Sage Marketing Advice with James Hipkin

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Too many SMBs think a new headline, a prettier design, or the latest AI tool will magically turn their website into a lead machine. In this episode, Mike Montague sits down with marketing veteran James Hipkin to explain why most underperforming websites don’t have a copy or design problem; they have a strategy problem. You’ll learn why “inside-out” marketing stalls growth, how to shift to an “outside-in” approach that meets buyers where they are, and why messaging built for boomers can repel younger audiences like Millennials and Gen Z.

James also shares the 80/20 rule for finding your most valuable customers, how to build content for people who have never heard of you, and practical ways AI can help you tailor messaging for different buyer personas without sounding robotic. If your business is stuck on a plateau, still relying too heavily on referrals, or wondering how to adapt to the self-service research habits of modern buyers, this conversation is a blueprint for building marketing that resonates, connects, and converts.

Key Takeaways

1. Most website problems are strategic, not cosmetic – Poor performance usually comes from a lack of a clear marketing strategy, not bad copy or visuals.

2. Adopt an “outside-in” marketing mindset – Build messaging and offers around your audience’s journey, not just your own story or features.

3. Your boomer-era marketing may repel younger buyers – Millennials and Gen Z expect self-service research and digital-first engagement, not phone calls and hard sells.

4. The 80/20 rule can unlock growth – Focus on the top 20% of customers who generate most of your revenue, and design campaigns to attract more like them.

5. Strangers need different messaging than referrals – Don’t assume new prospects know your values, reputation, or track record—build content that educates and builds trust from scratch.

6. AI works best when it’s trained on your voice and audience – Use AI to adapt content for different personas, not to mass-produce generic marketing.

7. Chatbots should provide value, not push for a call – Modern buyers will engage with bots if they get answers, resources, and useful guidance without pressure.

8. Meet customers where they are in their decision journey – Offer the right content at the right stage, from initial research to final decision, to keep prospects moving forward.

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