This work studies technological, business, and cultural development practices in the commercial Earth Observation (EO) sector. Increased access to space combined with growing demands for climate and natural resource monitoring, situational awareness, on-demand analytics, and sovereign data independence motivate the expansion of EO. The financial performance and culture of five public EO companies–iQPS, GOMSpace, Kleos Space, Planet Labs, and Satellogic–are analyzed. Time-series econometrics modeling indicates trends in how financial resources impact earnings and revenue, and the models are used to forecast future earnings and revenue with a high goodness-of-fit. A time-series DuPont analysis investigates how companies operate through conversion of different financial instruments, and corresponding corporate milestones contextualize these financial transactions. Informational interviews of four EO company executives provide clues about company culture and decision-making strategies. Recommendations tailored to the unique challenges and opportunities of the global EO sector are provided to help government partners, investors, and program managers estimate business performance given financial and cultural data.