the Genesis Framework.

What I have done is work within the context of a thriving WordPress community of developers, users, consultants and advocates.

I have lived in a city that has made it’s name on entrepreneurship and arts in Austin.

I have helped and supported entrepreneurs in their quest to build products in DC and find ways of succeeding both with and without investment money.

Moving Back to Baltimore

For some weeks now, I’ve made it clear that I’ve decided to move back from Austin to Baltimore. In 2008, I left Baltimore because I saw awesome things developing in technology in DC. At the time, there were guys like Peter Corbett who was just beginning to do technology advocacy work in the Nation’s Capital. By 2009, iStrategyLabs would launch the first Apps for Democracy contest that challenged contestants to create web and mobile applications with civic intent. That would morph into similar contest like Apps for America, etc.

You would also see some organizations that would flare out dramatically because of business model, ideas, weak leadership, lack of community involvement, etc.

I would then move to Austin where I would see a city immersed in technology. Lots of money flowing. Lots of incubator action, such as the products and entrepreneurs who would be graduated from the Capital Factory incubator. I would see ATX Startup Crawl occur several times a year as guests would have the opportunity to move around town and visit some of the great startups like TabbedOut, InfoChimps, uShip and more. Thousands of people would come through these offices and see the great technologies and ideas being built, all while enjoying local Texas beers and eats.

I would see awesome projects like We Are Austin Tech highlight influencers in that community (including myself) come up.

And I watched Baltimore grow as a technology community to the point where DC entrepreneurs started paying attention to their up and coming little brother 45 mins up I-95. I watched from afar as Dave Troy would put his heart and soul into building Baltimore as a center of entrepreneurship and tech. I’d watch as Greg Cangialosi would build his Blue Sky Factory marketing firm out and have a successful acquisition, all while continuing to personally invest more in the Baltimore scene.

I even watched great tragedies like the systematic destruction of Advertising.com by Aol.

I watched this all over the last 4 years and realized Baltimore was coming into it’s own. It had successes. It had failures. It had investors. It had bootstrap. It’s still not entirely cohesive, but from my seat, it looks promising.

So I’ve decided to move back to my home and put my money where my mouth is and see if I can take what I’ve gleaned from DC and Austin and apply it here in Baltimore. I may be one of those failures. Or I may not be, but I’ve got to try.

What Makes a Successful Community?

In the last few weeks, I’ve had several conversations with Baltimore business owners and entrepreneurs, and I’m finding a common question and point of discussion: What makes a successful community? The answers and opinions are intriguing. Again, I can’t say my opinion carries any authority. What I can say, however, is I’ve been in a bunch of communities and witnessed elements of success.

Some folks think a successful business community requires investors who are willing to commit their time and money. Anyone who has gone through the fundraising process knows that hands on investors are the best kind. If a VC or Angel investor can help a portfolio company supplement resources (human capital or otherwise) through their network, they bring quite a bit of upside to a startup. Investors who wire money and never pay attention to their portfolio companies, expecting the founders to execute according to plan, are in my opinion bad investors.

So in this light, some entrepreneurs here in Baltimore find the lack of investment money or engaged investors as detrimental to the community.

On the flip side of the coin, some entrepreneurs seem to be thinking that the mark of a good startup community is going to be in the number of entrepreneurs who are able to successfully bootstrap. There is some validity to this claim as well. The more you can do on your own, the less of your company you’re giving away (as I noted in the “Valleyboys” segment of this article a few weeks ago).

However, there is also value in bootstrapping and taking money, if the situation is right.

Other folks I’ve talked to feels the value is in the number of people attend professional meetups compounded by the sheer number of meetups. In Austin, we have a vibrant meetup community. From the Austin WordPress meetup to Austin on Rails to Austin Lean Startup to Refresh Austin and the list goes on.

My opinion is that a city startup community is built on all these things. It’s not money, really. Money will follow success. Perhaps Baltimore needs to have an IPO or high profile acquisition that allows the company to continue to operate and hire in Baltimore to put them on the map and in the conversation. I don’t really think it’s that, per se, but that certainly helps.

It would help if the State of Maryland was more business-friendly to small businesses, as Texas is. People come to Texas, and more specifically Austin, from California and New York because the environment is notably friendly to small business. More business would be created in Maryland with better business policy. It might even attract out of state growth.

Beyond that though, meetups are important but meetups don’t create value if the conversations end at the meetup. The idea of building something – a prototype – as you might get out of a Startup Weekend is good… if it continues afterwards from prototype to business product.

But I think the biggest thing that makes community grow is collaboration and the willing to share ideas without being defensive, sharing resources without being possessive, sharing physical space without being prohibitive. It takes more that an entrepreneurs flying solo behind his Macbook Pro in a coffee shop, but it takes less than structured office space with prohibitive managerial org charts.

It doesn’t take sacrificing lifestyle on the altar of work, but it does take entrepreneurs willing to gut out ideas by working with other entrepreneurs and customers and transparently sharing war stories of success and failure while helping to mentor others new to the space.

