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.
How to Break the Internet: A Data 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 third most-liked tweet plays to his strengths as a serial entrepreneur in the social app space. it’s a criticism of Instagram, which he claimed had 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. Because Greg has a track record on this topic, there’s a more direct connection between “oh this is an interesting point” and “oh this is someone I should be following.”
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’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.
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.
Greg’s Vision: Translating Social Reach Into A Community App
As Greg’s following grew, his strategy shifted from being where the people are (i.e. Twitter) to building something he can own (i.e. building a list for his newsletter). This is an important shift: it shows he felt he’d maxed-out the reach upside, and now wanted to build defensibility.
Why Greg Shifted Focus from Twitter to Substack
The data shows that Greg’s most-liked Tweet came in Jan 2021. In the intervening 20 months not a single Tweet has had the same reach. I suspect that Greg realized, like many, that Twitter can change it’s algorithm at any time. And rather than continuing to swing for the fences on reach, but build on unstable ground (Twitter), he shifted tacks toward securing his following on a platform he can own (i.e. email).
Why Greg Moved from Twitter to Substack to Podcast
The value of Twitter is reach. The value of a Substack is control. But why did Greg launch a podcast? In a recent podcast episode with Steph Smith, Greg and Steph laid out the thinking. Steph argues that people read blogs casually: they might read one post and never come back. Whereas podcasts are a much deeper and more intimate relationship: once someone forms a habit, they tend to listen to you every week. However podcasts have a discoverability problem. So the ideal roadmap is to build the top of funnel on a channel with huge distribution (i.e. Twitter) and then use a medium like Podcasts to create a deeper, intimate, and stickier relationship.
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.
Next: Build a Community
Greg failed to build a social app that had the social reach he aspires to, but it’s clear he’s building the prototype of a new type of community product. One that has individual influencers as the “anchors” of various communities.
Late Checkout just launched their own community. Separately he’s launched a community for AI. And I suspect we’ll see him partnering with other influencers to launch their own communities. Underpinning this will be a technology product that has the potential to displace Facebook Groups, Instagram, and TikTok as the dominant mobile social app of our generation.