Much has been written about the rise of the gig economy in which workers perform gigs under “flexible” arrangements, working only to complete a particular task, e.g. providing transportation rideshare services. The gig economy has been enabled by “work-on-demand via apps” and Internet-based platform companies such as Uber. The gig economy holds a great promise of matching the demand and supply in real time. However, the gig economy can create an imbalance in terms of risk-sharing vis-à-vis value-sharing for the supply-side. Using online ethnography, this research explores specific grievances of rideshare drivers that highlight these risks. The findings show that the specifics of the risks and downsides faced by the drivers are plentiful. These grievances are placed in the light of the rich organizational fairness lens and implications for the future of work are elaborated.