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This chapter examines the insider–outsider dynamics shaping Web3 technologies as they navigate entrepreneurial ecosystems and the technology diffusion process. It establishes insiders as the developers, founders, and investor communities driving Web3 innovation, often operating in regulatory grey zones with a techno-solutionist mindset. In contrast, outsiders include institutions, policymakers, and the broader public reacting to Web3’s experimental nature and socio-technical novelty. The chapter situates Web3 within frameworks of technology adoption, socio-technical imaginaries, and models of diffusion. It highlights the tendency of insiders to overlook social nuances while pursuing rapid commercialisation and adoption. The chapter presents two case studies: the first examines the regulatory friction encountered by Ripple Labs and its digital asset, XRP; the second chronicles the rise and fall of Art NFTs, from their promise of empowering artists to their eventual decline due to legal uncertainties, environmental concerns, scams, and clashing community values. This decline mapped onto public disillusionment with the technology despite, and perhaps because of, its utopian techno-libertarian premise. The chapter argues that Web3 must navigate complex insider–outsider tensions while introducing disruptive innovations within existing socioeconomic structures. It concludes with policy recommendations spanning regulatory frameworks, consumer protection, responsible innovation, and public education to foster a more balanced and sustainable Web3 ecosystem.