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Kit Chilvers started posting memes on Instagram when he was 14, treating the platform like a video game and obsessing over what made posts take off. A decade later, that experimentation has turned into Pubity Group, a bootstrapped social media company with roughly 170 million followers and hundreds of billions of annual views.

In a recent interview, Kit broke down how he cracked early Instagram growth, why wholesomeness turned out to be a massive business opportunity, and how he's trying to turn platform-native virality into durable media brands, original franchises, and real revenue.

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In some ways, it's never been a better time to be a standup comedian. In previous eras, aspiring standups had to slowly make their way up through the industry by performing in open mic nights and small venues, but now a few viral video clips on Instagram or TikTok can instantly thrust a new comedian into the spotlight.

But even if a standup has millions of followers on social media, it can be difficult to monetize their fanbase. There's no easy way to alert followers in a certain geographic area that you're performing at a local venue, and social media moderation algorithms consistently throttle reach, especially if a comedian talks about controversial topics.

Danny Frenkel and a co-founder launched Punchup in 2023 to solve these problems. His platform allows comedians to place their video content behind a gate that collects users' email addresses and locations. It also allows venues to sell tickets to events directly through Punchup. Comedians can even directly sell their standup specials on the site. Punchup has already attracted several big name comedians to its network, including Shane Gillis and Tom Segura,

In a recent interview, Danny walked through the economics of standup comedy, explained how his experience selling ads on Meta informed Punchup's service offerings, and outlined his longterm ambitions for the platform.

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In today's episode, we're speaking to Suryansh Tibarewala, the co-founder of Essentially Sports.

EssentiallySports began in 2014 as a bootstrapped passion project started by Suryansh and his co-founders while they were college students in India. It started as a simple WordPress site focused on tennis and Formula One. The site ran for four to five years with virtually no revenue, relying largely on volunteer contributors.

But then in 2018, the site's founders decided to quit their day jobs and go all in. They expanded the sports coverage, found reliable advertising partners, and eventually grew EssentiallySports into one of the largest sports sites ranked by Comscore – all without raising outside capital.

In a recent interview, Suryansh walked through the site's early days, its expansion into US sports, and its B2B live events strategy.