How a few college students bootstrapped one of the largest sports media websites in the world

My newsletter: https://simonowens.substack.com/   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.  

My newsletter: https://simonowens.substack.com/   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.  

My newsletter: https://simonowens.substack.com/   Roca News was founded on a simple premise: so much of news now is consumed on social platforms, with fewer and fewer internet users clicking through to article pages. After launching in 2020, it gained its initial success on Instagram, where it amassed hundreds of thousands of followers by distilling important news stories into swipeable images. It then launched a daily newsletter that's since grown to over 200,000 subscribers.   Most recently, the company has invested heavily in its YouTube channel, sending its on-camera hosts to far-flung locations to interview everyday people about their unique experiences. Each video racks up hundreds of thousands of views, and the channel has grown to close to 600,000 subscribers in a little over a year.   In a recent interview, co-founders Max Towey and Max Frost recounted Roca's origin story, walked through its initial Instagram strategy, and explained how they invented a unique documentary format for their YouTube channel.  

My newsletter: https://simonowens.substack.com/   When Shane Greer took over the magazine Campaigns & Elections in 2011, it was in a sorry state.    Founded back in 1980, the outlet had once been the gold standard for reporting on the political operatives who help candidates and corporations influence elections.   But by 2011, the magazine was limping along, with its print edition and events struggling to break even. That year, it was acquired by a private equity firm, which installed Greer to run it. In a very short period of time, he killed the print edition, expanded its online reach, and revived its events business.   Then in 2015 he and his business partner Shane D'Aprile acquired Campaigns & Elections, and they immediately set about expanding the company into new niches and regions. Today, there's not only Latin American version of C&E, but the company also bought a B2B media outlet that covers the cannabis industry.   In a recent interview, the two Shanes walked me through their initial strategies for righting the C&E ship, explained why they acquired the magazine, and outlined their plans to build out a B2B media empire.  

My newsletter: https://simonowens.substack.com/   The Kyiv Independent launched in 2021, and its timing was in some ways fortuitous, since it was only a few months later that Russia launched a full-scale invasion in Ukraine. Suddenly, the entire world was paying attention to the country, and the Kyiv Independent happened to be the most authoritative English-language outlet to be reporting on the ground. This attention not only resulted in a massive amount of traffic, but also a surge in membership donations as sympathetic Westerners sought out ways to support Ukraine's cause.   In a recent interview, Chief Operating Officer Zakhar Protsiuk discussed the early days of getting the Kyiv Independent off the ground, its shift from one-time donations to recurring memberships, and why the outlet has begun producing longform documentaries.  

My newsletter: https://simonowens.substack.com/   What if you took Morning Brew's approach to newsletter writing and applied it to local news? That was the original idea behind 6AM City, a company that launched its first newsletter in Greenville, South Carolina in 2016 and gradually expanded into over a dozen cities.   For most of its history, 6AM City's approach was to hire a handful of editors in each city and then gradually build up an audience and advertiser base. But in the last year, it developed a playbook for using AI to launch newsletters in smaller, less populated areas, with the goal of eventually hiring human editors once those newsletters reached certain thresholds.   In a recent interview, co-founder Ryan Heafy explained how these AI newsletters actually work, where they get their information, and what guardrails the company has put in place to ensure quality control.  

My newsletter: https://simonowens.substack.com/   When the media holding company Woven Digital purchased BroBible in 2012, the idea was that the guy-focused publisher would benefit from all the business synergies that come from being part of a larger media network. Instead, BroBible was neglected and undermonetized. So when Woven began unraveling its holdings in 2018, BroBible's staff banded together and bought it back. And what started out as a staff of seven has grown to 16 today, and the business is diversified across programmatic advertising, events, and sponsored social media posts.   In a recent interview, publisher Brandon Wenerd walked through Brobible's early blogging days, its transformation into a real business, and how breaking free of its parent company allowed it to adapt to the current media climate.  

My newsletter: https://simonowens.substack.com/   In 2008, Wade Wallace found himself living in Australia and laid off from the company that moved him there in the first place. With his visa in limbo, and not much else to do, he launched CyclingTips, a blog that covered both the professional and amateur aspects of the sport. What started out as a hobby eventually grew into a fully-staffed news website, one that eventually sold to the investment firm that owned Outside Magazine.   Then in 2022 he quit CyclingTips, raised some investment money, and then launched Escape Collective, which covers the exact same beat. Unlike CyclingTips, Escape Collective is fully funded through paid subscriptions, and when we recorded this interview it was on the verge of profitability.   In a recent interview, Wade walked through his early days building CyclingTips, why he grew unhappy at Outside, and how he grew Escape Collective to 15,000 paying members.  

My newsletter: https://simonowens.substack.com/   There was a time 20 years ago where if you filmed a horror movie on a tight enough budget, you could plausibly turn a profit from the DVD sales alone. Unfortunately for Chris Sharpe, his entry into the horror genre came just as the DVD market was collapsing, and so his career as a movie director fizzled out after he made only one film.    Luckily, one of the stars of that film, Hilah Johnson, had a strong onscreen presence and a penchant for cooking, and together they launched Hilah Cooking, a YouTube channel that eventually grew to over 450,000 subscribers. Then a few years later Chris teamed up with another co-star from that movie, Adriene Mishler, to launch Yoga With Adriene, which now has over 13 million subscribers on YouTube.   In a recent interview, Chris walked through how he and his collaborators launched both channels, why Hilah decided to eventually end her channel, and the massive success they've seen building a yoga streaming app.  

My newsletter: https://simonowens.substack.com/   When Tomiwa Aladekomo took over Big Cabal Media eight years ago, the company was little more than two promising publications that were read mostly within Nigeria. He stepped in not as a founder, but as someone who had spent years inside every corner of the media world, including music, advertising, brand strategy, and digital publishing. And he saw, even then, that Big Cabal had the potential to diversify its revenue and scale up into one of the most influential media companies in Africa.  In a recent interview, Tomiwa walked through how that early instinct turned into a 100-person company that now stretches across multiple countries and several lines of business. He also discussed how Big Cabal is navigating the same headwinds facing publishers everywhere—including shrinking social traffic and the rise of AI—while also confronting challenges unique to African media.