Over the past 200 years, Iowans have tilled more than 99% of the state’s native tallgrass prairie. Today, big bluestem, blazingstars, and purple coneflowers exist only in slivers, while industrial fields of corn and soybeans carpet the state. Academic and popular sources alike have thoroughly documented large-scale monoculture’s ecological effects, including decreased soil microbial diversity, contaminated waterways, and topsoil depletion. This paper begins from the observation that, as in other ecologies, new life forms and livelihoods are now emerging from this landscape of “capitalist ruins” (Tsing 2015). Across the state, beginning farmers are veering away from the arc of agricultural modernization to instead start small-scale, diversified farms targeting local markets. In many ways they resemble the kinds of smallholder farms that industrialization displaced during the 20th century, but contemporary beginning farmers are also entrepreneurs, subjects of late capitalism. These farmers often express antipathy to the commodity grain fields surrounding them, but their experiences cannot be summarily glossed as resistance. Drawing on 16 months of ethnographic fieldwork, this paper seeks to interrogate the pathways through which the values and expectations of Iowa’s industrial agricultural system entangles itself in the livelihoods of new alternative farmers. Offering not only an antagonistic foil, industrial farms also can provide material goods, equipment, and land that alternative farmers repurpose. Furthermore, interactions with grain farmers, agricultural economists, and other experts can influence the kinds of agricultural futures beginning farmers imagine for themselves and their land.