Stop Drowning in AI Pilots: Start Prototyping, Collaborating, and Scaling

Fred Grinstein & Kate Cook on creative ideation, Sean Wood's micro-change formula, The Grin Labs on finally escaping pilot purgatory, and Hiten Shah from Dropbox on AI beyond chat.

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This week, we're tackling creative chaos, marketing workflows, AI adoption anxiety, and pilot purgatory head-on. 

  • Fred Grinstein shows us how "GenJam" sessions turn weeks of creative effort into rapid-fire prototyping. 

  • Kate Cook demonstrates why truly transformative AI marketing demands deeper collaboration, not just automation. 

  • Sean Wood breaks down how small, manageable "micro-changes" quickly boost AI adoption and reduce team anxiety. 

  • Carl Miller and Marco Crolla give us practical strategies to escape pilot purgatory, ensuring every AI experiment drives measurable outcomes. 

  • Plus, inspired by a timely provocation from Dropbox's Hiten Shah, we wonder what comes next beyond traditional AI chat interfaces.

  • Also, don’t miss your chance to join our upcoming Just Curious Agency Symposium. Details below!

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🧭 The Just Curious Agency Symposium: A Hands-On AI Workshop

In early July, we’re planning a small-group, half-day virtual symposium for 12-15 agency leaders who want to understand—not just imagine—how AI can create real business value. Instead of panels or keynotes, you’ll join a select group of peers for hands-on working sessions led by 4–6 Just Curious AI experts. Each expert brings deep experience in applying AI to real agency challenges across operations, client management, finance, strategy, and creative.

We are currently designing the program with our experts and will start to market this next week. Want in?

Just reply with “Agency Symposium” and we’ll add you to the early invite list.

🎙 AI Expert of the Week: Fred Grinstein

Co-Founder, Machine Cinema

Fred Grinstein has shaped storytelling strategies at leading media brands, expertly blending traditional creativity with emerging technologies like AI and synthetic media. While Fred primarily advises creative companies and teams on AI adoption, his insights offer valuable adjacent learnings that businesses across industries can apply to enhance their own creative and strategic practices. 

In our conversation, Fred shared actionable strategies on rapidly prototyping new ideas, leveraging AI for creative acceleration, and significantly reducing time from ideation to execution.

🔥 Why Fred's Perspective Matters

"These events become this amazing way to just toss people into the pool, bump around, almost drown, grab the wall, be okay, and that's how you start to look around and see how we do this thing that we call storytelling with AI."

If your team feels creatively stuck or wants to significantly accelerate content development, Fred’s practical approach is a game-changer. His GenJam framework makes AI tangible and immediately useful, specifically for:

  • Creative and marketing teams looking to enhance their ideation and prototyping speed.

  • Content creators and producers eager to explore innovative storytelling methods.

  • Business leaders and entrepreneurs who want practical ways to boost creative productivity.

Fred emphasizes hands-on collaboration, using AI not to replace creativity but to amplify human ingenuity and accelerate creative processes. 

📺 Watch & Learn

🧠 5 Key Takeaways from Fred

  1. Rapid prototyping is your secret weapon.  Fred uses AI tools to quickly prototype multiple ideas, discarding weaker ones early and refining the strongest concepts immediately.

  2. Combine AI tools for maximum impact. Creative breakthroughs happen when tools for ideation, visuals, audio generation, and editing are seamlessly integrated into a unified workflow.

  3. Learning AI is like learning to swim. Fred describes "GenJams" as "pool parties," encouraging teams to dive directly into practical AI experimentation, rapidly learning through real-world use.

  4. Innovation thrives through hands-on collaboration. Events like GenJams provide environments where diverse teams experiment with AI in real-time, learning from peers in an interactive, engaging setting.

  5. Accelerate your creative decision-making. Reducing the ideation-to-approval process from weeks to hours allows creative teams to experiment more freely and discover superior ideas faster.

Fred’s method clearly demonstrates that thoughtful application of AI tools can dramatically improve creativity, efficiency, and innovation, particularly valuable to SMBs and creative teams aiming to enhance their content development capabilities.

🎥 From the Vault: 3 AI Conversations to Accelerate Your Business

This week, we're highlighting three conversations filled with practical insights for SMB leaders who want to unlock real business impact with AI:

  • Kate Cook on integrating AI into marketing workflows for higher creativity and measurable results.

  • Sean Wood on why micro-change management is key to overcoming resistance and scaling AI adoption.

  • Carl Miller on escaping pilot purgatory and driving real business outcomes through strategic alignment and governance.

Each offers tactical lessons and clear next steps—ready to apply today.

