Outsmarting entropy: Shipping beyond the playbook

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

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About the author

Marc Sirkin

Marc serves as Third Door Media’s CEO. He is a twenty+ year digital marketer with a proven track record of revenue & digital fundraising growth. He’s led high-growth change at a wide range of organizations, helping companies ranging from startups to large enterprises.

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