<?xml version="1.0" encoding="utf-8"?><feed xmlns="http://www.w3.org/2005/Atom" ><generator uri="https://jekyllrb.com/" version="3.10.0">Jekyll</generator><link href="https://kcalhoon.github.io/feed.xml" rel="self" type="application/atom+xml" /><link href="https://kcalhoon.github.io/" rel="alternate" type="text/html" /><updated>2026-03-19T12:08:04-07:00</updated><id>https://kcalhoon.github.io/feed.xml</id><title type="html">Ken Calhoon’s AI Blog</title><subtitle>Exploring AI, data science, and their real-world applications with occasional diversions.</subtitle><author><name>Ken Calhoon</name></author><entry><title type="html">Privacy &amp;amp; Security: The Real AI Enterprise Unlock</title><link href="https://kcalhoon.github.io/article/newsletter-march-2026/" rel="alternate" type="text/html" title="Privacy &amp;amp; Security: The Real AI Enterprise Unlock" /><published>2026-03-18T17:00:00-07:00</published><updated>2026-03-18T17:00:00-07:00</updated><id>https://kcalhoon.github.io/article/newsletter-march-2026</id><content type="html" xml:base="https://kcalhoon.github.io/article/newsletter-march-2026/"><![CDATA[<p><img src="/assets/images/article-security-ecosystem-20260319/ai-ecosystem-safety-lynchpin.png" alt="Privacy and Security: The AI Ecosystem Lynchpin" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Gemini
</p>

<p>The potential of AI has enterprises and hyperscalers alike racing to capture value — but the real unlock isn’t the technology. It’s solving privacy and security. Here’s the storyline in a few charts.</p>

<hr />

<p><strong>Hyperscalers are placing a $650B bet on AI infrastructure — and they need enterprise demand to justify it.</strong> The investment in AI compute and infrastructure is historic. The return depends on enterprises moving from experimentation to production at scale. <a href="https://www.ben-evans.com/" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/ben-evans-ai-investment.png" alt="Hyperscaler AI Investment" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Ben Evans
</p>

<hr />

<p><strong>But there is a significant gap between that massive infrastructure spend and actual enterprise AI spending, which sits at just $37B in 2025.</strong> The infrastructure is being built. Enterprise adoption is growing fast, but it pales in comparison to the infrastructure investment. Closing that gap is the central challenge for the AI ecosystem. <a href="https://menlovc.com/perspective/2025-the-state-of-generative-ai-in-the-enterprise/" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/menlo_ai_spending.png" alt="Enterprise AI Spending Gap" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Menlo Ventures
</p>

<hr />

<p><strong>Companies are seeing real ROI from AI — but it’s concentrated in a narrow set of use cases.</strong> The value is there. The opportunity is to expand it across a wider range of high-impact business problems. <a href="https://a16z.com/leaders-gainers-and-unexpected-winners-in-the-enterprise-ai-arms-race/" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/a16z-ai-roi.png" alt="AI ROI Today" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: a16z
</p>

<hr />

<p><strong>The key to unlocking broader ROI is automation — not just AI assistance, but redesigning how work gets done.</strong> High-performing AI implementers are much more likely to be redesigning workflows, including automation. <a href="https://www.mckinsey.com/capabilities/quantumblack/our-insights/the-state-of-ai" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/mckinsey-scaling-ai.png" alt="McKinsey: Scaling AI Through Automation" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: McKinsey
</p>

<hr />

<p><strong>Smart automation requires agents — and enterprise adoption is already accelerating rapidly.</strong> AI agents operate with increasing autonomy, executing multi-step tasks across systems. The question is no longer whether enterprises will use agents, but how fast. <a href="https://learn.g2.com/enterprise-ai-agents-report" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/g2-AI-agents-autonomy-levels.png" alt="G2: AI Agent Autonomy Levels" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: G2
</p>

<hr />

<p><strong>However, agents introduce a new category of risk that most organizations are not prepared for.</strong> AI tools are deployed in 73% of organizations, but real-time governance covers only 7%. Only 9% of organizations can intervene before an agent completes an action. <a href="https://www.cybersecurity-insiders.com/ai-risk-and-readiness-report-2026/" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/cyber-security-insider-readiness-runtime.png" alt="Cybersecurity Insiders: AI Governance vs. Deployment Gap" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Cybersecurity Insiders
</p>

<hr />

<p><strong>The result: data security and privacy is now the #1 concern for executives — and one of the few concerns that is still growing in importance.</strong> This is not a theoretical risk. It is the primary barrier between where enterprises are today and where they need to go. <a href="https://www.bain.com/insights/executive-survey-ai-moves-from-pilots-to-production/" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/bain-pilots-to-production-safety-concern.png" alt="Bain: Safety Concerns in AI Pilots to Production" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Bain &amp; Company
</p>

<hr />

<p><strong>The companies that solve this become the ones that win.</strong> PwC finds that 58% of executives report improved AI ROI from responsible AI programs, and organizations with mature governance are significantly more likely to rate their AI capabilities as effective. <a href="https://www.pwc.com/us/en/tech-effect/ai-analytics/responsible-ai-survey.html" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/article-security-ecosystem-20260319/pwc-impact-responsible-ai.png" alt="PwC: Impact of Responsible AI" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: PwC
</p>

<hr />

<p>Privacy and security aren’t the brakes on AI progress. They’re the accelerant. A comprehensive governance approach integrated with run-time security is what turns AI ambition into durable enterprise value.</p>]]></content><author><name>Ken Calhoon</name></author><category term="article" /><category term="enterprise" /><category term="security" /><category term="governance" /><category term="agents" /><category term="infrastructure" /><category term="ROI" /><category term="McKinsey" /><category term="Bain" /><category term="Menlo Ventures" /><category term="Andreessen Horowitz" /><category term="hyperscalers" /><category term="risk" /><category term="workflow" /><category term="adoption" /><category term="PwC" /><category term="Cybersecurity Insiders" /><summary type="html"><![CDATA[]]></summary></entry><entry><title type="html">The $650B Build-It-and-They-Will-Come Moment in AI</title><link href="https://kcalhoon.github.io/newsletter/newsletter-march-2026/" rel="alternate" type="text/html" title="The $650B Build-It-and-They-Will-Come Moment in AI" /><published>2026-03-12T05:00:00-07:00</published><updated>2026-03-12T05:00:00-07:00</updated><id>https://kcalhoon.github.io/newsletter/newsletter-march-2026</id><content type="html" xml:base="https://kcalhoon.github.io/newsletter/newsletter-march-2026/"><![CDATA[<p><img src="/assets/images/newsletter-2026-03/2026-03-newletter-field-dreams.png" alt="&quot;Field of Dreams&quot;" style="border: 1px solid #2E8B57; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Gemini
</p>

<h2 id="hyperscalers-make-big-bets-on-supply--and-big-waves-driving-demand">Hyperscalers make big bets on supply — and big waves driving demand</h2>

<p>According to Bridgewater, Big Tech hyperscalers plan a massive $650 billion AI infrastructure investment in 2026. Yet Menlo Ventures reports 2025 enterprise AI spending hit just $37 billion. That gap suggests suppliers expect a major surge in AI service spending. Or it’s just FOMO. Or both. <a href="https://www.reuters.com/business/big-tech-invest-about-650-billion-ai-2026-bridgewater-says-2026-02-23/" target="_blank" rel="noopener noreferrer">Reuters</a> <a href="https://menlovc.com/perspective/2025-the-state-of-generative-ai-in-the-enterprise/" target="_blank" rel="noopener noreferrer">Menlo Ventures</a></p>

<p><img src="/assets/images/newsletter-2026-03/ben-evans-ai-investment.png" alt="&quot;AI Capex&quot;" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Ben Evans
</p>

