Outsmarting entropy: Shipping beyond the playbook

In this episode of Playbook Broken, Will Allen of Cloudflare talks about re-thinking the business model for content creators and more.

By ,
Founder, Marc Sirkin Consulting
July 23, 2025 • 2 minutes read

Table of Contents

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    In this episode of Playbook Broken, we delve into the shifting landscape of business marketing and sales playbooks.

    We welcome Will Allen, VP of media and AI privacy products at Cloudflare, to discuss the evolution of content creation and AI in today’s dynamic environment.

    We explore the critical role of playbooks in navigating change, the impact of AI on content creators, and the necessity of clear communication and relentless shipping to succeed.

    Tune in for insights on redefining business models, the future of AI agents, and strategies to adapt in an ever-changing digital world.

    Episode guide

    00:00: Introduction and welcome
    00:22: Guest introduction: Will Allen
    01:10: Cloudflare and its origins
    03:18: The concept of playbooks
    04:50: Challenges and adaptations in playbooks
    11:31: AI and content creation
    13:49: The changing landscape of content monetization
    19:39: Cloudflare’s approach to AI and content
    21:39: The crux of the issue
    21:54: Writing for future AIs
    22:12: Developer documentation and AI integration
    22:43: Different approaches to content control
    23:10: Enforcing content policies
    24:33: The changing landscape of SEO and AI
    28:34: The rise of agents and bots
    33:30: The future of content and business models
    37:33: Overcoming challenges and shipping products
    40:31: Final thoughts and closing remarks/custom

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    Contributing authors are invited to create content for MarTech and are chosen for their expertise and contribution to the martech community. Our contributors work under the oversight of the editorial staff and contributions are checked for quality and relevance to our readers. MarTech is owned by Semrush. Contributor was not asked to make any direct or indirect mentions of Semrush. The opinions they express are their own.

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    Marc Sirkin
    Founder, Marc Sirkin Consulting

    Marc Sirkin is a former CEO, CMO, and digital transformation leader known for driving growth, innovation, and exits at iconic brands including Microsoft, PwC, and Autism Speaks. As Founder of Marc Sirkin Consulting and host of the “Playbook Broken” podcast, he helps executives navigate existential change by integrating AI, aligning teams, and accelerating outcomes. He led the integration of Third Door Media into Semrush post-acquisition by preserving editorial independence while transforming virtual events and launching AI-powered products.

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