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

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.

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

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.

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

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.