It’s a Bear Market for Citibin

In this week’s podcast, Liz Picarazzi explains why she ignored advice to focus on her main market and chose to also pursue a new market with a very high barrier to entry.

Good Morning!

Here are today’s highlights:

• Thanks to generative AI, it took the marketing head of a small, family business 10 minutes to go viral.

• You’re a CEO. You know you want your team using AI—but you don’t really get it yourself. You’re not alone!

• Unlimited PTO has always been something of a charade because employees are afraid to take it. Now, its proponents say it’s evolving.

• A Millennial couple's side hustle was failing until they decided to take a couple of loans. Would you have taken the same risks?

THE 21 HATS PODCAST

This week, Liz Picarazzi tells Jay Goltz and William Vanderbloemen that she’s had a couple of big breakthroughs: For Liz, it’s been a challenging few years dealing with the tariffs while also trying to break into a promising new market. Despite the advice of some very smart people who encouraged her to conquer her first market —urban areas plagued by rats—before expanding into additional markets, Liz has spent several years trying to position Citibin to serve towns, parks, and resorts that need trash bins strong enough to withstand bears. For that investment to pay off, however, Liz would have to outsmart her nemesis, an especially ferocious competitor that goes by the name of Seeley.

• Plus: Jay talks about the plight of small retailers trying to survive while their industry collapses around them. And William tells us how he’s trying to keep up in the AI arms race between employers and employees.

• You can subscribe to the 21 Hats Podcast wherever you get podcasts.