Strategy Stack: Weekly Tech Breakdown
👥 Featuring:
Guest: Kieron, Strategic Consultant, Substack Writer, and Creative Technologist
Host: Alex (The Strategy Stack)
Key Topics Covered
Kieron shared his journey from working at legendary creative agencies (like Wieden+Kennedy and Chiat\Day) to launching his Substack and consulting practice “Can’t Copy That Strategy,” focused on building uncopyable strategic positions.
Discussed the role of strategic subtraction—what you choose not to do—as a foundational lens. Shared his technique of “trajectory analysis” using image-based visualization to define where a company is today vs. its desired future.
Highlighted the shift from homepage-era “read-only” web (Web 1.0) to today’s delegated and agentic AI tools. Noted that despite tech changes, strategic fundamentals (values, clarity, constraints) haven’t changed.
Critiqued current AI tools for limitations rooted in their training on past data and their tendency to hallucinate or misrepresent. Reinforced that strategic thinking and storytelling are still uniquely human competencies.
Envisioned a near future where AI becomes an invisible collaborator—thinning the web, orchestrating tabs, and helping users navigate abstraction. Emphasized visual thinking as critical to strategy.
Warned that generative AI democratizes creation but doesn’t guarantee quality. It can widen the gap between those with strategic clarity and those overwhelmed by tools. Critical thinking remains a core differentiator.
Explored societal transitions, including the diminishing role of traditional “newsletters,” the problem of content remix culture, and Substack’s potential as a platform for original thinking beyond the algorithmic traps.
Spoke about how future employment models may shift toward decentralized, AI-augmented “value collectives” and DAOs. Recognized that tools can either empower or disorient people, depending on their ability to ask the right questions.
Argued for geopolitical and ecological awareness in product and energy innovation. Cited how combustion engines still power the world—and will continue to for decades—despite the EV push. Warned against media timelines disconnected from real infrastructure constraints.
💡 Takeaways
From Alex:
Strategy isn’t about predicting the future—it's about making clear choices in the present.
Visualization, not optimization, may become the most critical skill for the strategist.
In a world of overwhelming signals, agentic AI will enable a return to human connection and purposeful decision-making.
From Mike:
Good strategy = choice + sacrifice. Running toward hard decisions creates clarity.
Visualization unlocks strategic insight—image-based trajectory analysis helps teams align fast.
Vibe coding and AI tooling empower more creators, but can’t replace the need for narrative precision.
Substack enables authentic discourse outside social media’s algorithmic traps. Writing about strategy—not just how to write—is where real value lives.
Industrial and ecological shifts (like EVs vs. combustion) require realism. You can't replace an engine while the car is moving 120 mph.
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