In a recent LinkedIn post, Jasonfeifer discusses the often-contentious topic of brand redesigns, using the example of Pirates Booty’s new look to explore the challenges companies face when trying to evolve their image. Feifer highlights the disconnect between long-time consumers and the need for brands to capture a younger demographic.
Feifer opens by acknowledging the widespread criticism of the Pirates Booty redesign, noting his own initial reaction:
“Personally, I love the quirky old design and I think this new one is bland.”
However, Feifer quickly pivots to a more nuanced perspective, questioning whether this personal preference is a significant problem for the brand. He points out that the loudest critics of the redesign tend to be those in his own age group. This observation leads him to consider the strategic imperative for Hershey’s, the parent company of Pirates Booty, to look beyond its existing customer base.
The Generational Divide in Brand Perception
Feifer argues that a brand’s success hinges on its ability to attract and retain new generations, whose aesthetic preferences and values may differ significantly from older consumers. He uses his own children as a relatable example to illustrate this point.
As Jasonfeifer notes:
“I have a 7- and 11-year-old. They care 0% about what I find charming. I see it daily.”
This personal anecdote underscores his central thesis: that brands must prioritize future growth over the comfort of their current, established audience. The insights gained from observing his children’s reactions emphasize that what resonates with adults might be completely irrelevant to younger consumers. This generational gap is a critical factor in understanding the reception of a brand refresh.
Navigating the Risks of Redesign
Feifer delves into the inherent risks associated with brand redesigns, drawing parallels to other high-profile cases. He suggests that a successful redesign requires more than just a visual update; it demands a clear and deliberate mission.
According to Feifer:
“So here’s what I find fascinating: When a brand redesigns, it must look beyond the expected naysayers — and have faith in a clear and considered mission.”
He further elaborates on the potential outcomes, distinguishing between successful evolutions and notable failures. Feifer mentions Tropicana’s infamous packaging redesign as an example of a redesign gone wrong, a situation that resulted in significant backlash and a reversal of the changes.
In contrast, Feifer implies that when brands get it right, consumers eventually adapt and embrace the new identity. The success of a redesign, in his view, often depends on the brand’s ability to execute its vision effectively and connect with the target demographic, even if it alienates a portion of its existing user base in the short term.
Assessing the Pirates Booty Redesign
Returning to the Pirates Booty example, Feifer concludes that it is premature to definitively judge the success or failure of the new design. He advises cautious observation, particularly of how younger consumers respond.
As Feifer advises:
“But before you count it out, watch what the kids do first.”
This perspective encourages a longer-term view, suggesting that the ultimate validation of the redesign will come from its ability to resonate with the next generation of consumers, rather than immediate acceptance from the established audience. Feifer’s analysis provides a valuable framework for understanding the complexities of brand evolution in a rapidly changing market.
📝 About This Content
This article is based on insights shared by Jasonfeifer on LinkedIn.
📅 Originally posted on June 15, 2026 | View original post on LinkedIn →