Create a strategy which aims to put yourself out of business. Nonprofits exist to cure something, address an issue, or elevate a group of people. Not all of them are tackling issues with a clear potential solution on the horizon, but we do. It may be a big dream, but we can see a clear path to making voter registration a thing of the past (Hello, same day registration!). The most lasting legacy we could leave would be death by success.

For someone who wants to set aside money to establish a Philanthropic Foundation or Fund, what does it take to make sure your resources are being impactful and truly effective? In this interview series, called “How To Create Philanthropy That Leaves a Lasting Legacy” we are visiting with founders of Philanthropic Foundations, Charitable Organizations, and Non Profit Organizations, to talk about the steps they took to create sustainable success.

As a part of this series, I had the pleasure of interviewing Debra Cleaver, CEO of VoteAmerica.

Debra Cleaver is the founder and CEO of VoteAmerica, a nonpartisan national nonprofit leveraging research-driven campaigns to register and turnout the 100+ million Americans who are traditionally excluded by partisan outreach efforts. Debra is a serial founder whose organizations include (2016), (2018), Long Distance Voter (2008), and Swing the State (2004). Debra is an alum of Pomona College and Y Combinator, and a former Draper Richards Kaplan Fellow for Social Entrepreneurship. As a result of Debra’s work and commitment to the organization, VoteAmerica just won the Social Innovation Award from the Classy Awards, one of the most prestigious and largest social impact awards in the country.

Thank you for making time to visit with us about a ‘top of mind’ topic. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?

Both my parents were civil servants and proud union members. When I was just 5 years old, my mother brought me along with her and her union for a protest march in Washington, D.C. Experiences like those shaped who I am today as an adult. I learned from a very young age that when I recognize injustice in the world, sitting idle and assuming someone else will address it is not an option. The importance of speaking up and protesting has been rooted deeply in my upbringing for longer than I can remember.

You are a successful leader. Which three character traits do you think were most instrumental to your success? We would love to hear a few stories or examples.

  1. I’m physically incapable of staying silent in the face of injustice. It only fires me up to do more. We sue states when they limit voter’s rights (Kansas and Georgia most recently).
  2. I have a product management mindset. When I see a gap, I use technology to build a solution. In 2020, Texas was the most voter suppressive state in the country, lacking basic essential infrastructure to help citizens cast their ballot safely, like online registration and mail-in ballot tracking. Our team stepped up to build the lacking critical election tech for Texas voters, such as the ballot tracker.
  3. I believe in the importance of empathy & camaraderie in team dynamics. Even in a fully-remote world, it’s crucial to form interpersonal connections with your colleagues. The strongest team dynamics are created when we all know, care, and respect one another both inside and outside the office.

What’s the most interesting discovery you’ve made since you started leading your organization?

In 1993, the internet as we know it was “born.” That same year, the National Voter Registration Act was signed into law. Commonly referred to as the Motor Voter Act because it required state governments to offer a simplified voter registration process to any eligible person applying for or renewing a driver’s license, it essentially made the DMV the largest voter registration group in America.

Nearly 30 years later, this law which is the same age as the internet, is still the last major upgrade to our federal voter registration system. Think of how much the internet has grown and changed and evolved in that time! Yet our country’s approach to voter registration has not. That’s just wild to me.

Can you please tell our readers more about how you or your organization intends to make a significant social impact?

VoteAmerica’s goal is to be the largest, most efficient voter engagement organization in the country. There are numerous other groups doing fantastic work in this space, but most utilize traditional 1-to-1 grassroots tactics. We are hyper-focused on building exponentially scalable tactics which will instead allow us to reach voters on a scale of 1-to-millions.

I started VoteAmerica by posing this question to my team: If we woke up tomorrow and no one was registered to vote, how could we most quickly and efficiently reach and register everyone. There were about 240 million people eligible to voter in 2020, so unsurprisingly, no one said “grab a clipboard and start knocking on doors!”

As its core, voter registration is just paperwork. We are constantly made to fill out paperwork with the same basic information fields, so why not integrate voter registration into other paperwork-filing actions which are similar to renewing your driver’s license?

