The WhyNot Initiative is a program of Patriotic Millionaires which advocates for government-controlled healthcare, redistributing individual income, and gun control advocacy. The WhyNot Initiative primarily engages in funding elections research and advocacy training programs for left-of-center issues. The WhyNot Initiative also financially backs efforts to oppose Republican officials and Republican-backed causes. 
Alan S Davis
Alan S. Davis is the Director of the WhyNot Initiative and president of the Leonard and Sophie Davis Fund, which focuses on similar left-wing economic and social policies. Davis is also an advisory board member of the parent group Patriotic Millionaires.
On June 25, 2019, Davis was invited as the Director for the WhyNot Initiative to give opening remarks at an event hosted by the labor union-aligned think tank Economic Policy Institute titled “Taxing the (Very) Rich: Finding the Cure for Excessive Wealth Disorder.” 
Elections Funding Research
In 2014, the WhyNot Initiative funded research (along with several large left-wing foundations) into elections funding conducted by the William J. Brennan Center for Justice, a left-of-center think tank. 
WhyNot donated to the Democracy Initiative in 2018, including providing stipends to bring people to Washington, D.C. for the “Democracy Champions” training. The program trained activists for “democracy reform” for “workers’ rights, environmental justice, racial justice, LGBTQ rights” and liberal immigration reform.  Democracy Initiative leadership includes high level members from organizations including Greenpeace, the Sierra Club, AFL-CIO, and Common Cause.
The group donated to Common Cause through the George S. McGovern Great Government Endowment for efforts toward “democracy reform”. This also funded a conference by Common Cause in 2016 on Howard University campus in Washington D.C. which promoted left-wing economic and social policy.