Sourcing Crazy-Hot Digital Campfires on Reddit
5 ways to tap into and grow a community-first business using existing momentum
Greg Isenberg is an entrepreneur who has built and advised an impressive number of community-first businesses. The last two companies he founded, Islands (a chat app for college kids) and 5by (a video discovery app) were acquired by WeWork and StumbleUpon, respectively.
These days, he is co-founder of Late Checkout, a product studio that designs, creates and acquires internet communities (it was behind the recent viral phenomenon youprobablyneedahaircut.com) and also advises powerhouse platforms like TikTok on community growth strategies.
Greg—a mastermind at sniffing out robust passion communities and building thriving businesses around them—dropped so many digital campfire knowledge bombs during our recent conversation that it was hard to choose just five. Here are the ones that most stood out.
1. Do whatever it takes to be “at one” with your community
At the end of 2015, Greg founded messaging app Islands, based on the then-prescient concept that group chat was the new social network and would verticalize in the same way that social networking had.
Hoping to gain traction on college campuses, his team built the Islands software before realizing that in order to foster a thriving community on the app, he first needed to learn more about the community the app would be serving—and to do that he would have to leave Silicon Valley to embed himself in the community he wanted to serve.
Back then, the accepted wisdom for launching a social start-up was to bring fraternities and sororities onboard first, the way Tinder and Bumble had. But having gone to university in Canada before dropping out to build start-ups, all he knew about the U.S. college experience was what he’d seen in movies like Van Wilder and Old School.
Research told him the southern U.S. had the highest percentage of fraternities and sororities, and Tuscaloosa, Alabama was its mecca. So at 28, he re-located to Tuscaloosa, lived off-campus for a year and went from school to school across the southern U.S. asking pointed questions, taking copious notes, and studying the problem like an academic. His goal? To understand which communities mattered, the life cycles of their members, and elicit feedback on their product. That immersion process sparked more than a few epiphanies, the first of which was that if you want to build a community, you have to be at one with it.
2. The communities who need you most may be hiding in plain sight
During the embedding process, Greg pitched every fraternity and sorority on Islands, but his product didn’t resonate with those groups.
In retrospect, the reason why was obvious: they already had a built-in social network. It’s why people joined them.
Realizing his team had been too easily swayed by Silicon Valley’s marketing wisdom, he and his team went back to their mission statement—Connect The Disconnected—and changed course. The moment they threw out the accepted wisdom and started thinking about “how to give people homes who didn’t have them and which communities wanted their product the most, the numbers just took off.”
Following that logic, Greg realized that if you were gay and lived in a major city, you could easily find your people, but if you were gay and lived in Tuscaloosa, “to this day” it’s hard to find your community. So he and his team began creating group chats for LGBTQ communities. “They basically welcomed us with open arms and thanked us for giving them a home,” he says.
3. Listen to what your community is really saying
Most of the time your community isn’t going to tell you exactly what they want because often they don’t know what they want, says Greg, so you have to figure that out. So after asking people a zillion questions, distill answers to unearth subtext. During the embedding process, Greg asked product-related questions such as, “What do you like about what I’m doing? What don’t you like? But he also asked, How’s life? How happy are you? What could be better in your life? “Ultimately, when you’re building a community, you’re building something that satisfies a set of emotions, so you have to try to understand those emotions, and determine whether people are feeling lonely or sad or anxious. For instance, right now a lot of college students are anxious about going back to school. The question to ask yourself is, ‘Is there a community to be built around that?’”
4. There’s some element of science to “going viral”
In April, during the early days of the Covid-19 quarantine, when everybody’s hair was getting longer and shaggier, Greg’s team at Late Checkout took a deep dive into Reddit’s stylist and barber community. Two themes jumped out at them: a lot of people couldn’t afford their rent because they were out of work, and a lot were cutting their own hair and doing a lousy job. The team knew that a substantial majority of Americans were living paycheck to paycheck. They also knew the media was always looking for interesting stories, especially during quarantine. Their Reddit dive told them a marketplace of buyers and sellers existed, the buyers had a huge problem and the sellers would do their best to make a great impression virtually. So the team said, Let’s build something. And that’s how youprobablyneedahaircut.com was born. “We built something in a matter of two days using no code stuff, published it and it went viral.” (They messaged fifteen or twenty journalists, many via cold-emails, and practically all wanted to cover the story. The site was featured everywhere from the TODAY Show to ABC News and far beyond. “They responded to the strength of the idea,” says Greg, and the name, which is “super, super important” if you want word of mouth.) “Millions of people saw the app and thousands used it. We wouldn’t have come across those insights if we weren’t combing Reddit, no pun intended.”
5. We’re in the midst of a major moment for digital campfires sparked by the “unbundling of Reddit”
Greg believes we’re seeing this shift towards groups and communities today because people are seeking refuge from the larger platforms. “It turns out if you give everyone a microphone, the party gets pretty loud,” which is why communities like Reddit are in the midst of a large-scale “unbundling.”
While he thinks Reddit has done a good job of creating a cookie-cutter way for communities to come together, he believes a demand exists for more “bespoke” experiences. So how do you make a Reddit group bespoke? “By spending one hour a day for seven days in a Reddit sub-group getting to know their language, jokes and needs, “and then thinking about how to create a tool to super charge that community and design with them.”
To that end, every Thursday Greg’s product team picks a Reddit vertical that one member is passionate about, and discusses how they could unbundle it.
“If you look at building a community through that lens, it’s quite interesting because it allows you to cut the noise in a lot of ways,” says Greg. One caveat: if you do this, don’t simply create another cookie-cutter solution. “You need to listen, design for them and with them. You need to … create your community along with them.”
Want to hear more from Greg Isenberg? Check out our full hour-long conversation on The Digital Campfire Download here.
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Each month I’ll be putting a different BIPOC-run digital campfire in the spotlight and inviting you to donate, with the understanding that I will never ask you to donate if I have not already done so myself. This month, I’m spotlighting The Nap Minstry, an organization founded by Tricia Hersey that examines rest as a form of resistance and reparations as well as a radical tool for community healing through performance art, site-specific installations, and community organizing. If you’re in a position to donate, and would like to, please join me in directly supporting The Nap Ministry’s mission here or here.