We’ve zeroed in on the processes and platform with the largest possible reach and have been hard at work integrating our core tech tools into those major consumer software platforms. Our goal is that whenever someone e-files their taxes, checks their credit report, registers for a new class, changes their address, etc. they will also be prompted to check their voter registration status, and if needed, easily register to vote right then and there.

What makes you feel passionate about this cause more than any other?

I first became truly cognizant of how important voter turnout is in 2000. It was the second time I was eligible to vote in a presidential election. I was watching the returns late at night, after most of my friends had already gone to bed believing that Florida had gone blue, when suddenly a box of ballots was found in Broward County and everything changed. After a recount and several weeks of legal battles, the state was ultimately declared in favor of Bush. Watching the process unfold, I felt unnerved on so many levels, but what upset me most was that all of it stemmed from low voter turnout. Such low turnout, that the outcome of an American presidential election could be decided by the results of just one single county.

We’re still feeling the effects of that election’s fallout, having established a new low standard of confidence in our election systems. The presidential election should never come down to multiple recounts of ballots in a single county in America. I have a bias toward action, so witnessing this inspired me to do something about it, to somehow help ensure that our future elections would be more safe, secure, and most importantly, a fully honest reflection of the population. We all seem to have this vague sense that there are people addressing major systemic problems, but that’s often not true. If you can’t name the person who is actively working on fixing as issue, then it might as well be you.

Without naming names, could you share a story about an individual who benefitted from your initiatives?

In 2020, Americans had to navigate incredible hurdles to cast their ballots. The COVID-19 pandemic created an ever-changing world of new voting rules and processes. Ahead of the election, VoteAmerica piloted a text-based ‘Voter Helpline’ powered by Slack. By texting a shortcode, voters in all 50 states could be connected to one of our more than 300 volunteers who’d been trained to answer any questions and address issues they faced during the voting process. The platform organized incoming conversations so that volunteers could ‘adopt’ voters, giving them personalized attention and responding in near real-time to voters throughout their voting process. Both voters & volunteers were also able to later reconnect with the same exact person if they had further questions along the way.

During the 2020 General Election, our volunteers helped more than 14,000 voters from all 50 states and D.C. cast their ballots. These thousands of personal 1-on-1 engagements had an immense tangible impact, as seen in the many positive responses we heard from voters:

“I voted yesterday, and you made it happen! I’m 56, and it was my first time ever voting! Thank you for helping and empowering me!”

“Awesome, thank you so much! You rock! Wish I’d known about y’all during 2016. Can I give this texting number to friends if they have questions?”

We all want to help and to live a life of purpose. What are three actions anyone could take to help address the root cause of the problem you’re trying to solve?

  1. VOTE. In every election. Especially in local elections. And remind your friends & family to vote.
  2. Check your voter registration status. Any time. Don’t wait until the election to verify your information is up-to-date when you can do so year round.
  3. Don’t give up on democracy. Our system of government might not be perfect, but it’s worlds better than the alternative. Democracy only truly succeeds when we all participate.

Based on your experience, what are the “5 Things You Need To Create A Successful & Effective Nonprofit That Leaves A Lasting Legacy?” Please share a story or example for each.

