Jumpstarting a Design Community from Scratch

The internet has fostered digital communities for everyone, not least of whom are the very people who continue to build it. Designers and technologists from around the world gather in places like Hacker News and Designer News, Twitter and Reddit. No matter how isolated we are geographically from the major tech cities, we can still participate in the larger conversation.

We’ve created tools that enable us to live and work together at a distance in ways that were previously impossible. But, as important as digital communities are, there’s nothing quite like meeting with people face-to-face. Anyone who lives in San Francisco or New York can attest to the incredible energy that comes from being around other designers and engineers. Online, the level of intimacy — and serendipity — just isn’t the same as it is in-person.

I’ve been thinking a lot about community lately. I’m privileged to live in a part of the world which, though it isn’t a major tech hub, still has a robust community of designers, engineers, and entrepreneurs. (You may already know this. I’ve written about it previously ad nauseum.) The Hudson Valley Tech Meetup has almost 900 members; its meetups draw big names (the last event was keynoted by Dennis Crowley, founder of Foursquare); it’s given rise to a spinoff meetup aimed primarily at software engineers; and it’s already held a conference that drew attendees from around the world.

Dennis Crowley speaking at the Hudson Valley Tech Meetup

Dennis Crowley, founder of Foursquare, speaking at the Hudson Valley Tech Meetup

This wasn’t always the case. Just a few years ago, the Hudson Valley’s main connection to the broader tech world was the steadily-shrinking IBM headquarters. There was no local tech community, and any software or design industry was basically invisible. For me personally, returning to the region after college and trying to find some semblance of design culture, the outlook was bleak.

So what changed? How does a region’s design and tech industry go from being completely unorganized and isolated to unified and well-connected in less than two years? And how can people elsewhere replicate its success?

The Beginnings of a Community

To answer these questions, I went right to the source: Kale Kaposhilin, one of the founders and organizers of the Hudson Valley Tech Meetup. Kale is a magnetic personality; his enthusiasm for building communities is palpable and contagious. I suspect every community has someone in his mold — someone who can make magical things happen, just by introducing the right people to each other. He says:

We started Hudson Valley Tech Meetup in April of 2014 because it was obviously needed and didn’t exist already. We needed it so that we could connect with the other developers, technologists and startup founders and work with them. At the time we knew only a handful of people in web development in the Hudson Valley even though we’d been in the profession for a decade. [My business partner at Evolving Media Network] Dan Stone and I called up Daniel and Sabrina Schutzsmith [the founders of Digital Empire, another local digital firm] and said “we need to have a tech meetup in the Hudson Valley!” They said, “We were just saying the same thing!” There wasn’t any hesitation.

One of the quirks of running a tech meetup in the Hudson Valley is that the territory is divided by a river. It was decided early on that the meetup would split its time between the two sides, alternating venues between Kingston and Poughkeepsie, two of the larger cities in the region and its effective capitols. This would keep things central and accessible to everyone.

(Incidentally, if the name “Poughkeepsie” sounds familiar to you, it might be because of this Friends episode.)

Naming the group wasn’t as straightforward a process as you might expect. Kale and the other three organizers kicked around several names, but ultimately settled on one that mirrored the name of the New York Tech Meetup, the 49,000-member tech organization just a few hours downriver.

They were our heroes down the road. They were the city mice that could get 800 people to show up ever month and turn tech into a spectator sport. I wanted Hudson Valley Tech Meetup to be the country mouse to their city mouse so I fought for that more accessible (though possibly not as cute [as some of the other ideas we’d had]) name.

Kale is adamant that people are the most important aspect in building a community. He keeps coming back to the people who provided support early on, from those who acted as sounding boards to those who were early speakers and attendees. He goes on to talk about how anyone organizing a new community needs a group of reliable co-organizers to lean on:

If you want to start a tech meetup and a community you will need to start and grow a core team. We couldn’t have sustained the Hudson Valley Tech Meetup for this long without a team. It’s too much for just one or two people on their own. Creating the right team and adding to that team as time goes on is a key to sustainability IMHO. If everyone on the team can handle a small/medium size slice of the action then you increase your chances of avoiding burnout. Definitely avoid burnout. It’s pretty easy to burnout even with something as fun as throwing a tech event. If you load yourself up too much the pressure can be a problem. Don’t let that happen. Get help from others around you by listening to them and letting them develop any good ideas that they have which will help the community.

Create structure and responsibility but avoid hierarchy. Make decisions through consensus. Nobody runs this show. This show is for everybody.

Structuring the Meetup

Different design/tech meetups have different structures, based on the needs and interests of the particular group. The New York Tech Meetup, for instance, is built around numerous short startup demos, followed by a community mixer.

The Hudson Valley Tech Meetup typically opens with an hour of socializing, followed by two or three 20-minute talks. In between the talks are a chance for people to make announcements, and a time where people are encouraged to meet someone new. As Kale says: “We force them to co-mingle.” Often, the evening ends with a troop of HVTM members heading to a local restaurant or bar.

Your meetup, should you choose to start one, could mirror either of these formats, or do something else entirely. There’s no playbook offering a step-by-step guide for jumpstarting a new community, though Brad Feld’s Startup Communities comes awfully close.