It does takes the karmaic “pay it forward” approach without fiefdoms and regional rivalries to ensure that a rising tide raises all ships. What you put in to other companies you have no direct stake in, but can help with informal advice (when solicited) makes for a circle of life that encourages a community to exceed expectations and move from one level to the next. Mentorship is not an ROI term, but it is critical to the ecosystem.

Am I off-base in my thinking here?

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WordCamp Mid-Atlantic: Where It’s Been, Where It’s Going

Late in 2008, while I was transitioning from life in Baltimore to life outside of Washington, D.C., I was contemplating organizing the first WordCamp event in that area. Baltimore had begun to show signs of a healthy tech community and Washington had continued to flourish as a healthy communications scene. Philadelphia, just up I-95, had a healthy design and development community and I had become somewhat familiar with that city as well.

I made a point of making my event one that would set trends and challenge the status quo.

Mid-Atlantic

One thing I did think of early on was that I detested the trend that identified an event with a singular city, especially when there were multiple cities, all offering different, yet complementary modus operandi. I bucked the trend of identifying the event by a city, eschewing names like WordCamp DC or WordCamp Baltimore. These names, while celebratory of the city that hosts them, inherently bear the problem of inferred exclusivity.

From the very first WordCamp in the region, I challenged that designation and attempted to bring the cities together. It was called WordCamp Mid-Atlantic.

Three Cities, then Two

The original plan was to bring the three cities together in Baltimore for a WordPress event. Ideally, the result would be more collaboration and resources shared between the various communities. Ultimately, Philadelphia never bought into Mid-Atlantic (and in fact, ended up with their own successful WordCamp Philly). However, Mid-Atlantic was wildly supported by both Baltimore and DC. even garnering coverage in the Baltimore Sun business publication Maryland Daily Record.

For WordCamp Mid-Atlantic 2010, the event was geared mainly to the Washington Metro and Baltimore.

Keynotes That Challenge

In both events, I wanted to bring in someone from the WordPress leadership hierarchy as a Keynote as well as someone from outside of WordPress entirely to challenge the gathered attendees. This as quite controversial, actually. In 2009, I brought in Anil Dash, founder and former SVP at SixApart. Anil was known historically as somewhat of an antagonist, but did a wonderful job in sharing and illustrating the similarities between WordPress and SixApart who provided a competing platform. His message was one of learning from each other.

This past year, I opted to bring in Marco Tabini who has also been a frequent antagonist of WordPress. His message was one from the perspective of the PHP community and reconciling how the PHP core people could learn and help the WordPress core people, and vica versa. My inbox became a little tense in the weeks leading up to the event due to other incidents involving dissenting views about the GPL license and WordPress’ interpretation of it. Needless to say, Marco did an amazing job.

It’s Not My Baby

As most of you know, I have left the Baltimore/Washington region. As a result, this past WordCamp Mid-Atlantic was my last. People have asked me quite a lot about who I would pass the baton to. This is a tricky question because the event is not mine. It’s yours.

That said, this is not for just anyone to run. I cannot put any strings on who will run the next event but I do have the platform to voice my sentiments:

  • I want to see Mid-Atlantic stay in the event. I do not want to see a fractured event where there becomes a WordCamp Baltimore and a WordCamp DC. Both cities have user groups that meet frequently. I want to see the WordCamp Mid-Atlantic event retain it’s place as a regional/local event.
  • I want to see the idea of challenging (and even dissenting) opinions welcomed to the stage, like Marco… and Anil. We should not be scared of being shaken up. We should embrace it and learn from it. That said, future organizers should be sensitive as to who you have come and speak.
  • Retain the unconference. One of the amazing success stories of WordCamp Mid-Atlantic 2010 was the unconference, organized by Steve Fisher. Besides the pre-scheduled and organized tracks that are familiar to conference goers, we provided a separate, yet equal unconference for ad-hoc discussion and talks. The only thing I’d change is to make it true barcamp style and make a no-powerpoint rule.
  • No one organizer. I became the defacto organizer for both events. While I had varying degrees of help for both, I really became the guy for the event. This was not wise on my part. There should be an organizer in each city.

This is Baltimore’s event. This is Washington’s event. This event brilliantly integrated both communities. It really, really did. I want to see it continue (obviously with new leadership), but I want it to be with people who take it seriously and can make it better than it ever was. Put your own spin on it. Make it your own, not mine.

SixApart Engaging WordPress, and Other Thoughts on WordCamp Mid-Atlantic

It was a brilliant day on Saturday at University of Baltimore where Jimmy Gardner and I kicked off the inaugural WordCamp Mid-Atlantic. I have been to half a dozen or more WordCamps since the first one in San Francisco in July of 2006. Without being at all conceited, because it had nothing really to do with me, this was the best one yet.
Continue reading SixApart Engaging WordPress, and Other Thoughts on WordCamp Mid-Atlantic