Meet the 2019 Philanthropic 5
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Meet the 2019 Philanthropic 5

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June 19, 2019

Each year, United Way's Emerging Leaders honor five community leaders in their 20s, 30s and 40s who give, advocate and volunteer for change through the Philanthropic 5 Awards. The Philanthropic Youth award recognizes a youth community leader under 21 years old.

Meet our 2019 award winners: Liz Caldwell, Jilly Gokalgandhi, Mike Maschek, Jason Rae, Keith Stanley and Philanthropic Youth winner Erica Lofton.

Help us celebrate these winners at our annual Philanthropic 5 Awards event on Thursday, August 8th at Venue Forty Two. Register today!

Liz Caldwell is an assistant director and actuary at Northwestern Mutual. In this role, Liz is responsible for overseeing the reserves for long-term care insurance and disability income, as well as the new Principles Based Reserves requirements for life insurance. Liz is a passionate volunteer, coordinating a third-grade reading program and math outreach efforts at Northwestern Mutual. Liz also leads the nursery volunteers at Mercy Hill church and supports a number of community organizations, including Meta House, through donations and volunteerism. Liz has a bachelor’s degree from Purdue University and lives in the Bay View neighborhood of Milwaukee with her family.


Jilly Gokalgandhi works in community relations at Rockwell Automation, focusing on signature STEM volunteerism programs that empower underrepresented minorities and girls. As the 2019 curator of the Milwaukee Global Shapers, Jilly leads a cohort of young professionals who think globally and act locally by driving dialogue, action, and change. A Marquette graduate with a bachelor’s degree in international relations and economics, Jilly someday hopes to represent the U.S. as a diplomat. After 5 p.m. you can catch Jilly with a good book or a good friend.


Mike Maschek is vice president of finance and strategy at Sixteenth Street Community Health Centers and has more than 15 years of experience in the healthcare industry. To further his personal mission of providing access to health for all, Mike serves as acting board chair and treasurer at CORE El Centro and on the boards of the Wisconsin Primary Health Care Association and Planned Parenthood of Wisconsin.

Mike is passionate about small business development and acts as business liaison for Fund Milwaukee. He has personally invested in a number of small businesses including Sherman Phoenix, the Tandem Restaurant and Fyxation Bikes.



Jason Rae is the founder, president, and CEO of the Wisconsin LGBT Chamber of Commerce, an organization of more than 600 LGBT and allied-owned businesses. Jason has led the organization in numerous achievements and works with the National LGBT Chamber to support other LGBT Chambers around the country. Since 2004, Jason has been a member of the Democratic National Committee and, in 2017, was elected as DNC Secretary. Jason has always found time to give back to the community, serving on a number of nonprofit boards and committees including the Milwaukee County Human Rights Commission. Jason holds a degree from Marquette University and lives in Glendale with his husband Phillip and dog George Washington.



Keith Stanley is executive director of Near West Side Partners, Inc., where he’s charged with spearheading the organization’s efforts to revitalize Milwaukee’s Near West Side. Keith is also executive director of the Avenues West Association and was instrumental in the expansion of Near West Side BID #10, which resulted in a 300% increase in resources to enhance the community. In 2016, Keith was named a Milwaukee Business Journal 40 Under 40 winner. Keith holds a bachelor’s degree in business administration from Alabama State University.


Philanthropic Youth
Erica L. Lofton
is a facilitator, keynote speaker, mental health advocate, performer, and founder of Girls in Action, Inc. Foundation. Erica’s near peer support and advocacy with youth issues and girl’s leadership have been recognized by local and national leaders, including President Barack Obama.  In 2015 Erica was invited to the White House to accept the Champion of Change Award for Building Bridges Between Youth and Law Enforcement.

Erica is a 2019 graduate of University School of Milwaukee and will attend the University of Wisconsin – Madison beginning in fall 2019.


Help us celebrate the winners at our P5 event! Learn more and register to attend.


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