<p>To spur demand, Microsoft announced Copilot Cowork — an agentic application built with Anthropic’s help to automate non-engineering workflows. The agent executes plans in the background using Microsoft 365 data from Outlook, Teams, and SharePoint, while operating within enterprise security, privacy, and governance boundaries. <a href="https://www.microsoft.com/en-us/microsoft-365/blog/2026/03/09/copilot-cowork-a-new-way-of-getting-work-done/" target="_blank" rel="noopener noreferrer">link</a></p>

<p>The demand equation extends beyond direct enterprise implementations. Alphabet reported Google Search revenue grew 17% year-over-year to $63 billion, driven by AI Mode queries that have doubled since launch and run three times longer than conventional searches — creating new ad inventory as AI reshapes how people seek information. <a href="https://www.searchenginejournal.com/google-search-hits-63b-details-ai-mode-ad-tests/566613/" target="_blank" rel="noopener noreferrer">link</a></p>

<h2 id="security-moves-to-center-stage">Security moves to center stage</h2>

<p>That wave of new hyperscaler AI tools has already rattled markets. Announcements of Claude Code Security, Google CodeMender, and OpenAI Aardvark triggered a cybersecurity stock selloff — what Forrester called a “SaaS-pocalypse.” The anxiety isn’t unfounded: Google reports only 27% of security leaders feel equipped to secure applications against autonomous, agent-driven coding. <a href="https://www.forrester.com/blogs/claude-code-security-causes-a-saas-pocalypse-in-cybersecurity" target="_blank" rel="noopener noreferrer">Forrester</a> <a href="https://storage.ghost.io/c/44/95/449506ca-034e-480f-9725-fcde08ef1cc1/content/files/2026/02/The-state-of-AI-Security-and-Governance.pdf" target="_blank" rel="noopener noreferrer">report</a></p>

<p><img src="/assets/images/newsletter-2026-03/forrester-cybersecurity-stock-hit.png" alt="&quot;Forrester Cybersecurity Stock Hit&quot;" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Forrester Research
</p>

<p>The OpenClaw craze illustrates the stakes. The unleashed local agent sold out Mac Minis and racked up massive downloads — but also wiped a security researcher’s inbox against her explicit instructions. OpenAI has since hired founder Peter Steinberger to build next-gen personal agents, while transitioning OpenClaw to a foundation-supported open-source project. <a href="https://x.com/sama/status/2023150230905159801" target="_blank" rel="noopener noreferrer">X</a> <a href="https://blogs.cisco.com/ai/personal-ai-agents-like-openclaw-are-a-security-nightmare" target="_blank" rel="noopener noreferrer">Cisco</a></p>

<p><img src="/assets/images/newsletter-2026-03/stop-openclaw.jpg" alt="&quot;Stop OpenClaw&quot;" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Summer Yue/Simon Willison
</p>

<h2 id="the-tide-seems-to-be-rising">The tide seems to be rising</h2>

<p>The ROI picture remains murky. An Andreessen Horowitz survey finds enterprise AI returns mostly hovering between 1x (breakeven) and 1.5x — solid if not spectacular. <a href="https://a16z.com/leaders-gainers-and-unexpected-winners-in-the-enterprise-ai-arms-race" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-03/a16z-ai-roi.png" alt="&quot;a16z Enterprise AI ROI&quot;" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Andreessen Horowitz
</p>

<p>An NBER study of 6,000 global executives confirms the pattern: little AI impact to date, though firms predict three-year gains in productivity (1.4%) and output (0.8%), paired with a 0.7% employment drop. Employees are more optimistic, expecting a 0.5% employment boost. Notably, CEOs use AI more than the rest of the C-suite. <a href="https://www.nber.org/system/files/working_papers/w34836/w34836.pdf" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-03/NBER-ai-use-type.png" alt="&quot;NBER AI Use by Application&quot;" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: NBER
</p>

<p>To drive results, Google developed a KPI framework for production AI agents spanning operational reliability, adoption, and business value. Gartner adds five board-ready metrics — sales conversion rates, labor costs, time to value, collection efficiency, and employee NPS — to make the ROI case stick. <a href="https://cloud.google.com/transform/the-kpis-that-actually-matter-for-production-ai-agents" target="_blank" rel="noopener noreferrer">Google</a> <a href="https://www.gartner.com/en/articles/ai-value-metrics" target="_blank" rel="noopener noreferrer">Gartner</a></p>

<h2 id="wrestling-with-productivity">Wrestling with productivity</h2>

<p>Harvard Business Review reports that AI is intensifying work, not reducing it. Workers using AI tackle a broader range of tasks with less downtime and more multitasking. Getting this balance right is critical for both employees and the employers expecting efficiency gains. <a href="https://hbr.org/2026/02/ai-doesnt-reduce-work-it-intensifies-it" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Agency economic models are under pressure to evolve. S4 Capital’s Monks expects 25% of its revenue to be subscription-based by year-end — the logic being that as AI improves productivity, clients receive more output for the same fee rather than fewer billable hours. <a href="https://digiday.com/media-buying/the-billable-hour-does-not-allow-for-any-meaningful-innovation-s4-capital-builds-subscription-model-for-the-ai-age/" target="_blank" rel="noopener noreferrer">link</a></p>

<h2 id="working-on-workforce">Working on workforce</h2>

<p>Bain argues unlocking AI value requires simultaneously redesigning workflows and modernizing workforces. As agents deploy, work shifts from doing to planning and reviewing. The firm also notes that AI failures are often design flaws, not model errors — and perceived AI disruption risk is rising across all industries. <a href="https://www.bain.com/insights/want-more-out-of-your-ai-investments-think-people-first" target="_blank" rel="noopener noreferrer">link</a> <a href="https://www.bain.com/insights/executive-survey-ai-moves-from-pilots-to-production/" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-03/bain-workforce-workflow-modernization.png" alt="&quot;Bain Workforce and Workflow Modernization&quot;" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Bain
</p>

<p>Block is cutting 40% of its workforce and attributing it to AI. Wary observers suspect it’s mostly right-sizing after the company doubled its headcount between 2020 and 2024. Both can be true. <a href="https://x.com/jack/status/2027129697092731343" target="_blank" rel="noopener noreferrer">link</a></p>

<h2 id="swings-and-roundabouts">Swings and roundabouts</h2>

<p>Enterprise vendor trust is being tested. Anthropic refused Pentagon demands for unrestricted use of Claude and was blacklisted by the Trump administration. OpenAI signed a similar deal the next day, triggering 1.5 million #QuitGPT cancellations in 48 hours. For enterprise buyers, this raises real questions about vendor alignment. Meanwhile, Anthropic hit a $19B annualized run rate and Claude jumped to #1 on the App Store — the market rendering its own verdict. <a href="https://www.anthropic.com/news/statement-department-of-war" target="_blank" rel="noopener noreferrer">Anthropic</a> <a href="https://www.cnbc.com/2026/02/27/trump-anthropic-ai-pentagon.html" target="_blank" rel="noopener noreferrer">CNBC</a> <a href="https://www.cnbc.com/2026/03/03/openai-sam-altman-pentagon-deal-amended-surveillance-limits.html" target="_blank" rel="noopener noreferrer">CNBC</a> <a href="https://www.euronews.com/next/2026/03/02/cancel-chatgpt-ai-boycott-surges-after-openai-pentagon-military-deal" target="_blank" rel="noopener noreferrer">Euronews</a> <a href="https://finance.yahoo.com/news/anthropic-arr-surges-19-billion-151028403.html" target="_blank" rel="noopener noreferrer">Yahoo Finance</a></p>

