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Female Founders: Debra Cleaver of VoteAmerica On The Five Things You Need To Thrive and Succeed as a Woman Founder

An Interview With Candice Georgiadis

Extreme patience. You can’t predict the future. Things may work out exactly as you’d planned, but far more likely, they won’t. You will encounter roadblocks, changes, nay-sayers, critics, exhaustion, and failures. These things are inevitable. But if you trust your gut and believe in what you’re building, you’ll get where you’re going eventually.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Debra Cleaver.

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 Vote.org (2016), ElectionDay.org (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.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

The second presidential general election I was eligible to vote in was 2000. Even if you’re not a political junkie, surely you remember that presidential election: George W. Bush, Al Gore, and the “hanging chads.” 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. 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.

Can you share the most interesting story that happened to you since you began leading your company?

When I was first getting started in 2013, I was contacted by an independent research group which analyzes voter registration data. At the time, I was still working full-time at MySpace. I’d started this vote-by-mail group as an after-hours hobby, a way to blow off steam really.

This group had called to verify what the budget had been for my efforts (only about $5,200). They assumed I must’ve left off a zero because apparently the work I’d done had ultimately registered more than 100,000 voters. I’d inadvertently run one of the top 20 biggest voter registration campaigns in the country, on a fraction of the budget spent by others. There were groups who literally spent millions of dollars annually driving voter registration. I’d only spent about 80 hours of my personal time on the whole thing.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The funniest mistake I made was not realizing I was forming a company in the first place! When I first built Long Distance Voter, I didn’t recognize that I was forming what ended up becoming a critical part of the infrastructure for Vote.org. Before I paid myself a single dollar, I’d created what became the most authoritative source of information not just for voting by mail, but voting period.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

One of the best pieces of advice I ever received was from Sam Altman, who was at the time the President of Y Combinator. I’d been accepted into the Summer 2016 class of the organization, which provides seed funding and 3 months of intensive mentorship to select startups. About 10 weeks into each term is Demo Day, when all of the companies get the opportunity to pitch their product or service to a privately invited group of investors. Only a handful of nonprofits participate in Y Combinator and due to legal regulations, we’re the only ones allowed to ask for money during our 1 minute onstage. I needed $600,000 to properly fund what I wanted to accomplish at Vote.org, which I thought was an incredibly large sum. Several people advised me against directly asking for the investment, to instead focus on highlighting my organization’s cost-efficiency. It was Sam who told me to get up there and do exactly what I needed to. “People are going to raise millions of dollars today, for things that are far less important than U.S. democracy. If you need $600,000, don’t beat around the bush. Just ask for it. And in the future, never ask for anything less than exactly what you need. Ever.” That was a game changer.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Female founders are held to impossibly high standards. Men who have great ideas are seen as visionary. They’re funded for their ideas and potential alone. Whereas women who have great ideas are expected to also demonstrate at least a decade of proven accomplishment, or else we risk being seen as unprepared, unseasoned, just not ready for the challenge. It creates a chicken vs egg scenario. We need to prove what our vision can accomplish without funding, which can be almost impossible to achieve without the funding.

Men get funded for ideas alone, while women have their competence questioned every step of the way.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

As individuals, we need to recognize and correct the gendered differences between our expectations for male vs female founders.

Most male founders have a female partner at home, that is taking care of everything outside of work, often while also working a job themselves. The house, the children, their emotional wellbeing.

As females, we need to support other female founders. We’re held to the impossibly high expectation that we not only need to show significant success, competence, and drive, but also be nurturers. When considering some of the most successful male founders, their interpersonal demeanor almost never comes up. Yet female founders are expected to be warm & fuzzy at all times, then constantly criticized for our tone.

We all need to have an eye for these disparities, speak up, and push back.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

Women generally have a deep well of expertise that we don’t even recognize in ourselves. Without even acknowledging it, many women are able to have a successful professional career, while putting in the extra hours at home too.

Also, representation matters. The image of a founder is typically that of a techie in a hooded sweatshirt. The more we recognize successful women Founders, the more easily we can picture ourselves in that role as well.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

We idolize founders. They’re seen as larger-than-life visionaries capable of accomplishing things greater than we mere mortals can even dream of. But the truth is that the most successful founders can likely only do two or three things extremely well. The ability to bring their vision to life is necessary, but even more important is the ability to delegate crucial aspects of the business to people who know how to do them better than they do. You can’t become a successful founder alone. And your competence won’t be recognized unless you shout your successes from the mountaintops, demanding recognition.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

To be a founder, you have to be incredibly comfortable with uncertainty. Every day is highly varied and unique. As an employee, your days are fairly consistent. You start your day, do similar activities each day, and develop a deep expertise in those actions. But a founder needs to be more of a generalist, capable of rapidly and constantly learning new things to a point of competence but probably not excellence. Maybe you’re great at building apps but not at building publicity campaigns. You’ll still need to develop at least an intermediate understanding of the widely varied, often unrelated, skills necessary to make your company flourish, then hire someone who can do it even better than you to take it further. Unless you know the basics, you won’t know what to look for in that next hire, or how to properly recognize the difference between good and great.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)

  1. Confidence in your abilities. Recognize what you’re best at and double-down on these strengths. Conversely, be sure to reflect upon your weaknesses. Recognizing where you have gaps in skillset will allow you to recognize the roles you need to hire for first.
  2. Comfort with uncertainty. I can guarantee you that every day will be different from the last. You’ll have to put out more fires than you could ever dream of. So be prepared to roll with the punches and make constant adjustments to your strategy.
  3. A genuine excitement for learning. No matter how prepared you are, you will have to learn new things, constantly. If you are the type of person who approaches every opportunity with a growth mindset, no matter the outcome of our business, you’ll come out a winner.
  4. Extreme patience. You can’t predict the future. Things may work out exactly as you’d planned, but far more likely, they won’t. You will encounter roadblocks, changes, nay-sayers, critics, exhaustion, and failures. These things are inevitable. But if you trust your gut and believe in what you’re building, you’ll get where you’re going eventually.
  5. A network of other founders. No one can succeed in a vacuum. Having human resources you can connect with is essential. They may be going through the same struggles you are. Or they may help you view things through a completely different perspective. Either way, don’t forget to surround yourself with people who have a similar mission to build something for themselves.

How have you used your success to make the world a better place?

Every single day, I wake up and do my best to ensure that US democracy continues to exist 4, 40, and 400 years from now. We all deserve to have a voice and it’s my mission at VoteAmerica to make sure every single voice is heard.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

To bring the greatest good for all of us in the future, we need to work together to address climate change. I believe passionately in a fully engaged electorate, in building a world which is by the people, of the people, and for the people. But it’s crucial that we also protect the planet which we all occupy. Otherwise there may not be a future world for us to cast our votes in.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to meet the Prime Minister of New Zealand, Jacinda Ardern. Not only did she become the world’s youngest leader of a free nation when she took office, but then she was also the second elected world leader to give birth while in office, but then she went ahead and also did an exceptional job managing the COVID-19 pandemic in her country (while simultaneously raising an infant, alone). We could all learn some valuable lessons in time management and personal fortitude from her, without a doubt.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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