I think Barstool is a very interesting business story. From its origins as a free weekly in Boston to being a $450 million company, partly because of the end of the prohibition on sports gambling. Portnoy is a hustler, but his company's current value is in podcasts and he didn't see that at first. And Chernin made out. According to the article, it got at least half of the company for $25 million.
It's content on the internet that is valuable now. What are the internet-only news/information websites making money?
I don't see how it is a great investment going forward. Its has a polarizing public image that could end up killing it. Also, it appears that Barstool's value is in its attitude and its talent. Its readers/listeners/viewers are going to get older. It is going to have to replace people doing the popular podcasts. I don't think a media company with this specific of a attitude can both maintain its listeners and find the talent to keep people interested.