<p>OpenAI’s agentic commerce ambitions have hit their own friction. After launching in-app shopping to much fanfare, the company pulled back its “Instant Checkout” feature — scaling down to referral links rather than native transactions. According to Forrester, direct buying within answer engines remains consumers’ least-adopted AI use case. <a href="https://www.forrester.com/blogs/what-it-means-that-the-leader-in-agentic-commerce-just-pulled-back/" target="_blank" rel="noopener noreferrer">link</a></p>]]></content><author><name>Ken Calhoon</name></author><category term="newsletter" /><category term="enterprise" /><category term="ROI" /><category term="agents" /><category term="security" /><category term="productivity" /><category term="labor" /><category term="infrastructure" /><category term="strategic bets" /><category term="economics" /><category term="Anthropic" /><category term="OpenAI" /><category term="Google" /><category term="Microsoft" /><category term="Bain" /><category term="Andreessen Horowitz" /><category term="Forrester" /><category term="Menlo Ventures" /><category term="Benedict Evans" /><category term="S4 Capital" /><category term="SaaS" /><category term="risk" /><category term="hyperscalers" /><category term="workforce" /><category term="NBER" /><summary type="html"><![CDATA[]]></summary></entry><entry><title type="html">AI Pilot Purgatory Is an Orchestration Failure</title><link href="https://kcalhoon.github.io/ai-implementation/production-ai/ai-pilot-purgatory-orchestration/" rel="alternate" type="text/html" title="AI Pilot Purgatory Is an Orchestration Failure" /><published>2026-03-09T02:00:00-07:00</published><updated>2026-03-09T02:00:00-07:00</updated><id>https://kcalhoon.github.io/ai-implementation/production-ai/ai-pilot-purgatory-orchestration</id><content type="html" xml:base="https://kcalhoon.github.io/ai-implementation/production-ai/ai-pilot-purgatory-orchestration/"><![CDATA[<p>Most AI initiatives don’t die in the model. They die in the seams between teams.</p>

<p>I recently helped a client push two AI initiatives into live testing. The technology worked. What almost didn’t was the coordination — and the pattern is instructive because it applies broadly.</p>

<p>Getting an AI agent from prototype to production requires four parties in tight lockstep: <strong>domain experts</strong> making decisions on critical functionality, <strong>IT</strong> enabling data access and services, <strong>AI developers</strong> tuning agent accuracy and usability, and <strong>program management</strong> keeping everything synchronized. Remove any one from the cadence and progress fragments — not from a technical failure, but a coordination one.</p>

<p>What kept these two initiatives moving:</p>

<ol>
  <li><strong>Weekly status focused on achievement, not problem-solving.</strong> Every party in the room, every week. Keep it tight; surface blockers and route them, don’t analyze them.</li>
  <li><strong>Active interim follow-up.</strong> Four interdependent teams can’t afford to wait until next week. Gaps compound fast.</li>
  <li><strong>Disciplined scope.</strong> Generative AI invites endless “what if” conversations. Aspirations go in the backlog. Phase deliverables stay fixed.</li>
  <li><strong>Time-bound accountability.</strong> Every deliverable has an owner and a date. No ambiguity about who owes what by when.</li>
</ol>

<p>None of this is new. It is the same discipline that gets any cross-functional initiative across the line. But AI amplifies the coordination cost because the work spans domains that rarely share a natural operating rhythm — domain experts, IT, and AI developers operate on fundamentally different cadences and modes. That gap doesn’t close on its own.</p>

<p>The organizations shipping AI into production aren’t necessarily the ones with the best models. They’re the ones that treat orchestration as a core competency.</p>]]></content><author><name>Ken Calhoon</name></author><category term="AI-implementation" /><category term="production-AI" /><category term="enterprise" /><category term="implementation" /><category term="leadership" /><category term="agents" /><category term="orchestration" /><category term="program-management" /><summary type="html"><![CDATA[Most AI initiatives don’t die in the model. They die in the seams between teams.]]></summary></entry><entry><title type="html">AI Is Graduating from Pilots to Production — and the Data Shows What Separates Leaders</title><link href="https://kcalhoon.github.io/ai-strategy/production-ai/ai-pilots-to-production-bain/" rel="alternate" type="text/html" title="AI Is Graduating from Pilots to Production — and the Data Shows What Separates Leaders" /><published>2026-03-04T01:00:00-08:00</published><updated>2026-03-04T01:00:00-08:00</updated><id>https://kcalhoon.github.io/ai-strategy/production-ai/ai-pilots-to-production-bain</id><content type="html" xml:base="https://kcalhoon.github.io/ai-strategy/production-ai/ai-pilots-to-production-bain/"><![CDATA[<p>Bain’s longitudinal AI executive survey found that 80% of generative AI use cases met or exceeded expectations — yet only 23% of companies can tie those initiatives to measurable revenue gains or cost reductions. That gap defines the current moment.</p>

<p><img src="/assets/images/bain-combined-function-concerns.jpg" alt="&quot;AI pilot to production trends across business domains&quot;" style="border: 1px solid #2E8B57;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Bain
</p>

<p>The broader shift is accelerating: 74% of firms now rank AI a top-three strategic priority, up from 60% a year prior. Software development leads production scaling at 40%, customer service at 32%. In my client work, I see the same compounding dynamic — capabilities built for one function, say knowledge retrieval or invoice processing, transfer to others at lower cost and risk. Scale breeds scale.</p>

<p>Satisfaction rises sharply as companies move from AI-as-assistant to agentic workflow automation. Bain found respondents using agentic approaches were twice as likely to report results exceeding goals. But the risk profile shifts with it: security and privacy concerns climbed from 38% to 45% year-over-year, spiking to 49% among companies in production versus 35% still piloting. Automation unlocks the upside — it also demands tighter governance.</p>

<p>When use cases disappoint, the model is rarely the problem. Bain found a third of failures scaled poorly because designs didn’t accommodate real-world data and workflow complexity. Capturing those intricacies upfront — through shadow deployment and gradual rollout — separates durable production from a stalled pilot.</p>

<p>Leading firms share a common posture: defined vision, prioritized use case list, dedicated investment, and an iterative roadmap. Bain found 55% of leaders have all four in place, versus 40% of laggards who lack even a defined vision. The discipline isn’t just planning — it’s maintaining focus on shipping current initiatives while systematically identifying the next wave. That compounding effect is where the real ROI emerges.</p>

<p><a href="https://www.bain.com/insights/executive-survey-ai-moves-from-pilots-to-production/" target="_blank" rel="noopener noreferrer">Bain: Executive Survey — AI Moves from Pilots to Production</a></p>]]></content><author><name>Ken Calhoon</name></author><category term="AI-strategy" /><category term="production-AI" /><category term="Bain" /><category term="ROI" /><category term="security" /><category term="governance" /><category term="CAIO" /><category term="agents" /><category term="adoption" /><summary type="html"><![CDATA[Bain’s longitudinal AI executive survey found that 80% of generative AI use cases met or exceeded expectations — yet only 23% of companies can tie those initiatives to measurable revenue gains or cost reductions. That gap defines the current moment.]]></summary></entry><entry><title type="html">Golden Evaluation Sets: Enterprise AI’s Missing Feedback Loop</title><link href="https://kcalhoon.github.io/ai-implementation/production-ai/golden-evals-enterprise-speed/" rel="alternate" type="text/html" title="Golden Evaluation Sets: Enterprise AI’s Missing Feedback Loop" /><published>2026-03-04T01:00:00-08:00</published><updated>2026-03-04T01:00:00-08:00</updated><id>https://kcalhoon.github.io/ai-implementation/production-ai/golden-evals-enterprise-speed</id><content type="html" xml:base="https://kcalhoon.github.io/ai-implementation/production-ai/golden-evals-enterprise-speed/"><![CDATA[<p>AI moves fastest in software engineering for a structural reason: the model tests its own output instantly. Write code, run it, see if it breaks, iterate in seconds. The feedback loop is nearly frictionless.</p>

<p><img src="/assets/images/eval-set-image-speed.png" alt="Slow feedback loop" style="border: 1px solid #2E8B57;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Ken Calhoon
</p>

<p>Now consider what happens when AI moves into knowledge retrieval, invoice matching, or warranty validation. There is no compiler. No automatic pass/fail. The default iteration cycle becomes: developers tweak the system, sample outputs get generated, domain experts review them days later, and the cycle restarts. That loop is brutally slow — and the further AI scales beyond IT, the more consequential this drag becomes.</p>

