Tootsie Roll

Shaan's first short ever: betting against Tootsie Roll

Shaan recounts seeing a CNBC guest aggressively short Tootsie Roll (arguing nobody under 40 likes it and the 90-year-old owner would never sell). It became the first stock Shaan ever shorted; it dropped a few dollars, he made money and got out, and the stock has since risen.

“He's like, I'm shorting Tootsie Roll big. And I was like, what? This came out of nowhere. And he's like, I'm shorting Tootsie Roll. He goes, do you know anyone under the age of 40 who likes Tootsie Rolls? And he's like, yeah, Sam raises his hand, but he's like, he's like, kids don't like Tootsie Rolls. They don't even know about Tootsie Rolls.”

Buy out Tootsie Roll and relaunch it on TikTok

Shaan pitches buying the ~$2B Tootsie Roll, arguing it does none of what M&M's and Skittles do to stay relevant (pop-star partnerships, new variations, holiday themes). The plan: hire the best marketing agency, use TikTok as distribution, and bring the brand back with a vengeance.

“And so the idea would be to buy Tootsie Roll out, um, and bring it back with like— hire like the best marketing agency of all time and bring it back with a vengeance, uh, using TikTok as distribution.”

Steal thisAcquire a beloved-but-stale candy brand with a sleepy owner and revive it with modern culture marketing and influencer distribution.