How to Break the Internet: How Greg Isenberg Became “The Community Guy” and Amassed a 350K Following

Even before MrBeast announced his plan to roll up his businesses (Beast Burger, Feastables, etc.) into a public company, one person could already see the potential for upstart creators to threaten incumbent CPG brands.

That person is Greg Isenberg, founder of startup design studio Late Checkout and a student of culture and online community building.

Entrepreneurs like Nick Huber have discussed how becoming an influencer supercharged their business: allowing them to source talent from the crowd, get meetings with investors, and unlock new income streams. So in this recurring series, called #HowtoBreaktheInternet, I’ll seek to deconstruct how entrepreneurs like Greg rose to internet fame and how they monetized it.

Read on to see detailed data and analysis on the tweets that drove all that growth, and what we can learn about how to replicate it for ourselves.

From Tech Founder to Business Operator to Influencer

 Greg’s keen eye for product design and community-building was sharpened by his experiences founding and leading startups. In 2010 he was CMO at product design shop StressLimitDesign, then VP of product at Stock-Trak / WallStreetSurvivor.

From 2012 to 2015, he founded the social video app 5by, which was acquired by StumbleUpon in 2013. Then in 2016, he founded Islands, a social messaging app, that was later acquired by WeWork. He became the Head of Product Strategy at WeWork, consulted with TikTok, and eventually launched Late Checkout, “a product design agency, studio and fund that designs, creates and acquires community-based products”. I had followed Greg’s work passively, but really became interested in him when he started co-hosting the podcast Where It Happens.

One key insight: podcasts alone are really difficult to scale (there still aren’t easy ways to discover new podcasts). However what Greg did is achieve scale by building an audience on Twitter, getting to scale, and then pivoting into podcasts to deepen his relationship and bring a subset of that audience much closer.

Understanding His Content Brilliance: A Twitter Deep Dive

Greg joined Twitter in 2008, writing about topics ranging from advertising to creating landing pages, but his posts got little traction. In 2019, he started experimenting with Twitter threads. His most-engaged post that year was one on social media app predictions. This post played to his strengths: he was the CEO of social media app Islands at that time and had previously founded 5by and worked at StumbleUpon.

But it wasn’t until 2020 that his tweets started gaining more traction. A great example of such a tweet is his commentary on Fiverr’s US$5 billion valuation that year, where he encouraged ‘niche’ startups to keep grinding.

His growth began to accelerate in 2021, when he started creating ‘tweetstorms’ on marketing and business trends. This tweetstorm propelled his follower count from 30,788 in January 2021 to 80,665 by February: 

This tweet —his most-liked and most-retweeted of all time— had a deceptively simple premise: interviewing 5 billionaires. He explains some of the fundamental lessons he learned from them, including sacrificing friendships, understanding that ideas are always bound to get rejected, and that doubting oneself is natural.

A few observations:

• The packaging “5 billionaires in a week” evokes a feeling that we’re getting to peek behind a curtain.

• The thread mixes lofty ideas with grounded, relatable ones such as not needing an alarm clock.

• Despite it being a thread, each individual tweet is quite short—as though each one could have been a standalone bit of fortune cookie wisdom.

• The thread made me feel better about myself. I felt that I already have a lot in common with billionaires. This is really powerful: packaging content so the reader sharing it might play into their own sense of self-worth.

• One final observation: Greg’s been consistently posting after this tweet, and his audience has grown 15X since this tweet, but no other tweet has earned as many likes or helped him grow his following as dramatically. This surprised me: I would have expected that with so many more followers today, his tweets were today would consistently do better than those from 2 years ago. Put another way, it seems like Greg with 30K followers from 2021 and Greg with 450K followers in 2023 have roughly the same chance of going viral.

Greg’s second most-liked tweet showed the results of sleep quality based on changing certain factors of a couple’s daily activities.

A few observations:

• Interestingly, this was not original content: it was from a Reddit post that had appeared on the subreddit r/dataisbeautiful a few months earlier. Greg’s talked at length about unbundling Reddit or studying Reddit to understand what the community wants/needs. I suspect he noticed how well this Reddit post did, and then looked for a way to craft his own spin on it.

• The tweet was posted in November 2022—just in time for his subsequent podcast interview with Matteo Franceschetti, CEO of Eight Sleep, a tech company that creates smart mattresses. 

