Brian Halligan Proposes Strategic Illegibility in Response to the AI Era
Brian Halligan warns that founders competing to make their companies "legible" to AI may be commoditizing their own moats.
He points out that structuring internal data, workflows, and knowledge for AI agents will allow proprietary insights to be learned by vendors and turned into "best practices" that are disseminated across the market.
Halligan suggests adopting "strategic illegibility," intentionally preserving core advantages such as the founder's mental models, taste judgments, negotiation intuitions, and informal power networks to avoid complete exposure.
Source: Public Information
ABAB AI Insight
Brian Halligan, as a co-founder of HubSpot, has experienced the entire cycle of SaaS from early to mature stages. This discussion on strategic illegibility continues his long-term observation of the evolution of digitalization and competitive advantages in businesses. Earlier, HubSpot achieved rapid growth through knowledge base and process standardization but also faced the risk of being quickly replicated by tools like Copilot.
On the capital front, founders need to build both a human version of the company and an AI digital twin. However, Halligan advocates for retaining ambiguity at the key decision-making level. The strategic motive is to prevent AI vendors from generalizing a single client's playbook into common features, thus maintaining differentiated pricing power and long-term barriers.
Similar to Anne Miura-Ko's recent article discussing how legibility enhances power, companies like Zapier and Opendoor are already practicing building AI twin systems. The AI enterprise tools market is currently in the early stages of transitioning from a comprehensive legibility competition to selective ambiguity, with the influence of mature founders possessing strategic judgment on the rise.
Essentially, this is a reverse operation of technological substitution: AI will automate structured processes, but human unique judgment becomes the new scarce resource. The mechanism is that excessive legibility accelerates knowledge spillover and competitive homogenization, forcing pricing power to shift from transparent processes to deliberately retained "non-codable" advantages, accelerating capital concentration towards companies that can balance efficiency and uniqueness.
ABAB News · Law of Cognition
The more transparent a company is, the faster AI turns your moat into a standard feature across the industry. Legibility is productivity, but strategic illegibility is lasting competitiveness; ambiguity is the highest-level barrier. The sooner founders decide what should be hidden, the later they will be completely commoditized by AI tools.