<p>The fix is a golden evaluation set built before development begins: 50 to 100 examples covering standard flows and realistic edge cases, with expected inputs and desired outputs defined for substance, format, language, and latency. This creates a synthetic feedback loop that replicates the speed advantage coding environments enjoy natively.</p>

<p>The quality benefit is obvious. The speed benefit is routinely overlooked. With automated evaluation in place, developers receive immediate pass/fail signals on every iteration. Refinement cycles compress from days to minutes.</p>

<p>The catch is real: domain experts must invest meaningful time before a single line of code is written. That feels counterintuitive under pressure to start building. But hours of upfront definition save weeks of slow, reactive review cycles. The math is unambiguous.</p>

<p>Leaders should make this a hard prerequisite: no use case enters development without a golden test set and a documented workflow or SOP. The upfront discipline is not a brake on momentum — it is what makes downstream velocity possible.</p>]]></content><author><name>Ken Calhoon</name></author><category term="AI-implementation" /><category term="production-AI" /><category term="evaluation" /><category term="evals" /><category term="implementation" /><category term="workflow" /><summary type="html"><![CDATA[AI moves fastest in software engineering for a structural reason: the model tests its own output instantly. Write code, run it, see if it breaks, iterate in seconds. The feedback loop is nearly frictionless.]]></summary></entry><entry><title type="html">How I Stay on Top of AI: My Curated Podcast and Newsletter Sources</title><link href="https://kcalhoon.github.io/ai-strategy/podcast-newsletter-sources/" rel="alternate" type="text/html" title="How I Stay on Top of AI: My Curated Podcast and Newsletter Sources" /><published>2026-02-24T16:00:00-08:00</published><updated>2026-02-24T16:00:00-08:00</updated><id>https://kcalhoon.github.io/ai-strategy/podcast-newsletter-sources</id><content type="html" xml:base="https://kcalhoon.github.io/ai-strategy/podcast-newsletter-sources/"><![CDATA[<p>I get asked how I stay on top of AI developments. Here’s my 3-step system for tracking AI insights, plus my full curated list of top podcasts and newsletters.</p>

<p>Uncovering insights requires structure, not serendipity. Here is the framework I use to filter the AI ecosystem:</p>

<ul>
  <li><strong>Curate Aggressively:</strong> Limit inputs to high-authority voices.</li>
  <li><strong>Leverage Audio:</strong> Podcasts offer off-the-cuff insights you won’t find in written copy.</li>
  <li><strong>Automate Everything:</strong> I run GitHub Actions to fetch, parse, and email me summaries daily.</li>
</ul>

<p>My top five go-to sources span business strategy, news digests, technical research, and practical application:</p>

<table>
  <thead>
    <tr>
      <th>Source</th>
      <th>Type</th>
      <th>Focus</th>
    </tr>
  </thead>
  <tbody>
    <tr>
      <td><a href="https://stratechery.com/" target="_blank" rel="noopener noreferrer">Stratechery</a></td>
      <td>Newsletter</td>
      <td>Business strategy &amp; tech impact</td>
    </tr>
    <tr>
      <td><a href="https://www.beyondtheprompt.ai" target="_blank" rel="noopener noreferrer">Beyond The Prompt</a></td>
      <td>Podcast</td>
      <td>Enterprise AI strategy</td>
    </tr>
    <tr>
      <td><a href="https://www.ben-evans.com/newsletter" target="_blank" rel="noopener noreferrer">Benedict Evans</a></td>
      <td>Newsletter</td>
      <td>Weekly tech news digest</td>
    </tr>
    <tr>
      <td><a href="https://simonw.substack.com/" target="_blank" rel="noopener noreferrer">Simon Willison’s Newsletter</a></td>
      <td>Newsletter</td>
      <td>AI/LLM practical research</td>
    </tr>
    <tr>
      <td><a href="https://youtube.com/@howiaipodcast?si=3-R-tqSYtSUrEYd-" target="_blank" rel="noopener noreferrer">How I AI</a></td>
      <td>Podcast</td>
      <td>Practical AI workflows</td>
    </tr>
  </tbody>
</table>

<p>The full curated list is below, organized by topic. Sources marked <strong>Featured</strong> are my highest-value picks.</p>

<hr />

<h2 id="ai-news-digests--weekly-roundups">AI News Digests &amp; Weekly Roundups</h2>

<h3 id="featured--benedict-evans"><strong>Featured</strong> — <a href="https://www.ben-evans.com/newsletter" target="_blank" rel="noopener noreferrer">Benedict Evans</a></h3>
<p>Newsletter<br />
Weekly curation and analysis of what happened in tech that mattered.<br />
<strong>Author:</strong> Benedict Evans<br />
<strong>Subscription:</strong> Freemium (free Tuesday edition; $150/yr for premium Sunday edition)</p>
<blockquote>
  <p>If I read one source per week to keep track of trends, this is it. A collection of major happenings, data, etc.</p>
</blockquote>

<hr />

<h3 id="the-batch"><a href="https://www.deeplearning.ai/the-batch/" target="_blank" rel="noopener noreferrer">The Batch</a></h3>
<p>Newsletter<br />
Weekly digest of the most important AI research, industry news, and practical insights.<br />
<strong>Author:</strong> Andrew Ng / DeepLearning.AI<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>Useful weekly digest of major trends across AI.</p>
</blockquote>

<hr />

<h3 id="the-deep-view"><a href="https://www.thedeepview.com/" target="_blank" rel="noopener noreferrer">The Deep View</a></h3>
<p>Newsletter<br />
Tri-weekly summary of the most important AI news, tools, and tips in under 5 minutes.<br />
<strong>Author:</strong> The Deep View<br />
<strong>Subscription:</strong> Free</p>

<hr />

<h3 id="state-of-ai"><a href="https://nathanbenaich.substack.com/" target="_blank" rel="noopener noreferrer">State of AI</a></h3>
<p>Newsletter<br />
Monthly synthesis of key developments in AI, AI markets, and geopolitics plus the annual State of AI Report.<br />
<strong>Author:</strong> Nathan Benaich<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>Investor’s monthly perspective across disciplines, global.</p>
</blockquote>

<hr />

<h2 id="ai-strategy--industry-conversations">AI Strategy &amp; Industry Conversations</h2>

<h3 id="featured--beyond-the-prompt"><strong>Featured</strong> — <a href="https://www.beyondtheprompt.ai" target="_blank" rel="noopener noreferrer">Beyond The Prompt</a></h3>
<p>Podcast<br />
How organizations leverage AI to accelerate success, with creative strategies and actionable tactics.<br />
<strong>Presenters:</strong> Jeremy Utley &amp; Henrik Werdelin</p>
<blockquote>
  <p>Long form, very interesting and wide ranging guests and discussions. Bigger thinking and focus on enterprises, but also some practical tips.</p>
</blockquote>

<hr />

<h3 id="no-priors"><a href="https://linktr.ee/nopriors" target="_blank" rel="noopener noreferrer">No Priors</a></h3>
<p>Podcast<br />
Leading AI engineers, researchers, and founders discuss the biggest questions in AI and technology.<br />
<strong>Presenters:</strong> Sarah Guo &amp; Elad Gil</p>

<hr />

<h3 id="sharp-tech"><a href="https://sharptech.fm" target="_blank" rel="noopener noreferrer">Sharp Tech</a></h3>
<p>Podcast<br />
How technology works and the ways it is impacting the world, with weekly discussions.<br />
<strong>Presenters:</strong> Andrew Sharp &amp; Ben Thompson</p>

