Strategy Stack: Weekly Tech Breakdown
👥 Featuring:
Guest: Mike Goitein, Product Strategist, IT Consultant, and Substack Writer
Host: Alex (The Strategy Stack)
Key Topics Covered
Mike shared his unique journey from tennis strategy blogging in the '90s to leading IT and product strategy at major organizations like KeyBank.
Highlighted Linear as a modern "Jira killer," designed with elegance and deep UX empathy. Emphasized product decisions that favor unscalable, user-first experiences over A/B testing and ML-based feature optimization.
AI will be increasingly embedded into tools like OS interfaces and workflow systems—less as a standalone novelty, more as invisible infrastructure (citing Steve Jobs’ view of Dropbox).
Stressed that LLMs are only as good as the past data they were trained on. Strategy and product sense remain uniquely human and indispensable.
Envisioned a future where AI agents reduce noise and increase user efficiency by thinning the web—eliminating the clutter of 50 open tabs with personalized agent orchestration.
Cautioned that generative AI can empower small teams but doesn’t inherently elevate quality. The core challenge remains: are we solving the right problems, for the right people?
Discussed the shift from traditional capitalism to “cloud capitalism” where value flows through invisible infrastructures controlled by platforms like Apple and Google.
Compared the tech industry to “playing tennis without a net.” Advocated for balanced governance to maintain fair innovation, especially in highly regulated industries like finance and healthcare.
Strategy and product success hinge on what you choose not to do. Quoting Agassi’s late-career precision, Mike noted that great outcomes come from clear constraints and thoughtful subtraction.
Praised Substack as an algorithm-free, open platform that supports genuine discourse and thoughtful publishing. Cited his journey under the mentorship of Tim Denning.
💡 Takeaways
From Alex:
The future belongs to tools and systems that remove friction—especially in an age of digital overload.
Agentic AI may reintroduce healthy abstraction between humans and overwhelming digital interfaces.
Advocated for nuanced, geopolitical awareness in product development, particularly around tech sovereignty and global innovation equity.
From Mike:
Strategy is the master skill in a world where AI can build, code, and write. The remaining human edge is knowing what to build and why.
Linear’s approach—unscalable, beautifully crafted, human-first—shows the power of thoughtful product design over hyper-optimization.
Subtraction is the soul of great storytelling and product creation. It’s not about adding more; it’s about making the right strategic tradeoffs.
Vibe coding and AI-powered prototyping lower technical barriers, enabling more builders—but don't replace the need for critical thinking and narrative clarity.
Technological abundance doesn’t equal excellence. Great strategy still starts with sharp, essential questions.
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