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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.

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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.

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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.

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These days, every audio podcast has an accompanying video podcast, but Jefferson Graham was hosting video podcasts before the term even existed. In 2006, he started co-hosting a show with another USA Today colleague who lived on the opposite coast from him, and they'd physically FedEx the tapes back and forth so they could be edited. Jefferson then went on to host several video series for USA Today, including one where he'd interview celebrities about their favorite tech.

In 2021, after 30 years at USA Today, he decided to take a buyout so he could launch PhotowalksTV, a YouTube travel show where he'd visit different cities and instruct viewers on the best spots to take photos. In 2024, he signed a deal with Scripps News to broadcast the show on its FAST channels, and now new episodes air every Sunday at 10 am.

In a recent interview, Jefferson discussed what it was like to host a podcast when nobody knew what a podcast was, why he took the buyout from USA Today, and how he generates multiple revenue streams through his YouTube channel.

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If you attend any media industry conference, you'll hear lots of discussions from publishers about how they're trying to diversify their revenue streams, but Todd Scott took the opposite approach. A few years ago, he announced the National Business Review, the New Zealand media outlet he runs, would no longer accept advertising and instead monetize solely through paid subscriptions. NBR now has over 14,000 subscribers paying $499 New Zealand dollars a year. In 2025, it's projected to generate $4.5 million in revenue and is profitable.

In a recent interview, Todd walked me through how he acquired NBR, why he ditched advertising, and his plans to license his publishing technology to media outlets all across the world.

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Francesca Donner has had a somewhat unusual journalism career in that she never aspired to be a reporter or have her own bylines; instead, she started out her career as an editor and rose through the ranks of places like the Wall Street Journal and New York Times. But though she wielded some influence at these publishers, she was always frustrated by the lack of female viewpoints, both in terms of who was writing the articles and who was being interviewed for them. So in 2022, she launched the Persistent, a sort of online magazine that's written entirely by women.

In a recent interview, Francesca talked about her experience working in mainstream media, how she's trying to build an interactive community with the Persistent, and why she's been hesitant to lock content behind a paywall.

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One day in the 1990s, Alan Jay received a surprising phone call at work from Jeff Bezos's assistant, who said the Amazon founder wanted to meet with him during an upcoming trip to the UK. That meeting would eventually lead to Amazon acquiring IMDB, the movie database Alan had co-founded.

After the acquisition, Alan didn't rest on his laurels; over the next two decades, he went on to co-found two other media companies – one in entertainment and the other sports – both of which had their own successful exits. In a recent interview, Alan told the origin story of IMDB, walked through how he built the two other media properties, and explained why it's much harder to launch a media business today compared to 20 years ago.

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If Stuart Schuffman were in his early 20s today and building an independent media career, he'd probably be a TikTok influencer, but when he launched Broke Ass Stuart in the early 2000s, the natural medium was a print zine, one he printed out and stapled together himself. It was a San Francisco travel guide of sorts, and he trucked it all around the city and convinced coffee shops and bookstores to sell it on consignment.

The zine was never a huge moneymaker, but it landed him a book deal, and from there it expanded into an online media brand that's widely read by the city locals. In fact, Stuart can't walk through the streets of San Francisco today without being recognized.

In a recent interview, he told the Broke Ass Stuart origin story and explained how, bit by bit, it turned into a real business.

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By the time Eric Coffie launched his YouTube channel in 2016, he was already one of the most successful federal government contractors in the US and employed an entire team that specialized in erecting steel buildings. The YouTube channel came out of his frustration of having to repeat the same advice over and over again to those wanting to break into the industry; he figured he could just record some video explainers and send them to people.

But the success of the channel led to him expanding into podcasts, and then before he knew it Eric was operating an entire media company that spanned across video, podcasts, online courses, coaching, events, and even a paid community.

In a recent interview, Eric explained how he found an audience by going extremely niche and why he wants to shut down most of his media revenue streams so he can regrow his contracting business.

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The Coppell Chronicle isn't your average Substack newsletter. For one, the headlines are incredibly boring. Secondly, there's really no free version of it, since every issue that's sent out includes a paywall. But perhaps the most remarkable thing about it is that it's managed to convert upwards of 40% of its email list into paid subscribers, which is a conversion rate at least 10 times higher than the average Substack newsletter.

What's more, its owner Dan Koller achieved all this while maintaining his full time job. In a recent interview, Dan explained how he launched the newsletter, why it took off in his Dallas suburb, and whether he thinks other wannabe local news entrepreneurs could copy his model.

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If you ask Dave Anderson what he does for a living, he'll probably tell you he's retired, but that's not entirely true. While he did leave his last full-time job at Amazon back in 2020, he still writes a weekly newsletter on Substack about tech leadership. And even though he only works on the newsletter part time, it currently has over 2,000 paid subscribers. It turns out a lot of people want to tap into his insights gleaned from 20 years working in the tech industry, including over 10 at Amazon.

In a recent interview, Dave discussed the newsletter's origin story, how it found its audience, and why he doesn't have any ambitions to scale it into a larger media company.