In this chapter, the authors outline the historical evolution of trust and discuss how, for most of human history, trust and reputation have shaped personal relationships. They shed light on today’s sharing economy platforms’ activities in designing and operating reputation systems to leverage digital trust between peers. They further explore opportunities and challenges to foster trust based on blockchain technology and cryptocurrencies in the sharing economy, and analyze the public discourse in the Reddit community addressing these technological advances. They conclude that the advantages of blockchain technology and cryptocurrencies may offer several promising avenues for many sharing economy platforms, as they may allow for improvements regarding the decentralization of control. However, sharing economy platforms must leverage the potential of blockchain and cryptocurrencies with great care, and be aware of the challenges and downsides that these technologies may bring.