  1. Hire for your weaknesses. I’m a generalist, not a specialist (except when it comes to election laws). I have big ideas about our mission and how we’ll achieve it. Realizing that vision requires hiring and empowering a staff of trusted experts across departments. It would be a horrible use of my time (and we would probably fail) if I was in charge of things like conducting our financial audits, coding our robust toolset, or marketing the organization. So I feel incredibly lucky to have a team of incredibly talented, accomplished individuals dedicated to our success across their respective pillars.
  2. Buy, don’t build. See above. There are only so many hours in the day and my team is small. It’s important that every project we take on reinforces, rather than distracts from from our mission. If a tool or technology exists to make my team better at their job, we don’t spend time creating a work-around. We make it a resource and utilize it to the full extent.
  3. Create a strategy which aims to put yourself out of business. Nonprofits exist to cure something, address an issue, or elevate a group of people. Not all of them are tackling issues with a clear potential solution on the horizon, but we do. It may be a big dream, but we can see a clear path to making voter registration a thing of the past (Hello, same day registration!). The most lasting legacy we could leave would be death by success.
  4. Fundraise for longevity, not programs. Someone once said to me, ‘We’ve built a culture in non-profits where it’s a good thing if someone calls you scrappy. What that really means is you’re under-resouced.” If any small start-up had a successful first year, they’d receive more money to grow. When you work in the cyclical cycle of election politics, a killer election year does not result in more funding during the “off-years.” I reject the idea that “overhead” is an expense which detracts from our mission, instead seeing it as “core mission support,” essential to the success of our programs.
  5. Be goal-oriented and tactic-agnostic. I refuse to believe that low voter turnout is a result of high voter apathy. Voting is hard! We can increase turnout by simply making it easier, by clearing hurdles created by a lack of information access and antiquated regulations. My strategy to increase voter turnout has constantly evolved with the landscape. In 2008, it was fixing the lack of absentee ballot information on the internet, then states created online resources. In 2016, we launched the country’s first ever voter registration drive via text. Now you receive text reminders to vote from numerous organizations annually. Today, we’re building partnerships to scale our work and reduce costs long-term across the entire voter engagement lifecycle.

How has the pandemic changed your definition of success?

For the work we do at VoteAmerica, the truest form of success would be 100% voter registration and 100% voter participation in every election. It’s essentially an exit strategy! If we are truly successful, we won’t need to exist anymore. The integrations we’re building can live on in perpetuity, empowering millions of voters every day of every year. And the grassroots community organizations can reach every last remaining voter who may have been missed by our approach, in an even more targeted, efficient manner.

I began VoteAmerica in 2020 with this definition of success. We all knew it would take significant effort to achieve our goals, especially to convince multi-billion dollar companies that this was a consumer offering worth building into their product’s core offering. What we didn’t expect was how the pandemic would help shine a spotlight for the average citizen all of the many ways our elected officials actually make it more difficult for them to vote. I now consider it a major form of success that individuals are standing up more for their right to vote safely via any method available to them, and that companies have realized supporting Democracy is not only good for business. I see it as a major version of success that our citizens have become vastly more aware of the many ways their right to vote is suppressed and taken action to change that. For any significant change to be made in a society, citizen engagement is important but citizen empowerment is crucial.

How do you get inspired after an inevitable setback?

I’m a very stubborn person. And I believe passionately in the work I do. So I’m not easily deterred in pursuing my goals. When I face a setback or challenge, it reinvigorates my sense of purpose.

As a woman who has only ever lived in an America where I had the right to choose, I was very disappointed with the Supreme Court’s recent decision to overturn Roe v. Wade. All personal political views aside, I’m especially disappointed in this decision because I know 5 of our 9 current justices were appointed by presidents who actually lost the popular vote, so it doesn’t accurately reflect the values of our population’s majority. Furthermore, seeing how many people are newly politicized by this doesn’t just inspire me, it fuels me. I draw energy from it.

We are very blessed that very prominent leaders read this column. Is there a person in the world who you would like to talk to, to share the idea behind your non-profit? He, she, or they might just see this, especially if we tag them. 🙂

I would love to talk to Warren Buffett about the work we’re doing. I think anyone who can dedicate their entire life to being the best at one thing, without distraction, is so inspiring. And him especially because he’s a lifelong learner, who reads endlessly, and makes incredibly informed, educated decisions. It would be a dream come true to have his input on VoteAmerica’s strategy. Plus, we could do so much with even the smallest contribution from his 99% pledged charitable contributions.

You’re doing important work. How can our readers follow your progress online?

First, I also encourage your readers to take a few seconds to double check their voter registration status by visiting

They should also sign-up to receive election reminders at

Readers can also sign-up for email updates from VoteAmerica or follow us on social media.





To learn more about the Classy Awards:

Thank you for a meaningful conversation. We wish you continued success with your mission.