How being socially awkward helps me build thriving communities

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. 

The outsiders are coming in: The origin of Operator Collective

For most of my life, I’ve felt like an outsider. Whether it was being raised by immigrant parents who didn’t understand Western social norms, or my years as an awkward kid picked last for everything, or being one of the few women Chief Intellectual Property Counsels in the niche-y field of patent law, I’ve always been most comfortable working quietly in the background.

When you’re an outsider, you spend a lot of time observing. I’m often told I think outside the box, to which I silently respond it’s because I’m not enough of an insider to even know what the confines of the box are. And when you’re an outsider, you sometimes don’t even realize you have skills that would be useful to others.

Here’s an example. In 2008 I helped launch a venture-backed company we took from $0 to $100M and IPO in three years but I was such an outsider to venture that I didn’t realize this was unusual. There were the inevitable and valuable lessons learned during that period, and we ultimately grew the company to $300M.

After we sold the company ten years later, I started to spend more time with founders and VCs, mostly as part of the SaaStr community, which I’d been involved in from the early days (I’m married to the founder). And of course, I spent a lot of time where I’m most comfortable quietly observing. Here’s what I saw:  

  • The venture world revolves around VCs and founders. 
  • Roughly 90% of VCs and founders are white males, higher when you look at enterprise.
  • VCs and founders tend to hang out with other VCs and founders, and their networks don’t overlap much with operators, much less with women operators. 
  • Most b2b startups eventually want to sell their products to enterprise.
  • The majority of VCs and founders have either never worked in enterprise, or haven’t done so in decades.  

As I began to dip my toe in angel investing, I noticed something else: I was often the only woman on the cap table, and homogeneous groups were showing up again and again. I was bothered enough to ask a few founders if they’d noticed. These founders, to their credit, were horrified, and then even more distressed when they realized they hadn’t recognized it prior to my asking the question. They explained that they’d simply gone to their buddies for backing they didn’t know any women who might invest and could I please help.

The Buddy Syndrome strikes again
The fact is, they weren’t wrong. When you’re in the early days of starting a company, you turn to people you know the ones who trust you and are willing to take a chance. And people from your network tend to be people like you. (I call this the buddy syndrome.)

And beyond this, it’s a fact that fewer women invest. Women hold 71% of their assets in cash. They make up just 9% of venture decision makers and 22% of angel investors. And if you focus only on my area enterprise the numbers drop even more.

At the same time, I began asking my women friends: “Why don’t you angel invest?” Never been asked. Never had the opportunity. Didn’t occur to me that it was a possibility. No time to vet and not sure I know how to vet anyway.

Why aren’t more women investing?
I heard this over and over and from some of the most accomplished operators in the world, many of whom happened to be women… leaders who’d built the most successful tech companies in the world. In fact, many of today’s most respected operators are women.

Earlier this year one of our LPs, Reshma Saujani, Founder & CEO of Girls Who Code, released her book Brave, Not Perfect; this is based on the idea that from a young age, boys are praised when they take risks, while girls are expected to be perfect and steer clear of taking chances. Saujani’s experience is in the world of coding, but the translation to enterprise is clear: Women today are conditioned to be perfect at work, at home, and frankly in everything we do. As a result, we give 150% to our day jobs and 150% to our family and friends. We’re not looking to meet VCs and founders in the little time we have left over. Sprinkle in the gender pay equity gap and “gap table,” and the result is that most women don’t have the liquidity, much less the desire, to invest in people they don’t know and in startups they don’t have the time to vet. Yet they’re the very people with the backgrounds the venture world could use. So these women these ultra talented operators were also outsiders with no obvious path to get in.

On the flip side, there’s venture. Now the value of diversity has been well established, yet venture remains homogeneous not because no one wants the change, but because there hasn’t been a natural way for it to happen (birds of a feather, and all that). So what we wanted to do was help both sides of the equation: Give talented operators from diverse backgrounds a safe, comfortable way to join venture + make it easy for founders and VCs to bring in new experience and perspectives.

The origin of Operator Collective
The idea took hold quickly. Operators were thrilled at the idea (just look at the absurd amount of talent we’ve assembled), and they quickly referred their fellow operators. Even universities and foundations signed on as LPs, a rarity for a first-time fund. And of course as we operators have been trained to do, we built this fund to have immediate product-market fit to address that gaping lack of operational expertise in venture.

So here we go. The sidelines are bursting, and the outsiders are coming in.

Say hello to Operator Collective.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

Infographic: The absurd amount of talent in Operator Collective

It’s no secret venture capital is an exclusive and homogeneous group that’s hard for outsiders to crack. Yet VCs and founders don’t build companies — operators do. So why don’t they have a bigger voice to decide which founders get funded and how they’ll be supported?

That’s why we created Operator Collective, a new venture capital fund with a community of ultra-talented operators built right into its DNA. Operator Collective is making venture accessible to exactly the people the ecosystem needs now: leaders from diverse backgrounds with deep experience from building some of today’s most successful companies.

Our limited partners include 100+ respected operators who bring decades of experience growing and running the world’s most admired companies — from Zoom, Stripe, and PagerDuty to Salesforce, Slack, and beyond. They have more than 1500 years of collective operator experience; more than 60 of our LPs have built unicorns, more than 35 have taken their companies public, and more than 80 have steered their companies through acquisitions. The amount of revenue they own and people they lead is staggering.

Learn more in the graphic below. What an incredible team to have on your side.

Operator Collective Infographic

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.