Barstool lands a $450M valuation, thanks to a casino company

Cue the Sweet Caroline playlist... Penn National Gaming shelled out $163M for a 36% stake in Boston-raised Barstool Sports. You've heard of Barstool, the sports-culture blog/video/pod-producer famous for "irreverent" content. You probably hadn't heard of Penn National, which operates casinos like Tropicana and Margaritaville — its shares soared 11% on the news. Here's the deal:

• Barstool gets its valuation bumped close to half-icorn-worthy $450M (almost half a unicorn).
• Penn gets exclusive rights to use Barstool's brand in its sports-betting products (which its casino biz is going in big on).
• Barstool's founder (and fellow early employees) keep 28% ownership of the company.
• FYI we figured out the formula to all Barstool merchandise:

[Insider fan joke] + [Silhouette of athlete] = Barstool t-shirt

It's all about the eyes (and ears)... Media companies boil down to one word: Audience. That's where the real value is for them (and their investors) — Barstool brings in nearly $100M in revenues annually.

• Access: Since launching in 2003 as a Tom Brady-worshipping physical newspaper, Barstool hustled to build an audience of 66M "Stoolies."
• Special Access: That audience is particularly likely to be into sports/gaming (62% of Stoolies bet on sports, and 44% of those gamblers do it at least 1x/week).
• Brand: Penn wants more flat-brims in its life. "Sports betting attracts a new, younger demographic than traditional casino gaming." That's straight outta Penn's investment presentation deck.
• Conversion: Penn is betting it can convert Barstool's audience into its casinos and sports-betting app better if it owns the content and can promote itself there.