Mike Simmons



CEO and Founder

Blue Sky Strategies & Co.


Mike Simmons is an entrepreneur, public policy expert, and activist working at the intersection of policy, equity, and structural change.

Mike has shaped and written policy benefiting Chicago’s families for most of his career in senior policy roles in Chicago’s City Hall, including as Policy Director in the Mayor’s Office, and as Deputy Commissioner in the Department of Planning and Development, and as a legislative staffer on Capitol Hill for US Sen. Dick Durbin. Mike’s lasting impact on Chicago families and communities includes passing legislation to protect renters in foreclosed apartments, building new grocery stores in food deserts, and negotiating a general order with the Chicago Police Department and activists that protects transgender people.

Mike also did a stint at the Cook County Board of Commissioners where he was instrumental in designing and launching the Cook County Land Bank, which is charged with reactivating up to 55,000 vacant properties in struggling communities. He also led a budgetary audit of the $3 million Circuit Court foreclosure mediation program which found the program was not helping enough families avoid foreclosure in light of the volume of public dollars being spent. Mike also found unused dollars in the budget to reallocate to new violence prevention and street outreach work in Uptown.

Spurred by rapid change and gentrification happening in his home city, in 2017, Mike launched his own firm, Blue Sky Strategies & Co., a consultancy delivering expertise at the intersection of policy, urban planning, equity, and structural change that affects people who go unheard. Mike taps into his experience in helping his clients explore and reframe problems and find new ways of achieving goals. Mike believes with a radically honest approach and detailed planning and persistence, we can move beyond the status quo. As a lifelong Chicagoan, he brings to his work a strong patriotism for his home city, a no drama approach to work, and battle tested leadership to the table to achieve for his clients and the community at large.

Mike took a one year self-directed sabbatical in 2016 and 2017 where he traveled to West Africa to explore the ancestry of African-Americans throughout the Transatlantic Slave Trade, a journey that took him solo through 7 countries. He then traveled to Europe and contrasted developed countries in the west with less developed regions in the Balkans and used those observations as ingredients in assessing his experiences as an LGBTQ black person, as an American, and descendant of the slave trade. In 2019 he began several trips through the Deep South of the United States to identify parallels between West Africans and African-Americans living there. After the sabbatical, he launched his first public photo exhibit in 2018 which showcased themes of Black agency and intersectional experience, and displacement using the photographs he took while in Africa and Europe. He’s currently working on his first novel narrating his journey by foot, bus, and bike across 23 countries during his sabbatical.

Mike co-founded the Chicago chapter of New Leaders Council, and has served on the Local School Council, the board of Equality Illinois, and was an inaugural Impact Fellow and a 2016 Leadership Greater Chicago Fellow. He has been a guest on local and national podcasts, he was named one of 30 under 30 by Windy City Times, he has been profiled by Business Week, Time Out Chicago, WBEZ-NPR public radio, and in 2019 was recognized by Crain’s Chicago Business as a Notable LGBTQ executive in Chicago for his work with Blue Sky Strategies. Mike graduated from Amherst College in 2006 where he was president of the student body. Mike also was a US national debate champion.

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