Hudson Valley Tech Meetup

The January kickoff of the Hudson Valley Tech Meetup, with over 200 people in attendance.

The Challenges and Rewards

Building a community from scratch isn’t easy; as with many things, it seems like 20% of the people do 80% of the work. Those who are motivated to develop a community are the same people who are probably overcommitted elsewhere.

The most challenging part of Hudson Valley Tech Meetup has just been taking the time to work on the project away from our businesses. Our core team is also running small businesses that employ a few or as many as twelve full-time employees. That’s serious business and one generally must devote oneself to that business full time.

Kale doesn’t dwell on the challenges, though, and reframes them in terms of the rewards:

We love it though and some of us who shall remain nameless are obsessed with throwing events and event production. When there is something that you simply must do to feel complete, you do it. Making ends meet in the process has been the only downside. The rest has been an open door to new adventures with wonderful people in our now-far-reaching Hudson Valley tech community.

Embracing the Region’s Character

Every region is unique — what works in one place won’t necessarily fit the character or composition of another. I asked Kale about how the Hudson Valley’s particular zeitgeist has informed the meetup’s development:

The Hudson Valley is a wonderful place to live, work and play. We moved over to Kingston [a small city along the Hudson River, and one of the capitols of the region] in the late 90’s as it would clearly offer us the walkable live/work integration of friends and business that we wanted. Kingston was ready to rise and eager to be embraced and shaped by new energetic residents. We had energy and wanted to build community together with our values aligned friends and creative colleagues.

I think that you can find similar pockets of people all over the region and most of them are using technology to improve their communities. Speaking to the larger Hudson Valley, I think that residents are here primarily for the quality of life that exists at the intersection of family, arts and community. If we wanted to be in the most aggressive career scenarios we could roll down to the city and just do that. Many of us have done that in the past and retreated up here or just never wanted to get that aggressive to begin with.

If you work in tech and live in the Hudson Valley, I think you’ve probably made a conscious or subconscious choice to pursue a slightly more relaxed lifestyle where priorities are weighted towards community, open spaces and nearby local food. This character is expressed in our tech community.

The single most regular startup conversation that I’ve had in the past year has been about community platforms of various sorts. Another common conversation has been around the technology needed to bring locally grown foods direct to people with less fuel. We’ve also been involved in a lot of social entrepreneurship software discussions, urban renewal conversations, and generally the idea of technology innovation that will help people is more exciting than technology that will go IPO.

Moving Forward

From everything Kale has said, it sounds like starting a new design/tech organization is both deeply challenging and richly rewarding. As a long-time member of the HVTM (well, as long-time as one can be in a two-year-old organization), I can attest to its efficacy in building relationships and strengthening community. The Hudson Valley Tech Meetup is made in the image of the region, but the region itself is being remade — local government and community leaders have started getting involved, as have educators and investors, and nobody leaves unchanged. The tech community is leaving its imprint on the broader region.

To me, it seems like one of the most gratifying parts of organizing something like this would be having a front-row seat to the transformation that takes place when space is made for serendipitous encounters and the cross-polination of ideas. Kale seems to feel similarly. He says:

Bringing the tech and design community together in any area can be fun and rewarding if connecting with other people is enjoyable to you. I’m an extrovert for the most part so connecting, empathizing and learning from others is how I experience the splendor of the universe. If you want to convene the tech community on a regular basis you should probably have at least one person on your team who is like me in this respect. I go looking for how other people can engage with and be fulfilled by Hudson Valley Tech Meetup. A LOT of people are excited by it and want to help and if their ideas are good and they have follow through they should be encouraged to help.

Not too long ago, Kale recommended that I read a book called Startup Communities, by the venture capitalist Brad Feld. The book talks about how to develop an entrepreneurial ecosystem in a city, and is framed around Feld’s experience nurturing the tech community in Boulder, Colorado. Reading it was validating — so much of our experience in the Hudson Valley had mirrored his experience in Boulder. While there isn’t a playbook for doing this sort of work, resources like this are helpful for spreading knowledge and sharing ideas.

Perhaps you live in a place without a strong (or any) design/tech community. Perhaps you think you’re the only one practicing your craft. You may be right. Or, perhaps there are lots of people nearby who are thinking the exact same thing, and are just waiting for someone to take the initiative and start something new. If this idea gets you fired up — if you love the idea of community-building and want to see something like this in your region — then you’re already qualified to do so.

Go get started.

Thanks to Kale Kaposhilin for sharing his experience and insights. This interview has been abridged and slightly restructured for length and clarity.

Thanks to the organizers of the Hudson Valley Tech Meetup for doing what they do — Kale Kaposhilin, Dan Stone, Daniel Schutzmith, and Sabrina Schutzmith.

Photos were taken by Daniel Schutzmith at the January 2016 HVTM meetup.

Understand Your Compensation

Designer Monoculture

The State of Design Leadership

The Science of Product Design

Interview with Michael Flarup: Co-Founder and Lead Designer at Robocat

The Importance of Design Conventions

Interview with Aaron Quint: CTO-turned-Cookbook Author