The nature of farming is – still – an essentially biological, and thus volatile, system, which poses substantial challenges to its integration into financialized capitalism. Financial investors often seek stability and predictability of returns that are hardly compatible with agriculture – but which are increasingly seen as achievable through data and digital farming technologies. This paper investigates how farmland investment brokers engage with, perceive, and produce farming data for their investors within a co-constructive process. Tackling land’s ‘stubborn materiality’ for investment, I argue, has material and immaterial components: it includes the re-imagination of farming as a financial asset that delivers reliable income streams for investors; and the re-engineering of farmland’s concrete materialities with digital farming technologies. Farmland investment brokers develop investor-suitable farmland imaginaries, underpinned by storytelling as well as the calculative ‘evidence’ of (digital) data. At the same time, digital technologies have become a key tool for transforming farms into ‘investment grade assets’ endowed with the rich data on farm performance and financial returns requested by investors. I conclude that the assetization and digitization of farmland need to be seen as closely intertwined and mutually reinforcing processes and identify key areas for future research on this intersection.