Deanna Singh


Deanna Singh wants to live in a world where marginalized communities have power. As an expert social entrepreneur, she is obsessed with making the world a better place, and she will build or break systems to create positive change.  While tackling complex social challenges, Deanna gives audiences the tools and courage to imagine, activate, and impact the world as agents of change. Deanna is described as a trailblazer and dynamic speaker who is at the forefront of social change. She is an accomplished author, educator, business leader, and social justice champion who speaks to over 50,000 people annually!


Deanna has spent more than two decades researching, designing, and building asset-based solutions to complex social challenges while raising awareness for underserved populations. She is the Founder and Chief Change Agent of Flying Elephant, an umbrella organization for four social ventures, all of which are dedicated to shifting power to marginalized communities. Through Uplifting Impact, she empowers businesses and individuals to increase diversity, equity, and inclusion in their workplaces by offering consulting, coaching, and training - including a bi-annual Virtual Summit that draws more than 500 attendees. Delivering keynotes and trainings to entrepreneurs and teams who want to align their work to their purpose, Deanna’s Purposeful Hustle brand teaches the method and the mission by the book of the same name, which has sold more than 10,000 copies. Story to Tell Books, a children’s book imprint, features positive narrative and visual images of children of color, including three books authored by Deanna. Lastly, Birth Coach Milwaukee provides doula services to birthing people who otherwise could not afford it. 


Deanna’s current projects include serving as lead instructor for the Professional Certificate in Diversity, Equity, and Inclusion offered through University of Wisconsin’s Center for Professional and Executive Development and publishing two new books: Actions Speak Louder (Penguin Random House; release Spring 2022) and a new book for American Girl (release June 2021).


Because of her creativity, tenacity, and change-provoking honesty, Deanna Singh is in demand as a motivational speaker and educator for teams from a wide variety of organizations. She is regarded as an expert in leadership; entrepreneurship; and diversity, equity & inclusion and speaks frequently to corporate, university, and association groups on all three topics. She also visits schools to share her three children’s books, I am a Boy of Color, I am a Girl of Color, and Cloth Crown.


Singh earned her Bachelor of Arts in Urban Studies from Fordham University, a Juris Doctorate from Georgetown University, and a Master’s in Business Administration from the University of Wisconsin, Madison. She has been recognized by the Milwaukee Business Journal as one of the community’s most influential 40 Under 40 Leaders, the State of Wisconsin as a Women Who Inspires, and by Forbes as an African American Woman Everyone Should Know. 

"Passion is often masked as a luxury when it is really an essential ingredient in life."
-Deanna Singh



Deanna offered a remarkable Keynote to kickoff our AmeriCorps members' term of service. Her genuine warmth and excitement was absolutely motivational and truly set the stage. We continue to get stories and appreciation for her amazing presentation. We are so grateful to have shared a powerfully inspiring moment of growth with such a tremendous change agent!

Amy Porter, Event Planner


Deanna is an artful, honest storyteller. She weaves her stories into messages filled with wisdom and delivers those messages in ways that touch the heart and soul. Those who listen to her walk away with a greater awareness of their individual power and a greater confidence that they can translate that "power" into a substantive and meaningful change in their communities.

Christine Hill, Executive Director, Future Milwaukee


Deanna was authentic, engaging and delivered a message that was inspiring and uplifting - much needed given the major endeavors our agency currently faces.

Patty Metropulos, Executive Director & CEO, Kathy's House