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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.