Yolanda Caraway Joins the Legal Lens Podcast!

I had the pleasure and privilege of welcoming a living legend to The Legal Lens Podcast for a riveting and revelatory discussion: the esteemed political strategist, change agent, and co-author of the award-winning book For Colored Girls Who Have Considered Politics, Yolanda Caraway. With over fifty years of experience shaping Democratic politics and a proven track record of making a political impact, Yolanda offers a rare and invaluable perspective on where we’ve been, how we got here, and what it will take to secure a brighter future and the ever-evolving national landscape right now. Yolanda’s powerful insights are a wake-up call, providing a sobering look at the challenges we face while still offering a clear and hopeful path forward.

For a deeper, more convenient dive into these topics, I encourage everyone to listen to our 35-minute discussion on the Legal Lens Podcast. You can find us on Apple Podcasts, Spotify, Simplecast, and everywhere you get your podcasts for free. Alternatively, you can also listen in the player below:

Yolanda Caraway Joins the Legal Lens Podcast to Discuss the Rise United Network, Content Creators, & the Future of Democratic Politics

We made history with a woman whose life is fit for the history books this week by bringing Yolanda Caraway on the program for her first-ever podcast appearance! It is truly an honor.

I am sure you will be both enlightened and inspired by this candid discussion with the eminent and inimitable Yolanda Caraway, a woman who has witnessed and participated in many modern watershed moments in our nation’s history. Here are relevant timestamps and topics covered:

4:40 – Yolanda’s Political Roots & Pivotal Historical Moments
20:00 – The Genesis, Impact, and Inspiration of For Colored Girls Who Have Considered Politics
27:30 – The Rise United Network
12:40 – The Rise of Political Polarization
32:00 – A Heartfelt Message of Hope

Yolanda Caraway’s Political Roots & Pivotal Historical Moments

In many ways, Yolanda Caraway‘s incredible story is the story of modern American politics itself.

Her journey into politics began as a 13-year-old volunteer for Robert F. Kennedy’s 1960s presidential campaign. She found herself at the epicenter of some of the most pivotal moments in our nation’s history, including the assassinations of Dr. Martin Luther King, Jr. and Robert F. Kennedy.

It was a chaotic time, but as she reflected, it was also a beautiful one.

“It was a tough time, but it was also a beautiful time for Black people because we were coming into our own in so many ways,” reflected Caraway.

Her career continued to the halls of Congress, the Democratic Convention, and ultimately to the Rev. Jesse Jackson’s presidential campaigns, where she served as chief of staff.

It was in this whirlwind of political activity that she honed her skills in strategy and fundraising and discovered her unique talent for getting things done.

“I learned a lot about myself, and I learned that, along the way, I was good at asking people for money. I wasn’t afraid to ask for money. Some people are. I’m not. I was actually good at strategizing. I wasn’t shy, and I wasn’t afraid. That turned out to be a huge asset,” said Caraway.

This fearlessness led her to launch her own business, The Caraway Group, which she ran for 40 years, helping Fortune 500 clients while always remaining connected to the political world she loves.

The Genesis, Impact, and Inspiration of For Colored Girls Who Have Considered Politics

In 2018, Yolanda Caraway, along with her co-authors, Donna Brazile, Bishop Leah Daughtry, and Minyon Moore, published the NAACP Image Award-winning book, For Colored Girls Who Have Considered Politics.

The book, which was inspired by the poem by author Ntozake Shange (RIP) called For Colored Girls, was a heartfelt “love letter to Black women” that shared their collective experiences navigating the political landscape.

The book details their personal journeys and the challenges they faced, but also provides a love letter to Black women. It also includes a “Dear Sister Candidate” chapter that serves as a tutorial for Black women aspiring to run for office. This part of the book is full of valuable advice and insight.

One key piece of advice she shared from this chapter is for a candidate to hire a private investigator to do opposition research on themselves to see what the opposition will find.

Founding The Rise United Network

Yolanda Caraway is not just reflecting on the past; she is actively shaping the future. She is the co-founder of the Rise United Network, a groundbreaking initiative that works with content creators to educate them on civics and combat the rampant misinformation on social media.

Yolanda believes that since civics is no longer taught in school, we must find new ways to help people understand how our government and laws actually work.

The Rise United Network trains content creators on how to use their voices responsibly and how to discern truth from falsehood, especially as more and more people get their news from social media.

This groundbreaking initiative aims to equip a new wave of digital civil engagement strategists with the skills and knowledge necessary to elevate authentic democratic discourse online and expand the party’s reach.

The power of this strategy was on full display at the 2024 Democratic National Convention, where the DNC, for the first time ever, invited 200 content creators to be a part of the event.

“My understanding, what I was told was they got 700 million more views than any traditional media,” said Caraway.

This overwhelming success proves that content creators are the wave of the future, and Yolanda is on the leading edge of this crucial movement.

The Rise of Political Polarization

As a trailblazing political strategist who has been “in the room” for countless political battles, Yolanda Caraway offers a powerful diagnosis of our current political climate.

Caraway traces the beginning of the “snarkiness and the meanness” to the era of Newt Gingrich and Bill Clinton, a period that set the stage for a new, more aggressive brand of partisan politics. However, she believes the true inflection point came with the election of President 47.

“It’s like it’s been something that’s unearthed that they’ve been hiding. For one period, it was like, okay, we have to be politically correct. But since the last election, it’s kind of the first time they’ve come out of the woodwork to say it’s all okay. You have the green light to say whatever you want to say,” said Caraway.

This new reality, she argues, has erased the old lines of civil discourse, turning political disagreements into personal attacks. She remembers a time when Democrats and Republicans could be friends and work together, a far cry from the divisive, “us versus them” mentality that now dominates the national stage.

I asked Yolanda to reflect on her experiences at the DNC, where she worked closely with her dear friend and one of the most celebrated DNC chairmen in history, the late Ron Brown.

She shared a powerful lesson from his leadership that is more relevant now than ever that she learned during a contentious presidential primary season in the early 1990s when Ron Brown brought all the potential Democratic candidates together for a summit.

A Heartfelt Message of Hope

Despite the political turmoil and the challenges ahead, Yolanda left us with a powerful and resolute message of hope.

“We’ve all been through so much over the years, and I don’t want us to see ourselves go back to where we were 50 years ago. We have to continue to fight. I don’t know if that’s hopeful or not, but I, you know, I’m rolling up my sleeves and I am, if I’m 75 years old and I can still get out here and make something happen, everybody else can, too. You just cannot give up. It won’t always be this way. Remember that as you keep fighting for what’s right,” said Caraway.

Yolanda’s journey reminds us that the fight for justice and democracy is a long one, but it is not a lost one. It is a fight that has been and will continue to be waged by dedicated people who refuse to give up. Her continued work with the Rise United Network is a testament to her enduring belief in the power of a people united.

Do You Want to Hear More Powerful Insights from Legal Experts Like Yolanda Caraway? Subscribe to and Download the Legal Lens Podcast!

Firstly, we strongly encourage all of our listeners to go to www.riseunited.us to learn more about the amazing work Yolanda Caraway and her team are doing, especially if you are a content creator interested in working with this organization. We strongly encourage you to support them in any way possible. Our discussion with the legendary Yolanda Caraway offered a powerful reminder that our strength lies in unity and our ability to learn from history.

Caraway’s insights are a vital and poignant reminder that progress is possible when we organize, engage, and refuse to be silent. Stay informed, inspired, and empowered. Listen and subscribe to my podcast on Simplecast or by clicking below!

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This communication is not legal advice. It is educational only. For legal advice, consult with an experienced employment law attorney in your state or city.