<hr />

<h3 id="tech-unheard"><a href="https://www.arm.com/company/tech-unheard" target="_blank" rel="noopener noreferrer">Tech Unheard</a></h3>
<p>Podcast<br />
One-on-one conversations with industry leaders exploring pressing technology trends from AI to leadership.<br />
<strong>Presenter:</strong> Rene Haas (CEO of Arm)</p>
<blockquote>
  <p>Interesting interviews with tech leaders; not necessarily about AI.</p>
</blockquote>

<hr />

<h2 id="business-strategy--enterprise-ai">Business Strategy &amp; Enterprise AI</h2>

<h3 id="featured--stratechery"><strong>Featured</strong> — <a href="https://stratechery.com/" target="_blank" rel="noopener noreferrer">Stratechery</a></h3>
<p>Newsletter<br />
Weekly and daily analysis of the business, strategy, and impact of technology.<br />
<strong>Author:</strong> Ben Thompson<br />
<strong>Subscription:</strong> Freemium (free weekly; $12/mo or $120/yr for daily updates and podcasts)</p>
<blockquote>
  <p>Highly condensed, covering major tech industry trends including AI.</p>
</blockquote>

<hr />

<h3 id="featured--one-useful-thing"><strong>Featured</strong> — <a href="https://www.oneusefulthing.org/subscribe" target="_blank" rel="noopener noreferrer">One Useful Thing</a></h3>
<p>Newsletter<br />
Practical implications of AI for work, education, and everyday life from a Wharton professor.<br />
<strong>Author:</strong> Ethan Mollick<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>Wharton professor’s incredibly popular blog; practical perspectives.</p>
</blockquote>

<hr />

<h3 id="featured--applied-ai"><strong>Featured</strong> — <a href="https://www.theinformation.com/features/applied-ai" target="_blank" rel="noopener noreferrer">Applied AI</a></h3>
<p>Newsletter<br />
Reporting on how businesses are deploying AI to automate work across industries.<br />
<strong>Author:</strong> The Information<br />
<strong>Subscription:</strong> Paid ($199–399/yr subscription to The Information)</p>
<blockquote>
  <p>The Information is expensive, but this newsletter is free. Practical business application and implications.</p>
</blockquote>

<hr />

<h3 id="featured--bain-software"><strong>Featured</strong> — <a href="https://www.bain.com/insights/industry-insights/technology-insights/" target="_blank" rel="noopener noreferrer">Bain Software</a></h3>
<p>Newsletter<br />
Technology and software industry research and insights from Bain’s consulting practice.<br />
<strong>Author:</strong> Bain &amp; Company<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>They say in an email what others write a whole report on.</p>
</blockquote>

<hr />

<h3 id="enterprise-ai-executive"><a href="https://enterpriseaiexecutive.ai/" target="_blank" rel="noopener noreferrer">Enterprise AI Executive</a></h3>
<p>Newsletter<br />
Twice-weekly executive-level insights on generative AI, agentic AI, and enterprise AI strategy.<br />
<strong>Author:</strong> Enterprise AI Executive<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>‘Executive’ focused, leans on research from major consultants and SIs.</p>
</blockquote>

<hr />

<h3 id="the-change-constant"><a href="https://saanyaojha.substack.com/" target="_blank" rel="noopener noreferrer">The Change Constant</a></h3>
<p>Newsletter<br />
Weekly teardown of the biggest news in tech and finance for professionals.<br />
<strong>Author:</strong> Saanya Ojha<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>Somewhat snarky business POV on AI.</p>
</blockquote>

<hr />

<h3 id="me-myself-and-ai"><a href="https://sloanreview.mit.edu/audio-series/me-myself-and-ai/" target="_blank" rel="noopener noreferrer">Me, Myself, and AI</a></h3>
<p>Podcast<br />
MIT Sloan Management Review and BCG collaboration sharing practical AI implementation secrets and success stories.<br />
<strong>Presenters:</strong> Sam Ransbotham &amp; Shervin Khodabandeh</p>

<hr />

<h3 id="the-so-what-from-bcg"><a href="https://www.bcg.com/podcasts/the-so-what" target="_blank" rel="noopener noreferrer">The So What from BCG</a></h3>
<p>Podcast<br />
BCG leaders on trends, developments, and ideas that will shape and disrupt the future of business.<br />
<strong>Presenter:</strong> Georgie Frost</p>

<hr />

<h2 id="practical-ai-application--tips">Practical AI Application &amp; Tips</h2>

<h3 id="featured--how-i-ai"><strong>Featured</strong> — <a href="https://youtube.com/@howiaipodcast?si=3-R-tqSYtSUrEYd-" target="_blank" rel="noopener noreferrer">How I AI</a></h3>
<p>Podcast<br />
Live screen-sharing episodes where guests demonstrate specific, practical AI workflows you can copy immediately.<br />
<strong>Presenter:</strong> Claire Vo</p>
<blockquote>
  <p>Very practical on usage of AI by bleeding edge practitioners; also has audio podcast.</p>
</blockquote>

<hr />

<h3 id="ai-with-allie"><a href="https://aiwithallie.beehiiv.com/" target="_blank" rel="noopener noreferrer">AI with Allie</a></h3>
<p>Newsletter<br />
Turning AI buzzwords into actionable business tactics from a former Amazon AI leader.<br />
<strong>Author:</strong> Allie K. Miller<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>Techniques and tips for using AI tools.</p>
</blockquote>

<hr />

<h3 id="artificial-corner"><a href="https://artificialcorner.com/" target="_blank" rel="noopener noreferrer">Artificial Corner</a></h3>
<p>Newsletter<br />
Plain English explanations of AI tools and concepts, with practical how-to guides for using AI and Python, aimed at making AI accessible without a technical background.<br />
<strong>Author:</strong> Frank Andrade (The PyCoach)<br />
<strong>Subscription:</strong> Freemium (free weekly; $20/mo or $200/yr for courses, guides, and prompt libraries)</p>
<blockquote>
  <p>Semi-detailed how-tos — helpful for 0–60 learning.</p>
</blockquote>

<hr />

<h2 id="ai-research--technical-deep-dives">AI Research &amp; Technical Deep Dives</h2>

<h3 id="interconnects"><a href="https://www.interconnects.ai/subscribe" target="_blank" rel="noopener noreferrer">Interconnects</a></h3>
<p>Newsletter<br />
AI models, training methods, open-source developments, and AI research trajectory.<br />
<strong>Author:</strong> Nathan Lambert<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>AI researcher’s blog — very technical, but makes sense of broader AI trends.</p>
</blockquote>

<hr />

<h3 id="featured--simon-willisons-newsletter"><strong>Featured</strong> — <a href="https://simonw.substack.com/" target="_blank" rel="noopener noreferrer">Simon Willison’s Newsletter</a></h3>
<p>Newsletter<br />
AI, LLMs, Python, open source, data tools, and practical AI explorations from the co-creator of Django.<br />
<strong>Author:</strong> Simon Willison<br />
<strong>Subscription:</strong> Free</p>
<blockquote>
  <p>Practically <em>technical</em> perspective; tests the technology.</p>
</blockquote>

<hr />

<h2 id="future-of-work--management">Future of Work &amp; Management</h2>

<h3 id="managing-the-future-of-work"><a href="https://www.hbs.edu/managing-the-future-of-work/podcast/Pages/default.aspx" target="_blank" rel="noopener noreferrer">Managing The Future of Work</a></h3>
<p>Podcast<br />
HBS professors talk to leaders grappling with forces reshaping work including AI, automation, and labor markets.<br />
<strong>Presenters:</strong> Joe Fuller &amp; Bill Kerr</p>

<hr />

<h3 id="cold-call"><a href="https://hbr.org/2019/04/podcast-cold-call" target="_blank" rel="noopener noreferrer">Cold Call</a></h3>
<p>Podcast<br />
Harvard Business School’s legendary case studies distilled into audio with faculty discussing real-world business lessons.<br />
<strong>Presenter:</strong> Brian Kenny</p>

