How to Kickstart Communities – A Work-in-Progress

how to build a community, friends

I want to preface; I don’t have all the cards laid out in front of me. In many ways, I am still trying to figure this out for myself. But I count myself lucky to be able to learn from some of the best in building communities. That said, the below are my views alone and are not representative of anyone or any organization.

A good friend recently asked me, “I’m about to start a community. Do you have any tips for how to start one with a bang?”

She’s not alone. Communities have been a hot topic for the past few years. A product of the crypto and NFT craze, and the isolation people felt when the world was forced to go virtual in 2020. At the same time, starting a community and maintaining/managing a community are different. Just like starting a company and growing a company are two different job descriptions. As such, this essay was written with the intention of addressing the former, rather than the latter.

Common traits of great communities

A great community has value and values.

Value is the excuse to bring people together. Value answers the question: why should I join? And within the first week, they should also have the answer to: why should I stay? Two fundamentally different questions. Many communities frontload the value – provide great value at the beginning – facilitating intros, onboarding workshops and socials. Subsequently, answers the first question, but take the second for granted. A community is the gift that keeps on giving. Over time, as you want to be able to scale your time and as the community grows, you need others to help you provide the reason for Why should I stay. Invariably, it comes down to people. You have to pick uncompromisingly great people from the start. And they have to derive so much value from being a part of the community, that demands converts to supply.

  1. They refer others.
  2. They give back to the community – in the form of advice, hosting events, and more.

Value should also be niche – just like the beachhead market for any startup. You want people to self-select themselves out of it, and the only people who stick around are the ones who derive the most benefits from being in it. Take, for example, a community of founders isn’t niche. And there a dime a dozen of the above. A community of pre-seed female founders focused on getting to product-market fit, is.

Values, on the other hand, are the rules of engagement. Codify them early. Take no implicit agreement for granted. Better yet, make them explicit. Back in January 2020, I wrote about rules in the context of building startup culture. I find the same to be true when building communities. “Weak follow-through is another fallacy in creating the culture you want. What you let slide will define the new culture, with or without your approval.”

I don’t mean for you to be a hard-ass on everything. But figure out early on how much slack you’re willing to give, and how much you aren’t. I’ve written about this before. Every person will suck. Every organization will suck. And unsurprisingly, every community will suck. What differentiates a great community from a good community is that the great ones get to choose what they’re willing to suck at.

You should be exclusive

Moreover, my hot take is that you have to be exclusive. Or let me clarify… in the wealth of Slack groups and Discord servers, yet in the world where everyone still has a job (or two), friends, family, and other communities they’re already a part of that all already slice up their 24-hour day pie in so many different ways, you are competing for their attention. If you’re a community, you’re competing against Instagram, Twitter, TikTok, Friday happy hours, Saturday nights out with the girls, date night with their partner, eight hours of sleep, their workout routine, and so much more. And so, you have to be inclusive of those who have been excluded. As such, you have to exclude those who have historically been included.

I’m not saying that you should start a community for the underestimated just ’cause. It’s like starting a business because you want the title of CEO. Don’t do it. It’s not worth your time. It’s not worth your energy. But you have to be honest with yourself, are you adding more value in the world? Is there anyone else who would sacrifice their other commitments to belong in your community? And do you have the discipline and the drive to maintain this community in the long term? The worst thing you can do is create a new home for someone then take it away.

Building and rebuilding habits

When starting a community, you are asking individuals to build a new habit. One of your greatest competitors is the incumbent solution of existing habits and routine. Some research cites that it takes 21 days to break a habit. And about two months to build a new one. All in all, 90 days all things considered.

Elliot Berkman, Director of University of Oregon’s Social and Affective Neuroscience Laboratory, surmises that there are three factors to breaking a habit.

  1. The availability of an alternative habit
  2. Strength of motivation to change
  3. Mental and physical ability to break the habit

To break down the above:

The availability of an alternative habit

How available is the replacement behavior? Are there other communities out there that do the exact same thing? How well known are they? What are their barriers to entry?

If there is a readily available alternative community, the first question you need to answer is: why bother making another? Realistically, any one person only has enough time and attention to be in 2-3 communities – total. The second question you need to answer is: how do people normally learn of that community? And subsequently, is there a market or audience who doesn’t have access to this distribution channel? If so, what channels occupy most of their attention? Target those.

Strength of motivation to change

There’s a saying in the world of marketing that goes something along the lines of: People don’t buy products. They buy better versions of themselves. Therefore, as a community, you need to nail the value you provide. Is it aspirational? Does it get people to jump out of their seats and scream yes?

A simple litmus test is if you were to share the reason you created the community, do they respond with “How do I sign up for this now?” or “Let me think about it.”? If the latter, you haven’t nailed your value proposition. In other words, what you’re selling isn’t aspirational. Or if it is, you’re either talking to the wrong demographic or the value proposition is a 10% improvement in people’s lives, not a 10x. Sarah Tavel‘s “10x better and cheaper” framework (albeit for startups) is a great mental model for nailing your value prop. Your community must be:

  1. So much better than the incumbent solution or habit they regress to, and
  2. Easy to jump on (i.e. switching costs must be low enough for it be a no-brainer) – Sometimes this means you need to manually onboard every individual into your community. And sometimes all one needs is an accountability partner. Everyone wants be THE number that matters, not just A number. Make people feel special.

Mental and physical ability to break the habit

This is admittedly the factor that is most outside of your immediate control. Here, I regress to the below nerdy formula I made up in the process of writing this blogpost:

(how much work you need to put into each member) ∝ 1/(# of members)

The amount of work you need to put into inspiring each member to join is indirectly proportional to the number of members you can accommodate in your community. In other words, the less you need to convince people to join your community, the more members you can accommodate. The more time you need to inspire enough activation energy for a person to build a new habit, the smaller the initial cohort of members you can tailor to.

This is why I love the concept of the idea maze so much. Has your target community members put in blood, sweat, and tears trying to find the value that you are providing? Why does this matter?

  1. They’ve designed their life already around finding answers around your value prop. They’re going to be more engaged than the average individual. They’re intrinsically motivated to be curious.
  2. Shared empathy. They know how tough finding an answer is, such that they’re more willing to help others going through similar problems.

The shared struggles that people collectively and synchronously go through together build camaraderie and trust. No matter how small or big. The bonds of a sports team are built upon the sweats and tears of brutal training regimens, losses and wins. The trust of a Navy Seals class is built through Hell Week, pain, exhaustion, adversity, and (the likelihood of) death. And, the friendships between college freshmen are built through the unfamiliar environment of a new and daunting chapter of their life.

In closing

Starting a community is hard. 99% of communities (don’t quote me on this number, but I know I’m close to the mark) disappear into obsolescence after their founders lose their motivation. Oftentimes even prior. Not only are you cultivating a new habit yourself, but you are doing so for everyone else you want in your community. I hope the above was able to illuminate your thinking as much as it did for me. I continue to learn and iterate, and as such, will likely publish more content on this topic in the future. For now, this essay will be my thoughts encased in amber.

Photo by Simon Maage on Unsplash


A big thank you to everyone who’s influenced and will continue to influence my thoughts on community, including but not limited to Sam, Andrew, Mishti, Jerel, Shuo, and most recently, Enzo.


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.