Margin of Signal: June 8, 2025
Issue #1 | Where AI meets enterprise reality
Welcome to Margin of Signal
A weekly curation of the highest-quality content across investing, business, tech, and AI.
In a world flooded with AI-generated clickbait and endless noise, my mission is simple: cut through the clutter and deliver only the insights worth your time.
Think of this as your personal filter—I'll sift through the endless stream of content so you don't have to.
This series serves a dual purpose.
Selfishly, it forces me to stay organized and document my reading and research in one place.
More importantly, it's built on a core belief: while AI can instantly answer any question, the real power lies in compounding knowledge. Each week, I'll share resources rich with context, frameworks, and ideas that layer into your mental models.
The goal isn't just information. It's insights that compound.
You won't find generic stock picks here.
Instead, expect deep dives, contrarian perspectives, and the kind of signal that shapes how you think about business, technology, and markets.
🔍 The Definitive AI State of Play
Mary Meeker’s Artificial Intelligence Trends Report 2025
After a six-year hiatus, Meeker returns with what might be the most comprehensive analysis of AI's current landscape. This isn't another breathless AI hype piece. It's 300+ pages of data-driven insights on where we actually stand.
The report covers everything from compute infrastructure to enterprise adoption patterns, with the kind of rigorous analysis that made her Internet Trends reports legendary. Her charts cut through the hype, spotlighting where real dollars and R&D are converging—and what that means for next-gen winners.
Essential reading for anyone seeking to separate AI reality from the rhetoric. Here’s a great summary for folks short on time.
🎧 Inside the Mind of a Tech Titan
Steve Ballmer on Acquired Podcast
Ballmer unpacks his Microsoft years, the Clippers acquisition, and his contrarian views on tech's future. Fascinating insights from someone who's been in the room where billion-dollar decisions get made.
What struck me most were his presentation slides on the Microsoft days—it's funny how communications from the most successful leaders are always so simple.
No buzzwords, no fluff, just clear thinking distilled into actionable points.
📈 Beyond the Obvious: Second-Order Investment Thinking
Investing in Second-Order Effects - Morgan Stanley
While everyone's chasing first-order AI plays, the real alpha might be in the ripple effects. This piece explores how to identify and invest in the less obvious beneficiaries of major technological shifts.
The framework applies beyond just AI—think about how the iPhone created new winners in everything from mobile payment processors to rideshare companies.
📊 The Data Revolution's Next Chapter
Data Rules Everything Around Me (Matt Slotnick on Substack)
A deep dive into how enterprise software is evolving and why the next wave of SaaS applications will look nothing like the last. Slotnick argues that data and agents, not traditional UIs, will define the next generation of enterprise applications.
This shift dramatically increases the total work an organization can perform without a proportional increase in headcount
The author breaks down why a new “agentic” layer is emerging atop existing software stacks.
This piece changed how I think about the entire B2B tech landscape.
🎙️ Venture Capital's Reality Check
How the Smartest Founders Are Quietly Winning with AI - My First Million & Jason Lemkin (SaaStr)
A refreshingly candid discussion about what's actually happening in venture capital, beyond the headlines and LinkedIn theater. The conversation cuts through the usual VC posturing to discuss deal flow reality, AI startup valuations, and what's really working.
Key takeaway: AI agents—paired with human-in-the-loop feedback—are reshaping every facet of software, talent, and venture investing.
💡 Under-the-Radar SaaS Deep Dive
Kneat Analysis (Two-Part Series) - Capital Light Substack
An excellent analysis of an under-the-radar SaaS company with compelling unit economics.
This is how you research small-caps—thorough, skeptical, and actionable. The author digs deep into customer concentration risk, competitive moats, management quality, and valuation.
Full disclosure: I own Kneat shares.
🌏 Macro Meets Tech
China, AI Immigration, Rare Earths & Chips - BG2 w/ Bill Gurley & Brad Gerstner
A wide-ranging discussion covering the intersection of geopolitics and technology.
Gurley and Gerstner explore how trade tensions, immigration policy, and supply chain dynamics are reshaping the global tech landscape.
🏢 OpenAI's Enterprise Pivot
OpenAI's Strategic Shift Toward Enterprise (The Change Constant Substack)
OpenAI's recent moves signal a major strategic shift toward enterprise sales.
Enterprise-first feature launches
Rapid enterprise adoption
Building a moat through context and MCP support + Deep Research connectors
Vision: ChatGPT as the universal workflow surface
This analysis connects the dots on their pivot and what it means for the competitive landscape.
The single most important insight is that the real battleground—and future source of monopoly-level value—is the “agentic” orchestration layer: the software that seamlessly integrates data sources, AI agents, and human-in-the-loop workflows into a unified, context-aware interface.
If context and workflow integration become the core moats, are we moving toward a winner-take-most market where one or two orchestration platforms capture the lion’s share of enterprise AI value?
Context worth reading: a16z's services-led growth framework explaining why the Forward Deployed Engineer is the hottest job in startups and this insightful thread on the implications.
Connecting the Dots
Notice the thread running through this week's picks?
Meeker's data shows unprecedented AI adoption, while Slotnick explains why the next wave won't be traditional UIs but agentic layers.
OpenAI's enterprise pivot is the real-world execution of this shift. They're not just selling AI models, they're positioning to own the orchestration layer that Slotnick predicts will define enterprise software.
Meanwhile, the VC conversation reveals investors are finally catching on: the value isn't in the AI models themselves, but in the companies that can seamlessly integrate AI agents with human workflows. This is exactly the "second-order effect" that Morgan Stanley piece warns us to watch for.
The compounding insight?
We're not just seeing AI adoption—we're watching the birth of an entirely new software category.
Shouts to ChatGPT and Claude for research and editing help.
That’s a wrap for Issue #1. We’ll be back in your inbox next Sunday with another Margin of Signal.
Thanks for reading,
Chima