<hr />

<h2 id="product-management--growth">Product Management &amp; Growth</h2>

<h3 id="lennys-newsletter"><a href="https://www.lennysnewsletter.com/subscribe" target="_blank" rel="noopener noreferrer">Lenny’s Newsletter</a></h3>
<p>Newsletter<br />
No-nonsense advice on product management, growth, and career development with an accompanying podcast.<br />
<strong>Author:</strong> Lenny Rachitsky<br />
<strong>Subscription:</strong> Freemium (one free post/month; $200/yr for full access)</p>

<hr />

<h3 id="lennys-podcast"><a href="https://www.lennysnewsletter.com/podcast" target="_blank" rel="noopener noreferrer">Lenny’s Podcast</a></h3>
<p>‘Podcast<br />
Interviews with world-class product leaders and growth experts uncovering concrete, actionable advice.<br />
<strong>Presenter:</strong> Lenny Rachitsky</p>
<blockquote>
  <p>See also his newsletter.</p>
</blockquote>]]></content><author><name>Ken Calhoon</name></author><category term="AI-strategy" /><category term="podcasts" /><category term="newsletters" /><category term="resources" /><category term="productivity" /><category term="learning" /><category term="enterprise" /><category term="curation" /><category term="Stratechery" /><category term="Benedict Evans" /><category term="Ethan Mollick" /><category term="Simon Willison" /><category term="Andrew Ng" /><category term="Bain" /><category term="BCG" /><category term="HBS" /><summary type="html"><![CDATA[I get asked how I stay on top of AI developments. Here’s my 3-step system for tracking AI insights, plus my full curated list of top podcasts and newsletters.]]></summary></entry><entry><title type="html">No SOP, No AI Use Case</title><link href="https://kcalhoon.github.io/ai-implementation/no-sop-no-ai/" rel="alternate" type="text/html" title="No SOP, No AI Use Case" /><published>2026-02-19T01:00:00-08:00</published><updated>2026-02-19T01:00:00-08:00</updated><id>https://kcalhoon.github.io/ai-implementation/no-sop-no-ai</id><content type="html" xml:base="https://kcalhoon.github.io/ai-implementation/no-sop-no-ai/"><![CDATA[<p>It’s simple: no documented workflow, no AI use case.</p>

<p><img src="/assets/images/where-is-the-sop.png" alt="Checklist showing SOP, data readiness, and golden examples as prerequisites before AI development begins" style="border: 1px solid #2E8B57;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Ken Calhoon
</p>

<p>A pattern I keep encountering in stalled AI projects: the business reports “the AI is outputting wrong results.” Upon closer inspection, the AI is doing exactly what it was asked to do — it was just asked incorrectly. The sequence of steps is wrong, the calculations are fuzzy, the data source is off. The root cause isn’t the model. It’s that nobody documented what “right” looks like before development started.</p>

<p>Teams routinely assume the model will figure out what to do without the hard work of defining success. It won’t. The project pauses, developers sit idle, and the business scrambles to reverse-engineer the very workflow it should have documented upfront. Without a clear process, AI simply scales and automates existing confusion.</p>

<p>Three prerequisites before greenlighting any use case:</p>

<ol>
  <li><strong>Documented workflow with clear improvement targets.</strong> Map the current process end to end: steps, owners, decision points. Identify specifically where AI adds value. If you can’t write the SOP, the AI can’t execute it.</li>
  <li><strong>Confirmed and accessible data.</strong> Identify the exact systems, fields, and formats required. Verify access and accuracy before engineering begins. Assumed data availability is the fastest path to a stalled project.</li>
  <li><strong>Golden examples for the engineering team.</strong> Provide real, validated outputs that represent “good.” Development compresses dramatically when engineers build against concrete examples rather than iterating through ambiguous feedback loops.</li>
</ol>

<p>These three items require real investment from the business, not just the technical team. Process definition, data validation, and example curation are business responsibilities.</p>

<p>AI rewards preparation. It punishes ambiguity.</p>]]></content><author><name>Ken Calhoon</name></author><category term="AI-implementation" /><category term="evals" /><category term="implementation" /><category term="enterprise" /><category term="leadership" /><category term="SOP" /><category term="workflow" /><summary type="html"><![CDATA[It’s simple: no documented workflow, no AI use case.]]></summary></entry><entry><title type="html">When Killing an AI Project Is the Right Call</title><link href="https://kcalhoon.github.io/ai-strategy/killing-ai-project-success/" rel="alternate" type="text/html" title="When Killing an AI Project Is the Right Call" /><published>2026-02-17T01:00:00-08:00</published><updated>2026-02-17T01:00:00-08:00</updated><id>https://kcalhoon.github.io/ai-strategy/killing-ai-project-success</id><content type="html" xml:base="https://kcalhoon.github.io/ai-strategy/killing-ai-project-success/"><![CDATA[<p>A client recently killed an AI initiative targeting invoice processing. It was a good decision.</p>

<p>During scoping, the team uncovered critical workflow inefficiencies that had nothing to do with AI. Standard engineering — no neural networks required — fixed the data problem, delivered outsized ROI, and made the downstream human work dramatically easier. What remained was the genuinely hard AI problem: high-nuance exceptions that, at current cost and complexity, didn’t pencil out. Leadership did the math. Most of the gains were already captured. They redirected resources to projects where AI was more feasible and returns were clearer.</p>

<p>The meta-lesson is worth stating directly: sometimes the value of an AI initiative isn’t the model. It’s the rigorous process inspection that building the model requires. If you capture that value before deployment, the win is real; take it.</p>

<p>Too many organizations treat AI initiatives as commitments they can’t walk away from, as if stopping signals weakness or lack of vision. The opposite is true. Dogged pursuit of a marginal use case burns capital and talent that could be deployed where the technology actually fits.</p>

<p>Clear-eyed mid-project assessments separate organizations generating real returns from those accumulating expensive experiments. Sometimes the best AI strategy is a simpler solution.</p>]]></content><author><name>Ken Calhoon</name></author><category term="AI-strategy" /><category term="ROI" /><category term="implementation" /><category term="leadership" /><category term="project-governance" /><summary type="html"><![CDATA[A client recently killed an AI initiative targeting invoice processing. It was a good decision.]]></summary></entry><entry><title type="html">February 2026 Newsletter: Getting AI over the line in 2026</title><link href="https://kcalhoon.github.io/newsletter/newsletter-february-2026/" rel="alternate" type="text/html" title="February 2026 Newsletter: Getting AI over the line in 2026" /><published>2026-02-10T04:00:00-08:00</published><updated>2026-02-10T04:00:00-08:00</updated><id>https://kcalhoon.github.io/newsletter/newsletter-february-2026</id><content type="html" xml:base="https://kcalhoon.github.io/newsletter/newsletter-february-2026/"><![CDATA[<h2 id="you-cant-pilot-your-way-to-profitability">You can’t pilot your way to profitability</h2>

<p>According to BCG, the top 15% of CEOs are “Trailblazers” transforming AI from a CIO experiment to a business-led operating model. They invest ~1.7% of revenue—allocating 60% specifically to agentic AI—and upskill teams at double the average rate. They advocate simplicity, focus, and pushing through short-term pilot failures. <a href="https://web-assets.bcg.com/73/8e/cc44cbc14a3b81695f8a3de28ff1/ai-radar-2026-web-jan-2026-edit.pdf" target="_blank" rel="noopener noreferrer">link</a> <a href="https://the-so-what-from-bcg.captivate.fm/episode/special-episode-davos-wrap-up" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-02/bcg-flywheel.png" alt="BCG AI Trailblazer Flywheel" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: BCG
</p>

<p>With Apple officially tapping Google’s Gemini to power Siri, the tech giant is finally optimizing “buy vs. build.” The takeaway? Stop roadmapping the “uninvented.” Instead, lease commodity intelligence and double down on true differentiation—like Apple’s privacy layer—to build the most valuable product. <a href="https://www.nytimes.com/2026/01/12/technology/apple-google-ai-partnership.html" target="_blank" rel="noopener noreferrer">link</a></p>

