This study evaluates how welcoming thirty American cities--the twenty-five largest and five smaller "hotspots"--are to "nontraditional" problem-solvers and solutions. It assumes that the balky bureaucracies meant to improve K-12 education and hold leaders accountable are so calcified by policies, programs, contracts, and culture that only in the most exceptional of circumstances can they be fixed simply by top-down applications of new curricula or pedagogy. To determine the cities with the most reform-friendly ecosystems, analysts examined six domains that shape a jurisdiction's receptivity to education reform: (1) Human Capital; (2) Financial Capital; (3) Charter Environment; (4) Quality Control; (5) District Environment; and (6) Municipal Environment. Drawing on publicly available data, national and local survey data, and interviews with on-the-ground insiders, analysts devised a grading metric that rated each city on its individual and collective accomplishments in each of these areas. What did they discover? Few cities are rolling out the red carpet for education entrepreneurs. No cities were awarded As and just a handful of cities received Bs when measured for their hospitability towards reformers. The majority fell in the C range, half a dozen in the D to F range, and the remainder had too little data to judge (see Table 1, page 8). Low-scoring cities were characterized by lethargic district administration, inert political leadership, arcane staffing policies, and unsupportive (or silent) local business and philanthropic communities. They also found that cities are making greater strides in some areas than others: (1) They do best at drumming up sources of financial capital to advance reform: Nine cities earned As and ten earned Bs; support from outside the district is also strong, with municipal environment seeing nine As and eight Bs; (2) They fare least well when it comes to district environment, where a third got Fs; and (3) Grades were generally mixed with respect to human capital, charter environment, and quality control. Finally, substantial variation exists within states that had more than one city in the study. This suggests that entrepreneurial fate is not sealed by state lines: local officials, educators, and reformers can shape their own destiny. Appendices include: (1) Methodology; (2) Scoring Rubric; and (3) A list of organizations whose members helped to shape the study design and survey instruments. Individual sections contain footnotes and tables. [The foreword for this report was written by Chester E. Finn, Jr. and Amber M. Winkler. Funding for this paper was also provided by the Richard M. Fairbanks Foundation, Inc.]