🚀 Transform Marketing with AI Workflows

Kate Cook, Founder, Era Seven Partners

Kate explains why successful AI marketing initiatives require more than just new tools—they demand a shift in mindset. Companies that treat AI as a collaborative partner rather than simply automation see dramatically improved creativity and campaign performance.

Key Lessons:

  • Effective AI use demands building new "muscle memory" around human-AI collaboration.

  • AI workflows succeed when integrated into existing creative processes, not as standalone tools.

  • Real marketing impact comes from using AI for better, data-driven insights, not just automation.

Recommended Action:
Start small—use AI to quickly prototype new creative concepts, gaining buy-in by clearly demonstrating measurable impact from initial efforts.

🛠 An Introduction to Micro Change Management

Sean Wood, Founder, Human Pilots AI

Sean outlines a practical roadmap for introducing AI into your organization through micro-change management. By breaking AI adoption into small, incremental steps, organizations see higher engagement, reduced anxiety, and faster achievement of meaningful results.

Key Lessons:

  • Successful AI adoption starts with small, manageable "micro-changes."

  • Incremental wins create momentum and reduce employee resistance.

  • Clearly communicate these small wins throughout your organization, reinforcing their immediate value and building a positive AI culture.

Recommended Action:
Begin immediately with low-risk, high-value micro-changes (e.g., AI-driven meeting transcriptions), reinforcing early wins to build organizational confidence.

🌟 Escaping AI Pilot Purgatory: How to Achieve Real Business Impact

Carl Miller, Head of AI, & Marco Crolla, Co-Founder, The Grin Labs

Carl & Marco highlight why many organizations fail to scale beyond initial AI experiments and provide a clear strategy for achieving measurable, lasting business outcomes. AI success requires alignment with company goals, clear governance, and strong executive leadership.

Key Lessons:

  • Avoid AI stagnation by aligning pilot projects with measurable business objectives from day one.

  • Executive buy-in and transparent communication are essential for widespread AI adoption.

  • Build practical governance frameworks that allow for ongoing evaluation and iterative improvement.

  • Establish ongoing evaluation checkpoints to continually refine and adapt your AI strategy based on early results.

Recommended Action:
Prioritize AI projects with clear, immediate links to strategic business goals, ensuring visible and quantifiable outcomes from early stages.

✨ Based on conversations with: Fred, Kate, Sean, Carl, & Marco

🧠 Key Lessons for SMB Leaders

Here’s what stood out across conversations with Fred Grinstein, Kate Cook, Sean Wood, and Carl Miller. These fresh insights help SMBs practically apply AI to accelerate creativity, enhance marketing, and improve change management.

AI dramatically accelerates creative prototyping.
Integrating rapid prototyping with AI turns traditional, slow ideation into quick, iterative innovation.
Fred Grinstein, Co-founder, Machine Cinema

AI transforms marketing collaboration, not just automation.
Teams achieve breakthrough results when AI is treated as a true co-creator, reshaping workflows and creativity.
Kate Cook, Founder, Era Seven Partners

Micro-changes are key to rapid AI adoption.
Implementing small, incremental changes significantly reduces employee anxiety and accelerates sustainable adoption.
Sean Wood, Founder, Human Pilots AI

Effective AI governance is lightweight and flexible.
Clear yet adaptable governance structures link AI initiatives to measurable outcomes, fostering real, continuous innovation.
Carl Miller & Marco Crolla, The Grin Labs

These aren’t big bets, they’re actionable, practical next steps. SMB leaders can quickly apply these ideas to validate, scale, and integrate AI.

Rethink creativity, don't just automate it.
Use AI to completely redesign how your team approaches marketing workflows, shifting from task automation to creative collaboration.
Kate Cook, Founder, Era Seven Partners

Start small, validate fast.
Use quick wins like AI-generated content drafts or automated meeting notes to quickly prove value and build team confidence.
Sean Wood, Founder, Human Pilots AI

Make prototyping a daily habit.
Incorporate rapid, low-risk AI-driven creative tests into daily processes to accelerate decision-making and idea refinement.
Fred Grinstein, Co-founder, Machine Cinema

Establish clear, flexible AI governance.
Set up governance that's easy to follow, links clearly to business goals, and encourages—not hinders—innovation.
Carl Miller & Marco Crolla, The Grin Labs

🔍 My Favorite Things Last Week

As you’ll hear in my future interview with Amir Ouki of BOI, the chat interface of ChatGPT, Claude, etc, is both a blessing and a curse. I’m super interested in how we can break out of that form factor and explore the ways in which generative and agentic ai can be used to enable new experiences and value. 

This tweet from Hiten Shah, Head of AI Products @ Dropbox, is a great provocation.

🚀 Next Week: I’ll See You Here.

Curiosity is the spark. But momentum comes from small, strategic moves.

See you next week,

 - Stu

Ps. Please forward this to anyone curious about AI!