<p>The market is pricing this in. SaaS stocks lost ~$300 billion in market cap reflecting investor fears of AI workflow substitution. While the reaction was sharp, Goldman Sachs estimates the Agentic total addressable market will exceed SaaS by 2030. AI threatens to unbundle software, allowing enterprises to customize functionality less expensively. <a href="https://www.forbes.com/sites/donmuir/2026/02/04/300-billion-evaporated-the-saaspocalypse-has-begun/" target="_blank" rel="noopener noreferrer">Forbes</a> <a href="https://www.goldmansachs.com/insights/articles/ai-agents-to-boost-productivity-and-size-of-software-market" target="_blank" rel="noopener noreferrer">Goldman Sachs</a></p>

<p><img src="/assets/images/newsletter-2026-02/saas-agent-tam-goldman.png" alt="SaaS vs Agentic AI TAM Comparison" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Goldman Sachs
</p>

<p>“Pain is the new moat,” says OpenAI’s Kiriti Badam. Applied anthropologist Mikkel Rasmussen warns that if work feels easy, he gets “nervous.” The real competitive advantage lies in working through the hard-to-solve problems. <a href="https://youtu.be/hJjrywgVxM8?si=tjvVp8SfHkXoFT5M" target="_blank" rel="noopener noreferrer">YouTube</a> <a href="https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned" target="_blank" rel="noopener noreferrer">Lenny’s Newsletter</a></p>

<h2 id="fast-for-the-few">Fast for the few</h2>

<p>Development is shifting from coding to architecture and review. Anthropic shipped “Claude Cowork” in just 10 days with four engineers using AI to generate 90% of the codebase—then launched it as a desktop tool that gives non-engineers the same power, no terminal required. OpenAI similarly built Sora in 28 days. Product timelines are compressing by orders of magnitude. <a href="https://x.com/felixrieseberg/status/2010882577113268372" target="_blank" rel="noopener noreferrer">X</a> <a href="https://karozieminski.substack.com/p/claude-cowork-anthropic-product-deep-dive" target="_blank" rel="noopener noreferrer">Substack</a> <a href="https://claude.com/blog/cowork-research-preview" target="_blank" rel="noopener noreferrer">Anthropic</a></p>

<p><img src="/assets/images/newsletter-2026-02/plan-do-review-illustration.png" alt="Plan Do Review Workflow Illustration" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Ken Calhoon
</p>

<p>“That ship has sailed and good riddance,” said a veteran developer about manual coding in a UC San Diego study. While experts embrace AI agents, the paper reveals they reject “vibe coding,” instead choosing to “control” agents through rigorous planning and supervision to ensure quality. <a href="https://arxiv.org/html/2512.14012v1" target="_blank" rel="noopener noreferrer">link</a></p>

<h2 id="friction-for-the-many">Friction for the many</h2>

<p>Outside of elite engineering teams, however, general enterprise adoption faces friction. Workday finds AI carries a 37% “rework tax” for correcting low-quality outputs. To reclaim productivity, leaders must guide employees from augmentation to automation—refining prompts, curating reference content, and experimenting with different LLMs to fix instructions rather than results. <a href="https://forms.workday.com/en-us/reports/beyond-productivity-ai-value/form.html" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-02/workday_ai_training_quote.png" alt="Workday AI Training and Support" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Workday
</p>

<p>Microsoft sees this too. According to The Information, the company is reportedly offering large clients tens to hundreds of thousands of dollars to fund employee training and ensure Copilot adoption, concerned that customers aren’t getting enough value from its AI tools. <a href="https://www.theinformation.com/articles/applied-ai-microsoft-offers-training-funds-copilot-ai-customers" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Anthropic argues the biggest barriers aren’t model capabilities but data access and context aggregation. Companies with fragmented or siloed data will struggle to unlock sophisticated use cases regardless of technological advancements. <a href="https://cdn.sanity.io/files/4zrzovbb/website/cd77281ebc251e6b860543d8943ede8d06c4ef50.pdf" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Security risks compound these adoption challenges. Air Street Press highlights the growing conflict between innovation and safety following OpenClaw’s debut. Cisco deems the tool a “security nightmare,” yet Token Security found 22% of tracked users have installed it on corporate systems. <a href="https://press.airstreet.com/p/state-of-ai-february-2026-newsletter" target="_blank" rel="noopener noreferrer">link</a></p>

<h2 id="the-land-grab-continues">The land grab continues</h2>

<p>Google says Gmail is “entering the Gemini era,” powered by its Gemini 3 models. New features include an “AI Inbox” to prioritize VIPs and “AI Overviews” that let you ask your inbox questions naturally, turning the email client into a proactive personal assistant. <a href="https://blog.google/products-and-platforms/products/gmail/gmail-is-entering-the-gemini-era/" target="_blank" rel="noopener noreferrer">link</a></p>

<p>OpenAI is expanding on two fronts. It launched ChatGPT Health—a private workspace developed with over 260 physicians that connects with Apple Health and MyFitnessPal—after finding 230 million people already ask its models health questions weekly. And it will test ads in its free and $8/month “Go” tiers to monetize 900M weekly active users, with advertising crucial to fund $1.4 trillion in infrastructure commitments. <a href="https://openai.com/index/introducing-chatgpt-health/" target="_blank" rel="noopener noreferrer">OpenAI</a> <a href="https://seekingalpha.com/news/4529731-chatgpt-reaches-900m-weekly-active-users-but-gemini-adoption-continues-to-heat-up-report" target="_blank" rel="noopener noreferrer">Seeking Alpha</a> <a href="https://stratechery.com/2026/ads-in-chatgpt-why-openai-needs-ads-the-long-road-to-instagram/" target="_blank" rel="noopener noreferrer">Stratechery</a></p>

<h2 id="the-new-front-door">The “new front door”</h2>

<p>McKinsey warns the “new front door” to the internet is shifting: by 2028, AI could dominate 50% of search activity, influencing $750 billion in commerce. As decision-making moves pre-click, brands relying on traditional SEO risk a 20–50% traffic plunge, necessitating a pivot to AI-native strategies. <a href="https://www.mckinsey.com/capabilities/growth-marketing-and-sales/our-insights/new-front-door-to-the-internet-winning-in-the-age-of-ai-search" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Because AI search is answer-based, brands are scrambling to influence those answers. Ahrefs found the most detailed story wins, even if false. After seeding Reddit and Medium with fake narratives about a made-up brand, they found models like Gemini trusted third-party lies over the official FAQ, making GEO a critical new marketing frontier. <a href="https://ahrefs.com/blog/ai-vs-made-up-brand-experiment/" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-02/ahrefs-geo.png" alt="Ahrefs GEO Source Usage Analysis" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Ahrefs
</p>

<p>On the production side, Colgate-Palmolive worked with Google and BCG to produce video ads 4x to 6x faster using AI-generated imagery. BCG estimates fixing content inefficiencies can save marketers 10% to 30% of their total budget. <a href="https://business.google.com/us/think/ai-excellence/colgate-palmolive-gen-ai-marketing-pilot/" target="_blank" rel="noopener noreferrer">Google</a> <a href="https://www.bcg.com/publications/2025/for-cmos-the-future-starts-with-smarter-spending" target="_blank" rel="noopener noreferrer">BCG</a></p>]]></content><author><name>Ken Calhoon</name></author><category term="newsletter" /><category term="BCG" /><category term="Google" /><category term="Apple" /><category term="Anthropic" /><category term="OpenAI" /><category term="McKinsey" /><category term="Gemini" /><category term="Microsoft" /><category term="agents" /><category term="enterprise" /><category term="adoption" /><category term="productivity" /><category term="ROI" /><category term="infrastructure" /><category term="security" /><category term="marketing" /><category term="GEO" /><category term="search" /><category term="workflow" /><category term="AI use cases" /><category term="SaaS" /><category term="Goldman Sachs" /><category term="Workday" /><category term="vibe coding" /><category term="Colgate-Palmolive" /><summary type="html"><![CDATA[You can’t pilot your way to profitability]]></summary></entry><entry><title type="html">January 2026 Newsletter: Cooperation and Competition — AI flexes towards enterprise</title><link href="https://kcalhoon.github.io/newsletter/newsletter-january-2026/" rel="alternate" type="text/html" title="January 2026 Newsletter: Cooperation and Competition — AI flexes towards enterprise" /><published>2025-12-10T03:43:35-08:00</published><updated>2025-12-10T03:43:35-08:00</updated><id>https://kcalhoon.github.io/newsletter/newsletter-january-2026</id><content type="html" xml:base="https://kcalhoon.github.io/newsletter/newsletter-january-2026/"><![CDATA[<p><img src="/assets/images/newsletter-2026-01/menlo_ai_spending.png" alt="The $39B AI Market" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Menlo Ventures
</p>

