Only founder with two companies in the S&P 500. Currently leading Block's transformation into an AI-centered 'mini-AGI' organization, eliminating traditional hierarchy in favor of an intelligence layer. Known for high conviction bets (Cash App, Square lending) despite initial board/stakeholder opposition.
no scored calls yet — needs a stated position or a categorical verdict, with a matured window vs SPY
Jack Dorsey is aggressively transforming Block from a hierarchical organization into an intelligence-centered company where AI agents (Goose, Claude Code) handle information flow, reducing management layers from 5 to 2-3 and enabling every employee to query the company's world model in real time. He believes the company's limiting factor is its roadmap, and AI will let customers drive product development directly.
Bitcoin's open, leaderless consensus model and 16-year track record without downtime or security breaches make it a trustworthy currency for cross-border remittance and eventually everyday commerce, enabling internet-native business models that bypass traditional payment networks.
Twitter's rush to advertising monetization and centralized protocol ownership created vulnerability to government and advertiser pressure; an open protocol with user-chosen algorithms would have aligned incentives with users and resisted censorship.