• This tweetstorm included an affiliate link to Beam Dream Powder. So already in this small way, Greg was finding a way to monetize building his audience. It also made me wonder if the EightSleep podcast appearance had in some way been sponsored.

His third most-liked tweet is an interesting thread of criticism against Instagram, which he claims has shifted away from being a social media platform to becoming an advertising landscape that favors marketers instead of users. This, he says, is why many alternative social media platforms such as BeReal and Mastodon are trending. 

A few observations:

• This tweet once again plays to Greg’s core theme of being “the community guy” and leverages his strength: he’s one of the few people who have actually founded multiple social apps.

• There are so few shared moments in our culture anymore. We don’t all watch the same shows in primetime, we don’t all watch the Superbowl or the Oscars. But Instagram’s Feed changes are something nearly a billion people would experience together at the same time—and it’s something that wasn’t getting talked about enough. This, I’m sure, is a big factor driving this thread’s breakout success.

• Notice that he doesn’t “go negative” entirely: halfway through the thread he pivots to offering constructive suggestions and even tags the Head of Instagram Adam Mosseri by name. My takeaway: When engaging with business/professional content, your audience is more likely to amplify positive messages.

• Six hours after Greg’s thread, Adam Mosseri wrote his own thread confronting these same critiques. Greg quoted Mosseri and added it to his own thread, giving it more credibility.

Months later, Adam Mosseri eventually admitted that Instagram had focused too much on certain aspects, most especially its ‘Reels’ feature. In addition to being a TikTok competitor, Instagram has also positioned itself as an e-commerce platform and an NFT marketplace—a far cry from its original purpose of sharing photos and videos with your network.

Greg had another hit tweet in October 2022 when he launched The Pencil Case Project, which he describes as a free-to-mint NFT project that aims to ‘inspire creativity’. While it seemed like a change in direction for his content, it’s also an exercise in community building: he leveraged his status as a thought leader to stir interest in his project, and used the allure of exclusivity and early access to get people to generate sign-ups.

The last tweet we’ll look at is reminiscent of his most viral post—the one where he interviewed five billionaires in the same week. Both share the same premise: a list of digestible life lessons derived from real success stories.

In this thought-provoking thread, Greg gets introspective as he recalls the ups and downs he’s had as a business founder and leader. He shares what he has learned from his past business experiences, the traits aspiring leaders should have, the business lessons he had realized over the years—and a link to his Substack in case you want more. By giving his followers a peek at what his blog is about, he reassures them of the value he can provide and makes it more enticing to sign up.

From Tweets to Media: What Greg’s Content Is About

 Greg’s tweets encapsulate how tweets should be: informative yet with personality. He is clearly an expert of the “tweetstorm” format, which allows users to get richer insights from a social media platform that, at times, can be as chaotic as a public forum.

He’s also a pro at reeling in people to consume more of his content. Take for instance this tweet that explains the gamification strategy used by language-learning app Duolingo to reel in new users and retain them in the longer run. Instead of using a tweetstorm to elaborate, Greg invites the reader to subscribe to his Late Checkout newsletter, which focuses on business and product design. The tweet also utilizes a Twitter content strategy where the main tweet reels in users to check what’s next, which is often succeeded by a CTA or an irresistible offer—in this case, a free subscription to his newsletter.

Looking at his tweets and his podcast Where It Happens, the direction Greg is going for is clear: understanding the importance of community-based ventures and businesses. Much like how his Twitter insights are such a treat to his online followers, his podcast interviews with business leaders also consider the community an integral part of the discussion.

 Mixing Leadership Experience and Community Engagement

 If we were to sum up Greg Isenberg’s social media influence, we could say that he has mastered the combination of using his past leadership stints and network engagement to create content that matters not only to fellow business leaders but also to other users who might be seeing his insights for the first time.

 Despite his extensive business background, he knows how to look beyond the traditional tropes and recognizes the importance of disruptors in the scene. Greg understands the communal foundation of a variety of topics, from understanding the potential of creator-led businesses and doing email marketing in the new era to building hype for niche businesses, and more importantly, he translates these topics organically for the customer’s interest.

This is why Greg’s tweets punch through, and why they serve as a great example of how business leaders can ride the Twitter wave and stay relevant.