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Jonathan Skogmo has been working with user generated content since before the term “user generated content” even existed. Back in the 2000s, he moved to Hollywood and worked for what were called “clip shows,” where viewers would physically mail in funny home videos to have them compete for cash prizes. As it turned out, Jonathan’s entry into the industry coincided almost perfectly with the launch of YouTube. He was eventually able to leverage his skills to find viral clips on YouTube and license them to the media companies and brands that wanted to use them. His company Jukin Media eventually paid out over $50 million in royalties and in 2021 was acquired by the company that owns Readers Digest.

Now, Jonathan is building a new company focused on travel, and rather than growing it from scratch he’s acquired several existing media brands. In a recent interview, he walked me through his acquisition strategy and explained why physical travel guidebooks still have currency in an era where influencers seem to have captured the market.

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If you work in the live music business, there’s a decent chance you know of Josh Weidling, even though you probably wouldn’t recognize his face. That’s because he’s almost always been behind the camera as he interviewed literally thousands of musicians touring through the midwest. Josh launched his YouTube channel Digital Tour Bus in 2009, and over the next 15 years he dutifully uploaded upwards of five fresh interviews a week with musicians who walked the viewer through their tour bus and explained how they chose their musical instruments and gear.

In a recent interview, Josh dove into the origin story of the YouTube channel and explained how he turned it into a business. He also discussed why he decided to keep his day job rather than go all in on the franchise.

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Of all the media outlets to have launched in the last decade, Morning Brew has had one of the most impressive growth trajectories. Not only did it build its main newsletter to millions of subscribers, but it also spun off multiple B2B niche verticals and has had enormous success on platforms like YouTube and TikTok.

So it’s not surprising that when three of its early employees left to launch their own media company, there were plenty of high profile creators eager to work with them. Under the banner of Smooth Media Creative Holdings, these alums have built out an influencer marketing agency and also their own niche outlets.

In a recent interview, co-founder Josh Kaplan delved deeper into Smooth Media’s strategy, explained how it works with big YouTubers, and discussed why the company decided to acquire a 30-year-old B2B media brand.

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Food content is now a major staple on YouTube, but when baker Gemma Stafford launched her channel in 2014 there were hardly any professional chefs on the platform. This early mover advantage allowed her and her husband Kevin Kurtz to build up a massive audience that used Gemma’s tutorials in their own baking efforts. Then a few years ago they teamed up with media veteran Ronald Pruett, Jr. to launch the Bold Baking Network, a streaming platform that syndicates content from hundreds of baking creators all across the world.

In a recent interview, Kevin and Ron walked through the company’s origin story, how they monetized Gemma’s videos, and why they decided to expand beyond YouTube and build their own platform.

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The podcast company Sonoro launched in 2020 with a relatively simple thesis: that there were very few media companies geared toward the 62 million latinos within the US. Over the next four years, it built out a stable of dozens of podcasts across several formats ranging from serialized nonfiction to personality-led chat shows. In addition to the standard podcast monetization models, it also sought to further capitalize its IP by selling adaptations to Hollywood studios and developing its own merch lines. Today, the network generates over 100 million monthly downloads and works with some of the world’s biggest latino creators.

In a recent interview co-founder Joshua Weinstein explained how the company partners with talent and walked through all the ways it’s monetizing its IP.

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When the media covers business acquisitions, it’s usually only for huge deals involving VC-backed companies. Coverage of mergers for small, bootstrapped businesses is almost nonexistent. That’s where They Got Acquired comes in. Launched in 2021, it focuses on acquisitions in the $100,000 to $50 million range. Recently, it put out a detailed research report specifically focused on acquisitions of media outlets, which are typically sold at lower multiples than other kinds of online businesses.

In an interview, founder Alexis Grant walked through the experience she had selling two of her own media outlets and explained the steps a current media entrepreneur should take to maximize the selling price for their own business.

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Given the tumultuous economic landscape for local news, many outlets are turning to nonprofit models because they offer increased flexibility for generating revenue. But while these outlets have been adept at attracting foundation grants and small donor memberships, they’re not doing enough to cultivate relationships with the wealthy members of their own communities, many of whom can write much larger checks than your average reader.

At least that’s the thesis of Julie Rafferty. She not only has a deep background in consulting with nonprofits, but she also played an instrumental role in co-founding Brookline News, a nonprofit media outlet that operates outside of Boston.

In a recent interview, Rafferty walked through how she got wealthy members of her city to fork over $100,000 before the outlet even launched, and she gave some good advice on how other nonprofit newsrooms can identify and reach out to rich people in their own communities.

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If you work in the media industry, you’re likely aware of The New York Times tremendous success with its gaming vertical; in fact, millions of people subscribe solely so they can play games like Wordle and Connections.

But it’s not the only publisher that’s incorporated games into its business strategy. Hundreds of outlets ranging from Morning Brew to The New Yorker utilize a platform called Amuse Labs to build everything from crosswords to sudoku. In a recent interview, co-founder John Temple explained how publishers can leverage games to increase everything including time on site, repeat visits, advertising revenue, and paid subscription conversions.