5 tips for building a thriving community from scratch

Those pics up there? That was me when I was a kid. I was the third of four children born to immigrant parents who still don’t speak much English. We were just trying to make ends meet, and life was pretty simple – food, school, and of course piano.

American ways were quite foreign to us. I still have to make my fingers into a “b” and a “d” to figure out where my bread plate and drinking glass go, and I was told Westerners weren’t trustworthy since they often said things they didn’t mean, like “Let’s have lunch” and not follow through. Or “How are you,” but not wait for an answer.

In 8th grade I was 4’6” with a home perm, heavy bangs, and thick glasses. We didn’t have much money, so I had three outfits; I wore each for two days in a row before rotating. There are kids who don’t mind these “limitations,” but I wasn’t one of them. I desperately wanted to fit in, but this was tough: even beyond my awkwardness, I was pretty unremarkable. I’m one of the few people I know who had virtually no activities in high school (I do know every episode of Gilligan’s Island, though). Plus, as with many families back then, parents didn’t talk about “adult things” to kids. All this means I didn’t really begin to interact comfortably with adults until I was about 30. 

Fast forward to today: I’m on my fourth startup, all of which have incredibly strong communities with networking that’s core to their success – ChIPs (5,000 members and 19 chapters around the world), RPX ($0 to $100M and IPO in less than three years), SaaStr (world’s largest b2b software community), and Operator Collective. How does someone so socially awkward build such thriving communities? In many ways not being a cool kid growing up was the perfect training ground for constructing communities and building startups. Here are five tips.

1) Find your niche

Communities and products succeed because they have a focus. People need a personal connection, which might mean choosing an area that’s ignored or overlooked. ChIPs started out hyperfocused on women in patent law (there weren’t many of us). Only after nailing that niche did we expand to women in law, tech, and policy. The venture world typically revolves around VCs and founders – so at Operator Collective, we put operators front and center.

Think about my awkward former self who just wanted to fit in. What if I’d had a community of Gilligan’s Island Aficionados Who Love Velour? I would’ve fit right in and had a core group to identify with. Find an initial niche or addressable market and expand from there.

2) Start with the bellwethers

The first thing everyone wants to know is who’s involved. Having not naturally been a people magnet, I learned to involve the people others do want to hang out with, and build from there.

If you’re hosting a conference, the obvious way is to begin with the speakers. Find an anchor and build around her. How do you get that first speaker? Try starting with a “two-fer” – find two speakers with a connection or friendship. If someone can combine a speaking engagement with seeing people they don’t often get to spend time with, they’re more likely to say yes. At Operator Summit, we invited fantastic speakers, but paired them each with a friend – like Eric Yuan with Jennifer Tejada, and Claire Hughes Johnson with Leyla Seka. This also applies when building a customer base: Garner a few respected companies/leaders as early adopters.

3) Be deliberate from the first engagement

You always have to make people feel comfortable – including those who don’t often join in. Last September, we put together Operator Summit in just 4 weeks. We knew we wanted a high percentage of women and people from underrepresented backgrounds, so we were public with that intention and deliberately reached out to people in those categories. It wasn’t a women’s conference or one for people of color, but we ended up with 80% women and 50% people of color.

This was another place being socially awkward helped. What would it take to get me to come to an event that’s full of people I didn’t know? A personal invitation, first of all – not a bulk mailing. Plus we asked those who were coming for names of contacts who might be interested, and then specifically mentioned the referring friend in that invitation. By the time you get to a SaaStr Annual size of 20,000 attendees, personal invitations aren’t always possible, but you can still do it selectively. The same goes for selling a product. Each interaction should feel personalized, so every prospect gets the sense that you are connecting with them as an individual and understand their needs.

4) Make it easy to participate

When you’re selling a product, you make it easy to buy. When you’re putting together a community, you make it easy to join. Start with scheduling. We have a lot of women with young kids in our Operator Collective community, so we try to schedule meetings and events at family-friendly times. Operator Summit, for example, started at 10 and ended at 4:30. When we have update calls, we try to schedule them for when we know people have finished dropping off kids at school, over lunch, or during a commute time. If we’re scheduling a group, we’ll often send a poll to ensure a critical mass.

The other key is to give people a role. It can be scary to walk into a new meeting or conference, so introverts like me prefer to have a task. At SaaStr Annual, “braindates” are wildly popular. At Operator Summit, we encourage people to sign up for our small group Office Hours.

5) Obsess over every detail

No matter what you’re building, you can never assume people will buy, join, or participate. You have to make it worthwhile, which means obsessing over every detail. What’s the mix of people, who will they meet, and what will make them come back? What kind of content will you provide and where will everyone find value? What’s the reg process, what about dietary restrictions, and what kind of swag? Obsess over every detail, from how they buy to how the product is delivered to the entire user experience.

Get Building

From the day we enter the working world and actually well before the need to network is hammered into us. We have to put ourselves out there and expand our connections in order to advance our careers. But communities can be a haven for the socially awkward: a place for people to find their niche and feel comfortable. And if this kid can grow up to be a super connector who builds successful network-dependent companies, I’m here to tell you that anyone can.

P.S. If you want to see my awkwardness in action, join me on March 11 at SaaStr Annual, where Leyla Seka, Lexi Reese, Elisa Steele, and I will do battle in an unscripted debate to determine the #1 secret to building high-performance orgs. I’m terrified already.