Rebranding can make or break a business. For legacy companies like Cracker Barrel, bold moves designed to attract younger consumers can quickly backfire when they dilute the brand’s identity. Branding expert Bill Harper, CEO and Chief Creative Officer of BrandBossHQ, joins us on the latest episode of The Small Business Show to explain why even well-known companies struggle when they attempt major overhauls and what small business owners can learn from their missteps.
The pitfalls of rebranding
To start, Harper notes that when brands attempt sweeping changes without sufficient research, they risk alienating their existing customer base. Using Cracker Barrel as an example, he described how the restaurant’s recent brand revamp made it resemble competitors such as IHOP and Denny’s, stripping away the distinct qualities that had earned customer loyalty. According to Harper, companies often make changes based on operational efficiency or the goal of appealing to younger audiences, but these adjustments can result in a generic, unrecognizable brand.
"The only thing people think about when they buy a product is 'What's in it for me'...the only thing the product exist for is to get something that they're after."
Additionally, Harper highlights that executives may pursue rebranding as a high-stakes gamble, driven more by the pressure to succeed than by ego. CEOs entering new roles often feel the need to implement dramatic changes quickly, even if internal teams or customer research suggest a more measured approach. Misaligned leadership strategies and overconfidence in untested concepts can amplify the risk of failure.
The cost of poor research
One of the biggest mistakes Harper pointed out is investing heavily before testing ideas with the target audience. Cracker Barrel reportedly spent $700 million on its revamp before validating it with consumers. Harper stressed that brands must understand why customers stop engaging and identify what they truly value before implementing changes. Otherwise, rebranding can become a costly experiment with little to no positive impact.
Harper advised that small businesses focus on relevance and meaningful insights rather than flashy redesigns. Understanding what customers appreciate about existing products or services, and identifying where improvements are needed, enables precise and cost-effective adjustments. The goal is not to chase trends but to maintain the brand’s identity while enhancing its appeal to both current and prospective audiences.
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