Steven Sinofsky is a former president of Microsoft's Windows division, a board partner at Andreessen Horowitz, and the author of the Hardcore Software newsletter on the history and practice of the software industry.
Background
Sinofsky joined Microsoft in the late 1980s, before the release of Windows 3.0, as a software design engineer on the tools that became Visual C++. He later served as technical assistant to Bill Gates, worked on and eventually led the Microsoft Office team, and then led Windows through the development of Windows 7, Windows 8 and the Surface. Hardcore Software, which he began in December 2020, is a serialized first-person account of that period; he also co-wrote the book One Strategy (Source: hardcoresoftware.learningbyshipping.com).
Positions on AI policy
Sinofsky's AI-policy writing opposes what he calls preemptive regulation of the technology.
Executive Order 14110
In a 2023 essay, "Regulating AI by Executive Order," Sinofsky criticized President Biden's Executive Order 14110 as a document produced by aggregating inputs from interested constituencies while testing the legal limits of what could be done to slow AI without new legislation. He concluded that the order was about "stifling innovation and turning the next platform over to incumbents" in the United States, or more likely to companies in other countries, and argued that anyone claiming sufficient evidence of AI's dangers should make the case through the legislative process. Ben Thompson quoted the essay at length and endorsed its conclusion in his Stratechery article "Attenuating Innovation (AI)" (Attenuating Innovation (AI) — Ben Thompson (Stratechery, October 2023)).
Distillation enforcement
In a July 22, 2026 essay ("Distillation Is Not Anti-American, Weaponizing It Is"), Sinofsky argued that the Trump administration's push against Chinese distillation of US frontier models is "regulatory capture," writing that treating distillation as intellectual-property theft "is somewhat rich when you consider how [labs] acquired their training data" (Source: hardcoresoftware.learningbyshipping.com). The essay responded to OSTP Director Michael Kratsios's accusation that Moonshot AI distilled Anthropic's Fable model, and to Treasury Secretary Scott Bessent's statement that distillation sanctions were on the table. Its subtitle describes recent attempts to pursue government intervention over distillation as short-sighted and technically weak arguments aimed at regulatory capture, and its opening says it saddens him to see technology companies in IP litigation, more so when a company pursues it "under the cover of using the whole of government" (Source: hardcoresoftware.learningbyshipping.com). The full essay is behind a subscriber paywall.
AI in legal education and practice
In a July 11, 2026 essay, "Banning AI in Law School: We've Seen This Before," Sinofsky responded to the University of Chicago Law School's new AI strategy, which bans phones and laptops in class for first-year students. He compared it with Harvard Law School's 1982 decision, after students brought Osborne 1 portable computers to exams, to ban computers and word processors from exams, and argued that such restrictions are overtaken by students who adopt new tools regardless. He wrote that "preemptive regulation is the enemy of progress," that incumbents use "preemptive regulation" and "presumptive negatives" to slow technology adoption, and that controlling information tools is akin to controlling expression. On AI hallucinations in court filings, he cited a compilation of just over 1,000 cases in which hallucinations came to a judge's attention against a denominator of about 65 million new cases filed each year, and argued that AI remains governed by existing law, including liability, copyright, civil rights and antitrust (Source: hardcoresoftware.learningbyshipping.com). See Legal Services — AI Deployment and AI-Fabricated Citations.
Relationships
- contradicts: the administration's anti-distillation enforcement posture; see Distillation, Adversarial Distillation.
- related: Regulatory Capture in AI Policy, Microsoft.
- contradicts: Executive Order 14110 (RESCINDED) — criticized the 2023 order as a restraint on innovation
- supports: Attenuating Innovation (AI) — Ben Thompson (Stratechery, October 2023) — essay quoted and endorsed by Thompson
- related: Legal Services — AI Deployment, AI-Fabricated Citations, Andreessen Horowitz (a16z), Bill Gates