This dissertation explores the relationship between financial frictions and the real economy. It studies three channels of macro-financial transmission: market power of financial intermediaries, credit portfolio risk that originates from granular borrowers, and aggregate implications of countercyclical bank income risk. The first Chapter of the dissertation develops a quantitative model with financial intermediaries that are heterogeneous along four empirically-motivated dimensions: balance sheet size, credit market power, default risk, and efficiency. The framework highlights a trilemma for bank regulation: financial competition, efficiency, and stability are incompatible – no policy intervention can improve all three facets simultaneously...