Learning from the Worst Marketing Misfires

November 21, 2025

Is ChatGPT helping your sales... or sabotaging them?

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Bombora deepens integration with StackAdapt to power smarter B2B targeting

Bombora and StackAdapt have expanded their partnership: marketers can now access Bombora’s digital B2B audience data directly within StackAdapt. This includes highly customizable segments (using Bombora’s intent-based audiences) and global scale. Campaigns can run across multiple channels, while account-level measurement enables more precise ROI tracking.

Why it matters

This is a meaningful upgrade for B2B marketing. Instead of relying on proxy data or third-party layering, marketers now have seamless access to intent-rich audiences linked to real business signals. It means performance campaigns can be more precise, and ROI measurement can go beyond surface metrics. For content strategists, it also opens up opportunities: use intent data to tailor creative to the buyer journey, personalize messaging, and align content more closely with what decision-makers are researching in real time. Read more

Hotels face rising customer acquisition costs as competition intensifies

Hotel chains are seeing their customer acquisition costs (CAC) increase, driven by rising digital ad costs, more aggressive loyalty incentives, and pressure to fill rooms in a competitive market. The rising CAC suggests that traditional travel marketing levers are losing efficiency, and brands must rethink how they attract and retain guests.

Why it matters 

If acquiring guests is getting more expensive, marketers need to justify spend with long-term value. Loyalty programs must not just retain customers but drive profitability. Brands may need to shift part of their strategy from volume-driven acquisition to more targeted, data-driven segmentation. For content strategists, this means creating richer, more personal storytelling to deepen brand-guest relationships and reduce dependency on costly paid ads. Read more.

Michigan proposes tighter rules on online gambling ads to protect youth & ensure truthfulness

Michigan legislators have introduced Senate Bills 713 and 714, which aim to impose strict new regulations on online gambling and sports betting advertising. Under the proposed rules: ads must be pre-approved by the Michigan Gaming Control Board, include responsible-gambling disclaimers and helpline details, and must not target under-21 individuals. Violations could lead to fines or even license revocation.

Why It Matters

For marketers in regulated industries, the direction in Michigan is a strong signal. Stricter governance could become a model for other states. Brands will need to build compliance into their ad strategies — not as an afterthought, but as a core part of campaign planning. Agencies working in gambling or gaming must prepare for longer creative cycles (for pre-approval) and embed harm-reduction messaging. The broader lesson: consumer protection and brand trust are now deeply intertwined with regulatory risk. Read more.

Today’s Insight

Learning from the Worst Marketing Misfires

This piece highlights several failed campaigns — from AI-driven creatives that felt hollow, to tone-deaf wordplay, to insensitive rebrands. These failures stem from a few common issues: misunderstanding the audience, over-reliance on technology without emotional grounding, and poor crisis management.

Key Takeaways

  • Human connection beats gimmicks. Some of the worst campaigns tried to replace human expression with AI but ended up feeling cold or inauthentic.

  • Cultural sensitivity is non-negotiable. Campaigns that ignored social context or used problematic imagery faced backlash.

  • Representation needs substance. Using AI-generated models to “show diversity” can backfire if not backed by real commitment.

  • Clarity in crisis matters. When things go wrong, vague apologies or non-apology statements do more harm than good.

  • Measure experience, not just reach. With AI and automation becoming common, success should be measured by the quality of engagement (emotional resonance, sentiment), not just impressions.

    Click here to read this story.

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