AI & Content: Building What Can’t Be Summarized: Move beyond basic SEO to create unique value and actively feed AI. WebMD and Mayo Clinic structured their data to play nice with AI but then introduced dosage calculators, BMI calculators, and health risk assessment tools that can’t be easily digested. This dual strategy ensured their relevance to AI while reaffirming their stickiness to their audience.

New Revenue: The Power of Direct Relationships: Transition from volatile ad revenue to direct, resilient relationships with audiences who pay. The New York Times is the gold standard for this pivot. They saw the writing on the wall for print and went all-in on digital. They invested heavily in building unique value, most notably in games. They remade their offering into an indispensable part of readers’ lives and grew to over 10 million digital subscribers.

Audience First: Fans Over Fleeting Gains: Choose to build deep loyalty, even if it means saying ‘no’ to short-term cash. Spotify built hyper-personalization and loyalty with Wrapped while Barstool Sports embraced their community’s memes and built authentic connections and brand extensions. Both prioritized their audience and their users responded.

Triage & Transformation: Ruthless Focus Wins: Make the hard cuts and bold bets needed to align with the future. It means killing the ‘pretty good’ to protect the ‘essential’. Both Netflix (DVD -> Streaming -> Originals) and Adobe (Licenses -> Cloud) made uncomfortable, transformative bets, shedding old skins to dominate new markets.


Every successful pivot demonstrates the courage to make tough calls.

• Audience Intimacy: Deeply knowing who you serve.
• Strategic Confidence: Making bold bets and killing what doesn’t serve the future.
• Value Creation: Offering something genuinely unique.
• Adaptability: Evolving constantly, especially when it’s uncomfortable.

The window for gradual change has closed. This time of uncertainty requires bold and focused strategies that directly address the issues of AI, monetization, and audience. Are you equipped with the right playbook to compete? If not, let’s talk.