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From Cracker Barrel to Robinhood — When “Strategy” Turns Into Gambling
Why do smart companies make chaotic brand moves—and why do some “investors” treat markets like a casino? In this episode, Connor Malatesta and Ryan Bannister break down the Cracker Barrel branding dust-up, the consultant hamster wheel, and how quarterly pressure turns strategy into… a bet. Then we follow the thread to Robinhood and the rise of “push-button” gambling, asking what long-term thinking actually looks like in 2025.
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By Connor Malatesta and Ryan BannisterWhy do smart companies make chaotic brand moves—and why do some “investors” treat markets like a casino? In this episode, Connor Malatesta and Ryan Bannister break down the Cracker Barrel branding dust-up, the consultant hamster wheel, and how quarterly pressure turns strategy into… a bet. Then we follow the thread to Robinhood and the rise of “push-button” gambling, asking what long-term thinking actually looks like in 2025.