Progressive Politics

Episode Overview

On this episode of The Tote + Pears Podcast, we’re discussing women’s political presence and power — from the female voters who influenced the 2016 presidential race, to the rise of a new women’s movement and the issues facing women today with American blogger, writer, and CEO and founder of the digital agency, Do Big Things, Cheryl Contee.
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Topics Covered

A third-generation college graduate: Cheryl Contee grew up in Washington, DC, to a close-knit family that valued education. Her parents were both heavily rooted in their academic backgrounds — her father was a Harvard professor and her mother, a college professor and an early childhood education teacher. Cheryl picked up the mantle and continued the legacy of achievement with which she was raised. When accepted to both Yale and Princeton, Cheryl chose Yale, a university rich in history and privilege.

An invited guest: Often, minority groups find themselves questioning their presence at elite institutions like the Ivy Leagues. And for notable reasons. Recent studies show that 43% of white students at Harvard are legacy, “Dean’s interest list” or recruited athletes: 70% of those white kids would have been rejected without their connections. Cheryl reflects on the exclusivity and the feeling of being an invited guest as a black scholarship student. At the time, it didn’t occur to her to push back on a space that made her feel like an outsider. But given her strong academic background, she came to recognize, not only did she deserve to be there, she deserved to be there the most.

Jack and Jill Politics: During the George W. Bush Administration, Cheryl quickly discovered there was room for the voice of the black person sitting in the next cubicle: sharing thoughts on culture and politics. She co-founded Jack and Jill Politics, named one of the top 10 black blogs in 2008, where she transformed from friendly co-worker, Cheryl, to the progressive political satirist, writing under the pseudonym "Jill Tubman.”

The blog was satirical, entertaining, and controversial. It blew up in popularity and impact: the first A list political blog to come out in support of Obama’s candidacy. Jill Tubman put pressure on political leaders to meaningfully represent the interests of their constituents and fought against corrupt figures within Washington, a stance for which the blog gained critical acclaim and mass exposure.

Too familiar with the country’s history of hurting and silencing outspoken black people, Cheryl’s family felt protective of her when they learned she was at the center of this political phenomenon. They warned her not to interfere with her promising career in tech. She decided that she was willing to put her life on the line for her beliefs.

Progressive politics: She went on to launch startups focused on the strategic execution of cause and campaigns. Notably, hers was the first tech startup with a black female founder to be acquired by a NASDAQ-traded company: a social impact startup acquired by social impact organization.

Today, she is the CEO and co-founder of Do Big Things, a digital agency that uses new narrative and new tech to support big campaigns through strategic counsel, content development support, campaign and infrastructure design, data and research, and more. They have worked with presidential candidates and on high profile congressional campaigns.

Do Big Things is women-led: 70% of the executive team is female, 50% are people of color. They represent the emerging American demographic, which Cheryl emphasizes is not just a “nice to have,” but a strategic value because they can speak to key audiences from an informed perspective more powerfully. Cheryl is proud of the agency’s success working with female candidates who step forward to overturn the status quo that isn't serving women. She remarks that this freshman/person class of Congress is the most diverse in American history, particularly across gender lines.

Cheryl Contee

Cheryl Contee is the award-winning CEO and co-founder of Do Big Things, a digital agency that creates new narrative and new tech for a new era focused on causes and campaigns.

Cheryl was a co-founder of social marketing software Attentive.ly at Blackbaud, the first tech startup with a black female founder on board in history to be acquired by a NASDAQ-traded company.

Her prior company Fission helped write the early source code for Crowdtangle, earning sweat equity in a successful social enterprise startup acquired by Facebook in Dec 2016. Cheryl is proud to be a co-founder of the tech inclusion initiative #YesWeCode.

Connect with Cheryl on LinkedIn.


Produced by: Kai-Saun Anderson
Music by:
Podington Bear - Soft Driver and Rope Swing

About the host

Amber Anderson

Co-Founder + Head of Strategy
Amber Anderson is the co-founder of T+P where she specializes in strategy, marketing and product management.

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