<h2 id="ai-spending-is-growing-fast-but-the-value-equation-remains-uncertain">AI spending is growing fast, but the value equation remains uncertain</h2>

<p>Enterprise Gen AI spending hit $37B in 2025, capturing 6% of the SaaS market, according to Menlo Ventures. While $19B went to apps and $18B to infrastructure, architectures remain simple. Prompt engineering and RAG dominate implementation, with only 16% of enterprise deployments qualifying as true autonomous agents. <a href="https://menlovc.com/perspective/2025-the-state-of-generative-ai-in-the-enterprise/" target="_blank" rel="noopener noreferrer">link</a></p>

<p>While Gen AI spending has grown 3.2x this year, it represents less than 1% of the $4 trillion in 2024 U.S. corporate profits reported by the St. Louis Fed. Even stratospheric returns on AI spend won’t materially impact these aggregate profits for the foreseeable future. <a href="https://www.stlouisfed.org/on-the-economy/2025/apr/whats-driving-surge-us-corporate-profits" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Microsoft Copilot leverages corporate data in Teams and SharePoint, but users face a steep learning curve, according to The Information. Concerned that customers aren’t seeing enough value to renew subscriptions, Microsoft is now funding employee training, while OpenAI similarly offers resources to bridge the skills gap. <a href="https://www.theinformation.com/articles/applied-ai-microsoft-offers-training-funds-copilot-ai-customers" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Companies need “domain owners” who have built a “second muscle” in technology, according to McKinsey. With only 5% of senior leaders having held technical roles, these executives are vital for aligning data, platforms, and engineering talent to deliver successful AI transformations. <a href="https://www.mckinsey.com/capabilities/quantumblack/our-insights/building-the-ai-muscle-of-your-business-leaders" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-01/anthropic_econ-impact.png" alt="Expected Economic Impact" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Anthropic
</p>

<h2 id="whos-capturing-that-spend-anthropic-and-open-weight-models-surge-ahead">Who’s capturing that spend? Anthropic and open-weight models surge ahead</h2>

<p>Menlo Ventures also reports Anthropic has unseated OpenAI as the top enterprise model provider, capturing 40% of spend versus OpenAI’s 27%. Google also grew to 21%. Anthropic’s surge is powered by a dominant 54% share of the coding market and the success of Claude Code. <a href="https://menlovc.com/perspective/2025-the-state-of-generative-ai-in-the-enterprise/" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Anthropic also reports its engineers primarily use Claude for debugging and code understanding. Staff use the tool in 60% of their work, estimating a 50% productivity boost. Additionally, 27% of Claude-assisted work involves “nice-to-have” tasks that otherwise wouldn’t be completed. <a href="https://www.anthropic.com/research/how-ai-is-transforming-work-at-anthropic" target="_blank" rel="noopener noreferrer">link</a></p>

<p>A new analysis of the Hugging Face ecosystem details a “fundamental rebalancing” of AI power. As US corporate dominance wanes, Chinese developers have surged ahead, with DeepSeek and Qwen driving China’s download share to 17.1%, surpassing the collective output of American model builders for the first time. <a href="https://arxiv.org/abs/2512.03073v1" target="_blank" rel="noopener noreferrer">link</a></p>

<p>Exemplifying the above trend, Pinterest and Airbnb have fine-tuned open-weight models from Qwen and DeepSeek to match frontier performance. According to Applied AI, these models handle multi-modal jobs and customer support queries at less than 10% of the cost. <a href="https://medium.com/pinterest-engineering/on-the-re-prioritization-of-open-source-ai-86f7279481e3" target="_blank" rel="noopener noreferrer">link</a> <a href="https://finance.yahoo.com/news/airbnb-picks-alibabas-qwen-over-093000045.html" target="_blank" rel="noopener noreferrer">link</a></p>

<h2 id="despite-the-hype-most-implementations-remain-focused-on-the-basics">Despite the hype, most implementations remain focused on the basics</h2>

<p>OpenAI reports that technology, healthcare, and manufacturing are the fastest-growing AI adopters, with the tech sector surging 11x year-over-year. While professional services and finance continue to lead in absolute scale, a widening divide shows “frontier” firms now send twice as many messages per seat as the median enterprise. <a href="https://cdn.openai.com/pdf/7ef17d82-96bf-4dd1-9df2-228f7f377a29/the-state-of-enterprise-ai_2025-report.pdf" target="_blank" rel="noopener noreferrer">link</a></p>

<p><img src="/assets/images/newsletter-2026-01/openai-fastest-sectors.png" alt="AI Implementation by Sector" style="border: 1px solid #2E8B57; width: 67%; display: block; margin: 0 auto;" /></p>

<p style="text-align: center; font-size: 0.9em; color: #555;">
  Source: Anthropic
</p>

<p>While most usage remains in “predictable areas,” Anthropic highlights N26 and Thomson Reuters leveraging Amazon Bedrock for compliance and security. Anthropic calculated a 1% increase in input context length correlates with a 0.38% <em>increase</em> in output quality, demonstrating that robust, selective data aggregation, not just model power, is critical for success. <a href="https://cdn.sanity.io/files/4zrzovbb/website/cd77281ebc251e6b860543d8943ede8d06c4ef50.pdf" target="_blank" rel="noopener noreferrer">link</a></p>

<h2 id="come-together-right-now">Come together, right now</h2>

<p>AWS and Google announced a jointly developed service providing high-speed networking links between their competing clouds. This allows enterprises to host data in their preferred cloud while utilizing models from other providers, reducing connection setup times from weeks to minutes. <a href="https://stratechery.com/2025/openai-code-red-aws-and-google-cloud-networking/" target="_blank" rel="noopener noreferrer">link</a></p>

<p>The Linux Foundation is organizing the Agentic Artificial Intelligence Foundation to develop shared open-source standards, according to The Information. Initial technical contributions include OpenAI’s Agents.md, Block’s Goose, and Anthropic’s MCP. OpenAI, Google, Microsoft, and Anthropic have joined the group to ensure agent ecosystems can effectively connect. <a href="https://www.linuxfoundation.org/press/linux-foundation-announces-the-formation-of-the-agentic-ai-foundation" target="_blank" rel="noopener noreferrer">link</a></p>]]></content><author><name>Ken Calhoon</name></author><category term="newsletter" /><category term="Anthropic" /><category term="OpenAI" /><category term="Google" /><category term="Microsoft" /><category term="McKinsey" /><category term="Menlo Ventures" /><category term="enterprise" /><category term="agents" /><category term="infrastructure" /><category term="ROI" /><category term="productivity" /><category term="fine-tuning" /><category term="open source" /><category term="adoption" /><category term="data" /><category term="leadership" /><category term="economics" /><category term="AI use cases" /><category term="cloud services" /><category term="RAG" /><category term="DeepSeek" /><category term="Qwen" /><summary type="html"><![CDATA[]]></summary></entry></feed>