We are living in the “Anthropocene” the era in which human activities are responsible for severe damage to the resilience of the ecological and social systems, undermining the Earth’s autopoetic mechanism, integrity and ability to function as a healthy complex adaptive systems. The prevailing societal paradigm for business practices has yet to realise the reality of our current global unsustainable state – and the shift necessary to move us forward collectively. Startup companies have a unique opportunity to gain and leverage competitiveness and attractiveness for funding and customers through sustainability driven business strategies, models and value propositions. This research analyses literature, document and interview data to explore if and how current practices in the Lean Startup contribute to a sustainable society – and how a Strategic Sustainable Development approach might be introduced to enhance the resilience of Lean Startups. Therefore, our key recommendations for Lean Startups that want to introduce an SSD approach are: to raise awareness about the sustainability challenges and opportunities; utilise backcasting towards a vision framed by the Sustainability Principles; focus on fulfilling fundamental basic Human Needs; utilize strategic prioritization questions when pivoting and combine the FSSD ABCD process with the Lean BML cycle. Ultimately, this thesis proposes the use of Strategic Sustainable Trigger Questions to (re)design sustainable business models and value-propositions. We conclude that “asking the right questions - rather than giving answers up front” might spark conversations and innovations in Lean Startups, beneficial for the sustainability of both the individual startup the larger socio-ecological systems.